32789 Zip Code FL 3+ Acre Real Estate, Homes for Sale

2 Beds ⋅ 2 Baths ⋅ Whispering Waters/Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Enjoy the Winter Park lifestyle in this spacious 2-bedroom, 2-bath lakefront condo offering 1,900 square feet in the heart of downtown Winter Park. Enjoy serene lake views from the 120 sq ft screened porch—perfect for morning coffee or evening wine. The light-filled living area features soaring 8 ft 10 in ceilings, creating an open, airy atmosphere. A cozy family room offers built-in shelving and a wet bar, ideal for relaxing or entertaining. The galley kitchen features granite countertops, a natural gas range, and a convenient laundry closet with a stackable washer and dryer. The primary bedroom boasts a walk-in closet with ample storage, additional closet in the rear alcove, and a primary bath with dual sinks and a walk-in shower. The secondary bedroom includes an adjoining office alcove, while the secondary bath offers a walk-in shower. Neutral tones flow throughout the condo, and the dinette provides beautiful views of Lake Osceola. Completely rebuilt in 2011 with new plumbing, electrical wiring, air conditioning, and ductwork, this home offers modern efficiency and peace of mind. A covered boat slip (#15) with lift, two covered parking spaces in the gated underground garage accessible with a key access in the elevator, approximately 90 sq ft of private utility storage, and a community pool complete this exceptional offering. Just steps from Park Avenue, enjoy walkable access to premier shopping, dining, museums, and seasonal events, making this a rare opportunity for true lakefront living in one of Winter Park’s most desirable locations.

311 E Morse Boulevard Unit 2 - 5, Winter Park

$1,100,000

4 Beds ⋅ 3 Baths ⋅ Jenkins Add SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Sold. Lovely house. Large corner lot. Walking distance to Park Avenue.

1701 Palmer Avenue, Winter Park

$350,000

Lawndale SubDv. ⋅ 32789 Zip Code

Great buildable lot centrally located close to I-4 for easy access. Please consult the zoning and planning Dept. for info and guidelines for building. The lot has single family homes on both sides of it and faces a retention pond area across the street. Front half of the lot is cleared. Back half of the lot is wooded. Paved road frontage. Sign on the property. Bring your offers. Seller will not hold mortgage note.

2002 Indiana Avenue, Winter Park

$1,115,000

4 Beds ⋅ 4 Baths ⋅ Temple Estates SubDv. ⋅ 32789 Zip Code

In the heart of Winter Park, this extensively renovated modern farmhouse offers exceptional value for the location. A circular drive and inviting front porch welcome you into light-filled living spaces enhanced by all-new energy-efficient windows, custom millwork and designer finishes throughout. The functional layout includes a first-floor guest suite, additional well-appointed bedrooms and updated baths. The kitchen is updated, featuring custom cabinetry, stone countertops and stainless appliances. The family room flows to a covered lanai and summer kitchen, overlooking a paver deck, pool, fire pit and putting green, ideal for year-round entertaining. The fully fenced backyard offers privacy and access to a detached garage with additional storage. Upstairs, the primary suite features a private balcony, a sitting area, a walk-in closet, and a spa-inspired bath with a freestanding tub and an oversized shower. An additional upstairs fourth bedroom en suite, used as a gym, offers flexibility for a home office or nursery. Renovated with quality and intention, including updated systems and recent roofs. Ideally, across from Phelps Park and just a few blocks from Interlachen Country Club and Winter Park Racquet Club.

1673 Mayfield Avenue, Winter Park

$3,800,000

3 Beds ⋅ 5 Baths ⋅ Park Hill SubDv. ⋅ 32789 Zip Code

A refined, custom brownstone with an exclusive Park Avenue address, offering an unparalleled Winter Park lifestyle enhanced by the finest designer selections throughout. The timeless brick elevation and expansive windows evoke the charm of a favorite city street while preserving the tranquility of this sought-after setting. This three-story townhouse offers 4,237 square feet of thoughtfully designed living space, featuring three en-suite bedrooms, three full baths, two half baths, and a private elevator. Offered fully furnished for the most discerning buyer, the residence welcomes you through a hand-forged iron gate, gas lanterns, and a brick walkway. The open living, dining, and kitchen areas are ideal for entertaining and flow seamlessly to a private open-air courtyard filled with natural light. Custom lighted built-ins with glass shelving, an entertainment bar, and an antique glass entertainment center with sliding doors allow the space to beautifully showcase art or conceal the television. Designer window treatments include exquisite drapery and plantation shutters, complemented by beautiful backsplashes, countertops, fine wallpaper, and detailed trimwork throughout. An exquisite lighting package features designer fixtures and ambient lighting. The chef’s kitchen is equipped with Wolf and Sub-Zero appliances, a center island with ample prep and serving space, and a walk-in pantry, blending perfectly with the dining area and courtyard for effortless entertaining. The private primary suite is appointed with a morning station, dual closets, and a luxurious bath featuring floor-to-ceiling windows, double marble vanities, a spacious glass-enclosed steam shower, and a luxury bathtub. The intimate third-floor rooftop terrace offers a gathering space and exterior half bathroom for convenience. Additional features include a Control4 home automation system, an upscale air-conditioned garage with ceiling storage and custom cabinetry, newer third-floor HVAC and condenser, newer mini-split in the upstairs exterior bath, three-story block construction with soundproof floors, five AC units, and three tankless gas water heaters.

637 N Park Avenue, Winter Park

$4,800,000

5 Beds ⋅ 6 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

An extraordinary opportunity on the shores of Lake Osceola on one of Winter Park's most charming streets. This architecturally interesting lakefront estate offers breathtaking panoramic sunset views and an irreplaceable setting. Thoughtfully designed with the beautiful finishes. First time available in over three decades, this is rare chance to own a legacy property!

641 Bonita Drive, Winter Park

$1,635,000

4 Beds ⋅ 4 Baths ⋅ Windsong-Knowles Place SubDv. ⋅ 32789 Zip Code

Price reduction. Motivated seller! Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer with elegant lighting. This 4-bedroom, 3.5-bath home is loaded with upgrades. The office features beautiful wood and detailed, custom bookshelves, complete with a double-door entry for added privacy. The formal dining room features a pass-through to the Butler's Pantry, which leads into a chef's oasis—Wolf stainless steel appliances for the serious chef, and solid surface countertops. The gourmet kitchen opens up to the family room. This home is a Great floor plan for entertaining friends and family. Eat in nook is located off the kitchen for dinners together. The primary suite is located on the first floor with a spa-like ensuite. Double vanity, extra-large shower, large bathtub for when a relaxing bath is just what you need after a long day. Upstairs, you will find a bonus room, as well as the remaining bedrooms. off the bonus room is a bedroom and a full bathroom, great for guests. The other two bedrooms and bathroom are located on the opposite side of the upstairs to create a split floor plan. Large backyard for enjoying the Florida weather. New EV charger in garage, new A/C unit. Home includes surround sound. This home features numerous upgrades, too many to list. Windsong community offers a resort-style pool with lake views, a playground, lake for fishing. Close to restaurants, schools, and shopping.

1841 Harland Park Drive, Winter Park

$1,250,000

3 Beds ⋅ 3 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code

Experience the charm and endless convenience of Beloit Avenue, one of Winter Park’s most coveted streets! Just steps from the WP-9 Golf Course, and 2 blocks from the lively, renowned Park Avenue, this 3-bedroom/2.5-bath residence presents a unique opportunity for reimagination in a location that is simply unmatched. The 1-story home provides the ideal framework for function yet stylish living, with the existing open floorplan, detailed crown molding, and timeless hardwood floors. French doors off the rear family room lead to an open side courtyard, offering plenty of space to create an outdoor oasis that's perfect for relaxing or entertaining, all wrapped in a masonry wall for added privacy. Access the rear-facing two-car garage from a private brick-paved alley exclusive to Beloit homeowners. Combining charm, convenience, and the added perks of natural gas and a 4-year-old roof, this opportunity is a rare find in the very heart of Winter Park.

359 Beloit Avenue, Winter Park

$184,900

1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Lakefront Lifestyle in Winter Park—Under $200K! Live the resort life for less! This stunning, move-in ready retreat in the heart of Winter Park offers rare, direct access to the 239-acre, spring-fed Lake Killarney. Enjoy exclusive resident-only amenities, including a private boat launch, boat slips, an updated dock, and a tranquil lakefront gazebo. Perfectly located just minutes from the world-class shopping and dining of Winter Park Village, this home provides the ultimate balance of peaceful lakeside serenity and city convenience. The interior is just as impressive as the location. This charming, sun-drenched unit features an open-concept layout with gorgeous engineered wood flooring and a sleek kitchen upgraded with granite countertops. It’s a smart, stylish, and incredibly rare find that’s perfectly priced to sell. Whether you are looking for a low-maintenance home or a serene weekend getaway, this property delivers. Don't let this opportunity slip away—schedule your private showing today!

2500 Lee Rd. Unit 222, Winter Park

$369,900

3 Beds ⋅ 2 Baths ⋅ Temple Terrace SubDv. ⋅ 32789 Zip Code

MULTIPLE OFFER SITUATION - Welcome to this classic ranch home offering 3 bedrooms, 2 baths, and a wonderfully livable floor plan designed for everyday comfort, work-from-home flexibility, and easy entertaining. With 1,584 sqft of living space this home lives large and offers generous room sizes, plenty of storage, and a layout that simply makes sense. From the big front patio, step inside to a bright living area with cathedral ceilings and natural light, leading into an updated kitchen featuring granite countertops and newer cabinetry. Stacked bedroom layout, and the bathrooms feature tile finishes and oak cabinetry. Flooring includes tile throughout most of the home, wood laminate in the primary bedroom, and carpet in two bedrooms. The home also features updated double-pane insulated windows. Some of the highlights of this home are the expansive screened-in Florida room, perfect for relaxing, dining outdoors, or hosting friends —while enjoying fresh air. Outside, you'll find a huge, fully fenced backyard with mature oaks, palms, bananas, flowering cactus, and an aloe garden. There’s ample room for a pool, future expansion, and RV / trailer storage. A storage shed with electric adds even more convenience. The location truly can’t be beat — centrally located near downtown Winter Park, Maitland, Casselberry, restaurants, theaters, lakes, bike paths, museums, five golf courses, and endless shopping and recreation. Zoned for highly regarded schools including Dommerich Elementary, Maitland Middle, and Winter Park High, this is a setting many buyers specifically seek out. The neighborhood is on city utilities; this home currently uses septic which may not function properly and may need to be connected to city sewer which is already on the street. This is a conventional and cash-only sale and is being offered As-Is, with buyers responsible for their due diligence including verifying fees, taxes, and property details.

1816 Azalea Avenue, Winter Park

$4,450,000

5 Beds ⋅ 7 Baths ⋅ Stonehurst Estates SubDv. ⋅ 32789 Zip Code

SOLD DATA ENTRY ONLY Welcome to this exceptional custom residence located on one of Winter Park’s most desirable streets. Built in 2017 and impeccably maintained, this like-new home offers timeless architecture, modern luxury, and thoughtful design throughout. Offering 6 bedrooms, 6 full bathrooms, and 1 half bath, the home encompasses over 5,100 square feet of living space on a generous half-acre lot, providing both privacy and an impressive sense of scale. Upon entry, engineered hardwood flooring, high ceilings, and abundant natural light set the tone for the refined interiors.The open-concept floor plan seamlessly connects the main living areas, making the home ideal for both everyday living and entertaining. The kitchen is equipped with custom solid-wood cabinetry, premium Wolf and Sub-Zero appliances, a large center island, and ample storage, all opening to the family and dining spaces for effortless flow.The primary suite is located on the main level and offers a peaceful retreat with a spacious walk-in closet and a spa-inspired bathroom. Each additional bedroom is generously sized and features its own en-suite bath, ensuring comfort and privacy for family and guests. Multiple flex spaces throughout the home provide versatility for a home office, gym, or media room.Additional features include a Crestron lighting and sound system, a four-car garage with built-in cabinetry, a cement tile roof, and built-in closet systems throughout. The expansive backyard offers ample room for outdoor living and future enhancements. Ideally situated just minutes from Park Avenue, top-rated schools, dining, and shopping, this move-in-ready home presents a rare opportunity to own a nearly new estate in the heart of Winter Park.

1812 Stonehurst Road, Winter Park

$459,900

Golfview SubDv. ⋅ 32789 Zip Code

Ready to build your dream home or invest in one of Winter Park’s most desirable locations? This oversized, one-of-a-kind lot is ideally situated just across from Dubsdread Golf Course and only minutes from Park Avenue, Winter Park Village, dining, shopping, and entertainment. Enjoy convenient access to major roads while still being nestled in a highly sought-after neighborhood. Located within a top-rated school district, including Princeton Elementary. A rare opportunity in Winter Park—don’t wait to make this exceptional property yours.

3601 Midiron Drive, Winter Park

$409,000

3 Beds ⋅ 2 Baths ⋅ Magnolia Gardens Sub SubDv. ⋅ 32789 Zip Code

RARE OPPORTUNITY TO OWN A GREAT HOME IN WINTER PARK! MOTIVATED SELLER! Check out this spacious 3 bedroom, 3 bathroom home almost 1800 sq. ft. The home offers a great layout with abundant natural light, comfortable living spaces and timeless design elements. Enjoy central Florida living in one of Winter Park's most established neighborhoods, walking distance to dining, shopping, parks and top-rated schools. If you are an investor looking for a rare gem this will be a GREAT opportunity for you!

900 Carver Street, Winter Park

$899,000

Fairbanks Park SubDv. ⋅ 32789 Zip Code

Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and entertainment. Lots like this are seldom available. Whether you’re envisioning a custom residence or an investment in one of Central Florida’s most desirable neighborhoods, this is a truly rare opportunity in the heart of Winter Park.

731 Midget Drive, Winter Park

$2,600,000

6 Beds ⋅ 7 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code

Completed in 2020, this exceptional Winter Park lakefront estate blends refined architecture, thoughtful design, and effortless indoor-outdoor living on Lake Killarney. Beyond the gated courtyard-style entrance, the main residence offers 5 bedrooms, 4 full baths, and 2 half baths, complemented by a detached in-law studio ideal for guests, extended family, or a private home office, with a full bath, walk-in closet, and a dry bar with a mini refrigerator. Behind the home, the rear lawn stretches down to the lake where an oversized boat dock provides direct access to Lake Killarney for watersports or breathtaking sunset cruises. Enjoy a large deck, and an upgraded boat lift with 2 motors and a high-capacity cradle to accommodate a variety of boats. Throughout the home, a timeless neutral palette creates a warm and inviting space with modern elegance. An impressive open dining area greets you with soaring 2-story ceilings accented by exposed beams, and is adjoined to the kitchen by a well-appointed butler’s pantry for seamless hosting, complete with a dry bar and wine refrigerator, and a walk-in pantry. The kitchen is a true showpiece, with exceptional floor-to-ceiling cabinetry, 48” natural gas range with dual convection ovens, 2 dishwashers, and a built-in coffee/espresso machine. Anchoring the space, a large quartz-covered island offers 2 faucets plus a filtered water dispenser, and a butcher block prep space. The light-filled living room impresses with dramatic ceilings, a striking gas fireplace, and 10’ sliding glass doors that stack open to the covered lanai. A true extension of the home, the outdoor living experience is exceptional, featuring a summer kitchen, pool bath with an outdoor shower, and remote-controlled screens for year-round enjoyment. The resort-style pool and spa includes a sun shelf, all wrapped in travertine decking, overlooking the lake to provide a tranquil setting for relaxing with friends & family. Completing the main level is a private downstairs guest suite or home office, with a full bath and walk-in closet. Upstairs, the split-bedroom plan is separated by a versatile loft/bonus area with a dry bar and beverage fridge, ideal for a secondary living room, playroom, or study. Designed to embrace the home’s exceptional lakefront setting, the spacious primary retreat captures lake views through expansive glass doors, from the private balcony, and from the en-suite bath. The primary bath is luxurious, and thoughtfully designed to be a true sanctuary, with a freestanding soaking tub positioned to enjoy lake views, and a large glass-enclosed steam shower. Enjoy a very generous walk-in closet, with extensive built-ins and a center island that create a boutique-style dressing experience. The upper level also includes three additional bedrooms with wood floors, high ceilings, and easy access to 2 full bathrooms, plus a functional laundry room conveniently located off the bonus area. Perfectly positioned in Winter Park, with shopping, dining, and everyday conveniences just blocks away at the new and improved Winter Park Village, and the vibrant energy of the famed Park Avenue only minutes from your door, this lakefront home delivers the rare combination of newer construction and exceptional waterfront living—without compromise.

560 Country Club Drive, Winter Park

$4,250,000

4 Beds ⋅ 5 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform Twelve kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool. A wood-clad pergola shelters the lanai. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

1336 College Point, Winter Park

$420,000

1 Beds ⋅ 1 Baths ⋅ Park Aire Condo SubDv. ⋅ 32789 Zip Code

Location, Location, Location! Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz. Enjoy a large walk-in closet, one assigned carport space, and a private storage room. The community offers a sparkling saltwater pool, two third-floor outdoor patios, laundry facility, elevator, and a guest-quarters efficiency available to owners for a nominal fee. Just steps from Park Avenue shopping and dining, cafes, churches, Winter Park Golf Club, Rollins College and more. No pets.

640 N Park Avenue Unit 5, Winter Park

$1,500,000

2 Beds ⋅ 2 Baths ⋅ Trovillion Condo SubDv. ⋅ 32789 Zip Code

Located on the second floor of Villa Siena, this two-bedroom, two-bath residence offers 1,511 square feet of elegantly appointed living space with two balconies overlooking New England Avenue’s tree-lined brick streets in the heart of Winter Park. A split-bedroom layout ensures privacy, with wood flooring and tray ceilings defining the open-concept living and dining areas. The kitchen features solid wood cabinetry, granite countertops, a Sub-Zero refrigerator, and Wolf gas cooktop and oven. Both bedrooms include walk-in closets, tray ceilings, and direct access to private balconies via French doors. The primary bath is designed with dual vanities, a deep soaking tub, and a walk-in shower finished in natural stone. Travertine flooring continues through the entry, kitchen, and baths, while the full laundry room includes built-in cabinetry and utility closet storage. This residence includes one assigned space in the secured below-ground garage, and an additional ground-level garage space. Villa Siena amenities include a fitness center, rooftop terrace, club room with bar and outdoor seating, conference room, guest parking, and on-site management. Enjoy direct access to Park Avenue’s boutique shopping, dining, museums, and Central Park, with the Alfond Inn’s restaurant, café, and lounge just across the street.

315 E New England Avenue Unit 7, Winter Park

$615,000

3 Beds ⋅ 2 Baths ⋅ Orangewood Park SubDv. ⋅ 32789 Zip Code

Mid-Century Modern architecture meets modern comfort in this beautifully updated Winter Park home. Clean lines, open sightlines, and warm architectural details create a timeless aesthetic that feels both stylish and inviting from the moment you arrive. Inside, the home features an open-concept layout with multiple living areas—ideal for entertaining or everyday living. The renovated kitchen is the heart of the home, showcasing sleek cabinetry, stainless steel appliances, modern lighting, generous counter space, and a large island that flows seamlessly into the dining and living areas. Natural light fills each room, highlighting the home’s thoughtful design and functional layout. Step outside from the large, cozy family room into your private backyard oasis—an entertainer’s dream. The resurfaced pool (Dec 2025) and updated pool equipment (Dec 2025) provide worry-free enjoyment, while expansive patio areas, string lighting, and multiple seating areas create the perfect setting for relaxing or hosting gatherings. The outdoor space is both private and versatile, delivering true Florida living year-round. Garden enthusiasts will love the raised garden beds, established landscaping, and fruit trees, including mango, peach, fig, and Meyer lemon—perfect for anyone who enjoys homegrown produce and sustainable living. A charming garden pathway adds character and connects the outdoor spaces beautifully with a garden shed for your tools. Additional highlights include modern flooring throughout, updated bathrooms, flexible living spaces, and a layout that balances comfort with architectural character. Centrally located just minutes from Park Avenue, Rollins College, dining, shopping, downtown, and major roadways, this home offers the perfect blend of style, location, and lifestyle. A rare opportunity to own a Mid-Century Modern home with a private backyard setting and a gardener’s paradise in one of Winter Park’s most desirable areas. This is a welcoming, connected community where neighbors know one another and come together for festive street events throughout the holidays, creating a warm and inviting atmosphere.

2811 Eastern Parkway, Winter Park

$625,000

3 Beds ⋅ 3 Baths ⋅ Mc Intyre Place Condo SubDv. ⋅ 32789 Zip Code

Experience the ease of townhome living with the feel of a single-family residence. Nestled on a picturesque brick street shaded by mature trees, this well-maintained home offers prime access to Rollins College, Park Avenue, and the best of Winter Park. With 2,015 square feet of living space, the home offers three generously sized bedrooms and two and a half baths in a smart, comfortable layout. Step inside to a spacious living room featuring built-ins, soaring ceilings, a fireplace, and large windows with French doors that fill the room with natural light. Off the living room, enjoy the first of two serene patios—perfect for relaxing or entertaining. The living room flows seamlessly into the dining room and the kitchen, which includes a cozy breakfast nook and abundant storage. From the nook, step out onto the second patio to enjoy your morning coffee or an evening cocktail. Upstairs, the primary suite is a true retreat. It boasts its own fireplace and ample space for a desk, workout area, or sitting area. The ensuite bath includes dual vanities, a garden tub, a separate shower, and an impressive dressing area with extensive mirrored closet space. Down the hall, two additional bedrooms share a Jack-and-Jill bathroom. Zoned for Audubon K–8 and Winter Park High School, and just moments from Winter Park’s vibrant lifestyle amenities, this home blends comfort and convenience. Schedule your private showing today!

785 Mcintyre Avenue Unit 785, Winter Park

$1,300,000

Park Grove SubDv. ⋅ 32789 Zip Code

Amazing opportunity to build your dream home on large 0.35 acre lot in the premier Park Grove neighborhood, walking distance to Park Avenue and all that downtown Winter Park has to offer!

751 Williams Drive, Winter Park

$630,000

5 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort and its own ATTACHED 2bed/1 Bath IN-LAW SUITE!!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park

$1,575,000

4 Beds ⋅ 4 Baths ⋅ Tangerine Court SubDv. ⋅ 32789 Zip Code

Welcome to 1780 Mizell Avenue, a masterpiece where timeless charm meets modern luxury. This 4-bedroom, 4-bathroom plus office single-family residence offers 2,743 square feet of finely curated living space designed for the discerning buyer who values sophistication, comfort, and convenience. Perfectly positioned just moments from downtown Winter Park’s boutique shopping, fine dining, and Chain of Lakes; this home embodies the best of upscale Florida living. Step inside and experience the 10-foot ceilings, level 5 walls, hardwood flooring and upgraded designer lighting that set an elegant tone throughout. The first-floor master suite is a serene retreat featuring a custom walk-in closet and a spa-inspired bath with wall-to-wall tile, a frameless glass shower enclosure, Kohler three-way shower system, and a freestanding soaking tub. The chef’s kitchen is a masterpiece in itself, equipped with a Viking range, paneled Fisher & Paykel refrigerator, wine fridge, and granite countertops, all framed by sleek custom cabinetry and sophisticated finishes. Dual Trane HVAC systems with Nest smart thermostats ensure year-round comfort with effortless control. The home office, adorned with custom millwork and direct pool access, provides an inspiring space for work or study, ideal for today’s lifestyle. Outdoor living is equally impressive. Entertain in style with a 9-foot stainless-steel summer kitchen, outdoor shower, and a spacious backyard perfect for gatherings or quiet relaxation. Additional highlights include a two-car garage with an epoxy-coated floor, pre-wired EV charger, glass stair railing, and a cozy electric chimney feature adding warmth and character to the main living area. Located in one of Winter Park’s most established neighborhoods residents enjoy top-rated schools, tree-lined streets, and proximity to award-winning restaurants and the Chain of Lakes, all within walking distance. This is more than a home, it’s a statement of luxury, design, and lifestyle. Offered exclusively at 1780 Mizell Avenue, Winter Park, FL where sophistication meets everyday comfort.

1780 Mizell Avenue, Winter Park

$108,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. Brand new a/c unit. This condo is perfectly located in a desirable area with lots of nearby shopping, restaurants, and amenities

1695 Lee Road Unit E204, Winter Park

$445,000

4 Beds ⋅ 2 Baths ⋅ Blk C Pt Rep 02 SubDv. ⋅ 32789 Zip Code

Back on the market after buyer was unable to obtain financing; inspection was completed and seller has addressed multiple items identified during the inspection process. Exceptional opportunity This 4-bedroom, 2-bath property offers approximately 1,450 square feet of living space features a spacious backyard and is ideally located just minutes from Downtown Winter Park, within the highly desirable 32789 zip code. It is within close distance to Mead Botanical Garden and just over one mile from Rollins College. With ongoing redevelopment in the area this property presents strong upside potential amid Winter Park’s continued revitalization.

1347 Orchid Avenue, Winter Park

$2,100,000

5 Beds ⋅ 4 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Back on the market—an exceptional opportunity in Winter Park. Now offered below appraised value, this residence has been thoughtfully refreshed with new carpet, interior paint, and thoughtful enhancements. Presented for the first time, this beautifully appointed 2014 David Weekley home is tucked away on a large corner lot within a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. Featuring 5 bedrooms and 5 bathrooms, the home is designed for both refined living and effortless entertaining, this home includes a private office and expansive bonus spaces. A standout feature of this property is its exceptional and highly sought-after parking flexibility. In addition to the 3-car garage, a newly added driveway (2024) provides additional space for guests and everyday convenience. Beyond that, a gated parking area—discreetly tucked behind an accessible double gate—offers secure storage for a boat, jet skis, or additional vehicles, eliminating the need for off-site storage and enhancing both lifestyle and practicality. Inside, the home showcases a curated collection of upgrades, including custom built-ins throughout the living spaces, office, flex areas, and dining room; custom built closets in every room; and a thoughtfully redesigned pantry with pull-out shelving. Unique touches such as under-stair storage with a hidden “secret door,” custom barn doors, and a LaCantina slider elevate both function and design. Outside is an entertainer’s paradise. There is a covered custom-built summer kitchen with metal roof featuring a built-in LP Grill, Primo Kamodo Smoker, stainless steel storage drawers and cabinets, counter storage ice bucket and plenty of island space for dining. The large pool and adjoining hot tub provide ample space for hours of fun and entertainment. The backyard putting green adds a fun distinctive, resort-style touch. Additional enhancements include brand new luxurious Berber carpet, attic flooring, overhead garage storage, plantation shutters, landscape lighting, updated exterior paint and interior paint, a tankless gas water heater, updated designer lighting through the home and multiple bathroom updates. The roof was replaced in 2021 for added peace of mind. The kitchen is a cooks dream with abundant storage, ample counter space and two ovens. A GE Monogram Dual Fuel Range was added to the kitchen in 2023. The 2021 dining room renovation introduces a custom bar, added storage and striking raw-edge floating shelves—perfectly blending modern sophistication with everyday livability. With its prime location, elevated finishes, and rare combination of luxury and utility—particularly its unmatched parking and storage capabilities, this move-in-ready Winter Park home is truly a standout offering! Inspection report available upon request.

2503 Versailles Avenue, Winter Park

$1,130,000

3 Beds ⋅ 3 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Discover refined elegance in this meticulously updated 3-bedroom, 2.5-bath two-story residence in sought-after Winter Park. Offered at $1,200,000, this stunning home seamlessly blends modern luxury with thoughtful design. The heart of this home features a customized chef's kitchen with top-of-the-line Signature Kitchen Suite appliances, including both induction and electric ranges plus propane gas cooking. Sophisticated touches include in-cabinet and drawer lighting, a dedicated coffee station, and wine cooler—perfect for the culinary enthusiast. Enjoy main-floor living with a spacious primary bedroom suite featuring a spa-inspired ensuite bath with jetted tub and separate shower. Throughout this beautifully appointed home, you'll find 11-foot ceilings, fresh paint inside and out, new porcelain flooring on the main level, and designer light fixtures. A gas fireplace adds warmth and ambiance, while plantation shutters and custom draperies provide elegant window treatments. The second floor offers two generous bedrooms with charming Juliet balconies, connected by a convenient Jack and Jill bath. The versatile loft/bonus room features a built-in entertainment center with surrounding bookcases and beverage center—ideal as a media room, home office, or recreation space. A detached two-car garage opens to a private patio and backyard—perfect for entertaining. The unbeatable location offers walkability to the YMCA and Phelps Park. This turnkey residence represents the perfect blend of luxury, location, and lifestyle in Winter Park's vibrant community.

1600 Palmer Avenue, Winter Park

$899,000

2 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

560 Ololu Drive, Winter Park

$895,000

3 Beds ⋅ 3 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

Situated in the highly sought-after Winter Park area and surrounded by tree-lined streets, this stunning move-in ready home is waiting for its new owner. Set on one of the largest lots in the neighborhood, the property greets you with style and charm. Professional landscaping leads you to an inviting open floor plan designed for both family life and entertaining. The living room provides flexible space for formal gatherings or relaxed moments. The upgraded kitchen features newer stainless steel appliances, quartz countertops, and a wet bar complete with a wine refrigerator and extra cabinetry. The spacious dinette area can accommodate a larger dining table if desired. The owner’s suite is generously sized, featuring an updated bath with a glass-enclosed shower and modern sink. One secondary bedroom offers an en-suite bath, while a third full bath off the family room is perfect for guests. There's also an office or den with French doors that could easily be converted into a fourth bedroom. The family room, highlighted by accent ceiling beams, is ideal for watching games or spending time with friends and opens up to a remarkable backyard oasis. The expansive, fenced backyard is a rare gem—it boasts a beautiful pool, gazebo, and ample space for play and pets. Additional features include engineered hardwood floors throughout, a newer AC system, upgraded yard drainage, a two-car garage with tons of built in storage and ample driveway parking. Conveniently located a short distance from the YMCA, an A-rated elementary school, and just a short drive from Park Ave and other amenities, this location truly can't be beat.

1802 Arbor Park Drive, Winter Park

$420,000

4 Beds ⋅ 3 Baths ⋅ Temple Terrace SubDv. ⋅ 32789 Zip Code

32789 Zip Code! Welcome Home to 1847 Azalea Ave! Discover the charm and convenience of this beautiful one-story home located in the heart of Winter Park. The home is complete with 4 Bedrooms, 2.5 Bathrooms, and 1,477 square feet of living space. This recently renovated property offers brand new features throughout and is move-in ready, ideal for a first time home buyer or investor. Park Ave is minutes away plus close proximity to all of Winter Park's local shops, entertainment, and restaurants. Roof (2022) A/C (2020). Don’t miss the opportunity to own this move-in ready home, call today to schedule your private showing!

1847 Azalea Avenue, Winter Park

$1,150,000

4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Prime Location! Step into the charm of Old Winter Park in this uniquely designed one story, four bedroom, three bath home located off the Via’s in Lake Knowles Terrace. Built in 1951 and thoughtfully renovated in 1998, this home offers soaring ceilings, generous light from skylights, and a layout that embraces both privacy and togetherness. Enjoy two spacious en-suite bedrooms, ideal for multi-generational living or hosting guests. The open-concept living area flows into a large lanai with a cathedral ceiling and a screened-in lush garden courtyard featuring a fish pond, creating a seamless indoor-outdoor experience perfect for year-round entertaining. The lanai brings the total square footage of living space to over 3000 sf. Take in tranquil views of Lk Wilbar, nestled in a quiet, established neighborhood just a mile away from everything: Park Avenue shopping and dining, top-rated hospitals, the YMCA and two well known country clubs. This property of 9, 787 sf has endless opportunities to make it the perfect home for you and your family. Call to schedule a tour today!

1611 Walnut Avenue, Winter Park

$540,000

3 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

Beautifully situated on an elevated 50-by-106-foot lot in the Waterbridge community, this spacious single-story home enjoys a quiet cul-de-sac setting overlooking a small neighborhood park and is adjacent to a green space that enhances privacy. The property has wonderful curb appeal with mature trees, a wide driveway, an oversized two-car garage, and an inviting entrance courtyard that creates a sheltered transition into the home. Inside, the floor plan offers generous room sizes and excellent flow, beginning with a large foyer that opens to both the formal living room and the formal dining room. The 17’ x 12’ living room features a vaulted ceiling and large-format windows. The formal dining room is spacious and opens through sliding glass doors to a private side courtyard ideal for container gardening or quiet outdoor seating. The kitchen is sizable and well designed, with extensive counter space and abundant cabinetry, and offers convenient access to the side courtyard. The kitchen opens to the family room, allowing easy interaction between the two spaces, and extends into the Florida room beyond. The Florida room is one of the most charming areas of the home, with a brick façade along one wall, sliding glass doors, and views of the brick-covered and maturely landscaped backyard. This light-filled space is perfect for casual dining, a reading nook, or year-round indoor–outdoor living. The bedroom wing is thoughtfully spaced away from the main living areas. The primary suite is generously proportioned at roughly 21’ x 17’, with a vaulted ceiling, walk-in closet, and a spacious bathroom that includes a standalone tub, separate shower, long vanity with significant counter space, and a dedicated makeup area. Two additional bedrooms are comfortable in size with reach-in closets and share a full hallway bath with a long vanity and a tub-shower combination. Closet space and storage are abundant throughout the home, including hall storage, bedroom closets, built-ins, and a deep garage with workshop potential. Outdoor living is a highlight of the property. In addition to the front entrance courtyard and the private dining courtyard, the home features a lovely brick-paved backyard framed by mature landscaping, planting beds, and established greenery. The space is low-maintenance and provides multiple areas for seating, gardening, and relaxation. Recent updates include replacement of the electrical panels, which is set for final permit closing inspection; a 2017 HVAC; and a 2018 full home replumb. A current four-point inspection is available and will be updated to reflect the electrical panel replacement once the permit is closed. With its cul-de-sac location, elevated lot, multiple courtyards, flexible living areas, and desirable proximity to Park Avenue, Baldwin Park, the Cady Way Trail, the nearby dog park, and Downtown Orlando, the home enjoys an exceptional setting within a highly regarded Winter Park school zone. Meticulously maintained and built on excellent bones, it offers the uncommon opportunity to move right in or renovate with vision and create something extraordinary.

1817 Jessica Court, Winter Park

$622,500

2 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

Welcome to 1835 Jessica Court in Winter Park’s highly desired Waterbridge community. This beautifully maintained 2-bedroom, 2-bath residence offers a spacious, well-designed interior and a private pool, creating an exceptional blend of comfort, quality, and effortless Florida living. Recent enhancements include Roof 2023, A/C 2024, Pool Pump 2023, Pool Filter 2024, new flooring, fresh interior paint, upgraded baseboards, and an updated vanity in the guest bathroom, giving the home a refined and refreshed feel throughout. The open layout provides flexible living and dining spaces suited for a variety of lifestyles, while the 2-car garage adds convenience and valuable storage. A screened back patio extends the living area and offers a comfortable outdoor space overlooking the private pool, designed for serene enjoyment with minimal upkeep. Waterbridge residents enjoy access to community tennis courts and walkable surroundings. Centrally located between Park Avenue, Baldwin Park, and Audubon Park, this home provides quick access to dining, boutique shopping, local markets, and outdoor recreation. Nearby schools include Brookshire Elementary, Glenridge Middle School, and Winter Park High. This property delivers a rare combination of updates, location, and ease in one of Winter Park’s most convenient and sought-after neighborhoods.

1835 Jessica Court, Winter Park

$415,000

2 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 bath bungalow showcases an open floorplan with high-vaulted ceilings in the main living areas, plenty of natural light, and a separate indoor laundry room. The paver patio on the side of the home offers a nice added space for dining and entertainment. It is one out of only a handful of lots to have a view of MLK Park, made even better by our Florida sunsets, which can be seen right from the kitchen window! This home is perfect for anyone seeking a high-convenience and low-maintenance lifestyle. The location puts you right in the heart of town with scenic walks to Winter Park's famous Park Avenue, Hannibal Square, Winter Park Village, The WP9 Golf Course, Rollins College, and plenty more. There are endless options for shopping, entertainment, events, and dining. As the saying goes, "LOCATION, LOCATION, LOCATION!" Home Facts: Metal Roof (2019). AC (2018). Water Heater (2024). Vinyl Flooring (2025). Repiped supply and drain lines. Freshly painted living space. Washer and Dryer included. Spray foam insulation in attic to reduce energy bills. Turnkey and ready for her new Owner!

875 W Lyman Avenue, Winter Park

$290,000

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

151 N Orlando Avenue Unit #115, Winter Park

$3,000,000

5 Beds ⋅ 6 Baths ⋅ Sorensen Heights SubDv. ⋅ 32789 Zip Code

Welcome to the best of Winter Park living, where luxury meets lifestyle and every day feels like a getaway. This stunning custom home, built by Lundev, sits on a quiet, tree-lined street just a mile from Park Avenue and only steps from beautiful Lake Osceola. Imagine walking to brunch on Park Ave, then coming home to launch your paddleboard from the end of your street. From the moment you pull up, the home makes an impression from its striking architecture to the curved driveway that feels both elegant and inviting. Inside, it’s designed for the way people actually live and entertain today. The chef’s kitchen is the heart of the home, featuring a massive marble island, sleek custom cabinetry, and high-end appliances, all opening up to light-filled living spaces and three sets of French doors that flow seamlessly to the outdoors. Step outside and you’ll find your own private resort: a heated pool and spa, full summer kitchen, and a cozy cabana with a gas fireplace, all enclosed by automatic screens so you can enjoy the space year-round. Whether it’s a casual family dinner or a lively evening with friends, this backyard is one of the best in Winter Park. The first-floor primary suite feels like a spa retreat, with a soaking tub and peaceful views of the pool. Upstairs, each bedroom has its own en-suite bath, plus there’s a versatile bonus room and a large home gym that could easily flex into whatever you need, playroom, office, media space, or studio. Every detail was thoughtfully designed and beautifully executed, but what makes this home truly special is how it feels. Sophisticated yet comfortable. Private yet connected to everything that makes Winter Park so desirable. Just steps from Lake Osceola and moments from the charm of Park Avenue, this home offers a lifestyle that’s as effortless as it is exceptional.

473 Fletcher Place, Winter Park

$110,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

HUGE $15,900 PRICE DROP! Discover your perfect home in this two-bedroom, one-bath second-floor unit at Waterfall Cove, ideally situated in the heart of Winter Park. This inviting open-concept layout features large windows that fill the space with natural light, along with cozy carpeting throughout and stylish tile in the bathroom. Each bedroom offers a comfortable retreat, while sliding glass doors open to a spacious private balcony overlooking a serene, park-like setting with walking paths. Take comfort in knowing the unit is equipt with impact doors and windows for protection from flying debris, strong winds and forced entry. Waterfall Cove boasts beautiful grounds, including rolling lawns, a pool, and a dog park, all in a quiet community. Enjoy the convenience of being within walking distance to shopping centers, gyms, cinemas, and more. With easy access to Rollins College, UCF Valencia College, and major roads leading to theme parks, this unit is perfect for first-time buyers, those looking to downsize, or investors. The HOA covers exterior maintenance, including your balcony, cable, and internet as well as bi-monthly pest control. Don’t miss this opportunity!

1695 Lee Road Unit E211, Winter Park

$810,000

2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Lovely Orwin Manor home with custom pool and spa in the heart of Winter Park. Backyard oasis features a detached guest house (ADU) with a kitchenette, bathroom and two built-in murphy beds.

1314 Canterbury Road, Winter Park

$325,000

2 Beds ⋅ 2 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

PRICED TO SELL! Nestled in the heart of Winter Park, this updated 2 bedroom, 2 bath second floor corner unit offers the perfect blend of comfort and convenience. The renovated kitchen with its inviting counter seating seamlessly opens to the dining area and family room, highlighted by a cozy corner fireplace. The vaulted ceilings provide a generous feel to the living space. The spacious indoor laundry room adds practicality to your daily routine. The master suite impresses with a walk-in closet and a beautifully updated bathroom. The charming screened balcony off the second bedroom is perfect for enjoying the fresh air. The community features a refreshing pool that overlooks the picturesque Lake Killarney, along with a kayak and paddleboard rack providing easy access to enjoy adventures on the lake. EXCELLENT LOCATION! Walkable to Winter Park Village, Trader Joes and a variety of restaurants and shopping along the 17-92 corridor. Easy access to I.4 via Fairbanks or Lee Rds. This condo is not just a home; it’s a lifestyle waiting to be embraced. Don't miss out! Call today to schedule your showing!

520 Killarney Bay Court Unit 2, Winter Park

$300,000

1 Beds ⋅ 1 Baths ⋅ Whispering Waters SubDv. ⋅ 32789 Zip Code

Discover your new downtown Winter Park ground-floor pied-à-terre. Two blocks from Park Avenue, the 1960s mid-century modern Whispering Waters Condominiums are a Winter Park landmark. Your remodeled end-unit studio features an updated open kitchen with plentiful wood cabinets, ceramic tile flooring throughout, new dual-pane windows, a stylish updated bathroom with a step-in shower, and wood built-ins in the living room. Open to the living room is a sleeping alcove that accommodates a queen-size bed. An additional 9’ by 6’ enclosed room could be used as a bedroom, an office, or a lounging space. With easy access from your new pad to both Interlachen Avenue and Morse Boulevard, your downtown Winter Park adventures await.< Included is one assigned parking space in the secured underground garage, where you will also find a community laundry room. Enjoy mail and package delivery directly to your door. Electricity, gas, water, and sewer are included in your monthly condo fee for worry-free simplicity. Community amenities include: • Community swimming pool; • Lakeview social club room; • Outdoor patios overlooking Lake Osceola; • On-site management. Whispering Waters is a 55+ Community.

311 E Morse Boulevard Unit 6-3, Winter Park

$750,000

4 Beds ⋅ 3 Baths ⋅ Hills SubDv. ⋅ 32789 Zip Code

Charming traditional ranch located in the desirable “Hills” neighborhood of Winter Park! Step into a welcoming foyer that opens to a spacious floor plan accented by mid-century glass block dividers. The comfortable family room features an entertainment wall, a wood-burning fireplace, and a seamless connection to the well-designed kitchen with a peninsula island. Generous, ceiling-height maple cabinetry provides excellent storage, and the built-in oven and microwave add convenience. Just off the kitchen are the laundry room and powder bath, with direct access to the garage. The current garage has been divided to make a space for an office/flex space which can easily be removed if desired. The dining room offers a full wall of maple built-ins with display shelving and lower storage cabinetry. French doors lead to the covered lanai and pool area. Down the main hall you'll find the hall bath with double sinks and a glass-enclosed tub, along with the primary suite and three additional bedrooms. The spacious primary bedroom features French doors to the pool, a spacious bath with walk-in shower and jacuzzi tub, the custom walk-in closet is just off the bath. The backyard is privately fenced with a block/brick wall surrounding the open pool and expansive lanai. Recent updates include a 2022 roof, 2018 AC, re-plumbed, a tankless water heater, and a propane tank. Located in a fantastic neighborhood zoned for top-rated Maitland/Winter Park schools!

2632 Mandan Trail, Winter Park

$2,050,000

Temple Heights SubDv. ⋅ 32789 Zip Code

A rare estate-sized double lot in one of Winter Park’s most coveted and established neighborhoods—Temple Heights. This expansive property offers an exceptional opportunity to build a custom luxury residence in one of Central Florida’s most sought-after locations. Nestled in a quiet, tree-lined residential pocket, this oversized parcel provides the space, privacy, and prestige rarely available in the area. Whether envisioning a modern architectural showpiece, a timeless Winter Park estate, or a multi-structure compound, the generous lot size offers endless design possibilities for a truly one-of-a-kind dream home. The location is unmatched. Just minutes from Park Avenue, you’ll enjoy immediate access to Winter Park’s world-class dining, boutique shopping, renowned galleries, Rollins College, and the charm of the city’s historic brick streets. Nearby amenities include Kraft Gardens, the YMCA, and the Winter Park Racquet Club—placing recreation, culture, and convenience at your doorstep. Opportunities like this are exceptionally limited. This is your chance to secure a premium piece of land in one of Winter Park’s most desirable and tightly held neighborhoods, perfect for creating a custom estate tailored to your vision.

1205 Mayfield Avenue, Winter Park

$2,000,000

3 Beds ⋅ 3 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code

Once closed, call LA for Effective sales price. Totally traditional luxury single-story home is located in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre beautifully landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and COMPLETELY re-done. Multi-generational potential as this home has a complete attached guesthouse. Interior layout boasts formal living with bay window and tall ceilings, dining room with antiqued mirror set into extensive moldings and trim, plus a library/den with a tongue and groove wood vaulted ceiling and a wall of bookshelves and built-ins. The spacious family room with a white-washed brick, wood-burning fireplace wall and vaulted ceiling is all open to the breakfast area and kitchen. The gourmet kitchen features custom inset cabinet drawers and doors, white marble slab backsplashes, Kohler farmhouse sink and a large island with a deep prep sink. The kitchen is a chef’s delight with a 48-inch Viking gas range, Viking warming drawer, Jenn-Air refrigerator, wine refrigerator and a Bosch dishwasher. The kitchen also has amazing storage and two large pantries. There are a total of four bedrooms (the 4th is currently the living room of the in-law suite suite) and three full baths. Throughout the home are beautiful real ¾-inch-thick and 5-inch-wide plank walnut floors, beam and coffered ceilings, French doors, oversized picture windows and designer accents lighting. French doors off the family room open to seamlessly blend indoor and outdoor living, leading to a covered lanai with travertine stone tile overlooking a resort and entertaining backyard. Huge swimming pool and a 30-by-15-foot pergola with Bistro lighting, which is a wonderful spot to relax, dine and play, all on a tiny pebble surface, like an Italian driveway! French garden fountain, rose garden and synthetic turf for pets make the backyard a haven. The home’s floor plan offers a desirable layout with huge primary bedroom with a generously sized un-suite bath with dual sink counters, amazing Roman walk-in shower, jetted tub with bubblers and two large walk-in closets. Guest wing features a spacious bedroom and bath and the West Wing is a full In-law apartment, including a bedroom, handicapped bath, full kitchen and its living room (which would be easy to be converted back into the 4th bedroom - plans available). Imagine having a wonderful space for in-laws or an adult family member that needs space of their own. Just a short drive or bike ride from Park Avenue, this open and inviting home has easy access to downtown Winter Park, AdventHealth, downtown Orlando and is zoned for A-rated schools. Surround sound through most of the house and CAT 6 wiring throughout. Recent additional remodeling and updating have taken place including all new windows, paint inside and out, as well as a new roof and gutters in 2022. A detailed list of all renovations is available upon request.

1624 Barcelona Way, Winter Park

$750,000

3 Beds ⋅ 2 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Sold data entry.

1681 Woodland Avenue, Winter Park

$800,000

3 Beds ⋅ 4 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

Welcome to this rare find in the heart of Winter Park — a beautifully updated 3-bedroom, 3.5-bath townhome that lives like a single-family home, and best of all, there’s no HOA. Step inside to soaring 20-foot ceilings in the foyer and living room, complemented by elegant hardwood floors, crown molding, and expansive windows that fill the space with natural light. The open-concept design is both spacious and versatile, offering seamless flow and plenty of room to relax, entertain, and enjoy the Florida lifestyle. At the center of the home is a chef-inspired kitchen featuring crisp white cabinetry, solid granite countertops, stainless steel appliances, and a central island with built-in outlets and custom pull-out storage. The light-filled living room opens effortlessly into the dining area, where French doors lead out to a wood deck and a fully landscaped backyard oasis. Mature trees, curated garden beds, and decorative stone walkways create a peaceful retreat — perfect for indoor-outdoor entertaining. Upstairs, the generous primary suite is a true sanctuary, complete with double entry doors, a spa-like bath with jetted tub and shower, a walk-in closet, and a private balcony ideal for morning coffee or evening relaxation. Two additional guest suites each include their own ensuite bath, providing comfort and privacy for family, visitors, or a home office. A conveniently located upstairs laundry room completes the second floor. Additional Features: • Underground propane tank powering the stove, fireplace, BBQ grill, and new (2023) hot water heater • New roof (2022), new carpet (Nov. 2025) • Upstairs A/C replaced in 2023 • Tesla car charging station • Long private driveway with ample parking • No HOA — enjoy added freedom and low-maintenance living. Prime Location: Situated in Virginia Heights, one of Winter Park’s most coveted neighborhoods just minutes from Park Avenue’s renowned dining, shopping, and Central Park, along with Seven Oaks Park, Mead Botanical Garden, and Azalea Lane Tennis Center with adjacent kiddie park. Zoned for top-rated Audubon K–8 and Winter Park High School. Call today to schedule your private tour of this exceptional home in a premier Winter Park location. Floor Plan Attached!

1251 Arlington Place, Winter Park

$2,185,000

5 Beds ⋅ 5 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code

Under Construction. Masterfully designed new construction by LUIH Luxury Homes, where architectural elegance and refined livability meet an unbeatable lifestyle. Located in the Audubon Park School District just a short stroll from the iconic East End Market. From its captivating façade to its meticulously curated interiors, every element of this residence has been crafted for those who expect the exceptional. Step through the grand entry and into a home where natural light, texture, and scale set the tone for unforgettable living. The heart of the home is a chef’s kitchen featuring Quartz countertops, custom cabinetry full Thermador appliance suite, and integrated LED underlighting. It opens seamlessly to the dining and living rooms, creating a layout that makes everyday living feel elevated and hosting feel natural. The primary suite is not simply a bedroom, but a place to unwind at the end of the day. The primary bathroom features dual vanities, a freestanding soaking tub, a walk-in shower, and a spacious closet all crafted with a calming, spa-like atmosphere in mind. Beyond the interior, sliding glass doors reveal an outdoor sanctuary that unfolds like a private resort. A covered lanai expands into a summer kitchen built for lavish entertaining, while the pool and spa shimmer beneath Florida’s year-round sun. Positioned within the esteemed Audubon Park school district and mere steps from the iconic East End Market, the location offers a lifestyle that is both vibrant and intimate. Baldwin Park’s lakeside paths and cafés are minutes away, and Park Avenue Winter Park’s crown jewel of fine dining, boutiques, and culture is just a golf-cart ride from your front door. This is more than a home, it is a narrative of LUIH’s impeccable craftsmanship, elegance, and intentional design, crafted for those who understand that true luxury is not a statement, but a feeling.

2722 Eastern Parkway, Winter Park

$1,690,000

3 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Discover a fresh take on modern living in one of Winter Park's most admired neighborhoods - the "Tree Streets." This custom three-story LunDev home marries modern minimalism with subtle Dutch Colonial influences, creating a distinctive and inviting retreat. The carefully curated neutral palette sets a relaxed tone throughout, blending timeless design elements with contemporary sophistication—indoors and out. Step into an open-concept layout bathed in natural light that highlights generous room sizes and thoughtful transitions from space to space. The welcoming foyer flows into a great living area and gourmet kitchen featuring a premium Thermador appliance package, including a commercial gas range and double under-counter refrigerator drawers. Adjacent to the kitchen, a stylish powder bath and mudroom with abundant storage lead to a convenient two-car attached garage. The main level is anchored by a luxurious primary suite that features a spa-inspired bath and an expansive walk-in closet with dedicated laundry facilities, perfectly suited for busy lifestyles. From the great room, large garden doors open to a back lanai pool area, seamlessly integrating indoor and outdoor living. Enjoy extended entertaining options in the cabana pool house, complete with a TV and fireplace. Upstairs, two additional bedrooms, each with an ensuite and custom walk-in closet, share a beautifully appointed bonus room with a dramatic raked ceiling and a second laundry area, offering flexibility to suit your needs. The versatile third level features a private studio that can easily serve as a fourth bedroom, guest suite, or private home office, complete with a built-in closet and full ensuite bathroom. LunDev has masterfully created a residence that exudes sophistication and casual luxury, making this property a standout gem. Located near parks, lakes, and premier shopping at Park Avenue, Winter Park Village, and Whole Foods, this home offers an exceptional lifestyle opportunity. Schedule your private tour today to experience the allure of this exquisite Winter Park residence.

1630 Chestnut Avenue, Winter Park

$1,000,500

3 Beds ⋅ 2 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Desired Winter Park address. A 1950s bungalow on a spacious lot surrounded by multi-million-dollar homes, this is the last untouched original home left on this block. Short distance to Lake Sue, Winter Park schools and many parks in the area. The value is in the land.

210 E Rockwood Way, Winter Park

$2,195,000

5 Beds ⋅ 4 Baths ⋅ Lugano Terrace SubDv. ⋅ 32789 Zip Code

Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich Elementary. Inside, wide-plank engineered white pine flooring flows throughout, complementing vaulted ceilings, wood-burning fireplace in the living room, and a spacious open layout ideal for entertaining. The informal dining room overlooks the private backyard and resurfaced PebbleTec pool, while the chef’s kitchen impresses with dual islands, quartz countertops and full-height quartz backsplash, custom hood, Thermador appliances including a 48” six-burner gas range and French door refrigerator. The gorgeous, light filled family room showcases gas fireplace and a built-in bar with wine fridge. The expansive upstairs primary suite is a luxurious retreat, featuring a spa-like bath with a dual-entry shower with Infrared sauna, soaking tub, dual vanities with LED mirrors, expanded closets, and a sitting area. Also upstairs is a flexible loft or library space, an office/nursery with a private balcony, and a bonus exercise room or third closet. Three spacious bedrooms are located downstairs, including a second primary or guest suite with its own en-suite bath and pool access. Notable upgrades include a new roof (2021), PEX plumbing and water heater (2025), updated electrical panels, new propane tank, new AC supply grills and a new second AC system (2025). Additional features include Level 4 smooth drywall, custom trim and moldings, 8’ metal front and double back doors, custom wood interior doors, upgraded light switches and plugs, all-new designer light fixtures ( Regina Andrew, Visual Comfort, etc. ), fireplace surrounds, and custom metal and wood staircase. Black interior and exterior Anderson windows: Dual Pane Low-E Smart Sun Standard Argon Fill Simulated Divided Light (SDL). Outside, enjoy a fully fenced and gated backyard with turf and paver landscaping, updated pool coping, and a covered porch ideal for entertaining, new exterior paint and gas lanterns. The 2-car garage includes custom paneled doors, painted floor and workshop area. Located within walking distance to top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, and just minutes from Park Avenue and the Winter Park Racquet Club and Interlachen Country Club, this home offers exceptional quality, location, and lifestyle. NEW April 2026 Black Steel doors windows with low e-dual pane glass ($150k value!).

1885 Temple Drive, Winter Park

$1,430,000

3 Beds ⋅ 3 Baths ⋅ Palmer Park SubDv. ⋅ 32789 Zip Code

Location, Location, Location... Mid-Century Modern that's walking distance to Park Avenue and located in that very special Golden Triangle that is so desirable. This is a smart investment combined with a great lifestyle and ready to move in and enjoy. Open kitchen to living area, a family room that opens to a spacious deck and landscaped large private yard.

1011 Mckean Circle, Winter Park

$405,000

2 Beds ⋅ 1 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Don’t miss this rare opportunity to own a professionally landscaped, beautifully maintained home in Winter Park, perfect as a primary residence or a smart investment property! This 1950s bungalow seamlessly blends modern convenience with the historic charm of Winter Park. This light-filled 2-bedroom, 1-bath home features a bonus room, ideal as an office or a dining area. It offers original wood flooring with tile in the kitchen and bath and plantation shutters throughout. The eat-in kitchen boasts a full accompaniment of stainless-steel appliances as well as ample cabinet space. Recent updates include a 2018 roof, 2018 windows, 2018 A/C, 2019 septic system and 2019 rear sliding doors; providing added peace of mind. Step outside to a spacious and low maintenance yard, fully fenced backyard, ideal for entertaining and relaxing. Choose to expand or add future improvements with this sizable lot. The oversized driveway provides generous off-street parking, adding to the home’s convenience. Nestled in a desirable, well-established neighborhood with easy access to I4, shopping, and dining on Park Avenue; this property combines vintage appeal, modern functionality, and a prime location. Whether you're looking to move right in or add to your portfolio, this is a gem of a property!

1872 Biscayne Drive, Winter Park

$2,232,000

3 Beds ⋅ 4 Baths ⋅ Perle Du Lac SubDv. ⋅ 32789 Zip Code

Imagine waking, relaxing, and entertaining with serene lakefront views in this elegant ground-floor Perle du Lac residence. The refined 2,714-square-foot design includes hardwood and travertine flooring, ten-foot-high ceilings, and extensive millwork. The expansive open-plan living and dining room lets you configure your furniture however you’d like. A bank of glass doors leads to your covered lakefront patio, where you can enjoy al fresco meals and admire your boat in its personal covered slip with electric lift. The spacious kitchen offers new cabinetry, under-cabinet lighting, hardwood countertops, and a farmhouse sink. Built-in appliances include a Sub-Zero® Refrigerator, a Wolfe® Gas Cooktop, Dacor® Ovens, and a Bosch® Dishwasher. From the kitchen, you have access to the sizable adjacent library, with its wall-to-wall bookcases. Configure it as your office or a family room if you wish. A wall of glass doors and windows makes the lake a focal point in your primary bedroom suite. The en-suite bathroom features a jacuzzi bathtub, walk-in shower, two separate vanities, and a secluded Toto®-equipped water closet. A large walk-in closet completes the suite. Two more spacious bedrooms are on the opposite end of the residence. One includes its own en-suite full bathroom. Both share an outdoor patio space. Additionally, you’ll find a third full bathroom and a powder bathroom. The laundry room includes a Miele® washing machine and dryer set. In the secured garage, you have two assigned parking spaces and a sizeable storage room. Perle du Lac residents enjoy exclusive community amenities, including a heated swimming pool, hot tub, beautifully maintained grounds, and double-gated security for peace of mind. All of this is minutes from Park Avenue, Rollins College, and everything that makes downtown Winter Park famous.

660 Osceola Avenue Unit 101, Winter Park

$1,850,000

3 Beds ⋅ 4 Baths ⋅ Virginia & Morse Brownstones SubDv. ⋅ 32789 Zip Code

Experience refined townhome living in the heart of Winter Park. Designed by renowned architect Phil Kean, this three-bedroom, three-and-a-half-bath residence spans more than 3,000 square feet and delivers a seamless blend of privacy, luxury and convenience. A private elevator offers access to all levels, including a rooftop terrace designed for elevated outdoor living. The ground floor features a spacious office and a guest suite with a private bath. On the second level, the open-concept living area includes a designer kitchen appointed with Wolf and Sub-Zero appliances, a 36-inch gas range, quartz countertops, custom cabinetry, and a dry bar with wine refrigerator. The third-floor primary suite offers two walk-in closets, a private balcony, and a Carrara marble bath with a soaking tub and a frameless glass shower. An additional bedroom on this level features a private balcony, walk-in closet and en-suite bath. Additional enhancements include California Closets, custom built-ins, designer lighting and a Control 4 security system. The rooftop terrace, complete with an outdoor television, provides a private setting to enjoy Florida sunsets. Ideally near Park Avenue, Hannibal Square and Winter Park Farmers Market, this townhome offers a lock-and-leave lifestyle with proximity to premier dining, shopping and cultural attractions.

419 W Morse Boulevard, Winter Park

$6,111,000

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

Tucked away on a quiet and beautiful Lake Maitland lot in the highly desirable Green Oaks neighborhood, this stunning French Provincial residence offers magnificent water views from nearly every room. With one of the most private entrances and lots in all of Winter Park, this timeless home blends European charm with modern comfort. The light-filled, open floor plan features a downstairs primary suite and a gorgeous family room with gas fireplace, opening to the pool and lake. The gourmet kitchen, also facing the backyard, is the heart of the home. Featuring granite countertops, light cabinetry and gas cooktop. The open layout includes the eat-in breakfast area and family room. Multiple French doors to the pool and lakefront for everyday indoor-outdoor living and enjoy breathtaking views that make every moment feel like a getaway. Upstairs, two generously sized bedrooms-each with en-suite baths are joined by a cozy conversation area with lake views, a large bonus room and a private office/study that could easily be an additional bedroom. A connecting guesthouse offers a true retreat with two bedrooms, a full bath, living area and kitchen, perfect for hosting friends or family. Sparkling pool, lush landscaping, and private dock on Lake Maitland, enjoy awe-inspiring sunrise views over the Isle of Sicily. Craftsmanship is showcased throughout, from the millwork to the 4-car garage, with extensive updates: roof (2021), multiple A/C systems with UV lights (2020–2025), new flooring throughout downstairs and all bedrooms (2020), updated upstairs windows (2020), rebuilt balcony with Trex decking, new pool equipment (2020) and pool converted to salt (filter 2024), Generac whole-house generator, Trex deck and dock with new cables and 7,500-lb lift (2022), new primary, upstairs guest suites and powder baths (2025), marble porcelain fireplace surround, remote shades in the primary suite, and new lighting fixtures throughout. Surrounded by manicured grounds and minutes from downtown Winter Park, Park Avenue shopping and restaurants, Enzian Theater, library, bike paths, and top-rated schools, (Dommerich, Maitland Middle and Winter Park High School). Just around the corner from Park Maitland and near Lake Highland and Trinity Preparatory Schools. This lakeside masterpiece offers unmatched privacy, luxury, and timeless sophistication-a truly exceptional home. Ski, wakeboard, pontoon or cruise around Dog Island and Isle of Sicily on the chain of lakes. Enjoy the magic of the holiday season- festive boat parade and holiday light displays. 121 ft of lakefront on the Winter Park Chain of Lakes.

1860 Summerland Avenue, Winter Park

$2,500,000

3 Beds ⋅ 7 Baths ⋅ Camwood Sub SubDv. ⋅ 32789 Zip Code

Set across Lake Maitland on a street where every home is an architectural gem, this Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this 5,483 sq ft estate offers 3 bedrooms, 7 bathrooms, and 7 versatile bonus rooms, including a private guest casita and a fully finished basement. Total area including outdoor spaces: 6,821 sq ft. The exterior showcases a stone façade, barrel-tile roof, wrought-iron detailing, and lush courtyards. A gated entry with outdoor fireplace leads to the guest casita with full bath, ideal for extended family, live-in support, or private office use. Inside, arched walkways, travertine floors, and soaring ceilings define the main level. The formal dining room, executive office, and great room flow seamlessly to the resort-style pool and lanai. The chef’s kitchen features dual Sub-Zero refrigerators, separate freezer, hidden walk-in pantry, Dacor 6-burner gas range, double ovens, Sharp drawer microwave, and built-in Miele coffee station. A butler’s hallway, half bath, and custom laundry suite add function and refinement. The primary suite on the main level features marble flooring, French doors to a private courtyard, a spa bath with soaking tub, dual-entry shower, and boutique-style custom closet. Upstairs offers two bedrooms, each with en-suite bath and custom closets, plus two open seating areas/lofts and a half bath. One suite opens to arched French doors overlooking the courtyard, stone architecture, and partial Lake Maitland views. The finished basement completes the 7 bonus rooms, providing flexible space for a home theater, gym, game room, or recreation lounge. Outdoor living includes a heated pool and spa, summer kitchen (installed 2021) with gas grill, beer tap, coolers, hibachi station, and a full cabana bath with accent shower on astro turf. Roof 2024. Three SEER 22 high-efficiency HVAC units (2020). Perfectly positioned on the Winter Park side of Lake Maitland within the renowned Chain of Lakes, Villa Toscana offers exceptional privacy and timeless appeal. This exclusive address places you just five minutes from Park Avenue’s fine dining, boutiques, and cultural attractions, while surrounded by some of Central Florida’s most distinguished waterfront estates. With access to the Winter Park Chain of Lakes, top-rated schools, and the charm of the city’s historic brick streets, Villa Toscana embodies the essence of refined Winter Park living.

1401 Green Cove Road, Winter Park

$567,500

3 Beds ⋅ 2 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code

Welcome to this charming 3 bedroom, 2 bathroom home in desirable Winter Park, Florida. With over 1450 square feet of living space, this property is perfect for families or individuals looking for a cozy yet spacious place to call home.Upon entering, you'll be greeted by bright and airy living spaces that flow seamlessly between the dining area, kitchen, and sunken living room. The updated kitchen features stainless steel appliances, granite counter tops, and pendant accent lighting over the bar. In this SPLIT floor plan, the master bedroom boasts an en-suite bathroom with ample closet space, while the two bedrooms are perfect for guests and/or a home office. The home is just steps away from Park Ave, Hannibal Square, Seven Oaks Park, and Mead Gardens. With so many dining and entertainment options right outside your front door, you'll be able to take advantage of everything Winter Park has to offer. All of these amazing features and amenities are also linked to Winter Park's highly sought after public schools.

1010 Aragon Avenue, Winter Park

$1,589,000

4 Beds ⋅ 3 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Comfort, charm, and LOCATION are KEY for this unique, one-story, KEY West-style pool home with deeded access to Lake Virginia! Nestled on a brick-lined street in the highly sought-after Virginia Heights neighborhood, this location is truly one-of-a-kind, engulfed in the beloved culture and history of Winter Park, and within true walking distance of Rollins College, Park Avenue, and all the lively bustle of downtown Winter Park. Better yet, enjoy deeded lake access from the neighborhood lakefront park just a 3-minute walk from your front door, where neighbors gather for social events, holiday parties, and relaxing lake views. With a sprawling green lawn, dock, kayak/canoe storage racks, and picnic tables, the perfect daily retreat is just steps away. The home is move-in ready and bursting with charm, with over 2800 SF of thoughtfully designed space for everyday living and entertaining. The ideal, split-bedroom floorplan includes 3 bedrooms, 3 en-suite bathrooms, a private home office (or a 4th bedroom), cozy living room with a wood fireplace (piped for gas), dining room with a built-in lighted bar, large family room, and over 400 SF of covered lanai space overlooking the pool & backyard paradise. The oversized primary suite is truly special, with room for a sitting area, tons of built-in storage, and a mirrored barn door that opens to reveal a custom-designed spa bath, renovated down to studs in 2021. An absolute stunner, the primary bath features a large zero-entry marble shower, custom mahogany-topped vanity, maple board-and-batten walls, brass fixtures, and cypress vaulted ceilings, plus 2 walk-in closets and a third storage closet at the bedroom entrance. The sunny family room extends to the rear of the home, where French doors are equipped with retractable screen doors for enjoying the breeze indoors and out, in true Key-West style. Past the French doors, a travertine lanai stretches across the back of the home and overlooks a lagoon-style pool and travertine deck, with surrounding palms and lush tropical landscaping to create the perfect backyard oasis. The kitchen features Thermador appliances, with a gas cooktop and a brand new vent hood framed by a new marble backsplash, and new pendant lighting over the breakfast bar. Both secondary bedrooms have French doors that open to the covered lanai, and en-suite bathrooms. Other conveniences include a whole-house sound system with interior and exterior speakers, custom laundry room (renovated in 2021), and 2-car garage with built-in storage. Move-in ready, the home was completely replumbed in July 2025, with a new gas water heater, partial roof replacement (all new flat roof in Aug 2025), up-to-date electrical, and (2) recently serviced 2019 HVAC units with UV lights. Ask for list of improvements and a floorplan!

1450 Glencoe Road, Winter Park

$520,000

3 Beds ⋅ 2 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Mid-Century Modern Charm in the City of Winter Park! Enjoy living in one of the most sought after neighborhoods in Winter Park, adjacent to Baldwin Park and Audubon Park. This home blends timeless design with today’s updates—just minutes from shopping, dining, parks, and top-rated schools. Make this stylish retreat your own and experience the best of Winter Park living! Enjoy the comfort of this updated Mid-Century Modern home ready for you to make it your own! Featuring an oversized updated kitchen with a sleek black and stainless designed cabinet combination with frosted glass upper cabinets, and lots of granite countertops—perfect for entertaining or everyday living. All inclusive stainless steel appliances with a five-burner gas stove and hood and a breakfast bar with seating that flows into the bright and open great room. There the floor-to-ceiling windows make the room so special. The huge primary suite has double closets for lots of storage, room for a sitting area to relax and read or watch a show. The updated ensuite bath has a walk-in shower with beveled glass door and built-in shower seat. Other sought after features include an oversized walk-in pantry, large combined laundry/storage room, and covered carport. Newer double paned windows and sliders allow the home to be flooded with natural light, while a tankless water heater and recent AC adds modern efficiency.

3025 Northwood Boulevard, Winter Park

$3,390,000

5 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansive 0.30-acre lot, this residence captures attention from the moment you arrive, with its striking architectural details, a sweeping driveway, and detached garage that together set a tone of timeless sophistication. Inside, soaring 20-foot ceilings welcome you into a grand foyer framed by curved archways and exceptional millwork. The living room is a true showpiece, centered around a statement fireplace with built-in shelving and subtle LED underlighting that accentuates every detail. The chef’s kitchen is a work of art, showcasing quartz countertops, exquisite custom cabinetry, integrated LED lighting, a Wolf appliance suite, and a charming breakfast nook. The formal dining room captivates, with stunning coffered ceilings floor to ceiling windows, and an atmosphere perfectly suited for elegant entertainment. The primary suite is a private sanctuary, offering dual vanities with floating mirrors, a freestanding soaking tub, a walk-in rain shower, and a spacious custom closet. Each additional bedroom has been thoughtfully designed with generous proportions and its own en-suite bath, blending comfort with sophistication. Upstairs, a loft and secondary laundry area provide convenience and versatility, while the main level includes a full mudroom and butler’s pantry with an additional washer and dryer, tailored for effortless living. The outdoor living space rivals the most luxurious resorts. A covered lanai with retractable screens seamlessly extends the interior’s sophistication outdoors, offering a year-round retreat for dining or lounging. The expansive pool deck unfolds around a sparkling pool and integrated spa, complemented by a dedicated pool bath connected to the detached garage. From the curved archways to the meticulous millwork and layered LED lighting throughout, every inch of this home reflects the builder’s attention to detail and commitment to craftsmanship. It is more than a home, it is a statement of style, presence, and precision in the heart of Winter Park’s most coveted location.

1751 Glencoe Road, Winter Park

$1,475,000

4 Beds ⋅ 4 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

Opportunity awaits in the most desirable neighborhood! Buyers have cold feet. Nestled in the Elizabeth’s Walk subdivision in the highly coveted Windsong community of Winter Park, this renovated four-bedroom, four-bathroom pool home offers exceptional privacy and refined updates. Quiet interior street and mature landscaping the home feels secluded. Recent improvements include a new roof (2023), two new AC systems 4-ton Carrier Infinity downstairs and a 2.5-ton Trane upstairs (2025) and fresh exterior and interior paint in the kitchen and bathroom. The updated kitchen features a butcher block island and new cabinetry hardware. Beautiful wine storage room to showcase your finest wines. The newly redesigned powder bath includes hidden storage and a full shower. The living areas are open and welcoming, highlighted by recessed ceilings in the informal living room with distinctive wood beams in the family room giving the home character. The primary suite features dual closets plus a linen closet, fresh paint, new mirrors, tv, lighting, and UV film on doors to keep the suite very cool and save on electrical. The nursery showcases new paint, custom wallpaper, drapes, and remote shades, basically every detail thoughtfully considered. Upstairs, a generous loft serves perfectly as a playroom, exercise room or home office, along with two ensuite bedrooms and a large AC storage room. Outdoor living is private and inviting, with a newly refinished PebbleTec pool finish, new pool coping, gas fireplace, new screen enclosure and professionally updated landscaping (2024). The backyard feels like a personal retreat -quiet, enclosed, and perfect for both relaxing and entertaining. Other features include new insulation (2024), custom aluminum privacy gates with locks, Wi-Fi-enabled Schlage front door lock, touchscreen garage access, Ring cameras, and new thermostats. Living in Windsong offers a sense of community, exclusivity with access to the Winter Park Chain of Lakes, pools, a kids water park area, and playgrounds. Pontoon boat available for residents use. Just minutes from Park Avenue’s shops and restaurants, Baldwin Park, and top-rated schools including Brookshire Elementary, Glenridge Middle, Winter Park High. Great location for private schools- Lake Highland Prep and Trinity Prep.

1408 Chapman Circle, Winter Park

$2,025,000

4 Beds ⋅ 4 Baths ⋅ Maitland Shores SubDv. ⋅ 32789 Zip Code

BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, an opportunity priced 4-bedroom, 3.5-bath home to get into the coveted Winter Park Vias while adding your final touches to personalize this home while prioritizing location, schools, privacy and connectivity. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring a super spacious kitchen, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.

2299 Via Tuscany, Winter Park

$6,300,000

4 Beds ⋅ 6 Baths ⋅ Camwood SubDv. ⋅ 32789 Zip Code

Quintisential Lake Maitland Estate - first time available. Classic architecture with incredible and thoughtful details throughout. Private setting on over an acre captures sweeping views of Lake Maitland. Sought after location close to Park Avenue. This legacy property embodies the best of Winter Park Lakefront Living.

1308 Green Cove, Winter Park

$630,000

5 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park

$2,175,000

4 Beds ⋅ 5 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

This stunning LunDev-built pool home has been meticulously maintained and thoughtfully updated, blending timeless craftsmanship with modern style. The ideal floorplan features a first-floor primary suite, a private office, and an open kitchen and family room that flow effortlessly to the home’s exceptional outdoor living space. Outside, the spacious backyard is a private retreat complete with an oversized covered patio, gas firepit, and a fully equipped summer kitchen with a pizza oven, all surrounding a sparkling pool and heated spa. In 2022, the kitchen received a major renovation, showcasing a new island, updated countertops and backsplash, fresh fixtures and cabinet hardware, and elegant lighting that elevate the space. The primary bath renovation mirrors the same level of quality, with new custom vanities topped with quartz countertops, all-new tile, a glass-enclosed shower, a relaxing soaking tub, and classic lighting and mirrors. Additional improvements include a new roof (2021), newer hardwood floors throughout the 2nd floor, updated brick paver driveway, newer pool equipment, and fresh interior and exterior paint, each reflecting consistent care and attention to detail. Designed for both everyday comfort and effortless entertaining, this home is truly move-in ready and radiates pride of ownership inside and out.

2030 Versailles Avenue, Winter Park

$2,295,000

4 Beds ⋅ 6 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

Introducing a stunning new custom home by Ellsworth Gallimore and Butler Ridge Development, ideally situated in a prime Winter Park neighborhood. This residence combines timeless elegance with modern luxury, showcasing exceptional design and craftsmanship throughout. The thoughtfully designed home features a marble front façade and professional landscaping. Inside, you’ll find an open, bright layout with high ceilings, wide-plank white oak floors, oversized picture windows, and refined crown molding. A welcoming flex space—perfect as a sitting room or den—greets you at the entry, across from another room ideal for a private office. The great room, at the center of the home, offers 12-foot ceilings, a sleek fireplace, and a full wall of sliding glass doors that open to the resort-style backyard. Designed for both entertaining and daily living, the open-concept kitchen, dining, and living areas flow seamlessly together. The chef’s kitchen impresses with a striking waterfall island, premium Thermador appliances, a dual-fuel range with a 6-burner gas cooktop, a third oven plus convection microwave, and an expansive custom pantry. A stylish mudroom and decorative laundry room complete the main level’s amenities. The primary suite on the first floor features direct access to the pool, a spa-inspired bath with a soaking tub, multi-spray shower, dual sinks with a large vanity, and a spacious custom walk-in closet. Upstairs, a loft-style bonus room connects to three additional bedroom suites, each with custom closets and ample storage. Outdoor living includes a saltwater pool with an elegant fountain feature, marble pavers, a summer kitchen with a built-in grill, sink, and beverage fridge, an outdoor bathroom, and a lush grassy area perfect for play or pets. Additional highlights include a two-car garage and zoning for top-rated schools—Lakemont Elementary, Maitland Middle, and Winter Park High. Walk to the Winter Park YMCA and Phelps Park, and enjoy being just minutes from vibrant downtown Winter Park. Elegant design, modern luxury, and a prime location—this exceptional new home offers the very best of Winter Park living.

1661 Palm Avenue, Winter Park

$417,500

3 Beds ⋅ 2 Baths ⋅ 0000137281 SubDv. ⋅ 32789 Zip Code

Located in the desirable Winter Park area, this newly listed 3-bedroom, 2-bathroom home at 2148 Blossom Lane offers excellent value and investment potential. This well-maintained house features 1,685 square feet of comfortable living space, perfect for families or investors looking for a solid opportunity. The home's prime location puts you just minutes from Winter Park Village, with easy access to shopping, restaurants, and major roadways. Theme park enthusiasts will appreciate the convenient proximity to Orlando's world-famous attractions, making this an ideal choice for vacation rentals or permanent residence. Inside, you'll find a thoughtful layout with three bedrooms, including a spacious primary bedroom, and two full bathrooms. The 1,685 square feet provides plenty of room for comfortable living and entertaining. The property's practical design makes it move-in ready for new owners. The location truly sets this property apart, offering the perfect balance of suburban comfort and urban convenience. Whether you're looking for a family home or an investment property, this Winter Park house delivers on both fronts. With shopping, dining, and entertainment options nearby, plus quick access to major transportation routes, daily life becomes effortless. This is a great opportunity to own in one of Central Florida's most sought-after communities.

2148 Blossom Lane, Winter Park

$1,050,000

3 Beds ⋅ 2 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Incredible opportunity to rebuild on this 95’ x 125’ prime Winter Park corner lot in Timberlane Shores. Surrounded by multi-million dollar homes, and across the street from Lake Virginia! This property will have lake views from the second story of your future new home! A+ location that will not last long!

620 Virginia Drive, Winter Park

$266,000

2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Beautifully updated and meticulously maintained. Improvements done in late 2020. Kitchen Ceiling raised and recessed lights installed, new Cabinets, Quart Counters, Stainless Steel Samsung Appliances including Counter-depth Refrigerator. Wall opened into Living Room and Breakfast Bar Installed. Updated Master Bath includes new Vanity, Mirror and Lights, Commode and beautiful new Shower, Barn Door installed for Privacy. Guest Bath also updated. Luxury Vinyl and Bathroom Tiles replaced throughout. New Double Paned Windows and Sliding Door, 6" Floor Moldings, Knock-down Ceilings and Decorator Paint. A/C and water Heater done with rest of updates. This 2 Bedroom 2 bath End Unit is centrally located in Lakefront Community with covered Patio in private Courtyard! Enjoy Sunsets on Lakefront Deck, Private Lakefront Ramp Access to skiable Lake Killarney, Heated Pool, Saunas and walking access to Shops, Restaurants, Movies and short distance to Park Avenue, Farmers Market and Downtown Art Festivals. Don't miss seeing this "little bit of heaven"! Call today for private viewing!

1500 Gay Road Unit 9B, Winter Park

$5,700,000

5 Beds ⋅ 6 Baths ⋅ Thomas M Henkels Add SubDv. ⋅ 32789 Zip Code

SOLD DATA ENTRY.. Welcome to this timeless lakefront estate located on the shores of Lake Virginia, offering approximately 143 feet of private waterfront along the highly sought-after Winter Park Chain of Lakes. Situated on over an acre, this beautifully updated residence blends classic architecture with modern luxury and an exceptional indoor-outdoor lifestyle. Thoughtfully renovated in 2016, the home features spacious formal and informal living areas, high ceilings, custom millwork, and stunning lake views throughout.The chef’s kitchen is equipped with Wolf and Sub-Zero appliances, double ovens, built-in Miele coffee system, wine refrigeration, and additional refrigerator/freezer drawers. The kitchen opens to the main living space and flows seamlessly to the outdoor entertaining areas. The primary suite offers a serene lakefront setting with a spa-inspired bath and generous closets. Additional bedrooms are well-appointed and offer both privacy and flexible living arrangements.Step outside to a resort-style waterfront setting, complete with a large pool and spa, expansive terrace, summer kitchen, gas fire pit, and private boat dock with lift. Enjoy boating, paddleboarding, or sunset cruises right from your backyard. The property’s elevation provides exceptional views stretching across Lake Virginia toward downtown Orlando and Rollins College.Located on a quiet, private street just moments from Park Avenue dining, shops, and Winter Park’s most desirable amenities, this is a rare opportunity to enjoy lakefront living in one of Central Florida’s most distinguished neighborhoods.

374 Henkel Circle, Winter Park

$975,000

3 Beds ⋅ 3 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

Nestled in the heart of Winter Park, this exquisite 3-bedroom, 2.5-bath residence offers 2,557 square feet of beautifully designed living space along with a spacious 2-car garage. Situated on a charming, tree-lined brick street just minutes from Park Avenue, the home’s first level includes a welcoming living room, versatile bonus/flex space, dining room with built-ins, a well-appointed kitchen, and a laundry room with ample storage.The centrally located designer kitchen features a herringbone tile backsplash, custom wood-wrapped hood, decorative island, and an adjacent dining room with a built-in buffet. A double-sided wood-burning fireplace serves as a striking centerpiece, separating a flexible space with a wet bar from the spacious living room, which offers built-in cabinetry and French doors leading to the manicured backyard. The second level features the primary suite and two additional guest bedrooms. The primary suite impresses with vaulted ceilings, a wood-burning fireplace, a wall of custom built-ins offering abundant closet storage. The luxurious en-suite bath includes a walk-in closet, dual vanities, a freestanding clawfoot soaking tub, and a walk-in shower with a seamless glass enclosure. The two additional bedrooms share a Jack-and-Jill updated bathroom. The vinyl-fenced backyard with mature landscaping and a brick paver patio is perfect for outdoor entertaining. Additional features: 2024 roof, Rheem 80-gallon electric water heater (2008), Carrier heat pump AC system (2011). 2024 exterior paint, seamless gutters, garage door and opener. Located within close proximity to the golf course, Winter Park Village, and Park Avenue, this home offers direct access to upscale shopping, dining, art galleries, and cultural events in a vibrant, historic setting. Zoned for A-rated schools and offering convenient access to major roadways, this residence provides an exceptional blend of style, comfort, and location in one of Winter Park’s most desirable neighborhoods.

1150 Kenwood Avenue, Winter Park

$2,925,000

5 Beds ⋅ 6 Baths ⋅ Thomas M Henkels Add SubDv. ⋅ 32789 Zip Code

This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of the highly sought out after Winter Park Chain of Lakes. The property is just a short walk or drive to Park Avenue’s restaurants, boutiques, and local attractions. The main home features three bedrooms and five bathrooms, each bedroom offering its own en suite bathroom. A separate guest house (ADU) provides an additional 932 square feet with two bedrooms, one bathroom, newly refinished original hardwood floors, fresh paint and a wood burning fireplace perfect for guests or extended family. Inside the main residence, you’ll find solid wood and travertine flooring throughout the first floor, surround sound speakers, a wood burning fireplace and freshly painted interiors. The living room features large windows overlooking the lake, with an open floor plan that flows seamlessly into the dining room and kitchen. The gourmet kitchen showcases a beamed ceiling, Busby custom three tone cabinetry with granite countertops, a six burner gas cooktop, and a built in ice maker. The dining area offers easy access to the outdoor entertaining spaces, perfect for enjoying lakeside gatherings. The primary suite occupies the entire second level, offering dual bathrooms, individual walk in closets, and a private balcony with unobstructed lake views. Additional features include an inviting office/den with french doors and custom built ins, as well as a spacious laundry room with ample cabinetry, a 120 bottle wine fridge, and a secondary refrigerator for added convenience. An expansive paver driveway leads to covered parking that accommodates up to three vehicles. Traditional gas lanterns and built in landscape lighting enhance the home’s Mediterranean charm and highlight its mature, manicured grounds. Outdoor living is the centerpiece of this property, featuring durable composite board decking, a summer kitchen with an infrared grill, and a hot tub for relaxing and entertaining. Enjoy multiple inviting seating areas with stunning east facing lake views. The private boat dock includes a storage closet, boat lift, and the boat itself is included. This home offers relaxed luxury and timeless lakefront living in one of Winter Park’s most desirable neighborhoods.

516 Henkel Circle, Winter Park

$250,000

2 Beds ⋅ 1 Baths ⋅ Stansbury Estates SubDv. ⋅ 32789 Zip Code

Unlock potential in one of Central Florida’s most desirable pockets! This centrally located Winter Park home shines with major updates already completed including a 2018 roof, 2022 HVAC, and fresh interior paint. Just bring a little extra love to elevate the finishes and create instant equity. Perfect as a long-term rental, short-term investment, or a future flip with strong resale appeal. Live minutes from Winter Park shopping & dining, beautiful golf courses, and vibrant Downtown Orlando. Commuting stays easy with quick access to top employers, schools, and major roadways. Whether you’re crafting your next investment win or dreaming up a place of your own, this home delivers value, location, and endless opportunity. Investors welcome — ask us about Hard Money lending options!

2009 Cornell Avenue, Winter Park

$879,000

3 Beds ⋅ 3 Baths ⋅ Virginia Heights Pt Rep SubDv. ⋅ 32789 Zip Code

Experience the best of Winter Park living at 451 Fairfax Avenue, an exceptional townhouse in the sought-after Virginia Heights neighborhood. This elegant residence offers timeless style and the rare advantage of no HOA. Designed for comfort and convenience, this home features three spacious bedrooms, three full baths and a private two-car garage. Upon entry, you are greeted by an open-concept living and dining area that flows seamlessly into the well-appointed kitchen, creating the perfect space for everyday living and entertaining. A bedroom and full bath on the main level provide flexible living options for guests. The main level also features a well-equipped laundry room with a sink, ice maker and generous storage. A bright sunroom with abundant natural light offers a versatile space for an office, reading nook or cozy sitting area. Upstairs, the primary suite features a spacious bath and walk-in closet, along with a secondary suite with its own en-suite bath. Beyond its inviting spaces, this home has been meticulously maintained, with new landscaping and drip-line irrigation for all patio planters. Enhancements include a tankless gas water heater, newer windows and doors with transferable warranties, new air-conditioner heat pumps (2024 and 2025), interior/exterior painting, and honeycomb roll shades throughout. In one of Winter Park’s most desirable neighborhoods, you’re a short distance from Lake Virginia, Mead Botanical Garden, and the Winter Park Tennis Center. Stroll to Rollins College or enjoy the boutiques and dining along Park Avenue, all less than a mile away. A rare opportunity to own a low-maintenance, luxury residence in the heart of Winter Park. Zoned for Audubon K-8 and WP High School. Schedule your private showing today to experience 451 Fairfax Avenue for yourself.

451 Fairfax Ave., Winter Park

$775,000

Lakeview Terrace SubDv. ⋅ 32789 Zip Code

Discover a truly unique offering in the heart of Winter Park! 1770 Bryan Avenue is now on the market along with the adjoining lots at 1760 and 1780 Bryan Avenue, creating a rare opportunity to own three consecutive parcels in one of Central Florida’s most desirable communities. While each property is being sold and priced separately, buyers have the option to purchase one, two, or all three lots together — offering remarkable flexibility for future use. Together, these lots present endless possibilities: Combine all three to create a spacious 200' x 127' estate lot Split into two 100' x 127' homesites Develop individually as three 66.6' x 127' lots Use this prime location to build an estate-style residence, design a family compound, or develop multiple homes — the options are abundant. Whether you’re seeking a personal sanctuary or a high-potential investment, this offering delivers exceptional value and versatility. Ideally located just minutes from Phelps Park, Park Avenue’s shopping and dining, and top-rated schools, this property provides the perfect balance of convenience and exclusivity. Opportunities like this are exceptionally rare in Winter Park — don’t miss your chance to secure 1770 Bryan Avenue, with the option to expand your vision across all three premier lots.

1770 Bryan Avenue, Winter Park

$470,000

3 Beds ⋅ 2 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Live the Winter Park dream in this freshly updated 3-bedroom, 2-bath home—just steps from Lake Killarney and minutes to I-4, boutique shopping, and top dining spots. The interior has been freshly painted, creating a bright and welcoming feel throughout. The updated kitchen shines with white shaker cabinets, quartz countertops, a subway-tile backsplash, and stainless-steel appliances. It’s perfect for everyday cooking and effortless entertaining. Wood-look laminate floors flow through the spacious living and dining rooms and into the bedrooms, while the family room offers wood-look tile, a cozy fireplace, and sliding doors that open to the screened patio. Outside, a long driveway extends beyond the fenced yard to a side-entry oversized two-car garage with workshop area. Surrounded by mature trees, the backyard is a private retreat with a cozy firepit, utility shed, and a versatile concrete pad—ideal for basketball games or weekend gatherings under the stars. Zoned R-1A, the property also allows for an accessory structure such as a guest suite or studio (no kitchen permitted) Thoughtful updates, generous outdoor space, and an unbeatable location near Lake Killarney make this home a rare find. Come experience comfort, character, and convenience in the heart of Winter Park.

2381 Roxbury Road, Winter Park

$630,000

3 Beds ⋅ 2 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

"NEW PRICE" ON THIS MOVE-IN READY, 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH "NO HOA" & LARGE PRIVATE YARD, WINTER PARK, FL 32789. The Seller has already relocated and willing to work with a "Fully Pre-Qualified" Buyer to get this home sold quickly. AWESOME LOCATION just off Corrine Drive. WALKING DISTANCE to East End Market. TOP-RATED Audubon Park (K-8) & Winter Park High (Magnet Program) Schools. The Owners completed a HOME ADDITION & UPDATE in 2020 w/over $115,000.00 of improvements, including a NEW Roof, NEW Primary Bath, EXPANDED Great Room, NEWLY Enclosed Entry way w/mudroom & pantry, along with mechanical & finishing upgrades. Enter the home through a fully ENCLOSED FOYER which allows easy access to the new MUDROOM, as well as the ENORMOUS GREATROOM, which features an open Family & Dining Room area featuring a Wood Burning Fireplace, Decorative Shiplap Niche, Vaulted Ceiling and a dual French Doors leading to the HUGE Patio & Back yard. The CHEF'S KITCHEN was redesigned to include 42" Wood Upper & Lower SHAKER CABINETS w/Soft Close Drawers, Quartz Countertops, HUGE FARM-STYLE Deep Sink, Custom Tile Backsplash, "LG" Stainless Package including a French Style Refrigerator, Flat-Top Range, Microwave, Dishwasher, Wine Refrigerator, Decorative Shelves & a Mid-Century Modern Bungalow Pendant. The Primary Suite is the perfect COUPLES RETREAT which includes a Large Bedroom, Vaulted Ceiling, and a HUGE 14' LONG WALK-IN CLOSET w/Customizable Organizers to store all your Clothes & Accessories. The Primary Bathroom includes HIS & HERS Matching Vanities with Quartz Countertops, Recessed Sinks, Dual Mirrors & Hardware. Enjoy the luxury of a custom jetted soaking tub—ideal for unwinding after a long day or for families with young children, complete with a Tile Backsplash. The "WALK-IN SHOWER" features Frameless Glass, Custom Wall & Floor Tile and an OVERHEAD RAIN SHOWER. Finally, the bathroom features oversized 24"x24" Custom Floor Tile to complete the design features. Do you ENJOY OUTDOOR SPACE & like to Entertain? Do you need a SPACIOUS KIDS AREA for them to safely play? If so, you will FALL-IN-LOVE” with the fully fenced & enclosed back yard featuring two HUGE 12'x21' and 15'x27' OPEN PAVER PATIO areas perfect for all your outdoor furniture & equipment. Also enjoy your own PRIVATE TAVERN with an 8'x12' Bar designed with Corrugated Metal Panels, a Bar Top, Shelving & Concrete Floor. The Bar is OPEN FOR YOUR FRIENDS & FAMILY. The Backyard also includes (2) Separate Gate Entrances which will accommodate & secure your Boat, Trucks, Trailers, Work Equipment, etc. In addition, there is an 8'x8' and 5'x8' Storage Rooms. Addl Features: NEW Roof (2025), NEW Interior & Exterior Paint (2025), Tankless Water heater, Carrier HVAC System (2019), Updated Electric Panel (2019), Updated PEX Plumbing (2019), Newer 8"x36" Custom Tile Flooring, Newer Double Paned Windows (2019), NEW Drain field (2024), Block Construction, HUGE Laundry & Storage Room wCustom Organizers, 6" Baseboards, Window Treatments, Ceiling Fans & Lights, Open Carport (13'x21'), Covered Carport perfect for a Golf Cart (8'x17'), Irrigation System, Gutters & Downspouts, Decorative Bamboo & much more. Just minutes to Park Avenue, Fine Dining, Leu Gardens, Downtown Orlando, Municipal & OIA Airports, Hwy 436, 408, 418, Turnpike, UCF & the Beaches. Call for more info or to schedule your private showing.

3018 Northwood Boulevard, Winter Park

$1,100,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Residence 415 at The Cloisters offers a rare opportunity to own a comprehensively rebuilt home in one of Winter Park’s enduring lakefront communities. Set on the fourth floor, just one block from Park Avenue, this residence blends timeless architecture with newly reimagined design. Taken thoughtfully down to its original structure and meticulously reconstructed with longevity in mind, this two-bedroom, two-bath residence now reflects a highly customized living experience. Every surface, system and layout choice has been elevated, beginning with level 5 smooth drywall, Emtek polished nickel hardware, custom millwork, full-height solid-core doors and Panaget engineered hardwood flooring. Lutron lighting systems control dimmable LED lighting throughout. Bedrooms, as well as the family room, include prewiring for additional fixtures, and the primary suite features dedicated pendants over each nightstand, independently controlled bedside. The kitchen is anchored by a full suite of smart Thermador appliances, including an induction range, range hood and a full-height refrigerator with a convertible Flex drawer for additional refrigeration or freezer storage, an internal water dispenser, built-in compartment cameras and Thermador’s signature Diamond ice maker. Calacatta Laza quartz surfaces and full-height backsplash accentuate custom oak cabinetry featuring soft-close drawers, an integrated appliance station with interior outlets, and an oversized pantry for seamless storage. A breakfast bar opens to the dining and living areas, which comfortably accommodate full-size furnishings and create defined spaces for formal dining, casual living and media use. The primary suite offers two built-in closets and a spa-inspired bath with Fantasy Brown quartz countertops on a wall-to-wall vanity. A lighted medicine cabinet mirror with integrated speakers sits above the vanity, with interior power outlets for charging accessories. A fully tiled frameless shower features a lighted accent wall, overhead rain shower and wall-mounted handheld options. Additional built-in cabinetry provides deep storage for linens and supplies, as well as a dedicated laundry storage closet. The second bedroom functions as a guest suite, supported by a beautifully appointed bath in matching design. Additional highlights include custom-trimmed window casings throughout, ready for shades or shutters, and an entry closet that can double as storage or pantry overflow. The residence includes assigned covered parking and private storage. Residents of The Cloisters enjoy an amenity-rich lifestyle with on-site management, access to a heated pool, two fitness rooms with saunas, a clubhouse and manicured lakefront park space. This turnkey optional offering places you at the heart of Winter Park’s cultural, dining and retail corridor, where enduring architectural character meets elevated, modern living.

100 S Interlachen Avenue Unit 415, Winter Park

$490,000

3 Beds ⋅ 2 Baths ⋅ Shores Lake Killarney Sec 02 SubDv. ⋅ 32789 Zip Code

No HOA! Fully Renovated Home with Deeded Lake Access to Lake Killarney in Prime Winter Park Location! Welcome to this move-in ready gem nestled in one of Winter Park’s most coveted neighborhoods. This solid concrete block home has been thoughtfully updated with timeless finishes, featuring a brand-new kitchen with freshly painted cabinetry, quartz countertops, stainless steel appliances and a custom paver driveway. The layout is filled with natural light, showcasing refinished flooring and modern bathrooms with stylish upgrades. Key improvements include: new roof and AC (2019), re-piping (2005) and energy-efficient windows (2010). Enjoy the charming front porch, lush landscaping and unbeatable location, just minutes from I-4, Park Avenue, and Winter Park Village. Whether you’re looking for a primary residence or a smart investment, this home checks all the boxes. **This property also qualifies for a closing cost credit of up to 1% of the loan amount through the Seller’s preferred lender.** Schedule your showing today and make it yours!

259 Blossom Lane, Winter Park

$800,000

3 Beds ⋅ 2 Baths ⋅ Golfview Heights SubDv. ⋅ 32789 Zip Code

Rare opportunity in the heart of Winter Park! This property sits on a double lot (0.29 acres) — a true rarity in this highly desirable location. The existing 1953 concrete-block home (3 bed / 2 bath) with an attached garage apartment (studio + bath) and shared 2-car carport offers little to no current value and would require a complete renovation. Property will be sold as-is with no repairs. Furniture removal prior to closing is negotiable. The real value is in the land. With privacy at the end of a quiet street, and a doctor’s office next door, the property is ideally located steps from AdventHealth Winter Park Hospital, Lakemont Center, and just 5 minutes from Rollins College and Park Avenue’s shopping and dining. The property features a large tree-lined backyard, city water and sewer, cable, and electricity already available. Whether you choose to restore a solid 1950s block home or tear down and build your dream estate while saving on impact fees, this is a prime investment opportunity in one of Central Florida’s most sought-after areas.

1822 Greenwich Avenue, Winter Park

$162,000

1 Beds ⋅ 1 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Come take a lovely stroll to Mead Gardens(47 acres), located just around the corner from this adorable condo in one of Winter Park’s most popular communities! The pool is located directly behind this condo! This cozy first-floor unit features brand-new luxury vinyl flooring that gives it a fresh, welcoming feel. The spacious living room has sliders that open up to a nice-sized screened-in Florida room—perfect for sipping your morning coffee or relaxing at the end of the day and the best part the pool is located directly behind your Florida room! With the large Florida palm tree as a reference point you can see how close to the pool this condo is! After you enjoy taking a hike around Mead Gardens- then come home to a nice swim in the pool! And here’s some exciting news: the seller is offering seller financing! That means the deed will be in your name, and with just 20% down and flexible terms, it’s an incredible chance for first-time buyers, or to add to your rental portfolio, or anyone looking for a sweet second home. If you've been dreaming of having a Winter Park address, this is your moment! You’ll absolutely love the fantastic location of this condo, and let’s not forget this condo is located less than 2 miles to Advent Health hospital, the Orlando Science center, shopping, restaurants and all that Winter Park has to offer! Don’t miss out on this wonderful investment opportunity. Show and Sell!!

1250 S Denning #122 Street Unit 00122, Winter Park

$1,500,000

4 Beds ⋅ 5 Baths ⋅ Tangerine Court SubDv. ⋅ 32789 Zip Code

Just Reduced $100,000 below appraised value!!!!! Experience refined living in this completely remodeled single story residence located in the heart of Winter Park. Enjoy luxury living in this impeccably maintained home. This beauty offers three spacious bedrooms and three beautifully appointed baths in the main house and a 1bed/1bth studio apt above the garage. Enter the spacious floorplan featuring open living and dining areas separated by a gorgeous double sided fireplace. The kitchen is a chef's dream with updated appliances and stunning marble countertops complete with lots of storage and work space. The living room features a panel of french doors overlooking the professionally landscaped and pavered back yard complete with a large resort style pool and soothing heated spa. Enjoy your morning coffee and your favorite afternoon beverage on the pavered lanai featuring remote control exterior shades. A half pool bath is part of this amazing landscape. The 2+car detached garage features an upstairs studio apartment perfect for guests, a home office or rental income. It is complete with a kitchenette, large bathroom and washer/dryer. The large master bedroom boasts two walk in closets, open step in shower, a double vanitiy and water closet . Lots of natural light, too!! Enjoy the guest room complete with an en-suite bath and, of course, the 3rd bedroom is perfect for family. Your paradise is only 2 miles from Park Avenue known and loved by so many for it's art galleries, restaurants, upscale shopping and parks. Top rated medical facilities within a short distance. This is lifestyle living at it's finest !

132 Burks Circle, Winter Park

$505,000

3 Beds ⋅ 2 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code

Winter Park home for sale

1651 N Park Avenue, Winter Park

$555,000

3 Beds ⋅ 3 Baths ⋅ Park Shore SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Modern Comfort in the Heart of Winter Park! Built in 2019, this 3-bedroom, 2-bath, 1,798sf townhome offers the perfect blend of convenience and contemporary style in a private 12-unit community. Light and bright with high ceilings and tile floors, the open-concept living area features a quartz island kitchen with Samsung appliances, solid wood cabinetry, and a retractable sliding door that opens to a walled courtyard—ideal for dining and entertaining. Upstairs, you’ll find the spacious primary suite, two additional bedrooms, a secondary bath, and a laundry room. Additional features include a downstairs custom closet, upgraded sound system with subwoofer and speakers throughout the main living areas and patio, central vacuum, security system, and an attached two-car garage. Enjoy low-maintenance living close to I-4, College Park, Park Avenue, shopping, and dining.

1267 Michigan Avenue, Winter Park

$6,495,000

5 Beds ⋅ 7 Baths ⋅ Osceola Place SubDv. ⋅ 32789 Zip Code

Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

550 Palmer Avenue, Winter Park

$720,000

4 Beds ⋅ 3 Baths ⋅ Howell Forest SubDv. ⋅ 32789 Zip Code

Discover The Hills of Winter Park, a quiet, tree-lined community just minutes from Park Avenue. This beautifully updated single-family home offers 3,902 square feet of living space on a 0.20-acre lot. It features two spacious primary suites—one located upstairs with a vaulted shiplap ceiling, three walk-in closets, and a private balcony overlooking the pool and spa. The remodeled kitchen includes a 5’x10’ stone island, stainless steel appliances, a 42” Kenmore range, and opens to generous living and dining areas with a wood-burning fireplace. Additional highlights include a large recreation room with French doors leading to a screened lanai and private fenced backyard oasis, perfect for entertaining. Enjoy plenty of driveway and street parking, plus a dedicated area on the lot ideal for recreational storage—perfect for boats, trailers, or extra gear. While there is no garage, the home offers ample storage space throughout, including multiple walk-in closets and flexible indoor utility areas. Recent upgrades include a 2023 roof, indoor laundry room, and an American Home Shield warranty. A rare opportunity to live, work, and relax in the heart of Winter Park.

2955 Lolissa Lane, Winter Park

$359,900

3 Beds ⋅ 2 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Fantastic Opportunity / Dubsdread Heights in Winter Park! Do not miss out on this great opportunity to own a home in the desirable College Park area located in Dubsdread Heights. This charming 3-bedroom, 2-bath residence sits on an oversized 50 x 140 lot and offers 1,283 sq. ft. of air-conditioned living space. Featuring a split-bedroom floor plan, the home includes hardwood floors in several rooms, a spacious kitchen with tile flooring and wood cabinetry, and a dining room enhanced by a beautiful tongue-and-groove wood ceiling.The primary bedroom boasts wood floors, a tongue-and-groove wood ceiling, a wall closet, and an en-suite bath with dual sinks, a shower, and a laundry closet with a washer and dryer. The two additional bedrooms share a bright hall bath with a tub/shower combo. Just off the kitchen, a 12 x 16 enclosed porch overlooks the expansive backyard, which includes an adjacent patio and two storage sheds that convey with the property. Updates Include New Roof (August 2017), New Electrical Panel (August 2023), Septic System Fully Cleaned and Serviced (Early 2025) & HVAC System (2018) Located just one block from the Dubsdread Golf Course, this home is ideally situated minutes from I-4, Downtown Winter Park, Park Avenue, College Park, AdventHealth Hospital, and Downtown Orlando. Perfect as a primary residence or an excellent investment opportunity in a prime location.

780 Baffie Avenue, Winter Park

$1,399,500

4 Beds ⋅ 5 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code

GORGEOUS NEW CONSTRUCTION IN WINTER PARK! Discover sophisticated modern living at 607 Ellen Drive — a brand-new construction masterpiece by the acclaimed Lazarus Homes, perfectly positioned in the heart of Winter Park. At this new price, it's simply unmatched value for new construction in this location. This impeccably designed 2,812-square-foot residence showcases striking contemporary architecture with clean lines, soaring ceilings, and natural light pouring in from every angle. The open floor plan flows effortlessly from space to space, creating the ultimate backdrop for everyday living and unforgettable entertaining. The chef's kitchen is nothing short of a showstopper — outfitted with top-of-the-line Monogram appliances, a sleek Ruvati sink, built-in oven and microwave, and a professional gas range. Show-stopping Taj Mahal Quartzite countertops bring both drama and durability, and you'll have the flexibility to add a full-height wine refrigerator or extra cabinetry to make the space truly your own. The living room delivers modern warmth with an electric fireplace and walls of glass sliders that open wide to a covered lanai and your own private pool — Florida indoor-outdoor living at its absolute best. Love to entertain? The home comes pre-stubbed for an optional outdoor kitchen, ready when you are. Retreat to the luxurious first-floor primary suite, a true private sanctuary with a spa-inspired en suite bath — double sink vanity, walk-in shower, soaking tub, and an oversized walk-in closet with custom built-ins and washer/dryer hookups. Upstairs, the impressive layout continues with a spacious bonus room, a striking loft framed in glass walls, three more bedrooms, two full baths, and a second laundry area for effortless convenience. A dedicated pool bath rounds things out for easy poolside enjoyment. Tucked into the sought-after Lake Killarney Shores community, this home is the ultimate blend of peaceful retreat and unbeatable location. Enjoy a low HOA, private boat launch access to Lake Killarney, and a walkable stroll to Winter Park's best restaurants, boutiques, and cultural hotspots. New construction, lake access, unbeatable location, and a brand-new price — this move-in-ready modern luxury home won't last long!

607 Ellen Drive, Winter Park

$645,000

2 Beds ⋅ 2 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Discover the timeless allure of this enchanting 2 bedroom, 1.5 bath home, built in 1936 and nestled in the heart of historic Winter Park steps from Lake Mizell. Located on one of the area's iconic brick-paved streets and surrounded by majestic oak trees, this Winter Park bungalow is a rare find. The home's classic design features original hard wood floors, original glass windows, a cozy wood-burning fireplace, and an abundance of natural light blending vintage charm with practical functionality. With its warm character and unbeatable location, this delightful property captures the essence of Winter Park living at its finest.

224 Overlook Road, Winter Park

$479,000

2 Beds ⋅ 1 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Beautiful piece of property on Clay St. in Winter Park. Fantastic location. Nearly a third of an acre. Minutes to downtown Winter Park , Advent Health medical center on Rollins St. and Dubsdread golf course. *Double gate fence for boat or RV. *Newer A/C in 2017. *Newer roof in 2017. *Garage *Huge fenced-in backyard. *Wood floors. Enjoy this home or build new on this great piece of property. Come and imagine the possibilities. What's your offer?

1386 Clay Street, Winter Park

$1,700,000

Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

An exceptional opportunity to design and build your dream lakefront home in Winter Park. Positioned on the shores of Lake Berry, one of the area's private and pristine ski lakes with no public ramp, this property offers a rare combination of privacy, location and potential. Set on over a half-acre of lakefront land, the property features a four-bedroom, two-and-one-half bath, single-story residence with a covered boat dock, ideal for enjoying lake life immediately or while planning a future custom build. The northeast-facing front provides the ideal orientation to capture breathtaking sunsets across the water each evening. Whether you choose to renovate the existing home or build a new architectural masterpiece, this offering presents the ultimate canvas for creating a generational lakefront retreat. Within minutes of downtown Winter Park, Park Avenue and A-rated public schools, this property combines the best of convenience, serenity and luxury lakefront living. A special opportunity to bring your vision to life on one of Winter Park's desired private lakes.

633 Balmoral Road, Winter Park

$375,000

3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to your next chapter at 1007 Early Ave in Winter Park, a charming 3-bedroom, 2-bathroom home. Thoughtfully maintained, this home combines character with modern comfort. Step inside to find inviting living spaces and enjoy peace of mind with a roof replaced in 2019. The spacious backyard is perfect for entertaining, gardening, or simply relaxing under the Florida sun. With plenty of room to play, it’s a rare find in Winter Park and offers potential for future outdoor upgrades or expansion. Located just minutes from downtown Winter Park, you’ll have easy access to top-rated dining, boutique shopping, and cultural attractions. Whether you’re a first-time homebuyer, a growing family, or looking for a smart investment in Central Florida’s thriving market, this home checks all the boxes! Schedule your showing today!

1007 Early Avenue, Winter Park

$414,000

3 Beds ⋅ 2 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code

Welcome to this fully remodeled, move in ready home perfectly situated on a spacious corner lot in Winter Park, just blocks from the Dubsdread Golf Course and close to the shops, restaurants, and charm of College Park and downtown Winter Park. Every inch of this 3 bedroom, 2 bath home has been thoughtfully updated to blend modern comfort with timeless style. Step inside to find a bright, open layout with beautiful tile flooring throughout for a clean, cohesive look. The spacious living and dining areas flow seamlessly together, creating an inviting space that’s ideal for entertaining or relaxing at home. The updated kitchen is a showstopper, featuring shaker cabinets, quartz countertops, a farmhouse sink, stainless steel appliances, and elegant finishes that make it both stylish and highly functional. Whether cooking a weekday dinner or hosting friends, this kitchen will quickly become the heart of the home. The primary suite includes a modern barn door entry to the walk in closet and a renovated bathroom with fresh, contemporary finishes. Two additional bedrooms and another updated full bathroom complete the interior, providing comfortable accommodations for family, guests, or a home office. Step outside and enjoy your private backyard retreat, fully enclosed with Vinyl Fencing for privacy. Entertain under the gazebo or relax on the paver patio. Take advantage of the 10x15 shed with power, perfect for a workshop, studio, or extra storage. Major system updates ensure peace of mind for years to come including double pane windows throughout, a 2020 AC unit and a 2016 roof. With its prime location, modern upgrades, and turnkey condition, this home is priced to sell and ready for its next owner. Schedule your private showing today!

740 Baffie Avenue, Winter Park

$4,720,000

5 Beds ⋅ 6 Baths ⋅ Camwood Sub SubDv. ⋅ 32789 Zip Code

*Under Contract - Accepting Backup Offers* An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired foyer greets guests with precast stone-clad walls, inlaid marble flooring, and a Murano-style polyhedral chandelier. Two first-floor guest suites, each with its own bath, are adorned with rift-cut white oak millwork, curved ceilings, and crystal chandeliers. At the heart of the home lies the main salon, where oak detailing and a deco-style stone fireplace with a holographic insert create an atmosphere of understated grandeur. The two-tone oak kitchen, wrapped in natural quartzite and anchored by a curved island and custom hood, features a curated suite of professional-grade appliances: • ILVE range • Miele refrigerator, freezer, and dishwasher • Sub-Zero wine and beverage preservation systems Adjacent, a dining area glows under a custom chandelier, while the powder bath impresses with wood and marble accents, an integrated stone sink, and a Saint Louis crystal faucet by Kallista. A scullery expands the culinary capability with a chef’s sink, Samsung Bespoke laundry and refrigeration, Wolf microwave drawer, and additional Miele dishwasher—ideal for both entertaining and daily ease. The first floor primary suite, discreetly hidden behind millwork, offers a serene retreat with an opulent closet system and a marble mosaic-clad bathing suite featuring Kohler digital shower technology and MTI tub. Upstairs, two additional ensuite bedrooms, a bonus room with walk-in closet, and a secondary laundry continue the home’s standard of refined luxury. Outdoors, the residence embraces resort-style living with a natural gas summer kitchen, infinity-edge pool, and 360-degree raised glass-tile spa. A two-car garage and porte cochere, both EV-ready, provide elegant utility. Modern conveniences include Lutron HomeWorks lighting and shade prewire, built-in SONOS audio zones, pre-installed speakers, and a commercial-grade Ubiquiti WiFi network ensuring flawless connectivity throughout. A feast for the senses, The Maybourne is more than a home—it’s a statement of artistry and craftsmanship, conceived for the most discerning Winter Park resident.

1302 Raintree Place, Winter Park

$586,000

2 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code

RARE CORNER TOP-FLOOR CONDO WITH AMAZING VIEWS – FULLY FURNISHED AND IN THE HEART OF WINTER PARK! Discover the perfect blend of comfort, style, and unbeatable location! This beautifully maintained 2-bedroom, 2-bath corner unit sits on the top floor of the desirable Villages of Winterset, offering expansive views and abundant natural light throughout. Enjoy the convenience of two elevators, a private storage unit on the same floor, and on-site laundry just steps from your door. Your assigned covered parking keeps your car cool and protected, and the secured mid-rise building features key access, a call box for guests, and a welcoming lobby lounge. Step outside and you’re just a short walk to everything that makes Winter Park special — Park Avenue’s boutique shops and restaurants, Rollins College, the Morse Museum, Winter Park Golf Course, and the SunRail station. Central Park is right there for art festivals, concerts, and weekend strolls! Relax at home by the sparkling community pool, enjoy the sun deck or BBQ area, and soak in the charm of one of Winter Park’s most beloved communities. Winterset is owner-occupied only, where rentals and pets are not permitted ensuring peace, privacy, and pride of ownership all around. Come see why homes at Winterset rarely hit the market — and fall in love with your new Winter Park lifestyle!

265 E Canton Avenue Unit GE, Winter Park

$105,000

2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code

Charming 2-bedroom, 1-bath condo located in the heart of Winter Park. This well-maintained unit offers comfortable living with an open layout, ample natural light, and convenient access to shopping, and dining. Enjoy the community pool and beautifully landscaped grounds, perfect for relaxing or entertaining. Ideal for first-time buyers, investors, or anyone looking to enjoy the Winter Park lifestyle.

1695 Lee Road Unit C214, Winter Park

$745,000

3 Beds ⋅ 2 Baths ⋅ Northwood - Winter Park Oasis SubDv. ⋅ 32789 Zip Code

An incredible location close to Park Avenue, this freshly renovated home exudes modern style and the walkable lifestyle that Winter Park is known for. This timeless Florida ranch features one-level living and is in a charming downtown neighborhood that is fresh and turnkey. Experience an open living concept with seamless flooring and designer selections throughout creating great spaces and function. The kitchen features clean-lined, neutral-toned cabinetry with a large island topped with quartz counters and bar seating with gold-toned, oversized pendants that take center stage. The adjacent bar area includes a built-in pantry, open shelving and a wine refrigerator, adding a touch of luxury to your everyday life. Just beyond the kitchen/living room, you'll discover a fantastic dining area and two well-appointed bedrooms. The shared bath is fully renovated with current selections, making it a retreat for family and guests. A desirable split plan with owner's suite is on opposite side of the home, adorned with beautiful light and airiness. A space-saving built-in wardrobe lines one wall, while the en-suite bath showcases stunning design elements, including a walk-in shower, dual sinks and a private water closet. The backyard invites you out through clear glass sliders to a charming backyard with a brick patio and a fully fenced backyard, lined with bamboo, which offers the privacy you desire. Entertain with shaded dining and lounging on sunny days with newer retractable awning (2021) controlled by a convenient remote. Additional features that make this home stand out include a newer roof (2020), newer air conditioner (2020), plumbing updated 2018, electrical panel update (2023), new backyard sod and irrigation (2025), freshly painted, a two-car garage with a new electric car charger (2022), a custom workbench and storage cabinets added in 2021. And let's not forget the incredible location, a couple of blocks from Winter Park 9 Golf Course, Park Avenue, Winter Park Village and Saturday farmers market, with Whole Foods, Publix and the Enzian just minutes away, this home is your private oasis in the heart of Winter Park.

630 Northwood Circle, Winter Park

$360,000

3 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

RARE FIND! MUST SEE! PRIME LOCATION! NO HOA! Check out this 3 bedroom 2 bath gem in the heart of beautiful Winter Park. This home is conveniently located close to shopping, dining, medical. Only minutes from Downtown Orlando and only a short drive to any of the Orlando amusment parks and airport. Home has been used as a rental for many years. Roof is 2020. HVAC replaced 2021. Whether you are looking to occupy or an investor looking for your next investment, this is it! Schedule your showing now!

611 Ololu Drive, Winter Park

$1,850,000

4 Beds ⋅ 5 Baths ⋅ Flora Park 2nd Add SubDv. ⋅ 32789 Zip Code

Welcome home to 1612 Magnolia Avenue. Built by the renowned custom home builder Lundev, this beautifully crafted transitional residence blends thoughtful design with luxurious comfort. From its striking exterior to the serene backyard oasis, every detail is designed to impress even the most discerning buyer. Upon entry, a dedicated office sits just off the foyer with custom floor-to-ceiling cabinetry and dual workstations, perfect for working from home. Across the hall, the formal dining room offers an elegant setting for entertaining and connects to the kitchen through a temperature-controlled wine cellar with storage for more than 400 bottles. The chef’s kitchen is a culinary dream featuring top-of-the-line appliances, a spacious island ideal for food preparation and presentation, and an open concept that flows seamlessly into the family room. A cozy gas fireplace anchors the family room, which opens through French doors to the covered lanai. Enjoy year-round outdoor living with a fully equipped summer kitchen that includes a grill, Green Egg BBQ, refrigerator, and wraparound counter space for hosting while overlooking the sparkling pool. The backyard is a private sanctuary complete with a luxurious pool and a large cabana with a wood-burning fireplace. The first-floor primary suite offers peaceful views of the backyard and a spa-like bath with dual sinks, a soaking tub, and a separate shower leading to an oversized walk-in closet with built-in storage. A mudroom, laundry room, powder bath, and convenient pool bath complete the well-planned first floor. Upstairs, three additional bedrooms provide ample space for family or guests. Two bedrooms share a Jack and Jill bath, while the third enjoys its own private en suite. This home has been extensively upgraded, combining comfort, sophistication, and modern convenience. Ideally located on a tree-lined street in one of Winter Park’s most desirable neighborhoods, it is minutes from the Winter Park Racquet Club, Park Avenue’s shopping and dining, YMCA, top-rated hospitals, and excellent public and private schools. Do not miss this rare opportunity to own a home that truly has it all. Welcome to the best of Winter Park living.

1612 Magnolia Avenue, Winter Park

$1,650,000

4 Beds ⋅ 3 Baths ⋅ Stonehurst Estates SubDv. ⋅ 32789 Zip Code

Nestled on a magnificent oversized lot in the heart of Winter Park, this 4-bedroom, 3-bath home offers plenty of space and opportunity. The backyard is a true highlight, featuring a large swimming pool and additional green space tucked just beyond the back hedges, adding a sense of privacy and flexibility for the outdoor area. Inside, the home showcases hardwood floors that flow throughout the living room, dining room, kitchen, family room, and bedrooms, creating a warm and inviting feel. A spacious family room with a cozy fireplace serves as the centerpiece of the home, while French doors open onto a vaulted screened porch, perfect for unwinding or entertaining with a view of the backyard. The kitchen offers stone countertops, and recent updates to the electrical, plumbing, and roof provide peace of mind for the next owner. This property is ideal for someone looking to renovate or update to their personal taste, or even to build a new home on this generous lot. Its location is hard to beat, set on a nice and quiet Winter Park street close to Park Avenue’s shops and dining, Rollins College, top-rated schools, and the area’s many lakes and parks. It’s a wonderful investment in both lifestyle and location.

1915 Stonehurst Road, Winter Park

$1,129,000

3 Beds ⋅ 3 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

RARE OPPORUNITY to Experience refined living in the heart of Winter Park with this exceptional and spacious 3-bedroom, 3-bath END UNIT residence at the highly sought Douglas Grand. This unit INCLUDES A DEEDED STORAGE UNIT AND 3 PARKING SPACES. Combining timeless elegance with modern comfort, this spacious home features high ceilings, an open-concept design, and exquisite finishes throughout. The gourmet kitchen is perfect for entertaining, offering custom cabinetry, stone countertops, premium stainless-steel appliances. The primary suite is a serene retreat with a spa-style bath, dual vanities, a soaking tub, and an expansive walk-in closet. Two additional bedrooms provide ample space for guests, an office, or a den. Enjoy the convenience of three designated parking spaces and a deeded storage unit, providing both practicality and peace of mind to store those holiday accessories and more. Residents of The Douglas Grand enjoy secure building access and maintenance-free living just steps from Park Avenue’s upscale shops, fine dining, and cultural attractions. Building is very well maintained with newer roofs recently completed in the last few years. This rare offering captures the essence of Winter Park luxury — convenient and perfectly located.

100 S Virginia Avenue Unit 314, Winter Park

32789 Zip Code 3+ Acre Real Estate & Homes

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