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$450,000
5 Beds 4 Baths Ridge High 1st Add SubDv. 32792 Zip Code
Welcome to 2181 Linden Road, where modern updates meet the everyday convenience of Winter Park living. Thoughtfully renovated and designed with flexibility in mind, this home offers a versatile layout, contemporary finishes, and a private separate-entry suite that adds valuable space for guests, a home office, or additional living arrangements. With no HOA, the property offers added flexibility rarely found in this sought-after area. The location is a standout. Enjoy easy access to Winter Park’s renowned Park Avenue, with its boutiques, restaurants, cafés, galleries, and local events, while nearby Winter Park Village adds even more shopping, dining, entertainment, and everyday conveniences. Outdoor enthusiasts will appreciate close access to the Cross Seminole Trail, Lake Baldwin Park, the Winter Park Chain of Lakes, scenic parks, and recreational opportunities. Downtown Orlando, major employment centers, Advent Health Winter Park, Rollins College, Full Sail University, SR-436, SR-426, and I-4 are also conveniently accessible. Winter Park continues to invest in its future, with ongoing improvements to Park Avenue, expanded infrastructure and streetscape enhancements, and a citywide Parks & Recreation Master Plan focused on improving parks, trails, open spaces, recreation, and community facilities for years to come. This is more than a renovated home it is an opportunity to enjoy the lifestyle, connectivity, character, and continued growth that make Winter Park one of Central Florida’s most desirable places to call home.

2181 Linden Road, Winter Park

$475,000
2 Beds 2 Baths Winter Park Pines Rep SubDv. 32792 Zip Code
Welcome to this charming 2 bedroom, 2 bath home, with light and bright open floor plan, spacious rooms and many updates and upgrades. Roof was replaced (2019), new A/C (8/26), fully renovated kitchen with quartz counters, cabinetry, and stainless appliances. Pella double pane windows (2020), new French doors and interior doors, and new soffits and gutters in 2025. Enjoy outdoor living in the lanai overlooking a large fenced backyard with native landscaping. This highly desired neighborhood offers excellent schools, quiet streets, community pool, hiking and biking trails, and nearby public golf course. Live minutes from Advent Hospital, city conveniences, downtown Park Avenue shops and restaurants. Also easy access to neighboring towns, Orlando and airports. This is a perfect starter home or downsize home for those want all the comforts and privacy of a home, neighborhood and community in smaller space and are not ready for an apartment and high HOA fees.

2824 Prince John Road, Winter Park

$600,000
4 Beds 2 Baths Arrowhead Cove SubDv. 32792 Zip Code
Welcome to this fully renovated four-bedroom, two-bathroom pool home offering close to 2,000 square feet of beautifully updated living space on an expansive .36-acre pie-shaped lot in the established Arrowhead Cove neighborhood. Thoughtfully renovated throughout, this move-in-ready residence combines modern finishes, an ideal split floor plan and exceptional outdoor living with a location zoned for top-rated Winter Park schools. Inside, brand-new windows and sliders, installed in 2026, fill the home with natural light while wood laminate flooring, fresh interior paint, and recessed lighting create a polished, comfortable atmosphere. The renovated 2025 kitchen features crisp white shaker-style cabinetry, quartz countertops, brand-new stainless steel appliances and a spacious stainless sink, creating a stylish and functional centerpiece for everyday living and entertaining. The private primary suite is thoughtfully separated from the secondary bedrooms and offers dual built-in closets and an updated ensuite bathroom with a double quartz vanity, beautifully tiled shower and separate water closet. Three additional bedrooms share a renovated hall bathroom featuring a double quartz vanity, tiled tub/shower and convenient direct access to the pool area. Step outside to your own private backyard retreat, where a spacious screened lanai overlooks the sparkling in-ground pool. Resurfaced in 2025, the chlorine-generated pool also features a new pump, light, steps and filter. A separate gazebo provides another inviting space for outdoor dining or relaxing, while the fully fenced .36-acre pie-shaped lot offers plenty of room to enjoy the outdoors. A two-car garage adds everyday convenience and storage. Ideally located just five minutes from Full Sail University and SR 417, approximately 15 minutes to UCF and 20 minutes to Orlando International Airport, this exceptional home also offers easy access to Target, Costco, grocery stores and abundant retail. With extensive 2025-2026 renovations, a private pool and an oversized lot in a highly desirable Winter Park school zone, this is a rare opportunity to enjoy turnkey living in a prime Central Florida location. ROOF - 2023 HVAC - 2018 PLUMBING - 2025 WATER HEATER - 2017

7525 Lodge Pole Trail, Winter Park

$529,000
3 Beds 2 Baths Garden Lake Estates Unit 1 SubDv. 32792 Zip Code
Updated Winter Park home with 2,047 sq ft of heated/cooled living space, a huge backyard, and NO HOA. This is an owner-updated home—not a flip—with quality improvements completed over the past several years and professionally completed permitted work. Major improvements include a 2021 roof, 2021 whole-house repipe, 2021 exterior stucco and paint, 2020 HVAC, 2023 kitchen remodel, 2023 permitted 400 sq ft heated/cooled sunroom addition, 2024 permitted 20’ x 10’ storage building, and 2025 hurricane-impact windows. The expanded kitchen features granite countertops and backsplash, newer appliances, and a massive storage expansion. The bright 400 sq ft sunroom features wall-to-wall windows, a four-panel sliding glass door, and permanent AC and heat. A separate 200 sq ft tiled screened room provides additional outdoor living space. The property also offers a large backyard with plenty of room to enjoy, entertain, or expand. Located in a desirable Winter Park area with great schools and convenient access to shopping, dining, parks, and major roads. Extensive owner-quality improvements, major systems already updated, permitted additions, and no HOA. Buyer to independently verify all measurements, square footage, permits, schools, and other property information.

1660 Gladiolas Drive, Winter Park

$750,000
4 Beds 4 Baths Meadows At Hawks Crest SubDv. 32792 Zip Code
Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacious open floor plan with a private backyard setting and a layout that offers exceptional versatility. The main level includes the primary suite, dedicated study, laundry room, kitchen, and principal living areas, making day-to-day living possible without the need for stairs. The gourmet kitchen features quartz countertops and 42-inch cabinetry, while 8-foot interior doors add height and proportion throughout. Large sliding glass doors open to an oversized screened and covered patio with eastern exposure, morning sun, and no rear neighbors. Built in 2020, the home also offers the advantages of newer construction, complemented by a tile roof. Upstairs, the 4-bedroom, 3.5-bath floor plan includes three bedrooms, one serving as a second primary suite, along with a large bonus room and separate loft. Hawks Crest is set along Lake Howell and offers a clubhouse, fitness center, community pool, splash pad, parks, walking trails, grilling and picnic areas, and a pier with lake access. Park Avenue, shopping, dining, recreation, and major roadways are all within convenient reach.

1287 Verdant Glade Place, Winter Park

$860,000
5 Beds 4 Baths Lake Ann Estates Unit 3 SubDv. 32792 Zip Code
Virtually Staged. Set on nearly an acre in Winter Park, this stately two-story home offers five bedrooms and three and a half bathrooms across more than 3,200 square feet of elegant living space. A dramatic two-story foyer with a sweeping staircase welcomes you into light-filled formal and casual living areas, including a spacious great room anchored by a fireplace. The gourmet island kitchen features rich cabinetry, stainless steel appliances, and generous counter space, flowing effortlessly to the surrounding living and dining spaces finished with wood-look flooring. The expansive primary suite provides a spa-like bath with a soaking tub and a separate glass-enclosed shower, while four additional bedrooms offer ample room for rest or a home office. Outside, a screened, in-ground pool and spa are framed by a paver deck and a large fully fenced yard, complemented by a covered patio and an oversized three-car garage. A rare offering of space and comfort on a generous, secluded lot. Included 100-Day Home Warranty with buyer activation

120 Longbranch Road, Winter Park

$439,000
3 Beds 2 Baths Village Green SubDv. 32792 Zip Code
Virtually Staged. This is the one!! Welcome home to this beautifully updated 3-bedroom, 2-bath POOL HOME with NO HOA!! RECENT MAJOR IMPROVEMENTS include a durable 2022 metal roof, a 2023 whole-house repipe, a 2023 A/C system, 2023 hot water heater, a 2022 pool filter, and a 2021 pool pump. Additionally the windows were replaced in approximately 2012 and the electric panel was replaced in 2011/2012. Inside, the RENOVATED KITCHEN is literally at the heart of the home and features stainless-steel appliances, granite counters, solid wood soft-close cabinetry and a farmhouse sink looking out to the pool area. Luxury vinyl plank flooring enhances the main living areas and BRAND NEW carpet adds comfort to the bedrooms. Both bathrooms have been UPDATED and the guest bathroom has been fitted with a walk-in accessible Jacuzzi tub. The freshly painted exterior provides attractive curb appeal. Step outside to your FULLY FENCED private backyard and swimming pool...perfect for relaxing, entertaining, and enjoying the Florida lifestyle. A storage shed is also included. Located in Seminole County with a desirable Winter Park address, the home is convenient to shopping, dining, parks, Full Sail University, UCF, SR 417, and Aloma Avenue. It is zoned for TOP RATED Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High School. With major improvements already completed, this inviting pool home is ready for its next owner. Schedule your showing today!!

7640 Village Green Dr, Winter Park

$765,000
4 Beds 4 Baths Meadows At Hawks Crest SubDv. 32792 Zip Code
Welcome to 1246 Verdant Glade Place in The Meadows at Hawk’s Crest, where luxury, thoughtful design, and resort-style living come together! This beautifully maintained original-owner 4-bedroom, 3.5-bath home showcases exceptional upgrades, including LVP flooring on both levels, plantation shutters, 8-foot first-floor doors, 5.25-inch baseboards, upgraded cabinetry, custom woodwork, and updated black iron stair railing. The impressive kitchen features quartz countertops, wall oven and microwave, stainless steel appliances, externally vented hood, marble tile backsplash, above- and under-cabinet lighting, and crown molding in the kitchen, dining room, foyer, and half bath. A stunning two-story custom built-in with electric fireplace, display shelving, and storage creates a dramatic focal point in the living area. The first-floor primary suite offers a tray ceiling and custom closet cabinetry, while one upstairs bedroom also features a custom closet. A private office/bonus space and upgraded laundry cabinetry add flexibility and function. Step outside to your own private resort featuring a spectacular saltwater pool and spa with sunshelf, pebble finish, fountains, and bubbler, all within a screened enclosure. Additional highlights include an epoxy-coated garage floor and overhead storage racks. The Meadows includes lawn care, a community pool, splash pad, fitness center, and gated entry. Conveniently located near shopping, dining, major roadways, Winter Park, parks, and trails. This is the Florida lifestyle you’ve been waiting for—come see it now!

1246 Verdant Glade Place, Winter Park

$415,000
3 Beds 2 Baths Autumn Glen Ph 3 SubDv. 32792 Zip Code
Welcome to this inviting 3-bedroom, 2-bathroom pool home in the Autumn Glen neighborhood of Winter Park, offering over 1,100 square feet of comfortable living space. As you step through the front door, you are immediately greeted by the bright, open-concept design, with natural light flowing throughout the home and creating a warm and welcoming atmosphere. To your left, the kitchen takes center stage with beautiful marble countertops, stainless steel appliances, an abundance of cabinetry and storage, and a charming farmhouse sink. The kitchen seamlessly opens to the dining area and living room, creating one connected space that is perfect for entertaining, relaxing, and making memories. Just off the entryway to your right, French doors open to one of the bedrooms, currently being used as an office, offering flexibility for a home office, guest room, or additional space to fit your lifestyle. Continuing into the living room, you'll find the primary bedroom tucked just beyond, offering a comfortable retreat filled with natural light. The primary suite features a closet and a private bathroom complete with a walk-in shower and stylish gold accents throughout. From the living room, follow the hallway to the third bedroom, which features its own closet, with the guest bathroom conveniently located nearby for easy access from both the bedrooms and main living areas. As you make your way outside, the home truly comes to life with a fully fenced backyard designed for enjoying the Florida lifestyle. The pool and hot tub combination creates the perfect place to cool off, unwind, or entertain, while the spacious patio provides plenty of room for soaking up the sun, gathering with friends, or enjoying late-night fires under the stars. Whether you're enjoying your morning coffee in the bright kitchen, relaxing in the living room, or spending summer evenings by the pool, this home offers a comfortable and inviting space to create memories. Conveniently located near shopping, dining, major highways, and Seminole County schools, this home offers the perfect blend of comfort, lifestyle, and convenience in Winter Park.

1533 Springtime Loop, Winter Park

$569,000
4 Beds 2 Baths Lake Waunatta Woods SubDv. 32792 Zip Code
Under contract-accepting backup offers. Move-In Ready Pool Home! This beautifully maintained 4-bedroom, 2-bath home features a split-bedroom floor plan with bright, open living spaces. The kitchen features soft-close cabinetry, stainless steel appliances, a pantry, ample counter space, and a breakfast nook/flex space. A screened patio overlooks the pool, fire pit, and fully fenced backyard. Both bathrooms were just renovated! The primary en-suite bath has dual sinks, a large walk-in shower, and direct pool access. The hall bath features dual sinks, a soaking tub, and a linen closet. Additional highlights include double-pane windows, an inside laundry room with utility sink, and a 2-car garage with EV charging outlet. Conveniently located near shopping, dining, parks, medical facilities, and is zoned for highly desirable schools. Schedule your private showing today!

4033 Tenita Drive, Winter Park

$219,900
3 Beds 3 Baths Hidden Oaks Condo Ph 01 SubDv. 32792 Zip Code
MOTIVATED SELLER...Welcome To This Beautifully 3 Bedroom, 2.5 Bathroom Condominium Located in the Desirable Hidden Oaks Community. Offering Updated Living Space, This Home Combines Comfort, Style, and an Unbeatable Location. Step Inside to a Spacious and Inviting Family Room Featuring Beautiful Laminate Flooring, Abundant Natural Light, and an Open, Welcoming Atmosphere. The Updated Kitchen Is Sure to Impress with Quartz Countertops, Stainless Steel Appliances, and A Sliding Glass Door That Opens to a Private Patio—Perfect for Relaxing or Entertaining. Upstairs, You'll Find All Three Bedrooms and Two Full Bathrooms, including a Generously Sized Primary Suite with a Walk-In Closet and Large Front-Facing Windows That Fill the Room with Natural Light. Residents of Hidden Oaks Enjoy a Peaceful Setting with Access to a Community Swimming Pool, Assigned Parking, And Plenty of Guest Parking. Ideally Located Just Minutes from Major Highways 408 And 417, This Home Is Only 4 Minutes from Full Sail University, Minutes from the University of Central Florida (UCF), Downtown Orlando, and Conveniently Close to Valencia College, Rollins College, Winter Park Shopping and Dining, Restaurants, and Everyday Conveniences. The Property Is Also Zoned for Highly Desirable Winter Park Schools, Making It an Excellent Choice for Homeowners and Investors Alike. Don't Miss This Move-In-Ready Opportunity in One of the Area's Most Convenient Locations!

7413 Belle River Court Unit 3, Winter Park

$495,000
3 Beds 2 Baths Woodcrest Unit 5 SubDv. 32792 Zip Code
Welcome to 5316 Halyard Court, a beautifully updated pool home nestled in the heart of Winter Park. This move-in-ready residence offers the perfect blend of modern finishes, comfortable living spaces, and an incredible backyard designed for enjoying the Florida lifestyle. From the moment you arrive, you'll appreciate the inviting curb appeal, updated front entry, and thoughtfully maintained interior. Inside, the home features an open and functional layout accented by luxury wood-look flooring throughout, neutral designer colors, crown molding, recessed lighting, and abundant natural light. The spacious living areas flow seamlessly together, creating an ideal setting for both everyday living and entertaining. The generously sized bedrooms provide flexibility for families, guests, or a home office, while the updated bathrooms offer clean, contemporary finishes. The primary suite serves as a comfortable retreat with its own private en-suite bath. Step outside to your own private oasis featuring a sparkling in-ground pool surrounded by an expansive travertine paver deck, a screened lanai perfect for year-round relaxation, and a fully fenced backyard shaded by mature trees. Whether you're hosting weekend barbecues, enjoying a quiet evening by the pool, or letting pets and family play, this outdoor space offers endless possibilities. Additional upgrades include owned solar panels for enhanced energy efficiency and long-term savings, an attached two-car garage, and a spacious lot that provides both privacy and room to enjoy the outdoors. Ideally located, this home is just minutes from Downtown Winter Park and the renowned Park Avenue shopping and dining district, Rollins College, Full Sail University, AdventHealth Winter Park, UCF, Valencia College, and numerous parks, golf courses, and recreational amenities. Convenient access to SR-417, SR-436, University Boulevard, and Aloma Avenue makes commuting throughout Central Florida simple and efficient. Combining an exceptional location with modern updates and resort-style outdoor living, 5316 Halyard Court is a rare opportunity you won't want to miss.

5316 Halyard Court, Winter Park

$399,900
3 Beds 3 Baths Grayson Square SubDv. 32792 Zip Code
Welcome home to this beautifully maintained, nearly new Pulte Townhome in the heart of Winter Park! Built in 2023, in the gated community of Grayson Square, this stylish two story residence offers 3 bedrooms, 2.5 bathrooms, and an attached one car garage, combining modern design with everyday convenience. The open-concept main living area is perfect for entertaining, featuring elegant quartz counter-tops, Whirlpool stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas. Enjoy the upgraded smart home technology, high speed internet and cable already included into the low HOA, making working from home and streaming effortless. Upstairs, you will find a spacious primary suite complete with a generous walk-in closet and a private en-suite bathroom designed for comfort and relaxation. Two additional bedrooms provide plenty of room for family, guests. or a dedicated home office. Also to note is that there are no direct rear neighbors, allowing you to enjoy peaceful outdoor views on the back covered patio. The community is beautifully maintained and offers a resort-style pool and cabana and sidewalks for evening strolls. One of the homes most desirable features is the one thing you need the most but comes unseen is the 10 year transferable Pulte home warranty. Located just minutes from Winter Parks renowned shopping, dining, entertainment, parks and top commuter routes like 417, you'll enjoy easy access to everthing Central Florida has to offer while coming home to a quiet, friendly neighborhood. If your looking for a modern, energy efficient home with premium finishes and virtually maintenance free simple living, this is the one youve been waiting for!

2017 Canny Cove, Winter Park

$1,999,990
4 Beds 4 Baths Kenilworth Shores Sec 01 SubDv. 32792 Zip Code
Thoughtfully designed with an uncompromising commitment to quality, craftsmanship, and detail, this exceptional new construction residence is an expression of luxury living. Defined by its striking architecture and refined contemporary design, the home makes an unforgettable first impression with a dramatic two-story foyer featuring soaring ceilings, a statement staircase with custom millwork, designer lighting, and LED accent illumination. Just beyond, a custom wine display with Dekton surfaces and integrated lighting, creates a sophisticated focal point while introducing the exceptional finishes found throughout the home. Designed for both everyday living and effortless entertaining, the expansive great room is anchored by a floor-to-ceiling custom millwork feature wall with integrated LED lighting and a sleek electric fireplace. Oversized sliding glass doors create a seamless connection to the outdoor living spaces, while the chef's kitchen serves as the heart of the home with custom cabinetry, quartz countertops, extensive under-cabinet LED lighting, a premium appliance package, and an oversized walk-in pantry. Located on the main level, the primary suite offers a peaceful retreat with direct access to the lanai and pool. The spa-inspired bath features dual vanities with backlit mirrors, a freestanding soaking tub, an expansive walk-in shower, and a custom walk-in closet. Upstairs, a spacious loft provides an ideal secondary gathering space complete with a stylish dry bar and built-in wine refrigerator. Three additional bedrooms offer generous accommodations for family and guests, each finished with the same exceptional attention to detail. Outdoor living is equally impressive with a massive covered lanai featuring a fully equipped summer kitchen, an additional electric fireplace, and generous space for dining and relaxation. Beyond, a resort-style pool with a spillover spa is complemented by an expansive backyard and side yard. Ideally located just minutes from Cady Way Park, AdventHealth Winter Park, and the shopping, dining, and charm of Park Avenue, this exceptional residence offers the perfect blend of luxury, convenience, and lifestyle. With craftsmanship and design rarely found at this price point, this is a home that is both timeless and unforgettable.

525 S Lakemont Avenue, Winter Park

$1,450,000
4 Beds 5 Baths Talman Mews Ph 2 SubDv. 32792 Zip Code
Under contract-accepting backup offers. RARE & GORGEOUS MEDITERRANEAN ESTATE located on a private, OVERSIZED CUL-DE-SAC LOT in Talman Mews, featuring a heated pool and spa with waterfall and water features, private office, loft, bonus/game room, and home gym room. Custom double wood doors open to a breathtaking two-story foyer with a motorized chandelier lift, curved staircase, and private elevator that goes up to the second floor. The first level features 10-foot ceilings, travertine flooring, custom columns, and crown molding in the formal living spaces. The kitchen is outfitted with upscale appliances including a Thermador separate paneled refrigerator and freezer, 6-burner gas range, chef style built-in microwave and convection oven, two paneled dishwashers, exotic granite countertops, center island, and custom walk-in pantry. The family room, anchored by a gas fireplace, opens through French doors to a covered lanai and resort-style backyard. A game room with a pool table and full en-suite bath can function as a second primary suite or in-law retreat, and a first-floor bedroom adds flexibility for guests or remote work. The garage's third bay was converted to be used as a home gym, with the option to reconvert for additional vehicle storage. Upstairs, every bedroom has a private en-suite bath. The primary suite includes a tray ceiling, sitting area, wet bar, private large sized balcony (great place to watch the rocket launches!) and it also has direct stair access downstairs to the pool. The primary bath features a jetted garden tub, gorgeous columns, separate walk-in shower, custom wood cabinetry with granite countertops, and an oversized walk-in closet. A loft, private study, upstairs laundry room, and additional bedrooms (one with its own sitting area) complete the second floor. The backyard includes tropical landscaping, vinyl privacy fencing, a heated pool and spa with water features, and a covered lanai pre-plumbed for a future summer kitchen. Additional features include a side-entry garage with epoxy flooring and workbench, barrel tile roof with radiant barrier, double-pane thermal windows, tankless water heater, security system, and surround sound pre-wire. Located 5 minutes from the prestigious Trinity Preparatory School. This home offers easy access to Downtown Winter Park, Downtown Orlando, UCF, Orlando International Airport, premier shopping, dining, and entertainment, the perfect blend of luxury, comfort, and convenience. THIS HOME REPRESENTS THE FINEST OF WINTER PARK LIVING!

2138 Talman Court, Winter Park

$669,900
3 Beds 2 Baths Winter Park Pines SubDv. 32792 Zip Code
Welcome to this beautifully updated three-bedroom, two-bathroom POOL home offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, resurfaced, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021

433 Gilbert Road, Winter Park

$425,000
3 Beds 2 Baths Eastbrook Sub Unit 06 SubDv. 32792 Zip Code
Discover the epitome of comfortable living in this fantastic single-family home situated on a generous and spacious corner lot. This meticulously renovated property features 3 bedrooms and 2 bathrooms, offering a perfect blend of modern style and cozy charm. Step inside to experience the allure of an open floor plan that seamlessly connects the living spaces. The kitchen, fully renovated and boasting a contemporary design, is the heart of this home—a perfect gathering place for family and friends. Indulge in the luxury of a private backyard oasis, where tranquility meets outdoor enjoyment. A delightful retreat awaits with a nice backyard, ideal for entertaining or simply unwinding under the stars. Plus, your vehicles and recreational gear are well taken care of with a 2-car garage and an additional boat space. The charm continues outdoors with a great covered lanai, providing the perfect setting for al fresco dining or cozy evenings by the fireplace. Every detail of this home has been thoughtfully curated to enhance your lifestyle. Don't miss the opportunity to make this Winter Park residence your own—where spacious living, thoughtful design, and comfort converge. Schedule your tour today and envision the possibilities that await in this truly remarkable home!

1886 Clematis Lane, Winter Park

$365,000
3 Beds 2 Baths Eastbrook Sub Unit 8 SubDv. 32792 Zip Code
Don't miss this opportunity to own a beautifully updated home with a sought-after Winter Park address! Priced to sell, this move-in-ready 3-bedroom, 2-bath home offers the perfect combination of comfort, style, and location. Enjoy being just minutes from Park Avenue, Baldwin Park, Cady Way Park and Trail, Winter Pines Golf Club, shopping, restaurants, and major roadways, making it easy to enjoy everything Winter Park and the surrounding area have to offer. Inside, you'll love the open floor plan that's perfect for everyday living and entertaining. The updated kitchen features quartz countertops, stainless steel appliances, a large single-basin sink, beautiful cabinetry, and plenty of counter space. It opens to the spacious dining area and family room, creating a bright and welcoming space where everyone can gather. Tile flooring is featured in the foyer, kitchen, bathrooms, and the large open living area just off the kitchen, while warm wood flooring flows through the formal dining room, family room, hallway, and all three bedrooms for a clean, updated look. The primary suite offers a spacious closet and an oversized walk-in shower designed for comfort and convenience. Step outside to the oversized screened lanai overlooking a fully fenced backyard that's perfect for entertaining, pets, play, or simply relaxing after a long day. A large storage shed provides plenty of room for lawn equipment, tools, bikes, or seasonal storage. Recent updates include a 2021 roof and 2022 HVAC system, giving the next owner added peace of mind. Security bars on the windows provide an extra layer of protection and may qualify for insurance discounts. If you've been looking for an updated home in Winter Park that offers great value, this is one you won't want to miss!

2511 Eastbrook Boulevard, Winter Park

$399,000
3 Beds 3 Baths Grayson Square SubDv. 32792 Zip Code
Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen boasts stainless steel appliances, gray cabinetry, and quartz countertops. Upstairs, the spacious primary suite offers a walk-in closet and a private in-suite bath with dual quartz vanities, while two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Relax on the covered lanai and enjoy the privacy of this home's cul-de-sac location. The HOA includes landscaping, exterior maintenance and repairs, high-speed internet, and access to the gated community, providing low-maintenance living. With no CDD, this home is an excellent option for both homeowners and investors. Ideally located in highly desirable Winter Park, Grayson Square is just minutes from SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and top-rated Seminole County schools nearby. Park Avenue is only a short drive away, making this home the perfect combination of convenience, comfort, and value.

2033 Canny Cove, Winter Park

$99,900
2 Beds 2 Baths Winter Park Woods Condo SubDv. 32792 Zip Code
Under contract-accepting backup offers. Move-in ready! Fully updated 2 bedroom/2 bath condo located in Winter Park for under 100k! Conveniently located on the first floor for easy access. Open kitchen overlooks the spacious great room and features white cabinets, Stainless Steel appliances, Granite counters, and breakfast bar. Split bedroom plan with 2 full baths featuring Granite counters and beautiful tiled showers/tubs. Neutral wood look laminate flooring throughout. Sliding doors lead to a private patio, providing a relaxing outdoor space, plus a private laundry room with washer/dryer and extra storage space with shelving. This unit offers a premium location with pool, clubhouse, and tennis right behind this building. Residents enjoy low-maintenance living with HOA coverage that includes building exterior and landscaping maintenance, pest control, water, access to two community pools, a playground, and tennis courts. Located in the desirable Winter Park area, this condo offers easy access to downtown Winter Park retail and restaurants, Full Sail, UCF, Valencia College, Rollins College, and Highways 417 and 408 for easy commuting. Also nearby are Sam's Club, Costco, Publix, Sprouts, Target, Walmart, and the Cady Way Trail for walking/biking. Zoned for highly rated Winter Park schools! This condo is perfect as a primary residence, vacation getaway, or investment opportunity with very strong rental demand. Note - NEW appliances are being installed around August 3 - refrigerator, range, microwave, and dishwasher.

145 Scottsdale Square, Winter Park

$729,995
4 Beds 3 Baths Landings At Hawks Crest SubDv. 32792 Zip Code
Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.

1418 Lone Feather Trail, Winter Park

$370,000
4 Beds 2 Baths Suburban Homes First Add SubDv. 32792 Zip Code
$10,000 Price Drop + $5,000 Buyer Credit | Updated Winter Park 4-Bed Home with No HOA. Welcome to this turn-key, move-in-ready 4-bedroom, 2-bath single-family home with major updates already completed. Improvements include a new roof, two new A/C systems, new tankless water heater, upgraded insulation, and new dual-pane energy-efficient windows, offering buyers improved comfort along with peace of mind on several big-ticket items. Additional updates include remodeled bathrooms, fresh interior and exterior paint, upgraded baseboards, and terrazzo and ceramic tile flooring throughout. This single-story home offers a split four-bedroom layout with direct exterior access, creating exceptional flexibility for multi-generational living, a private guest retreat, or a dedicated home office. The galley-style kitchen features stainless steel appliances, solid wood cabinets, and a decorative backsplash, with easy flow to the dining and living areas. Outside, the large fully fenced yard provides valuable usable space for entertaining, gardening, pets, or a future pool, while the attached carport includes covered parking and a convenient laundry/storage room. Centrally located in Winter Park near shopping, dining, parks, major Orlando commuter routes, and currently zoned for Winter Park High School, this no-HOA home offers major capital upgrades, strong functionality, energy-efficient improvements, and a $5,000 buyer credit for qualified buyers.

4965 Orange Avenue, Winter Park

$605,000
4 Beds 2 Baths Preserve At Hawks Crest SubDv. 32792 Zip Code
Nestled within the gated community of Hawks Crest, this thoughtfully designed single-story residence offers an exceptional blend of comfort, style and convenience in the heart of Winter Park. Spanning 1,920 square feet, this home features an open-concept floor plan that seamlessly connects the living, dining and kitchen areas, creating an inviting setting for both everyday living and entertaining. The kitchen serves as the centerpiece of the home, appointed with granite countertops, stainless steel appliances and a spacious center island with seating. The private owner's suite offers a walk-in closet and a well-appointed bath, while three additional bedrooms provide flexibility for guests, a home office or evolving lifestyle needs. A covered lanai overlooks the tranquil pond, creating the perfect backdrop for outdoor relaxation and year-round Florida living. Residents of Hawks Crest enjoy access to an impressive collection of amenities, including a clubhouse, fitness center, resort-style pool, splash pad, dog park, playgrounds, virtual guard gate and private access to Lake Howell for kayaking and paddleboarding. Ideally located just minutes from highways, Park Avenue, downtown Maitland, top-rated schools, Foxtail Coffee and Kelly's Ice Cream, this residence offers the opportunity to enjoy one of Winter Park's most sought-after gated communities.

2087 Laurelwood Way, Winter Park

$793,500
4 Beds 3 Baths Winter Park Pines SubDv. 32792 Zip Code
Completely reimagined with an extensive top-to-bottom renovation, this stunning four-bedroom, three-bathroom pool home offers over 2,300 square feet of beautifully curated living space in one of Winter Park's most desirable locations. Every detail was thoughtfully selected to blend timeless design with modern functionality, creating a truly move-in-ready home. Inside, large wood-look plank tile flooring installed throughout in 2024 creates a seamless flow, complemented by recessed lighting, plantation shutters, all-new designer lighting and ceiling fans, and energy-efficient windows replaced in 2024. A cozy wood-burning fireplace provides character to the beautiful living space while French doors installed in 2024 provide effortless access to the outdoor living space. Additional upgrades completed in 2024 include blown-in insulation and a gas tankless water heater. The showstopping kitchen was completely remodeled in 2024 and is designed to impress. Custom hardwood cabinetry accented with elegant gold hardware is paired with luxurious quartz countertops and a dramatic full-height quartz backsplash. A large center island with seating for four, a black farmhouse sink, pot filler, and abundant prep space make this kitchen equally suited for everyday living and entertaining. Split from the secondary bedrooms for added privacy, the spacious primary suite is a peaceful retreat featuring French doors leading directly to the pool, a dedicated makeup vanity, walk-in closet, and a beautifully renovated ensuite bathroom with a double vanity and an oversized tiled shower enclosed by frameless glass. All three bathrooms were tastefully remodeled in 2024 with timeless, high-end finishes. The oversized laundry room is as functional as it is attractive, offering built-in cabinetry for exceptional storage along with an included washer and dryer. Step outside to your own private backyard oasis situated on a beautifully landscaped .26-acre lot. The screened in-ground pool was resurfaced with mini pebble finishes in 2025, while a custom flagstone outdoor shower with a decorative rock bed creates a true resort-inspired atmosphere. Additional exterior improvements completed in 2024 include new exterior doors, gutters, French drains, and an updated two-car garage featuring epoxy flooring along with new torsion springs and rollers. Ideally located just minutes from UCF, Rollins College, Full Sail University, AdventHealth Winter Park, the Crosby Wellness Center, Winter Park Pines Golf Club, and the Cady Way Trail, residents also enjoy access to Cady Way Park with its community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Zoned for highly rated Aloma Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines a remarkable renovation with an unbeatable Winter Park lifestyle. ROOF - 2024 HVAC - 2024 ELECTRICAL - 2024 PLUMBING - 2024 TANKLESS WATER HEATER - 2024

729 Monmouth Way, Winter Park

$179,900
2 Beds 3 Baths Hidden Oaks Condo Ph 09 SubDv. 32792 Zip Code
Under contract-accepting backup offers. Move right in and enjoy low-maintenance living in the desirable Hidden Oaks community of Winter Park. This meticulous maintained and nicely updated 2-bedroom, 2.5-bath townhome-style condo features two spacious primary suites, each with its own private en-suite bathroom, offering a flexible floor plan and exceptional functionality. The open and inviting layout includes an oversized great room, 12-inch ceramic tile flooring, and a well-appointed kitchen with maple cabinetry, Corian countertops, flat-top range, stainless steel refrigerator, and new microwave, new blinds throughout. The washer and dryer are included, making this home truly move-in ready. Both bathrooms have been tastefully updated, maple cabinetry, one with granite & one with Corian countertops for a cohesive, modern look. Enjoy outdoor living on the private rear patio, complete with space for grilling and an additional storage closet. Hidden Oaks is a beautifully maintained community featuring mature landscaping, a community pool, and a convenient Winter Park location near shopping, dining, entertainment, major employers, and highly rated Winter Park schools. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities, creating an easy lock-and-leave lifestyle. Conveniently located near Full Sail University, the University of Central Florida, Downtown Winter Park, and major roadways, this home offers an excellent opportunity for owner-occupants, those seeking a second home, or buyers looking for a long-term investment property. Don't miss the chance to own a well-maintained and move-in-ready home in one of Winter Park's most convenient locations.

3381 Cedar Springs Place Unit 151, Winter Park

$453,040
4 Beds 2 Baths Suburban Homes SubDv. 32792 Zip Code
4 BEDROOM | 2 BATH | 1,863 SQ FT + TINY HOUSE GUEST SUITE | CUSTOM BUILD | NO HOA | WINTER PARK | Located just minutes from the charm and energy of Downtown Winter Park, this exceptional custom-built residence offers a rare opportunity to enjoy thoughtfully crafted living in one of Central Florida's most convenient and desirable corridors. Built in 2011 in a quiet community with no HOA restrictions, the home combines quality construction, modern aesthetics, and an outstanding lifestyle location that is difficult to replicate at this price point. From its welcoming front porch to its expansive backyard retreat, the property is designed for both comfortable everyday living and effortless entertaining. Situated on a generous 70-foot wide lot, the double-wide driveway, attached garage, and extra-wide side yard with a double-wide 11'6" gate provide exceptional utility for those with a boat, RV, or trailer — a rare and coveted feature with no association limitations. Throughout the interior, custom solid wood built-ins and cabinetry lend a warmth and permanence seldom found in production construction. The kitchen serves as the true centerpiece of the home, featuring custom solid wood cabinetry with pull-out pantry shelves, an extra-large entertaining island with abundant storage, solid stone countertops, and a striking tray ceiling with LED lighting that creates an elevated, modern ambiance. The open layout connects seamlessly to the living spaces and flows naturally toward the screened rear porch and the large, private backyard beyond. The private primary suite offers a genuine retreat experience, complete with a tray ceiling, generous walk-in closet, and a beautifully appointed en-suite bath featuring both a separate shower and soaking tub. Custom built-ins throughout the additional bedrooms add function and character at every turn. At 1,863 square feet, the main residence is complemented by a fully finished 156-square-foot backyard suite constructed in 2022, complete with a kitchenette and full bathroom — bringing the total living footprint to just over 2,000 square feet. Whether utilized for guests, extended family, a home office, or income-generating potential, this additional structure adds a remarkable dimension of flexibility and value rarely found in this market. The durable metal roof and quality of construction throughout speak to a home built with longevity in mind. Freshly painted and brand new, high-end Waterproof Laminate flooring throughout. Energy efficiency is woven into the fabric of the home as well, with open-cell spray foam insulation in the attic and a smart water heater working together to meaningfully reduce utility costs — a genuine and ongoing financial benefit that discerning buyers will appreciate. All of this, positioned less than ten minutes from Publix, Starbucks, and Costco, and within fifteen minutes of the boutique dining, shopping, and cultural offerings of Downtown Winter Park.

5350 Orange Avenue, Winter Park

$1,725,000
6 Beds 6 Baths Lake Florence Preserve SubDv. 32792 Zip Code
Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. This stunning 6-bedroom, 5+ bath pool home sits on the shores of private, Lake Florence, offering a rare opportunity for true waterfront living. Step inside to a grand two-story entry with soaring 10-foot ceilings and an open-concept layout designed for effortless entertaining. Natural light fills the expansive living, dining, and kitchen spaces, highlighting the home’s high-end finishes and thoughtful design. At the center of the home is a chef’s kitchen featuring an oversized 11’ x 5’ island, gas range with vent hood, premium Samsung and GE appliances, and an impressive 10’ x 4’ walk-in pantry, perfect for hosting or daily convenience. With six generously sized bedrooms, including a private in-law suite, this home offers flexibility for multigenerational living or guests. Upstairs, the spacious primary suite boasts lake views, a large ensuite bath, and dual walk-in closets. You’ll also find a versatile 19’ x 18’ game room with a 17' wide balcony overlooking the pool and lake, along with an oversized second-floor laundry room. Outdoor living is where this property truly shines. Enjoy direct access to Lake Florence from your private dock with electric boat lift, ideal for boating, jet skiing, or peaceful sunset cruises. The backyard is designed for relaxation and entertaining, complete with a saltwater pool, fully fenced yard, tiki hut featuring an outdoor kitchen and outdoor shower fitted with hot and cold water. Additional highlights include a 3-car garage, tankless water heater, custom closets throughout, and upgraded lighting and ceiling fans. Ideally located just minutes from SR 436, the 417, and only 15 minutes to Park Avenue, this home offers both convenience and exclusivity within a sought-after gated community. This is a rare opportunity to own a true lakefront retreat. Schedule your private showing today.

2914 Reef Knot Place, Winter Park

$1,262,500
4 Beds 4 Baths Kenilworth Shores Sec 07 SubDv. 32792 Zip Code
Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Completely reimagined and renovated, this stunning 4-bedroom, 4-bath residence offers the rare combination of modern construction quality and an established Winter Park location just minutes from Baldwin Park, Park Avenue, Rollins College, and top-rated schools. From the moment you arrive, the circular driveway, modern architecture, and professional landscaping create a memorable first impression. Inside, soaring natural light and oversized porcelain tile floors lead you through an open-concept floor plan designed for both everyday living and entertaining. The heart of the home is an extraordinary chef's kitchen featuring premium Bosch appliances, an oversized quartz island, custom cabinetry, a walk-in pantry, and a stylish wet bar. Whether hosting holiday gatherings or enjoying a quiet morning coffee, this space was designed to bring family together. The private owner's retreat feels like a luxury resort, offering direct pool access, a spa-inspired bathroom, soaking tub, oversized walk-in shower, custom closet, and a private beverage station for added convenience. Step outside and discover what truly sets this property apart. The backyard was designed for Florida living at its finest, featuring a sparkling pool, expansive covered lanai, outdoor dining area, and a fully equipped summer kitchen complete with grill, refrigeration, storage, and sink. It's the perfect setting for family gatherings, weekend entertaining, or relaxing after a long day. A dedicated office, versatile flex room, pool bath, and guest suite provide the flexibility today's buyers demand for work, fitness, hobbies, multigenerational living, or media space. Beyond the home itself, you'll enjoy a lifestyle few locations can match. Walk or bike to nearby parks and trails, spend evenings dining on Park Avenue, explore Baldwin Park's restaurants and shops, and enjoy quick access to Downtown Orlando and Orlando International Airport. With luxury finishes, smart-home upgrades, resort-style outdoor living, and a premier Winter Park address, this is more than a home—it's a lifestyle opportunity rarely available in Kenilworth Shores. Schedule your private showing today and experience the difference for yourself.

2015 Summerfield Road, Winter Park