Homesinorlando.forsale Search Results

$575,000

A rare opportunity in Winter Park’s coveted 32789! This stunning fee-simple townhome offers the feel of a private retreat with the architectural pedigree of Fugelberg Koch (FK Architecture), the freedom of NO HOA FEES, and an extraordinary setting overlooking the 80-acre Howell Creek Preserve. Tucked away in a highly desirable Winter Park location, this 2-story end-unit lives much larger than its 1,701 square feet and delivers a lifestyle that is truly hard to replicate. The heart of this home may just be its incredible outdoor living space. Step through the living area and onto the expansive deck, where a covered canopy creates a year-round outdoor room overlooking the lush Howell Creek Preserve. With a firepit, market lighting, and treetop views stretching across the native Florida landscape, this is the kind of space that begs you to linger—morning coffee surrounded by nature, afternoon cocktails with friends, or evenings gathered around the fire under the lights. The elevated vantage point places you virtually eye-level with the cypress canopy, creating a dreamy sense of privacy and connection to nature that is rarely found in townhome living. And perhaps best of all, this is a view that cannot be renovated into another home. Inside, soaring 14-foot ceilings and dramatic picture windows fill the living room with an abundance of natural light while framing beautiful views of the preserve. The open, airy design makes the home feel exceptionally spacious and brings the outdoors in. The stunning kitchen features gorgeous Spanish tile flooring, solid wood cabinetry, granite countertops, and a new backsplash. The dining room adds character with built-in cabinetry and French doors, while the spacious indoor laundry room provides exceptional everyday convenience. Upstairs, two generously sized bedrooms and two full bathrooms provide a comfortable private retreat. A convenient powder room is located downstairs for guests. The coveted end-unit location also offers additional outdoor space along the side of the home, beautifully enhanced with brick hardscaping and room for relaxing, grilling, entertaining, or overflow parking. Parking is another standout feature, with a one-car garage plus two designated parking spaces—a rare convenience in this setting. And then there is the location. Situated in the prestigious 32789 zip code, this home puts you within walking distance of the Winter Park Racquet Club, the Winter Park Chain of Lakes, and surrounded by some of Central Florida’s most sought-after real estate. Enjoy the best of Winter Park while coming home to your own private perch above the trees. Fee-simple ownership. No HOA fees. Exceptional architecture. Preserve views. Incredible outdoor living. Coveted Winter Park location. This is far more than a townhome—it is a lifestyle.

2 Beds ⋅ 3 Baths ⋅ Temple Trail Village SubDv. ⋅ 32789 Zip Code

A rare opportunity in Winter Park’s coveted 32789! This stunning fee-simple townhome offers the feel of a private retreat with the architectural pedigree of Fugelberg Koch (FK Architecture), the freedom of NO HOA FEES, and an extraordinary setting overlooking the 80-acre Howell Creek Preserve. Tucked away in a highly desirable Winter Park location, this 2-story end-unit lives much larger than its 1,701 square feet and delivers a lifestyle that is truly hard to replicate. The heart of this home may just be its incredible outdoor living space. Step through the living area and onto the expansive deck, where a covered canopy creates a year-round outdoor room overlooking the lush Howell Creek Preserve. With a firepit, market lighting, and treetop views stretching across the native Florida landscape, this is the kind of space that begs you to linger—morning coffee surrounded by nature, afternoon cocktails with friends, or evenings gathered around the fire under the lights. The elevated vantage point places you virtually eye-level with the cypress canopy, creating a dreamy sense of privacy and connection to nature that is rarely found in townhome living. And perhaps best of all, this is a view that cannot be renovated into another home. Inside, soaring 14-foot ceilings and dramatic picture windows fill the living room with an abundance of natural light while framing beautiful views of the preserve. The open, airy design makes the home feel exceptionally spacious and brings the outdoors in. The stunning kitchen features gorgeous Spanish tile flooring, solid wood cabinetry, granite countertops, and a new backsplash. The dining room adds character with built-in cabinetry and French doors, while the spacious indoor laundry room provides exceptional everyday convenience. Upstairs, two generously sized bedrooms and two full bathrooms provide a comfortable private retreat. A convenient powder room is located downstairs for guests. The coveted end-unit location also offers additional outdoor space along the side of the home, beautifully enhanced with brick hardscaping and room for relaxing, grilling, entertaining, or overflow parking. Parking is another standout feature, with a one-car garage plus two designated parking spaces—a rare convenience in this setting. And then there is the location. Situated in the prestigious 32789 zip code, this home puts you within walking distance of the Winter Park Racquet Club, the Winter Park Chain of Lakes, and surrounded by some of Central Florida’s most sought-after real estate. Enjoy the best of Winter Park while coming home to your own private perch above the trees. Fee-simple ownership. No HOA fees. Exceptional architecture. Preserve views. Incredible outdoor living. Coveted Winter Park location. This is far more than a townhome—it is a lifestyle.

2881 Temple Trail, Winter Park

$1,625,000

Discover this exceptional custom-designed modern pool home, ideally situated in one of Winter Park's most sought-after neighborhoods. Located on a quiet street, this spacious residence offers 5 bedrooms, 4.5 bathrooms, and a large upstairs loft—providing the perfect blend of luxury, comfort, and functionality. From the moment you enter, you'll be captivated by the abundance of natural light and stunning hardwood floors that flow throughout the main level and continue upstairs into the loft and primary suite. The thoughtfully designed floor plan includes a downstairs bedroom and full bath, ideal for guests, in-laws, or a private home office. Designed with the entertainer in mind, the gourmet kitchen is a true showstopper—featuring quartz countertops, an oversized island, Jenn Air appliances including a double oven, and generous cabinet space. A large butler’s pantry with an additional sink offers even more storage and prep space. Seamlessly transition from indoor to outdoor living with the sliding glass doors that open to a covered lanai, private pool, and expansive fenced in backyard—perfect for relaxing or hosting gatherings year-round. Upstairs, the luxurious primary suite includes a walk-in closet and a spa-like bathroom with dual sinks, a soaking tub, and a separate walk-in shower. Three additional bedrooms, two full bathrooms, and a spacious laundry room with more storage complete the upper level. Additional features include a dedicated mudroom with built-in bench seating and storage, and an air-conditioned two-car garage with insulated doors and epoxy floors. All of this, just minutes from the Winter Park Racquet Club, Park Avenue’s boutique shopping and dining, and top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High. Don’t miss this rare opportunity to own a one-of-a-kind home in one of Winter Park's premier neighborhoods.

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

Discover this exceptional custom-designed modern pool home, ideally situated in one of Winter Park's most sought-after neighborhoods. Located on a quiet street, this spacious residence offers 5 bedrooms, 4.5 bathrooms, and a large upstairs loft—providing the perfect blend of luxury, comfort, and functionality. From the moment you enter, you'll be captivated by the abundance of natural light and stunning hardwood floors that flow throughout the main level and continue upstairs into the loft and primary suite. The thoughtfully designed floor plan includes a downstairs bedroom and full bath, ideal for guests, in-laws, or a private home office. Designed with the entertainer in mind, the gourmet kitchen is a true showstopper—featuring quartz countertops, an oversized island, Jenn Air appliances including a double oven, and generous cabinet space. A large butler’s pantry with an additional sink offers even more storage and prep space. Seamlessly transition from indoor to outdoor living with the sliding glass doors that open to a covered lanai, private pool, and expansive fenced in backyard—perfect for relaxing or hosting gatherings year-round. Upstairs, the luxurious primary suite includes a walk-in closet and a spa-like bathroom with dual sinks, a soaking tub, and a separate walk-in shower. Three additional bedrooms, two full bathrooms, and a spacious laundry room with more storage complete the upper level. Additional features include a dedicated mudroom with built-in bench seating and storage, and an air-conditioned two-car garage with insulated doors and epoxy floors. All of this, just minutes from the Winter Park Racquet Club, Park Avenue’s boutique shopping and dining, and top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High. Don’t miss this rare opportunity to own a one-of-a-kind home in one of Winter Park's premier neighborhoods.

2407 Lafayette Avenue, Winter Park

$4,650,000

Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind residence by Vimaro Homes. Set within the highly sought-after Park Grove neighborhood and designed by renowned architect Gary Hancock, the home makes an unforgettable first impression with a stately front façade, manicured grounds, dual porte cochere’s, and a motor court leading to a two-car garage. Every element has been thoughtfully considered to create a residence that feels as though it has always belonged in Winter Park. Inside, exceptional craftsmanship takes center stage. A marble mosaic entry introduces interiors defined by chevron-pattern hardwood flooring, refined millwork, natural stone, and carefully curated finishes. The floor plan is equally impressive, balancing grand entertaining spaces with an effortless sense of livability. The main level features a dedicated library/home office, formal dining room, and expansive gathering room overlooking the private courtyard. At the heart of the home, the chef’s kitchen pairs Calacatta marble countertops with a full suite of Thermador appliances, a statement ILVE range, and an oversized butler’s pantry offering exceptional prep and storage space. The first-floor primary suite is a private retreat with direct access to the courtyard and an incredible spa-inspired bath finished in marble. Dual vanities, Perrin & Rowe fixtures, a freestanding soaking tub, walk-in shower, and an expansive dressing room elevate the suite to another level. Upstairs, four generously proportioned bedrooms each feature an ensuite bath and walk-in closet, surrounding a spacious central loft ideal for an additional living or entertaining space. Continuing to the third level, a fully finished attic space provides an unexpected bonus room perfectly suited for a private gym or a game room. The outdoor living experience is just as remarkable. At the center of the home is a spectacular courtyard-style pool, creating a private resort atmosphere framed by the residence and lush landscaping. An expansive covered cabana provides multiple areas for dining and lounging, complemented by a fireplace and full summer kitchen for year-round entertaining. Beyond the courtyard, ample yard space adds another layer of usability rarely found with such an intimate outdoor design. This home also offers the rare opportunity to enjoy one of Winter Park’s most desirable residential settings while remaining within walking distance of the boutiques, acclaimed restaurants, cafés, and vibrant atmosphere of Park Avenue. Hannibal Square and Winter Park Village are also just moments away, placing some of the city’s best dining, shopping, and entertainment within effortless reach. Timeless in its architecture and uncompromising in its execution, this home is destined to become one of Winter Park’s most distinguished residences.

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

Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind residence by Vimaro Homes. Set within the highly sought-after Park Grove neighborhood and designed by renowned architect Gary Hancock, the home makes an unforgettable first impression with a stately front façade, manicured grounds, dual porte cochere’s, and a motor court leading to a two-car garage. Every element has been thoughtfully considered to create a residence that feels as though it has always belonged in Winter Park. Inside, exceptional craftsmanship takes center stage. A marble mosaic entry introduces interiors defined by chevron-pattern hardwood flooring, refined millwork, natural stone, and carefully curated finishes. The floor plan is equally impressive, balancing grand entertaining spaces with an effortless sense of livability. The main level features a dedicated library/home office, formal dining room, and expansive gathering room overlooking the private courtyard. At the heart of the home, the chef’s kitchen pairs Calacatta marble countertops with a full suite of Thermador appliances, a statement ILVE range, and an oversized butler’s pantry offering exceptional prep and storage space. The first-floor primary suite is a private retreat with direct access to the courtyard and an incredible spa-inspired bath finished in marble. Dual vanities, Perrin & Rowe fixtures, a freestanding soaking tub, walk-in shower, and an expansive dressing room elevate the suite to another level. Upstairs, four generously proportioned bedrooms each feature an ensuite bath and walk-in closet, surrounding a spacious central loft ideal for an additional living or entertaining space. Continuing to the third level, a fully finished attic space provides an unexpected bonus room perfectly suited for a private gym or a game room. The outdoor living experience is just as remarkable. At the center of the home is a spectacular courtyard-style pool, creating a private resort atmosphere framed by the residence and lush landscaping. An expansive covered cabana provides multiple areas for dining and lounging, complemented by a fireplace and full summer kitchen for year-round entertaining. Beyond the courtyard, ample yard space adds another layer of usability rarely found with such an intimate outdoor design. This home also offers the rare opportunity to enjoy one of Winter Park’s most desirable residential settings while remaining within walking distance of the boutiques, acclaimed restaurants, cafés, and vibrant atmosphere of Park Avenue. Hannibal Square and Winter Park Village are also just moments away, placing some of the city’s best dining, shopping, and entertainment within effortless reach. Timeless in its architecture and uncompromising in its execution, this home is destined to become one of Winter Park’s most distinguished residences.

857 Brock Street, Winter Park

$2,495,000

Under contract-accepting backup offers. Under Construction. Experience exceptional craftsmanship and timeless design in this brand-new luxury custom home being built by FG Schaub Custom Homes. This residence will feature 5 bedrooms, 5.5 bathrooms, and 3,656 square feet of thoughtfully designed living space, blending modern architecture with everyday comfort. The open-concept floor plan highlights a gourmet chef’s kitchen equipped with a premium Wolf/Sub-Zero appliance package, custom cabinetry, a walk-in pantry, and a large center island overlooking the spacious great room. Expansive sliding glass doors lead to a covered outdoor living area complete with a summer kitchen, roll-away screen, and mini-split A/C—perfect for year-round entertaining. The outdoor space also includes a private pool, creating a seamless indoor–outdoor flow ideal for the Florida lifestyle. The first floor offers a primary suite with a spa-inspired bath and a generous walk-in closet, along with a private guest suite—ideal for visitors or multigenerational living. Upstairs, 3 additional bedrooms each include en-suite baths and walk-in closets, providing comfort and privacy for family or guests. Additional features include a two-car garage with epoxy flooring and an EV charger, premium landscaping, and vinyl fencing for added beauty and privacy. Conveniently located and zoned for Audubon K-8 and Winter Park High School, this home offers exceptional access to top-rated schools, local parks, and the vibrant shops and dining of Downtown Winter Park. **Estimated completion: October 2026.**

5 Beds ⋅ 6 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Under Construction. Experience exceptional craftsmanship and timeless design in this brand-new luxury custom home being built by FG Schaub Custom Homes. This residence will feature 5 bedrooms, 5.5 bathrooms, and 3,656 square feet of thoughtfully designed living space, blending modern architecture with everyday comfort. The open-concept floor plan highlights a gourmet chef’s kitchen equipped with a premium Wolf/Sub-Zero appliance package, custom cabinetry, a walk-in pantry, and a large center island overlooking the spacious great room. Expansive sliding glass doors lead to a covered outdoor living area complete with a summer kitchen, roll-away screen, and mini-split A/C—perfect for year-round entertaining. The outdoor space also includes a private pool, creating a seamless indoor–outdoor flow ideal for the Florida lifestyle. The first floor offers a primary suite with a spa-inspired bath and a generous walk-in closet, along with a private guest suite—ideal for visitors or multigenerational living. Upstairs, 3 additional bedrooms each include en-suite baths and walk-in closets, providing comfort and privacy for family or guests. Additional features include a two-car garage with epoxy flooring and an EV charger, premium landscaping, and vinyl fencing for added beauty and privacy. Conveniently located and zoned for Audubon K-8 and Winter Park High School, this home offers exceptional access to top-rated schools, local parks, and the vibrant shops and dining of Downtown Winter Park. **Estimated completion: October 2026.**

2812 Mulford Avenue, Winter Park

$2,190,000

Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs transformation, virtually every major component is new—giving this approximately 2,400-square-foot residence the quality, systems and finishes of a modern custom home. Framed by mature live oaks and sweeping 180-degree water views, the home combines refined craftsmanship and extraordinary lakefront serenity with warm European Contemporary architecture influenced by Belgian design and Organic Modern principles. Expansive, minimalist-profile windows frame the water from nearly every principal living space, while a dramatic 12-foot sliding glass wall connects the open living area to approximately 1,500 square feet of additional outdoor living. Multiple terraces, an integrated outdoor kitchen and beautifully landscaped surroundings create an exceptional setting for waterfront entertaining or quiet mornings beneath the oak canopy. Inside, natural wood, matte black accents, architectural lighting and tactile materials establish a cohesive, warm and inviting aesthetic. Custom white oak wall panels made in Spain, hand-cut white oak beams and architectural transitions, a textured brick feature wall, built-in Sonos audio and a dedicated entertaining bar reflect the attention given to every detail. The European-inspired kitchen features full-height cabinetry incorporating materials imported from Portugal, extensive integrated pantry storage, a Thermador appliance suite with a 36-inch range and griddle, and a Miele steam oven. Positioned at the heart of the living area, the kitchen creates an effortless setting for everyday life and entertaining, always with the lake close at hand. Each of the home’s three bedrooms includes a private en-suite full bath, with an additional powder room serving the common areas. A flexible lake-view office—currently used as a fitness and sauna studio—offers an inspiring setting for work, wellness or creative pursuits. The primary suite opens through nearly eight feet of accordion-style glass doors to a private rooftop terrace, inviting morning coffee, yoga, sunbathing or evening movies beneath the sky. Beyond its architectural design, the comprehensive transformation includes a new roof and roof components, electrical wiring, plumbing and piping, four-zone HVAC system, windows, stucco, drywall, flooring, kitchen and bathrooms. The result combines the character, proportions and established setting of an Old Winter Park home with the quality, efficiency and peace of mind expected from a modern custom residence. Turnkey, distinctive and intimately connected to the water, this exceptional home brings together architectural vision, modern livability and the coveted Winter Park lifestyle on the shores of Lake Sylvan.

3 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs transformation, virtually every major component is new—giving this approximately 2,400-square-foot residence the quality, systems and finishes of a modern custom home. Framed by mature live oaks and sweeping 180-degree water views, the home combines refined craftsmanship and extraordinary lakefront serenity with warm European Contemporary architecture influenced by Belgian design and Organic Modern principles. Expansive, minimalist-profile windows frame the water from nearly every principal living space, while a dramatic 12-foot sliding glass wall connects the open living area to approximately 1,500 square feet of additional outdoor living. Multiple terraces, an integrated outdoor kitchen and beautifully landscaped surroundings create an exceptional setting for waterfront entertaining or quiet mornings beneath the oak canopy. Inside, natural wood, matte black accents, architectural lighting and tactile materials establish a cohesive, warm and inviting aesthetic. Custom white oak wall panels made in Spain, hand-cut white oak beams and architectural transitions, a textured brick feature wall, built-in Sonos audio and a dedicated entertaining bar reflect the attention given to every detail. The European-inspired kitchen features full-height cabinetry incorporating materials imported from Portugal, extensive integrated pantry storage, a Thermador appliance suite with a 36-inch range and griddle, and a Miele steam oven. Positioned at the heart of the living area, the kitchen creates an effortless setting for everyday life and entertaining, always with the lake close at hand. Each of the home’s three bedrooms includes a private en-suite full bath, with an additional powder room serving the common areas. A flexible lake-view office—currently used as a fitness and sauna studio—offers an inspiring setting for work, wellness or creative pursuits. The primary suite opens through nearly eight feet of accordion-style glass doors to a private rooftop terrace, inviting morning coffee, yoga, sunbathing or evening movies beneath the sky. Beyond its architectural design, the comprehensive transformation includes a new roof and roof components, electrical wiring, plumbing and piping, four-zone HVAC system, windows, stucco, drywall, flooring, kitchen and bathrooms. The result combines the character, proportions and established setting of an Old Winter Park home with the quality, efficiency and peace of mind expected from a modern custom residence. Turnkey, distinctive and intimately connected to the water, this exceptional home brings together architectural vision, modern livability and the coveted Winter Park lifestyle on the shores of Lake Sylvan.

1420 Aloma Avenue, Winter Park

$610,000

Under contract-accepting backup offers. Rare opportunity to own a home in one of Winter Park's most sought-after neighborhoods. This charming 3 bedroom, 2 bathroom home sits on a 52x150 lot and is full of endless potential. Whether you are looking for the perfect starter home or an exceptional investment to build your dream home, this property offers an unbeatable combination of location, lifestyle, and value. The kitchen was beautifully remodeled with white custom cabinetry and gorgeous granite countertops. The oversized lot allows you plenty of room to expand, entertain, or simply just enjoy friends and family around the custom built fire pit. There is a large shed in the backyard to store all of your yard needs. Leave the car behind and enjoy one of Central Florida's most walkable neighborhoods. You are just steps away from East End Market, unique local shops, an incredible dining scene, including several Michelin-recognized restaurants and the top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. This desirable pocket of Winter Park offers a true community where neighbors know one another and local events bring them together. This is more than just a home-it's an opportunity to invest in an exceptional lifestyle while making a smart long-term investment in one of Winter Park's most desirable areas. Property being sold AS-IS. This is one not to miss!

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

Under contract-accepting backup offers. Rare opportunity to own a home in one of Winter Park's most sought-after neighborhoods. This charming 3 bedroom, 2 bathroom home sits on a 52x150 lot and is full of endless potential. Whether you are looking for the perfect starter home or an exceptional investment to build your dream home, this property offers an unbeatable combination of location, lifestyle, and value. The kitchen was beautifully remodeled with white custom cabinetry and gorgeous granite countertops. The oversized lot allows you plenty of room to expand, entertain, or simply just enjoy friends and family around the custom built fire pit. There is a large shed in the backyard to store all of your yard needs. Leave the car behind and enjoy one of Central Florida's most walkable neighborhoods. You are just steps away from East End Market, unique local shops, an incredible dining scene, including several Michelin-recognized restaurants and the top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. This desirable pocket of Winter Park offers a true community where neighbors know one another and local events bring them together. This is more than just a home-it's an opportunity to invest in an exceptional lifestyle while making a smart long-term investment in one of Winter Park's most desirable areas. Property being sold AS-IS. This is one not to miss!

2719 Woodside Avenue, Winter Park

$1,775,000

Charming and Sophisticated, this single-story home combines the old with the new in such a seamless manner, you will walk through the etched glass front door and immediately have the desire to sit down with a glass of wine, listen the player piano, and you will never want to leave. Welcome to this Completely Renovated Custom Home in the highly coveted area of Winter Park, just a few blocks from Phelps Park, the YMCA, and a beautiful walk to the Park Avenue shops and restaurants. Walking up the paver drive, over the travertine front patio and stepping into this gorgeous home, you are greeted with the formal living room featuring a player piano, a beautiful marble wood burning fireplace, and hardwood floors that flow throughout the home. Turning to your right you will find 3 large bedrooms, 2 full bathrooms and 1 half bath. You will note one of these secondary bedrooms presents as an en-suite with a full bathroom. The other 2 bedrooms share a full bathroom, along with an auxiliary half bath. Moving forward through the living room you step into the stunning oversized dining room, complete with a wall-bar custom made in Italy along with a wine dispensing machine (picture the Wine Room) which conveys with the sale. From the dining room we step down into a chef's kitchen like no other. Stunning 42"white wood cabinets, quartz countertops, white subway tile backsplash, a 6-burner natural GAS RANGE, double oven, and the largest center island with a microwave and beverage cooler on either end. This magnificent kitchen opens up to a large family room with French doors, surround sound speakers and large sunlit windows. Walking through the family room you will find the primary suite tucked away in the back of the house for the ultimate private sanctuary. Along with the generously sized bedroom with French doors giving access to the backyard and pool, you will be in absolute awe of the incredible primary bathroom, featuring his and hers sinks, a standalone tub, and a double-sided walk-in shower with 2 showerheads and storage benches. The on-demand hot water heater servicing this bathroom means you will never run out of hot water! Oversized His and Hers closets are the proverbial icing on the cake to this primary retreat ("Hers" is the size of a bedroom!). Stepping outside to the cozy covered patio, you will be drawn to the heated, saltwater pool built new in 2023, along with a summer kitchen, electric fireplace, and outdoor TV entertainment, also featuring the cutest pool half bath (no more dripping wet indoor bathroom trips!). Complementing the pool area is a fully fenced backyard for the 2-legged and/or 4-legged kiddos, large privacy hedges, and NO REAR NEIGHBORS. This home comes complete with a whole house Sonos system and speakers playing music throughout the house, even on the back patio, along with a whole house security system including 2 cameras and a Ring doorbell through Vivint. The 2-car garage easily fits both of your vehicles and has amble overhead storage along with attic access. Freshly painted exterior in 2026! Roof is 2018, AC's are 2018, hot water heater is 2026, and an updated irrigation system supported by a private well. Zoned for the BEST SCHOOLS, you can walk to Lakemont Elementary! Middle school is Maitland Middle, and of course, Winter Park High School. Only one lucky family will be able to call this turn-key custom Winter Park home theirs. Make an appt today so that lucky family is yours!

4 Beds ⋅ 5 Baths ⋅ Osceola Or Lakeview Deed SubDv. ⋅ 32789 Zip Code

Charming and Sophisticated, this single-story home combines the old with the new in such a seamless manner, you will walk through the etched glass front door and immediately have the desire to sit down with a glass of wine, listen the player piano, and you will never want to leave. Welcome to this Completely Renovated Custom Home in the highly coveted area of Winter Park, just a few blocks from Phelps Park, the YMCA, and a beautiful walk to the Park Avenue shops and restaurants. Walking up the paver drive, over the travertine front patio and stepping into this gorgeous home, you are greeted with the formal living room featuring a player piano, a beautiful marble wood burning fireplace, and hardwood floors that flow throughout the home. Turning to your right you will find 3 large bedrooms, 2 full bathrooms and 1 half bath. You will note one of these secondary bedrooms presents as an en-suite with a full bathroom. The other 2 bedrooms share a full bathroom, along with an auxiliary half bath. Moving forward through the living room you step into the stunning oversized dining room, complete with a wall-bar custom made in Italy along with a wine dispensing machine (picture the Wine Room) which conveys with the sale. From the dining room we step down into a chef's kitchen like no other. Stunning 42"white wood cabinets, quartz countertops, white subway tile backsplash, a 6-burner natural GAS RANGE, double oven, and the largest center island with a microwave and beverage cooler on either end. This magnificent kitchen opens up to a large family room with French doors, surround sound speakers and large sunlit windows. Walking through the family room you will find the primary suite tucked away in the back of the house for the ultimate private sanctuary. Along with the generously sized bedroom with French doors giving access to the backyard and pool, you will be in absolute awe of the incredible primary bathroom, featuring his and hers sinks, a standalone tub, and a double-sided walk-in shower with 2 showerheads and storage benches. The on-demand hot water heater servicing this bathroom means you will never run out of hot water! Oversized His and Hers closets are the proverbial icing on the cake to this primary retreat ("Hers" is the size of a bedroom!). Stepping outside to the cozy covered patio, you will be drawn to the heated, saltwater pool built new in 2023, along with a summer kitchen, electric fireplace, and outdoor TV entertainment, also featuring the cutest pool half bath (no more dripping wet indoor bathroom trips!). Complementing the pool area is a fully fenced backyard for the 2-legged and/or 4-legged kiddos, large privacy hedges, and NO REAR NEIGHBORS. This home comes complete with a whole house Sonos system and speakers playing music throughout the house, even on the back patio, along with a whole house security system including 2 cameras and a Ring doorbell through Vivint. The 2-car garage easily fits both of your vehicles and has amble overhead storage along with attic access. Freshly painted exterior in 2026! Roof is 2018, AC's are 2018, hot water heater is 2026, and an updated irrigation system supported by a private well. Zoned for the BEST SCHOOLS, you can walk to Lakemont Elementary! Middle school is Maitland Middle, and of course, Winter Park High School. Only one lucky family will be able to call this turn-key custom Winter Park home theirs. Make an appt today so that lucky family is yours!

890 N Phelps Avenue, Winter Park

$3,199,000

Under Construction. Perfectly positioned along one of Winter Park's most picturesque tree-lined cobblestone streets, this exceptional new construction residence offers a rare opportunity to own a home where timeless architecture, refined craftsmanship, and an unrivaled location come together. A striking marble mosaic foyer creates an unforgettable first impression, immediately setting the tone for the level of detail found throughout the residence. Just off the entry, a dedicated home office provides the ideal space for working remotely or enjoying a quiet retreat. Beyond, the thoughtfully designed floor plan unfolds into expansive living spaces filled with natural light and connected by effortless flow. The great room serves as the heart of the home, highlighted by a custom-built entertainment wall with integrated LED lighting, a sleek electric fireplace, and oversized sliding glass doors that blur the line between indoor and outdoor living. Designed for both everyday living and elegant entertaining, the chef's kitchen is a showpiece. Taj Mahal quartzite countertops are paired with an exceptional suite of Thermador appliances, including a paneled built-in refrigerator, while extensive custom cabinetry provides an abundance of storage without compromising the clean, sophisticated aesthetic. The adjoining dining room creates an inviting setting for gatherings and is complemented by a beautifully appointed dry bar complete with a wine refrigerator, making entertaining effortless. Privately situated on the main level, the primary suite is a true retreat with direct access to the lanai through expansive sliding glass doors. The spa-inspired bath showcases exquisite marble mosaic tile, dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous custom walk-in closet, creating a space that feels both luxurious and serene. Upstairs, three spacious guest bedrooms are thoughtfully arranged alongside a comfortable secondary living area and an expansive bonus room, offering remarkable flexibility for a media room, game room, fitness studio, or additional gathering space. The outdoor living experience is equally impressive. A spacious covered lanai is designed for year-round enjoyment, featuring a fully equipped summer kitchen, generous space for alfresco dining and entertaining, a sparkling pool and spa, and ample green space for recreation or relaxation. While the home's finishes and craftsmanship are exceptional, it is the location that truly sets it apart. Enjoy the rare privilege of walking to the boutiques, award-winning restaurants, and vibrant atmosphere of Park Avenue, the campus of Rollins College, Virginia Park, and the acclaimed East End Market. Zoned for highly sought-after Audubon K-8 and surrounded by the charm and character of the Lake Sue District, this is more than a home; it's a statement of luxury Winter Park living.

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

Under Construction. Perfectly positioned along one of Winter Park's most picturesque tree-lined cobblestone streets, this exceptional new construction residence offers a rare opportunity to own a home where timeless architecture, refined craftsmanship, and an unrivaled location come together. A striking marble mosaic foyer creates an unforgettable first impression, immediately setting the tone for the level of detail found throughout the residence. Just off the entry, a dedicated home office provides the ideal space for working remotely or enjoying a quiet retreat. Beyond, the thoughtfully designed floor plan unfolds into expansive living spaces filled with natural light and connected by effortless flow. The great room serves as the heart of the home, highlighted by a custom-built entertainment wall with integrated LED lighting, a sleek electric fireplace, and oversized sliding glass doors that blur the line between indoor and outdoor living. Designed for both everyday living and elegant entertaining, the chef's kitchen is a showpiece. Taj Mahal quartzite countertops are paired with an exceptional suite of Thermador appliances, including a paneled built-in refrigerator, while extensive custom cabinetry provides an abundance of storage without compromising the clean, sophisticated aesthetic. The adjoining dining room creates an inviting setting for gatherings and is complemented by a beautifully appointed dry bar complete with a wine refrigerator, making entertaining effortless. Privately situated on the main level, the primary suite is a true retreat with direct access to the lanai through expansive sliding glass doors. The spa-inspired bath showcases exquisite marble mosaic tile, dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous custom walk-in closet, creating a space that feels both luxurious and serene. Upstairs, three spacious guest bedrooms are thoughtfully arranged alongside a comfortable secondary living area and an expansive bonus room, offering remarkable flexibility for a media room, game room, fitness studio, or additional gathering space. The outdoor living experience is equally impressive. A spacious covered lanai is designed for year-round enjoyment, featuring a fully equipped summer kitchen, generous space for alfresco dining and entertaining, a sparkling pool and spa, and ample green space for recreation or relaxation. While the home's finishes and craftsmanship are exceptional, it is the location that truly sets it apart. Enjoy the rare privilege of walking to the boutiques, award-winning restaurants, and vibrant atmosphere of Park Avenue, the campus of Rollins College, Virginia Park, and the acclaimed East End Market. Zoned for highly sought-after Audubon K-8 and surrounded by the charm and character of the Lake Sue District, this is more than a home; it's a statement of luxury Winter Park living.

361 E Kings Way, Winter Park

$2,390,000

Custom-built Santa Barbara-style estate set on one of Winter Park's most coveted brick-paved streets, just moments from Park Avenue's boutiques, galleries and celebrated restaurants, Winter Park Golf Course, Winter Park Racquet Club, historic Rollins College and vibrant Winter Park Village. Built in 2010, this four-bedroom, 4.5-bath residence spans 3,661 square feet across two floors, with cathedral ceilings, a cozy fireplace and colonial windows and French doors, which frame the resort-style pool retreat. A gracious main-floor primary suite offers dual vanities and a large walk-in closet. The double-island chef's kitchen features a gas range and premium Thermador appliances, anchoring an open-plan living, dining and kitchen design, modeled for everyday ease and effortless entertaining. A flexible bonus space is ideal for a home office, formal dining or gym. Upstairs, three additional spacious bedrooms each offer their own en-suite bath and walk-in closet. The home wraps around a covered courtyard leading to the heated saltwater pool and spa, creating a private outdoor enclave. Parking is a breeze with an oversized two-car garage, additional golf cart parking, plus utility pad. Ample storage and workspace complete the rear of the property, which is also wired for a future whole-home generator. A rare offering in the heart of Winter Park, where timeless design meets an unmatched lifestyle.

4 Beds ⋅ 5 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code

Custom-built Santa Barbara-style estate set on one of Winter Park's most coveted brick-paved streets, just moments from Park Avenue's boutiques, galleries and celebrated restaurants, Winter Park Golf Course, Winter Park Racquet Club, historic Rollins College and vibrant Winter Park Village. Built in 2010, this four-bedroom, 4.5-bath residence spans 3,661 square feet across two floors, with cathedral ceilings, a cozy fireplace and colonial windows and French doors, which frame the resort-style pool retreat. A gracious main-floor primary suite offers dual vanities and a large walk-in closet. The double-island chef's kitchen features a gas range and premium Thermador appliances, anchoring an open-plan living, dining and kitchen design, modeled for everyday ease and effortless entertaining. A flexible bonus space is ideal for a home office, formal dining or gym. Upstairs, three additional spacious bedrooms each offer their own en-suite bath and walk-in closet. The home wraps around a covered courtyard leading to the heated saltwater pool and spa, creating a private outdoor enclave. Parking is a breeze with an oversized two-car garage, additional golf cart parking, plus utility pad. Ample storage and workspace complete the rear of the property, which is also wired for a future whole-home generator. A rare offering in the heart of Winter Park, where timeless design meets an unmatched lifestyle.

645 Pansy Avenue, Winter Park

$4,750,000

There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the product of meticulous vision, extraordinary craftsmanship, and an unwavering commitment to quality. Every space has been curated to create one of the most refined and meticulously executed homes to ever come to market in Winter Park. Situated on an expansive 15,000-square-foot homesite in the coveted Park Grove neighborhood, just moments from the boutiques and acclaimed dining of Park Avenue, the home immediately captivates with its striking architectural presence and a sweeping double-entry driveway. Beyond the front doors, a breathtaking foyer unfolds beneath soaring 22-foot ceilings, where an elegant, curved staircase, intricate marble mosaic flooring, oversized windows, and meticulous millwork establish a level of craftsmanship rarely found in today's market. Chevron-pattern engineered hardwood flooring extends throughout, complemented by exquisite natural marble and thoughtfully curated designer finishes at every turn. Designed to impress while remaining effortlessly livable, the grand living room features illuminated tray ceilings, a custom-built entertainment wall, and a sleek electric fireplace. The chef's kitchen is a true showpiece, anchored by dramatic Calacatta Viola marble countertops and backsplash, a complete Thermador appliance suite with paneled refrigerator and freezer, and a stunning ILVE range. An expansive butler's pantry with a second sink, double oven, warming drawer, dishwasher, and abundant preparation space elevates both entertaining and everyday functionality, while formal and casual dining spaces provide the perfect setting for gatherings of any scale. The primary suite is a private sanctuary designed for ultimate comfort, featuring its own coffee bar, an extraordinary custom dressing room. The primary also features a spa-caliber bath appointed with striking marble finishes, a dramatic illuminated walk-in shower, freestanding soaking tub, and Perrin & Rowe fixtures. A first-floor guest suite or dedicated office offers exceptional flexibility, while upstairs, three spacious en-suite bedrooms with walk-in closets are complemented by a hidden bonus room. Pocketing glass doors create a seamless transition to an exceptional outdoor retreat complete with a covered lanai featuring retractable screens, a fully equipped summer kitchen, resort-style pool and spa, expansive backyard, and professionally curated landscaping. Located just minutes from Park Avenue and surrounded by top-rated schools, this residence is more than a luxury home, it is a statement of artistry, craftsmanship, and timeless design that redefines what luxury new construction can be in Winter Park.

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

There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the product of meticulous vision, extraordinary craftsmanship, and an unwavering commitment to quality. Every space has been curated to create one of the most refined and meticulously executed homes to ever come to market in Winter Park. Situated on an expansive 15,000-square-foot homesite in the coveted Park Grove neighborhood, just moments from the boutiques and acclaimed dining of Park Avenue, the home immediately captivates with its striking architectural presence and a sweeping double-entry driveway. Beyond the front doors, a breathtaking foyer unfolds beneath soaring 22-foot ceilings, where an elegant, curved staircase, intricate marble mosaic flooring, oversized windows, and meticulous millwork establish a level of craftsmanship rarely found in today's market. Chevron-pattern engineered hardwood flooring extends throughout, complemented by exquisite natural marble and thoughtfully curated designer finishes at every turn. Designed to impress while remaining effortlessly livable, the grand living room features illuminated tray ceilings, a custom-built entertainment wall, and a sleek electric fireplace. The chef's kitchen is a true showpiece, anchored by dramatic Calacatta Viola marble countertops and backsplash, a complete Thermador appliance suite with paneled refrigerator and freezer, and a stunning ILVE range. An expansive butler's pantry with a second sink, double oven, warming drawer, dishwasher, and abundant preparation space elevates both entertaining and everyday functionality, while formal and casual dining spaces provide the perfect setting for gatherings of any scale. The primary suite is a private sanctuary designed for ultimate comfort, featuring its own coffee bar, an extraordinary custom dressing room. The primary also features a spa-caliber bath appointed with striking marble finishes, a dramatic illuminated walk-in shower, freestanding soaking tub, and Perrin & Rowe fixtures. A first-floor guest suite or dedicated office offers exceptional flexibility, while upstairs, three spacious en-suite bedrooms with walk-in closets are complemented by a hidden bonus room. Pocketing glass doors create a seamless transition to an exceptional outdoor retreat complete with a covered lanai featuring retractable screens, a fully equipped summer kitchen, resort-style pool and spa, expansive backyard, and professionally curated landscaping. Located just minutes from Park Avenue and surrounded by top-rated schools, this residence is more than a luxury home, it is a statement of artistry, craftsmanship, and timeless design that redefines what luxury new construction can be in Winter Park.

1525 Granville Drive, Winter Park

$1,849,900

**Third, Fifth, and Sixth MLS photo's are virtually rendered showing the potential of an off white painted exterior if painted** A rare opportunity to own a piece of Winter Park history in the coveted College Quarter. Built in 1922 and recognized as a designated historic residence, 318 Vitoria Avenue is a distinctive Mission Revival home offering timeless architecture, remarkable craftsmanship, and an exceptional lifestyle near Lake Virginia, Rollins College, and Park Avenue. Set on an elevated homesite along one of Winter Park’s picturesque brick streets, this 3-bedroom, 2.5-bath residence offers 2,036 square feet thoughtfully oriented to embrace natural light and breezes from nearby Lake Virginia. Its Mission Revival architecture is showcased through graceful arches, classic stucco construction, barrel-tile accents, distinctive balconies, and a secluded courtyard framed by custom ironwork created by a local master craftsman. Inside, original oak and heart-pine floors preserve more than a century of character. The expansive great room serves as the heart of the home, featuring 10-foot exposed-rafter ceilings, dramatic arched windows with handblown glass, a wood-burning fireplace, and French doors that create a seamless connection to the courtyard and pool. The kitchen features an oversized butcher-block island, imported tile, oak cabinetry, a breakfast nook, and adjoining pantry and laundry areas. Uniques details continue with custom coquina flooring on the porch and intricate tilework in the Florida room, both created by a Disney Imagineer and adding an exceptional layer of artistry and one-of-a-kind craftsmanship to the home. Upstairs, three bedrooms feature original heart-pine flooring, abundant natural light, built-in storage, balconies, and select views toward Lake Virginia. An unfinished basement provides valuable additional storage—an uncommon feature in Central Florida. Thoughtful improvements complement the home’s historic character, including a roof completed in 2021, air-conditioning system installed in 2020, recently updated tankless water heater, and a 2026 electrical panel upgrade with whole-home surge protection. Outside, mature landscaping surrounds the private plunge pool and courtyard, creating an intimate setting for relaxing and entertaining. College Quarter residents enjoy exclusive access to a private neighborhood park and dock on Lake Virginia, providing a wonderful connection to kayaking, paddleboarding, boating, and Winter Park’s Chain of Lakes. Rollins College, Park Avenue, Central Park, museums, restaurants, boutiques, and many of the city’s most celebrated destinations are all close at hand. Held by the same family for 46 years, 318 Vitoria Avenue represents a rare convergence of historic architecture, bespoke craftsmanship, meaningful modern improvements, private outdoor living, lake access, and an extraordinary Winter Park location. A distinctive residence ready for its next chapter.

3 Beds ⋅ 3 Baths ⋅ College Place Rep SubDv. ⋅ 32789 Zip Code

**Third, Fifth, and Sixth MLS photo's are virtually rendered showing the potential of an off white painted exterior if painted** A rare opportunity to own a piece of Winter Park history in the coveted College Quarter. Built in 1922 and recognized as a designated historic residence, 318 Vitoria Avenue is a distinctive Mission Revival home offering timeless architecture, remarkable craftsmanship, and an exceptional lifestyle near Lake Virginia, Rollins College, and Park Avenue. Set on an elevated homesite along one of Winter Park’s picturesque brick streets, this 3-bedroom, 2.5-bath residence offers 2,036 square feet thoughtfully oriented to embrace natural light and breezes from nearby Lake Virginia. Its Mission Revival architecture is showcased through graceful arches, classic stucco construction, barrel-tile accents, distinctive balconies, and a secluded courtyard framed by custom ironwork created by a local master craftsman. Inside, original oak and heart-pine floors preserve more than a century of character. The expansive great room serves as the heart of the home, featuring 10-foot exposed-rafter ceilings, dramatic arched windows with handblown glass, a wood-burning fireplace, and French doors that create a seamless connection to the courtyard and pool. The kitchen features an oversized butcher-block island, imported tile, oak cabinetry, a breakfast nook, and adjoining pantry and laundry areas. Uniques details continue with custom coquina flooring on the porch and intricate tilework in the Florida room, both created by a Disney Imagineer and adding an exceptional layer of artistry and one-of-a-kind craftsmanship to the home. Upstairs, three bedrooms feature original heart-pine flooring, abundant natural light, built-in storage, balconies, and select views toward Lake Virginia. An unfinished basement provides valuable additional storage—an uncommon feature in Central Florida. Thoughtful improvements complement the home’s historic character, including a roof completed in 2021, air-conditioning system installed in 2020, recently updated tankless water heater, and a 2026 electrical panel upgrade with whole-home surge protection. Outside, mature landscaping surrounds the private plunge pool and courtyard, creating an intimate setting for relaxing and entertaining. College Quarter residents enjoy exclusive access to a private neighborhood park and dock on Lake Virginia, providing a wonderful connection to kayaking, paddleboarding, boating, and Winter Park’s Chain of Lakes. Rollins College, Park Avenue, Central Park, museums, restaurants, boutiques, and many of the city’s most celebrated destinations are all close at hand. Held by the same family for 46 years, 318 Vitoria Avenue represents a rare convergence of historic architecture, bespoke craftsmanship, meaningful modern improvements, private outdoor living, lake access, and an extraordinary Winter Park location. A distinctive residence ready for its next chapter.

318 Vitoria Avenue, Winter Park

$3,895,000

From the moment you enter this custom residence you feel welcomed home by the understated elegance and gracious living spaces. SE corner location affording abundant natural light. From the underground private two car garage through the three living levels and up to the roof top terrace, each floor is serviced by a window wrapped staircase and your own private elevator. Creature comforts include a Lutron lighting system, home audio system and programmable shades, all set to your schedule by the Control4 home automation system. You approach the double entry doors via a gated, spacious terrace. The main level offers spacious living and dining areas opening to a Chef’s Dream Kitchen. Here you find solid wood cabinetry, quartz countertops, custom backsplash, Wolf five-burner natural gas cooktop, integrated Sub Zero refrigerator, Wolf wall oven and microwave, Bosch dishwasher, Sub Zero full size, dual zone wine refrigerator and a large island with counter seating. The adjacent sitting room faces East for starting your day with morning light or winding down your day with your favorite beverage. The wall mounted television adds to the convenience of this versatile space where you can catch up on the morning or evening news. The main living level also offers your guests the convenience of a private powder room. The second level is dedicated to the generous Primary Suite. This level offers a spacious bedroom, a custom walk-in closet, a gracious primary bathroom with a walk-in shower, double sinks, a custom vanity/makeup area, and a private water closet with automatic Toto Washlet. The Primary Suite level also features a customized office/lounge area with built-in cabinetry and a refrigerator. Adding to the convenience, you’ll find the laundry area integrated into the Primary Suite level. You are greeted to the Third Level through an open media room. The media loft area is adjacent to the two spacious and private ensuite bedrooms. Both bedrooms 2 and 3 feature walk-in closets and private bathrooms. Wait, there’s more! Up one more level you will find the incredible rooftop terrace. This approx. 800 sq. ft. space, serviced by your private elevator, is perfect for entertaining family and friends – no matter the size of the party! An entertainer’s delight, you will enjoy the outdoor kitchen with stainless 36” DCS natural gas grill, exhaust hood, refrigerator and sink. Adding to the convenience of entertaining on your private rooftop, this terrace has its own powder room. Additionally, there is an air-conditioned storage closet perfect for keeping dry and safe items you want protected from the weather. Going back downstairs to the underground garage, you’ll enjoy the security of your own oversized two-car garage. Not only does this level of Residence #1 offer you a private garage, you’ll also love the convenience and security of your own air-conditioned 9x13 storage room and another private foyer. The building’s garage area is accessed through a separate gated entrance. This underground parking area includes guest parking spaces. This exquisite residence is mere steps from all the dining, shopping and community amenities along Park Avenue and the adjacent Boulevards that make downtown Winter Park so coveted. Residence 1 of 125 South Interlachen Place is that rare opportunity to own an exquisite and perfectly located home offering the lock and leave lifestyle. All measurements are approximate and Buyer is responsible for verifying all dimensions.

3 Beds ⋅ 5 Baths ⋅ South Interlachen Place SubDv. ⋅ 32789 Zip Code

From the moment you enter this custom residence you feel welcomed home by the understated elegance and gracious living spaces. SE corner location affording abundant natural light. From the underground private two car garage through the three living levels and up to the roof top terrace, each floor is serviced by a window wrapped staircase and your own private elevator. Creature comforts include a Lutron lighting system, home audio system and programmable shades, all set to your schedule by the Control4 home automation system. You approach the double entry doors via a gated, spacious terrace. The main level offers spacious living and dining areas opening to a Chef’s Dream Kitchen. Here you find solid wood cabinetry, quartz countertops, custom backsplash, Wolf five-burner natural gas cooktop, integrated Sub Zero refrigerator, Wolf wall oven and microwave, Bosch dishwasher, Sub Zero full size, dual zone wine refrigerator and a large island with counter seating. The adjacent sitting room faces East for starting your day with morning light or winding down your day with your favorite beverage. The wall mounted television adds to the convenience of this versatile space where you can catch up on the morning or evening news. The main living level also offers your guests the convenience of a private powder room. The second level is dedicated to the generous Primary Suite. This level offers a spacious bedroom, a custom walk-in closet, a gracious primary bathroom with a walk-in shower, double sinks, a custom vanity/makeup area, and a private water closet with automatic Toto Washlet. The Primary Suite level also features a customized office/lounge area with built-in cabinetry and a refrigerator. Adding to the convenience, you’ll find the laundry area integrated into the Primary Suite level. You are greeted to the Third Level through an open media room. The media loft area is adjacent to the two spacious and private ensuite bedrooms. Both bedrooms 2 and 3 feature walk-in closets and private bathrooms. Wait, there’s more! Up one more level you will find the incredible rooftop terrace. This approx. 800 sq. ft. space, serviced by your private elevator, is perfect for entertaining family and friends – no matter the size of the party! An entertainer’s delight, you will enjoy the outdoor kitchen with stainless 36” DCS natural gas grill, exhaust hood, refrigerator and sink. Adding to the convenience of entertaining on your private rooftop, this terrace has its own powder room. Additionally, there is an air-conditioned storage closet perfect for keeping dry and safe items you want protected from the weather. Going back downstairs to the underground garage, you’ll enjoy the security of your own oversized two-car garage. Not only does this level of Residence #1 offer you a private garage, you’ll also love the convenience and security of your own air-conditioned 9x13 storage room and another private foyer. The building’s garage area is accessed through a separate gated entrance. This underground parking area includes guest parking spaces. This exquisite residence is mere steps from all the dining, shopping and community amenities along Park Avenue and the adjacent Boulevards that make downtown Winter Park so coveted. Residence 1 of 125 South Interlachen Place is that rare opportunity to own an exquisite and perfectly located home offering the lock and leave lifestyle. All measurements are approximate and Buyer is responsible for verifying all dimensions.

125 S Interlachen Avenue Unit 1, Winter Park

$4,750,000

Under contract-accepting backup offers. Privately nestled on 1.32 acres (1.1+ acres HIGH & DRY) along the tranquil shores of Lake Temple, this remarkable residence is a true compound where architecture, craftsmanship, and nature exist in perfect balance. Completed in 2019 by Gallimore Homes and enhanced with more than $300K in upgrades, this home was designed to feel secluded and private while serving as the ultimate destination for entertaining. This unique property offers a 4,060+ SF main residence (4 beds / 3.5 baths plus bonus room for a future 5th bedroom), a detached 480+ SF guest house (1 bed / 1 bath), and resort-style outdoor living overlooking peaceful water views and a rolling backyard. Designed for exceptional privacy, the home is positioned well back from the street and buffered by mature landscaping, a private courtyard wall with a security gate, and hurricane-impact windows and doors throughout. Additional highlights include an oversized three-car garage, parking for 15+ vehicles, and space to park a boat or RV next to the conservation area. Inside, soaring ceilings and premium finishes create an immediate sense of warmth and sophistication. Ten-foot-tall EuroWall folding glass doors span 15 feet across the great room, seamlessly blending indoor and outdoor living while framing beautiful backyard and water views. The chef's kitchen showcases professional-grade Sub-Zero and Wolf appliances, an oversized gathering island with prep sink, ice maker, waterfall countertops, a 48-inch Wolf six-burner dual-fuel range, dry bar with refrigerated drawers, and a spacious walk-in pantry. The open-concept design flows effortlessly into the great room and dining area, making everyday living and entertaining equally inviting. The split-bedroom floor plan offers exceptional privacy, highlighted by a spacious first-floor primary suite with 2 walk-in closets (totaling 175+ SF) and a spa-inspired bath. The first floor also includes a guest suite, two additional bedrooms with a Jack-and-Jill bath, and a powder/pool bath with access to the lania. Upstairs, the bonus room provides flexibility for a media room, game room, home office, and pre-plumed for a bath and kitchenette for a future 5th bedroom. Equally impressive is the detached guest house, complete with its own covered front porch, full kitchen, living room, bedroom, full bath, and beautiful backyard views…ideal for multigenerational living, extended guests, a private office, or long-term visitors. The covered lanai was designed for year-round outdoor living with three Phantom Screens spanning nearly 45 feet, an authentic Argentine wood-fired grill, and a built-in wet bar. The heated saltwater infinity-edge pool features a sun shelf, LED lighting, and a composite wood sun deck overlooking the water. The expansive lawn gently slopes to the shoreline beneath a magnificent 100+ year-old oak tree, enhanced by mature landscaping and landscape lighting that creates an unforgettable setting for intimate evenings and large-scale gatherings too. Located less than three miles from Interlachen Country Club and a few blocks from the Winter Park Racquet Club, this property offers a rare combination of privacy, flexibility, and estate-style living on more than an acre of waterfront in Winter Park. (*Ask for a Floorplan, List of Improvements, and Survey. Click the Virtual Tour link to see a video of the property! )

5 Beds ⋅ 5 Baths ⋅ Lake Maitland SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Privately nestled on 1.32 acres (1.1+ acres HIGH & DRY) along the tranquil shores of Lake Temple, this remarkable residence is a true compound where architecture, craftsmanship, and nature exist in perfect balance. Completed in 2019 by Gallimore Homes and enhanced with more than $300K in upgrades, this home was designed to feel secluded and private while serving as the ultimate destination for entertaining. This unique property offers a 4,060+ SF main residence (4 beds / 3.5 baths plus bonus room for a future 5th bedroom), a detached 480+ SF guest house (1 bed / 1 bath), and resort-style outdoor living overlooking peaceful water views and a rolling backyard. Designed for exceptional privacy, the home is positioned well back from the street and buffered by mature landscaping, a private courtyard wall with a security gate, and hurricane-impact windows and doors throughout. Additional highlights include an oversized three-car garage, parking for 15+ vehicles, and space to park a boat or RV next to the conservation area. Inside, soaring ceilings and premium finishes create an immediate sense of warmth and sophistication. Ten-foot-tall EuroWall folding glass doors span 15 feet across the great room, seamlessly blending indoor and outdoor living while framing beautiful backyard and water views. The chef's kitchen showcases professional-grade Sub-Zero and Wolf appliances, an oversized gathering island with prep sink, ice maker, waterfall countertops, a 48-inch Wolf six-burner dual-fuel range, dry bar with refrigerated drawers, and a spacious walk-in pantry. The open-concept design flows effortlessly into the great room and dining area, making everyday living and entertaining equally inviting. The split-bedroom floor plan offers exceptional privacy, highlighted by a spacious first-floor primary suite with 2 walk-in closets (totaling 175+ SF) and a spa-inspired bath. The first floor also includes a guest suite, two additional bedrooms with a Jack-and-Jill bath, and a powder/pool bath with access to the lania. Upstairs, the bonus room provides flexibility for a media room, game room, home office, and pre-plumed for a bath and kitchenette for a future 5th bedroom. Equally impressive is the detached guest house, complete with its own covered front porch, full kitchen, living room, bedroom, full bath, and beautiful backyard views…ideal for multigenerational living, extended guests, a private office, or long-term visitors. The covered lanai was designed for year-round outdoor living with three Phantom Screens spanning nearly 45 feet, an authentic Argentine wood-fired grill, and a built-in wet bar. The heated saltwater infinity-edge pool features a sun shelf, LED lighting, and a composite wood sun deck overlooking the water. The expansive lawn gently slopes to the shoreline beneath a magnificent 100+ year-old oak tree, enhanced by mature landscaping and landscape lighting that creates an unforgettable setting for intimate evenings and large-scale gatherings too. Located less than three miles from Interlachen Country Club and a few blocks from the Winter Park Racquet Club, this property offers a rare combination of privacy, flexibility, and estate-style living on more than an acre of waterfront in Winter Park. (*Ask for a Floorplan, List of Improvements, and Survey. Click the Virtual Tour link to see a video of the property! )

2525 Temple Drive, Winter Park

$3,275,000

1811 Oneco Avenue — an architectural presence unlike anything around it. A canopy of mature pines and oaks lines the approach, and the home reveals itself at the end of a quiet dead-end street. Step inside — more than 4,500 square feet across three levels. The foyer sets the tone — twin chandeliers above, white oak floors below. The eye is pulled past the curved staircase, straight into the gathering room, where French-pane glass opens the wall to a full-length lanai. The gathering room is the center the rest of the home answers to. A floor-to-ceiling fireplace anchors the space, framed by twin illuminated arches with chevron oak detailing and custom built-ins. The kitchen is a destination. Custom floor-to-ceiling white oak cabinetry. A statement fluted island wrapped in stone commands the center beneath brass pendants. A Viking gas range, double ovens, and custom hood complete a space designed to be lived around as much as admired. Coffee becomes conversation. Ordinary evenings become occasions. Behind the kitchen, a scullery reveals one of the most thoughtful luxuries — rich custom wood detailing, wine refrigeration, and dedicated prep space. The dining room sits beneath a vaulted ceiling with exposed beams, warm wood detailing, and a statement fixture above the table, a full wall of glass drawing a picturesque setting into every gathering. The primary suite is the most personal expression of luxury. A tray ceiling crowns the room while an alabaster chandelier casts a warm glow across the space. Beyond frosted glass doors, the bath unfolds in marble, warm brass, designer lighting, and custom cabinetry — a freestanding soaking tub anchoring the room, an oversized walk-in shower beyond. Dual custom walk-in closets complete the suite, the dressing room anchored by a center island beneath floor-to-ceiling cabinetry. Off the foyer, a steel-and-glass door reveals one of the home's most unforgettable spaces, walls of windows flooding the interior with natural light. With its own bath and walk-in closet, it serves just as easily as a fifth bedroom. Then the powder bath — scenic mural wallpaper climbs above elegant paneling, a sculptural fluted marble vanity beneath wall-mounted brass fixtures. Unforgettable. Beyond the glass, the home extends into its finest space. A full-length covered lanai runs beneath wood-clad ceilings, opening to a fully equipped outdoor kitchen with grill, beverage refrigeration, and storage. Beyond it, the pool stretches long and clear, framed in natural stone, a fire feature anchoring the lounge. Mature greenery closes the yard on every side — neighbors behind, never beside. A third of an acre of privacy this close to Park Avenue is its own kind of rare. This is the heart of Winter Park's 32789 — minutes from Park Avenue, in one of the area's most sought-after school zones: Lakemont Elementary, Maitland Middle, Winter Park High. Five bedrooms. Five and a half baths. More than 4,500 square feet. A three-car tandem garage. New construction, complete and ready. You can find another new-construction home. You will not find this lot, this design, and this floor plan together again at this number. Come see it. You will not forget it. Schedule your showing today.

5 Beds ⋅ 6 Baths ⋅ Flora Park 2nd Add SubDv. ⋅ 32789 Zip Code

1811 Oneco Avenue — an architectural presence unlike anything around it. A canopy of mature pines and oaks lines the approach, and the home reveals itself at the end of a quiet dead-end street. Step inside — more than 4,500 square feet across three levels. The foyer sets the tone — twin chandeliers above, white oak floors below. The eye is pulled past the curved staircase, straight into the gathering room, where French-pane glass opens the wall to a full-length lanai. The gathering room is the center the rest of the home answers to. A floor-to-ceiling fireplace anchors the space, framed by twin illuminated arches with chevron oak detailing and custom built-ins. The kitchen is a destination. Custom floor-to-ceiling white oak cabinetry. A statement fluted island wrapped in stone commands the center beneath brass pendants. A Viking gas range, double ovens, and custom hood complete a space designed to be lived around as much as admired. Coffee becomes conversation. Ordinary evenings become occasions. Behind the kitchen, a scullery reveals one of the most thoughtful luxuries — rich custom wood detailing, wine refrigeration, and dedicated prep space. The dining room sits beneath a vaulted ceiling with exposed beams, warm wood detailing, and a statement fixture above the table, a full wall of glass drawing a picturesque setting into every gathering. The primary suite is the most personal expression of luxury. A tray ceiling crowns the room while an alabaster chandelier casts a warm glow across the space. Beyond frosted glass doors, the bath unfolds in marble, warm brass, designer lighting, and custom cabinetry — a freestanding soaking tub anchoring the room, an oversized walk-in shower beyond. Dual custom walk-in closets complete the suite, the dressing room anchored by a center island beneath floor-to-ceiling cabinetry. Off the foyer, a steel-and-glass door reveals one of the home's most unforgettable spaces, walls of windows flooding the interior with natural light. With its own bath and walk-in closet, it serves just as easily as a fifth bedroom. Then the powder bath — scenic mural wallpaper climbs above elegant paneling, a sculptural fluted marble vanity beneath wall-mounted brass fixtures. Unforgettable. Beyond the glass, the home extends into its finest space. A full-length covered lanai runs beneath wood-clad ceilings, opening to a fully equipped outdoor kitchen with grill, beverage refrigeration, and storage. Beyond it, the pool stretches long and clear, framed in natural stone, a fire feature anchoring the lounge. Mature greenery closes the yard on every side — neighbors behind, never beside. A third of an acre of privacy this close to Park Avenue is its own kind of rare. This is the heart of Winter Park's 32789 — minutes from Park Avenue, in one of the area's most sought-after school zones: Lakemont Elementary, Maitland Middle, Winter Park High. Five bedrooms. Five and a half baths. More than 4,500 square feet. A three-car tandem garage. New construction, complete and ready. You can find another new-construction home. You will not find this lot, this design, and this floor plan together again at this number. Come see it. You will not forget it. Schedule your showing today.

1811 Oneco Avenue, Winter Park

$525,000

Beneath mature oak trees in The Quarters at Winter Park, this townhome-style condominium presents a rare opportunity to own a spacious, architecturally distinctive residence in one of Winter Park's most established communities. Priced to reflect its as-is condition, the home offers exceptional potential for a buyer ready to personalize the space. A gated brick courtyard and covered front porch lead to light-filled living and dining areas featuring engineered hardwood flooring and a wrought-iron staircase. The kitchen offers granite countertops, a gas range and opens to the family room, where a gas fireplace and skylight create a welcoming gathering space. A private screened courtyard connects the residence to the detached two-car garage. Upstairs, the primary suite spans more than 300 square feet and features a custom walk-in closet and dual-sink en-suite bath. Two additional bedrooms include one with a private en-suite bath and another with access to a balcony overlooking the tree-lined street. Ideally just minutes from Park Avenue, Rollins College and Seven Oaks Park, this residence offers the opportunity to renovate and customize a home in one of Winter Park's most sought-after communities. Sold as is, with an inspection report available upon request.

3 Beds ⋅ 4 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code

Beneath mature oak trees in The Quarters at Winter Park, this townhome-style condominium presents a rare opportunity to own a spacious, architecturally distinctive residence in one of Winter Park's most established communities. Priced to reflect its as-is condition, the home offers exceptional potential for a buyer ready to personalize the space. A gated brick courtyard and covered front porch lead to light-filled living and dining areas featuring engineered hardwood flooring and a wrought-iron staircase. The kitchen offers granite countertops, a gas range and opens to the family room, where a gas fireplace and skylight create a welcoming gathering space. A private screened courtyard connects the residence to the detached two-car garage. Upstairs, the primary suite spans more than 300 square feet and features a custom walk-in closet and dual-sink en-suite bath. Two additional bedrooms include one with a private en-suite bath and another with access to a balcony overlooking the tree-lined street. Ideally just minutes from Park Avenue, Rollins College and Seven Oaks Park, this residence offers the opportunity to renovate and customize a home in one of Winter Park's most sought-after communities. Sold as is, with an inspection report available upon request.

1134 Washington Avenue Unit 13C, Winter Park

$1,995,000

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

4 Beds ⋅ 4 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

922 N Pennsylvania Avenue, Winter Park

$1,595,000

In the heart of Winter Park's vibrant Hannibal Square, this exceptional one-story residence, completed in 2022, offers the ideal blend of contemporary design, refined finishes and an unbeatable accessible lifestyle. Thoughtfully designed with three bedrooms, two and one-half baths, and an open-concept floor plan, the home showcases clean architectural lines, soaring ceilings and walls of glass that fill the interior with natural light while framing views of the beautifully landscaped grounds. The chef's kitchen serves as the centerpiece of the home, featuring premium Wolf and Sub-Zero appliances, custom cabinetry, a center island with seating, and workspace for everyday living and entertaining. The adjoining dining area flows seamlessly into the spacious great room, where custom-built library shelving creates a striking focal point and adds warmth and character to the modern design. Beautiful polished concrete floors extend throughout the residence, providing a cohesive and sophisticated aesthetic. Designed with privacy in mind, the split-bedroom floor plan places the primary suite in its own secluded wing. This spacious retreat offers direct access to the covered rear patio and features a beautiful bath with dual vanities, an oversized walk-in shower, private water closet, and an impressive custom walk-in closet measuring approximately 11 by 9 feet. Conveniently accessible from the primary bath and laundry room, the thoughtfully designed closet enhances everyday functionality. On opposite side of the home, two additional guest bedrooms are connected by a well-appointed Jack-and-Jill bath, while a stylish powder bath is ideally located for visitors. Outdoor living is equally inviting with a covered patio with a privacy bamboo hedge that creates a peaceful backdrop for relaxing or entertaining. An attached two-car garage completes this beautifully appointed residence. Ideally near the acclaimed restaurants, wine bars, coffee shops, and boutiques of Hannibal Square, this home offers one of Winter Park's desirable lifestyles. Visit the renowned shopping, dining, galleries and sidewalk cafés of Park Avenue, enjoy nearby Central Park and community events, or take advantage of the proximity to Rollins College, the Winter Park Farmers' Market and major roadways providing convenient access throughout Central Florida. This is a rare opportunity to enjoy nearly new construction in one of Winter Park's sought-after neighborhoods, where modern luxury and exceptional accessibility come together.

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

In the heart of Winter Park's vibrant Hannibal Square, this exceptional one-story residence, completed in 2022, offers the ideal blend of contemporary design, refined finishes and an unbeatable accessible lifestyle. Thoughtfully designed with three bedrooms, two and one-half baths, and an open-concept floor plan, the home showcases clean architectural lines, soaring ceilings and walls of glass that fill the interior with natural light while framing views of the beautifully landscaped grounds. The chef's kitchen serves as the centerpiece of the home, featuring premium Wolf and Sub-Zero appliances, custom cabinetry, a center island with seating, and workspace for everyday living and entertaining. The adjoining dining area flows seamlessly into the spacious great room, where custom-built library shelving creates a striking focal point and adds warmth and character to the modern design. Beautiful polished concrete floors extend throughout the residence, providing a cohesive and sophisticated aesthetic. Designed with privacy in mind, the split-bedroom floor plan places the primary suite in its own secluded wing. This spacious retreat offers direct access to the covered rear patio and features a beautiful bath with dual vanities, an oversized walk-in shower, private water closet, and an impressive custom walk-in closet measuring approximately 11 by 9 feet. Conveniently accessible from the primary bath and laundry room, the thoughtfully designed closet enhances everyday functionality. On opposite side of the home, two additional guest bedrooms are connected by a well-appointed Jack-and-Jill bath, while a stylish powder bath is ideally located for visitors. Outdoor living is equally inviting with a covered patio with a privacy bamboo hedge that creates a peaceful backdrop for relaxing or entertaining. An attached two-car garage completes this beautifully appointed residence. Ideally near the acclaimed restaurants, wine bars, coffee shops, and boutiques of Hannibal Square, this home offers one of Winter Park's desirable lifestyles. Visit the renowned shopping, dining, galleries and sidewalk cafés of Park Avenue, enjoy nearby Central Park and community events, or take advantage of the proximity to Rollins College, the Winter Park Farmers' Market and major roadways providing convenient access throughout Central Florida. This is a rare opportunity to enjoy nearly new construction in one of Winter Park's sought-after neighborhoods, where modern luxury and exceptional accessibility come together.

462 W Lyman Avenue, Winter Park

$569,000

Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

3 Beds ⋅ 3 Baths ⋅ Fairshores Place SubDv. ⋅ 32789 Zip Code

Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

2803 Riddle Drive, Winter Park

$3,395,000

Come tour this brand new, elaborately finished luxury home in Winter Park! Designed and constructed by a well-established, award-winning custom home builder, no expense has been spared. This home is truly a leader in its class! Located just a short walk to the esteemed Audobon K-8 school, East End market, restaurants, shopping, Blue Jacket Park, Baldwin Park. Just a short drive to Park Avenue restaurants and shopping. As you pull up to this vast estate home, the dimensional architectural detail on the home on a huge lot boasts a commanding presence. The 12 foot ceilings on the first floor and 10 foot ceilings on the second floor give the home a voluminous feel throughout. The first floor features a huge master suite with an accessible washer and dryer off the giant walk-in closet, plus an additional full guest suite and separate office. The gourmet kitchen features luxury custom cabinets, an accent island with exotic granite counter tops. Thermador appliances outfit the main kitchen as follows: Large 30” refrigerator and 30” freezer towers, 48” dual oven gas range with ornamental hood, dishwasher and microwave drawer. Flanking the main kitchen is a spacious Butler’s pantry with its own sink, refrigerator and dishwasher. Just off the Butler’s pantry is both a mudroom just inside the garage, and additional air-conditioned storage room. Over the garage is a separate bonus/flex room with its own full bath and closet. Upstairs is a huge loft living area plus three full bedroom suites and laundry room. The home is ornamented with expensive fit and finishes as follows: extensive architectural ceiling detail with cove lighting, lighting fixtures, plumbing fixtures, hardware, tile, level 5 smooth drywall finishes, designer wallpaper, and more! Designed with energy efficiency in mind, Natural gas fuels two tankless water heaters, the kitchen range, summer kitchen grill and pool/spa heater. Elaborate landscaping provides beautiful accents and plenty of privacy in the rear outdoor living area. Outdoor living includes a huge covered lanai with retractable screens, summer kitchen, and heated salt-water swimming pool with integrated spa and pool deck, plus outdoor shower and separate pool bath. 10' tall pocket sliding glass doors can open the great-room wall completely to integrate your indoor and outdoor entertaining. Great fortune comes to those who TAKE IMMEDIATE ACTION when opportunity presents itself! Come tour your magnificent new luxury home today!

6 Beds ⋅ 8 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Come tour this brand new, elaborately finished luxury home in Winter Park! Designed and constructed by a well-established, award-winning custom home builder, no expense has been spared. This home is truly a leader in its class! Located just a short walk to the esteemed Audobon K-8 school, East End market, restaurants, shopping, Blue Jacket Park, Baldwin Park. Just a short drive to Park Avenue restaurants and shopping. As you pull up to this vast estate home, the dimensional architectural detail on the home on a huge lot boasts a commanding presence. The 12 foot ceilings on the first floor and 10 foot ceilings on the second floor give the home a voluminous feel throughout. The first floor features a huge master suite with an accessible washer and dryer off the giant walk-in closet, plus an additional full guest suite and separate office. The gourmet kitchen features luxury custom cabinets, an accent island with exotic granite counter tops. Thermador appliances outfit the main kitchen as follows: Large 30” refrigerator and 30” freezer towers, 48” dual oven gas range with ornamental hood, dishwasher and microwave drawer. Flanking the main kitchen is a spacious Butler’s pantry with its own sink, refrigerator and dishwasher. Just off the Butler’s pantry is both a mudroom just inside the garage, and additional air-conditioned storage room. Over the garage is a separate bonus/flex room with its own full bath and closet. Upstairs is a huge loft living area plus three full bedroom suites and laundry room. The home is ornamented with expensive fit and finishes as follows: extensive architectural ceiling detail with cove lighting, lighting fixtures, plumbing fixtures, hardware, tile, level 5 smooth drywall finishes, designer wallpaper, and more! Designed with energy efficiency in mind, Natural gas fuels two tankless water heaters, the kitchen range, summer kitchen grill and pool/spa heater. Elaborate landscaping provides beautiful accents and plenty of privacy in the rear outdoor living area. Outdoor living includes a huge covered lanai with retractable screens, summer kitchen, and heated salt-water swimming pool with integrated spa and pool deck, plus outdoor shower and separate pool bath. 10' tall pocket sliding glass doors can open the great-room wall completely to integrate your indoor and outdoor entertaining. Great fortune comes to those who TAKE IMMEDIATE ACTION when opportunity presents itself! Come tour your magnificent new luxury home today!

2905 Parkland Drive, Winter Park

$824,500

Life is simply better when everything is just around the corner. Perfectly positioned in the heart of Winter Park, this beautifully maintained David Weekley home offers the rare opportunity to enjoy one of Central Florida's most desirable lifestyles. Located just four blocks from Park Avenue and one block from Winter Park Village, you'll also enjoy close proximity to Hannibal Square, Central Park, Publix, the Winter Park Farmers' Market, acclaimed restaurants, boutique shopping, museums, cafés, and everyday conveniences. Built in 2017, this thoughtfully designed home blends timeless architecture with modern luxury across a spacious and functional floor plan. The first floor features three generously sized bedrooms and two full bathrooms, including a private primary suite complete with a spa-inspired bath and an expansive walk-in closet. Upstairs, the home's open-concept living spaces are designed for both everyday comfort and effortless entertaining. Natural light fills the expansive living and dining areas, while the chef's kitchen serves as the centerpiece of the home. Featuring premium Jenn-Air stainless steel appliances, a natural gas cooktop, generous cabinetry, beautiful countertops, and a large center island, it's a space equally suited for hosting friends or preparing a quiet dinner at home. Sliding glass doors extend the living area to an oversized balcony with Trex decking, creating an inviting outdoor retreat for morning coffee, evening cocktails, or dining under the stars. Built with quality and efficiency in mind, the home includes double-pane windows, great insulation, and a gas tankless water heater. The homeowners association further enhances the low-maintenance lifestyle by providing lawn and shrub care, irrigation water, and maintenance of the community perimeter wall, allowing you to spend more time enjoying your home and less time maintaining it. More than just a beautiful residence, this home offers an exceptional opportunity to experience the very best of Winter Park. Enjoy dinner on Park Avenue, spend Saturday mornings at the Farmers' Market, explore the boutiques of Hannibal Square, relax in nearby parks, or meet friends for coffee, all just moments from your front door. This is a home where luxury, convenience, and one of Winter Park's most sought-after locations come together beautifully.

3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code

Life is simply better when everything is just around the corner. Perfectly positioned in the heart of Winter Park, this beautifully maintained David Weekley home offers the rare opportunity to enjoy one of Central Florida's most desirable lifestyles. Located just four blocks from Park Avenue and one block from Winter Park Village, you'll also enjoy close proximity to Hannibal Square, Central Park, Publix, the Winter Park Farmers' Market, acclaimed restaurants, boutique shopping, museums, cafés, and everyday conveniences. Built in 2017, this thoughtfully designed home blends timeless architecture with modern luxury across a spacious and functional floor plan. The first floor features three generously sized bedrooms and two full bathrooms, including a private primary suite complete with a spa-inspired bath and an expansive walk-in closet. Upstairs, the home's open-concept living spaces are designed for both everyday comfort and effortless entertaining. Natural light fills the expansive living and dining areas, while the chef's kitchen serves as the centerpiece of the home. Featuring premium Jenn-Air stainless steel appliances, a natural gas cooktop, generous cabinetry, beautiful countertops, and a large center island, it's a space equally suited for hosting friends or preparing a quiet dinner at home. Sliding glass doors extend the living area to an oversized balcony with Trex decking, creating an inviting outdoor retreat for morning coffee, evening cocktails, or dining under the stars. Built with quality and efficiency in mind, the home includes double-pane windows, great insulation, and a gas tankless water heater. The homeowners association further enhances the low-maintenance lifestyle by providing lawn and shrub care, irrigation water, and maintenance of the community perimeter wall, allowing you to spend more time enjoying your home and less time maintaining it. More than just a beautiful residence, this home offers an exceptional opportunity to experience the very best of Winter Park. Enjoy dinner on Park Avenue, spend Saturday mornings at the Farmers' Market, explore the boutiques of Hannibal Square, relax in nearby parks, or meet friends for coffee, all just moments from your front door. This is a home where luxury, convenience, and one of Winter Park's most sought-after locations come together beautifully.

439 N Capen Avenue, Winter Park

$449,000

Under contract-accepting backup offers. Tucked away on a quiet dead-end street just off Lake Killarney, this solid block 1960's ranch at 2611 Lotafun Avenue offers over 1,800 SF of living space with room to make it your own. Featuring 3 bedrooms and 2 full baths, this home boasts a charming front living room with a wood-burning fireplace, PLUS a spacious family room/sunroom with its own fireplace — perfect for cozy nights or entertaining. The primary bedroom features an en suite bath, while the hall bath charms with original tilework. Step outside to your private pool, set on a generous 0.24-acre lot with a backyard shed for extra storage. Additional highlights include an attached 2-car garage with bonus storage room, interior laundry, and a 2022 roof. All new electrical was just installed in June 2026 by Skolfield Homes, giving buyers peace of mind on one of the big-ticket items. Enjoy the tranquility of this established neighborhood while staying close to major roadways, shopping, and dining. Homes with this much character and potential in Winter Park don't come around often — bring your vision and make this one shine!

3 Beds ⋅ 2 Baths ⋅ Justamere Camp Rep SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Tucked away on a quiet dead-end street just off Lake Killarney, this solid block 1960's ranch at 2611 Lotafun Avenue offers over 1,800 SF of living space with room to make it your own. Featuring 3 bedrooms and 2 full baths, this home boasts a charming front living room with a wood-burning fireplace, PLUS a spacious family room/sunroom with its own fireplace — perfect for cozy nights or entertaining. The primary bedroom features an en suite bath, while the hall bath charms with original tilework. Step outside to your private pool, set on a generous 0.24-acre lot with a backyard shed for extra storage. Additional highlights include an attached 2-car garage with bonus storage room, interior laundry, and a 2022 roof. All new electrical was just installed in June 2026 by Skolfield Homes, giving buyers peace of mind on one of the big-ticket items. Enjoy the tranquility of this established neighborhood while staying close to major roadways, shopping, and dining. Homes with this much character and potential in Winter Park don't come around often — bring your vision and make this one shine!

2611 Lotafun Avenue, Winter Park

$575,000

Under contract-accepting backup offers. Completely reimagined in 2025, this stunning 2-bedroom, 2.5-bath townhome offers the perfect blend of modern luxury and an unbeatable Winter Park location. Just minutes from Rollins College, Park Avenue, boutique shopping, award-winning dining, and everything that makes Winter Park so desirable, this move-in-ready home has been thoughtfully renovated from top to bottom with timeless, designer-selected finishes. The heart of the home is the beautifully redesigned kitchen featuring Sarah Sherman Samuel cabinetry and hardware, gorgeous marble countertops, a custom marble ledge, and all-new appliances. Throughout the home, you'll find new flooring, smooth-finished walls, fresh interior paint, recessed lighting with dimmers, updated electrical, new interior doors and hardware, and new baseboards, creating a clean, sophisticated aesthetic. Upstairs, both spacious bedrooms feature beautifully updated en-suite bathrooms, while the primary suite includes a custom marble-top vanity and a thoughtfully designed built-in closet system. Every bathroom has been fully renovated with high-end finishes that elevate the home's overall design. Step outside to your own private outdoor retreat featuring a large covered patio with low-maintenance turf—perfect for entertaining, relaxing, or enjoying your morning coffee year-round. Major mechanical updates provide added peace of mind, including a 2023 air handler, 2024 water heater, all-new A/C ductwork, and added attic insulation for improved energy efficiency. With nearly every surface and major system thoughtfully updated, this exceptional Winter Park townhome offers luxurious, turnkey living in one of Central Florida's most sought-after neighborhoods.

2 Beds ⋅ 3 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Completely reimagined in 2025, this stunning 2-bedroom, 2.5-bath townhome offers the perfect blend of modern luxury and an unbeatable Winter Park location. Just minutes from Rollins College, Park Avenue, boutique shopping, award-winning dining, and everything that makes Winter Park so desirable, this move-in-ready home has been thoughtfully renovated from top to bottom with timeless, designer-selected finishes. The heart of the home is the beautifully redesigned kitchen featuring Sarah Sherman Samuel cabinetry and hardware, gorgeous marble countertops, a custom marble ledge, and all-new appliances. Throughout the home, you'll find new flooring, smooth-finished walls, fresh interior paint, recessed lighting with dimmers, updated electrical, new interior doors and hardware, and new baseboards, creating a clean, sophisticated aesthetic. Upstairs, both spacious bedrooms feature beautifully updated en-suite bathrooms, while the primary suite includes a custom marble-top vanity and a thoughtfully designed built-in closet system. Every bathroom has been fully renovated with high-end finishes that elevate the home's overall design. Step outside to your own private outdoor retreat featuring a large covered patio with low-maintenance turf—perfect for entertaining, relaxing, or enjoying your morning coffee year-round. Major mechanical updates provide added peace of mind, including a 2023 air handler, 2024 water heater, all-new A/C ductwork, and added attic insulation for improved energy efficiency. With nearly every surface and major system thoughtfully updated, this exceptional Winter Park townhome offers luxurious, turnkey living in one of Central Florida's most sought-after neighborhoods.

1122 Washington Avenue Unit 7B, Winter Park

$250,000

Perfect Property for Builder or Investor Nestled in the sought-after Karolina on Killarney neighborhood, this classic 1935 bungalow offers timeless character and an exceptional opportunity to create your dream home in one of Central Florida's most desirable locations. Situated on a generous lot, this 2-bedroom, 1-bath residence features approximately 1,408 square feet of living space with a flexible floor plan ready for your personal vision. Original architectural details provide a warm foundation for renovation, restoration, or expansion, while the spacious backyard offers ample room for outdoor entertaining, gardening, or future additions. Whether you're a homeowner looking to customize a historic property or an investor seeking your next project, this home presents outstanding value in a neighborhood surrounded by beautifully updated residences. Ideally located just minutes from Park Avenue's renowned dining, boutique shopping, museums, and year-round events, you'll also enjoy convenient access to Downtown Orlando, College Park, Winter Park Village, major hospitals, and top commuter routes. With no HOA and a prime location in the heart of Winter Park, opportunities like this are increasingly rare. Bring your imagination and unlock the incredible potential this charming property has to offer!

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

Perfect Property for Builder or Investor Nestled in the sought-after Karolina on Killarney neighborhood, this classic 1935 bungalow offers timeless character and an exceptional opportunity to create your dream home in one of Central Florida's most desirable locations. Situated on a generous lot, this 2-bedroom, 1-bath residence features approximately 1,408 square feet of living space with a flexible floor plan ready for your personal vision. Original architectural details provide a warm foundation for renovation, restoration, or expansion, while the spacious backyard offers ample room for outdoor entertaining, gardening, or future additions. Whether you're a homeowner looking to customize a historic property or an investor seeking your next project, this home presents outstanding value in a neighborhood surrounded by beautifully updated residences. Ideally located just minutes from Park Avenue's renowned dining, boutique shopping, museums, and year-round events, you'll also enjoy convenient access to Downtown Orlando, College Park, Winter Park Village, major hospitals, and top commuter routes. With no HOA and a prime location in the heart of Winter Park, opportunities like this are increasingly rare. Bring your imagination and unlock the incredible potential this charming property has to offer!

1960 Biscayne Drive, Winter Park

$1,625,000

Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exceptional 4-bedroom, 4-bath pool home with a dedicated office offers timeless design, thoughtful updates, and an unbeatable location. A welcoming covered front porch provides the perfect spot to enjoy your morning coffee. Inside, soaring ceilings, extensive moldings, travertine and hardwood floors, and abundant natural light create an elegant first impression. Just off the foyer, French doors open to a private office, ideal for working from home. A secondary bedroom and full bath with a walk-in shower are conveniently located on the main level. The spacious kitchen flows seamlessly into the family room and features granite countertops, solid wood soft-close cabinetry, a gas cooktop, wall oven, breakfast bar, wet bar, walk-in pantry, and a sunny breakfast nook overlooking the lanai and pool. The adjoining family room is anchored by a gas fireplace and French doors leading outdoors. The covered lanai showcases a tongue-and-groove ceiling and remote-controlled screens, creating the perfect setting for year-round entertaining. The generous first-floor primary suite offers space for a sitting area and features two custom walk-in closets, dual vanities, a soaking tub, separate shower, and private water closet. A beautiful wrought-iron staircase leads upstairs to two generous en-suite bedrooms and a cozy loft. The private backyard is designed for relaxation and entertaining, featuring a saltwater pool and spa surrounded by lush landscaping. Additional highlights include two newer HVAC systems (2022 and 2023), a gas water heater (2022), central vacuum system, built-in Home Team pest defense system, and plantation shutters throughout. Located within the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home is ideally situated between Park Avenue and Corrine Drive, with downtown Orlando just minutes away.

341 E Reading Way, Winter Park

$499,000

Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Huge back yard with plenty of potential space for ADU! Move in ready, no HOA, and just a short stroll from Rollins College and beautiful Park Avenue. A rare must see opportunity!

2 Beds ⋅ 1 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code

Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Huge back yard with plenty of potential space for ADU! Move in ready, no HOA, and just a short stroll from Rollins College and beautiful Park Avenue. A rare must see opportunity!

981 Aragon Avenue, Winter Park

$1,025,000

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

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

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

1138 S Pennsylvania Avenue, Winter Park

$1,099,000

Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character with all-new finishes and systems. An open living, dining, and kitchen core opens to a light-filled sitting area, with white oak floors and designer lighting and ceiling fans throughout. The kitchen stuns with Taj Mahal quartzite counters and KitchenAid stainless appliances. Out back, an expanded patio overlooks a private, fenced yard built for gathering. Everything is new: roof, windows, 200-amp electrical, plumbing with new water heater, HVAC ductwork, and Nest thermostat. Best of all, you can live it on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. A turnkey classic in one of Winter Park's most established, walkable neighborhoods.

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

Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character with all-new finishes and systems. An open living, dining, and kitchen core opens to a light-filled sitting area, with white oak floors and designer lighting and ceiling fans throughout. The kitchen stuns with Taj Mahal quartzite counters and KitchenAid stainless appliances. Out back, an expanded patio overlooks a private, fenced yard built for gathering. Everything is new: roof, windows, 200-amp electrical, plumbing with new water heater, HVAC ductwork, and Nest thermostat. Best of all, you can live it on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. A turnkey classic in one of Winter Park's most established, walkable neighborhoods.

3006 Northwood Boulevard, Winter Park

$2,475,000

Nestled within the highly sought-after Kenilworth Shores neighborhood, this extraordinary new construction home represents a rare opportunity to own one of Winter Park's finest new builds. Thoughtfully designed with an exceptional floor plan and uncompromising level of craftsmanship, detail, and finishes. This home is located just minutes from everything Winter Park has to offer. Step through the front doors into a breathtaking two-story foyer where soaring ceilings, and a statement chandelier create an unforgettable first impression. Designed for both everyday living and effortless entertaining, the floor plan is one of the home's most desirable features. Rare for Winter Park, the residence offers a luxurious primary suite, private guest suite, and dedicated office all on the main level. The expansive living room serves as the heart of the home, showcasing extensive custom trim work, an electric fireplace, and bespoke built-in cabinetry with LED underlighting. Walls of glass create a seamless connection to the outdoor living spaces while filling the home with natural light. The chef's kitchen is a true showpiece, designed to satisfy even the most discerning culinary enthusiast, featuring stunning Calacatta quartz countertops, custom cabinetry, a paneled built-in refrigerator, and a complete suite of Thermador appliances. Adjacent to the kitchen, the formal dining room creates an elegant setting for entertaining, featuring a custom dry bar complete with a wine refrigerator. Privately tucked away, the primary suite serves as a true retreat, featuring sliding glass doors leading directly to the backyard oasis, creating a seamless indoor-outdoor connection. The spa-inspired primary bath features marble mosaic tile, floating mirrors above dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous walk-in closet. The upper level continues the home's thoughtful design with a spacious loft, accompanied by three generously sized bedrooms. Outdoor living is equally impressive, a covered lanai creates the perfect setting for year-round entertaining and is fully equipped with a summer kitchen. The beautifully designed backyard retreat showcases a sparkling pool and spa surrounded by lush green space, offering the ideal balance of recreation, relaxation, and privacy. Perfectly positioned in the heart of Winter Park, residents enjoy tree-lined streets while remaining just a golf-cart ride from the boutiques, award-winning restaurants, and cafés, of Park Avenue. The home is also conveniently located near Winter Park High School, Advent Health Winter Park, and the beloved Cady Way Park, where tennis courts, soccer fields, baseball fields, walking trails create one of Central Florida's most desirable active lifestyles. Don't miss out on this amazing new home!

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Nestled within the highly sought-after Kenilworth Shores neighborhood, this extraordinary new construction home represents a rare opportunity to own one of Winter Park's finest new builds. Thoughtfully designed with an exceptional floor plan and uncompromising level of craftsmanship, detail, and finishes. This home is located just minutes from everything Winter Park has to offer. Step through the front doors into a breathtaking two-story foyer where soaring ceilings, and a statement chandelier create an unforgettable first impression. Designed for both everyday living and effortless entertaining, the floor plan is one of the home's most desirable features. Rare for Winter Park, the residence offers a luxurious primary suite, private guest suite, and dedicated office all on the main level. The expansive living room serves as the heart of the home, showcasing extensive custom trim work, an electric fireplace, and bespoke built-in cabinetry with LED underlighting. Walls of glass create a seamless connection to the outdoor living spaces while filling the home with natural light. The chef's kitchen is a true showpiece, designed to satisfy even the most discerning culinary enthusiast, featuring stunning Calacatta quartz countertops, custom cabinetry, a paneled built-in refrigerator, and a complete suite of Thermador appliances. Adjacent to the kitchen, the formal dining room creates an elegant setting for entertaining, featuring a custom dry bar complete with a wine refrigerator. Privately tucked away, the primary suite serves as a true retreat, featuring sliding glass doors leading directly to the backyard oasis, creating a seamless indoor-outdoor connection. The spa-inspired primary bath features marble mosaic tile, floating mirrors above dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous walk-in closet. The upper level continues the home's thoughtful design with a spacious loft, accompanied by three generously sized bedrooms. Outdoor living is equally impressive, a covered lanai creates the perfect setting for year-round entertaining and is fully equipped with a summer kitchen. The beautifully designed backyard retreat showcases a sparkling pool and spa surrounded by lush green space, offering the ideal balance of recreation, relaxation, and privacy. Perfectly positioned in the heart of Winter Park, residents enjoy tree-lined streets while remaining just a golf-cart ride from the boutiques, award-winning restaurants, and cafés, of Park Avenue. The home is also conveniently located near Winter Park High School, Advent Health Winter Park, and the beloved Cady Way Park, where tennis courts, soccer fields, baseball fields, walking trails create one of Central Florida's most desirable active lifestyles. Don't miss out on this amazing new home!

426 Worthington Drive, Winter Park

$779,000

Under contract-accepting backup offers. Beautiful corner 4 bedroom home in the heart of Kenilworth Shores in Winter Park.

4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Beautiful corner 4 bedroom home in the heart of Kenilworth Shores in Winter Park.

1826 Banchory Road, Winter Park

$1,849,900

Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park