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Welcome to 5415 N Lake Burkett Lane, a beautiful home located in the desirable Trinity Bay community of Winter Park, with a neighborhood boat slip, dock, and lake access! Offering 3 bedrooms, 2.5 bathrooms, and 2,027 square feet of thoughtfully designed living space, this home makes a lasting first impression with its soaring vaulted ceilings and inviting atmosphere. The open, well-designed floorplan creates a natural flow throughout the main living areas, making it perfect for both everyday living and entertaining. The downstairs features spacious living and dining areas, a convenient half bathroom, a dedicated laundry room, and direct access to the attached two-car garage. Upstairs, you'll find all three bedrooms, offering a comfortable separation between the main living spaces and private retreats. The layout provides a wonderful balance of functionality and comfort, with plenty of room to accommodate a variety of lifestyles. Step outside to enjoy the screened-in rear patio, the perfect spot to enjoy your morning coffee or unwind in the evenings while taking in the outdoors. Beyond the patio, you'll find a generously sized backyard with endless possibilities! Whether you envision creating your dream outdoor entertaining space, adding a garden, designing a play area, or simply enjoying the extra room to relax, this backyard is a blank canvas waiting for your personal touch. With its spacious layout, soaring ceilings, and fantastic potential, this Trinity Bay home is an opportunity you won't want to miss!

3 Beds ⋅ 3 Baths ⋅ Trinity Bay Ph 2 SubDv. ⋅ 32792 Zip Code

Welcome to 5415 N Lake Burkett Lane, a beautiful home located in the desirable Trinity Bay community of Winter Park, with a neighborhood boat slip, dock, and lake access! Offering 3 bedrooms, 2.5 bathrooms, and 2,027 square feet of thoughtfully designed living space, this home makes a lasting first impression with its soaring vaulted ceilings and inviting atmosphere. The open, well-designed floorplan creates a natural flow throughout the main living areas, making it perfect for both everyday living and entertaining. The downstairs features spacious living and dining areas, a convenient half bathroom, a dedicated laundry room, and direct access to the attached two-car garage. Upstairs, you'll find all three bedrooms, offering a comfortable separation between the main living spaces and private retreats. The layout provides a wonderful balance of functionality and comfort, with plenty of room to accommodate a variety of lifestyles. Step outside to enjoy the screened-in rear patio, the perfect spot to enjoy your morning coffee or unwind in the evenings while taking in the outdoors. Beyond the patio, you'll find a generously sized backyard with endless possibilities! Whether you envision creating your dream outdoor entertaining space, adding a garden, designing a play area, or simply enjoying the extra room to relax, this backyard is a blank canvas waiting for your personal touch. With its spacious layout, soaring ceilings, and fantastic potential, this Trinity Bay home is an opportunity you won't want to miss!

5415 N Lake Burkett Lane, Winter Park

$739,000

Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer featuring soaring ceilings of nearly 20 feet, creating an impressive and light-filled living space. The open layout seamlessly connects the main living areas, ideal for entertaining and family gatherings. This thoughtfully designed home features 4 spacious bedrooms and 3.5 bathrooms, including dual primary suites—one conveniently located on the main level and another upstairs—providing flexibility for multi-generational living or guest accommodations. A dedicated private office on the first floor offers the perfect work-from-home environment. Step outside to a beautifully maintained backyard with water view—perfect for relaxing or enjoying Florida’s outdoor lifestyle year-round. Extensively upgraded throughout, the home showcases high-quality finishes with a solid wood staircase. This is a rare opportunity to own a meticulously upgraded home in a prime Winter Park location—ideal as a primary residence or a high-potential investment property.

4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code

Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer featuring soaring ceilings of nearly 20 feet, creating an impressive and light-filled living space. The open layout seamlessly connects the main living areas, ideal for entertaining and family gatherings. This thoughtfully designed home features 4 spacious bedrooms and 3.5 bathrooms, including dual primary suites—one conveniently located on the main level and another upstairs—providing flexibility for multi-generational living or guest accommodations. A dedicated private office on the first floor offers the perfect work-from-home environment. Step outside to a beautifully maintained backyard with water view—perfect for relaxing or enjoying Florida’s outdoor lifestyle year-round. Extensively upgraded throughout, the home showcases high-quality finishes with a solid wood staircase. This is a rare opportunity to own a meticulously upgraded home in a prime Winter Park location—ideal as a primary residence or a high-potential investment property.

2315 Kestrel Perch Place, Winter Park

$1,949,000

Improved! Positioned on a charming brick-lined street in historic Winter Park adjacent to Windsong, this custom-built residence pairs solid architectural craftsmanship with extensive modern upgrades. Refinished Mahoghany double doors open to 12-foot ceilings, soft curved archways and a thoughtful layout finished with travertine on the main level and reclaimed maple and beech hardwoods upstairs and in the primary suite. The expansive, open family room centers around a gorgeous gas fireplace and flows seamlessly into a true chef’s kitchen featuring a new marble tile backsplash, Rejuvenation drum chandelier, granite countertops, prep island, custom lighted cabinetry, a six-burner gas range with pot filler, double ovens with warming drawer and a Thermador French-door refrigerator. An adjoining butler’s pantry with wine fridge and wet bar connects directly to the formal dining room, complemented by a newly constructed dedicated wine room and a quiet main-level office or library. The first-floor primary suite offers a private retreat with detailed tray ceilings, dual walk-in closets, a jetted soaking tub, twin vanities and direct French-door access to the outdoor living area. Upstairs, three spacious bedrooms and two full baths including a private en-suite accompany a classic Juliet balcony overlooking the pretty front yard. Designed for effortless Florida living, the covered summer kitchen is perfect for relaxing with friends and watching football, featuring a built-in grill, custom copper hood and beverage fridge, while the second covered lanai is perfectly situated for a hot tub. Both look out over a private saltwater pool framed by maintence-free turf, lighting and a newly planted podocarpus privacy hedge. Recent capital improvements include new dual HVAC units, a tankless water heater, whole-home surge protection, central vacuum, smart-home automation for pool, security and irrigation, six new exterior fixtures, complete interior and exterior repainting, epoxy-coated garage floors, extensive kitchen renovations, refinished front entry doors and fully refreshed landscaping. Enjoy no HOA dues, seasonal neighborhood block gatherings and quick access to Lake Mizell, premier schools (Brookshire, WPHS, Park Maitland, Lake Highland, Geneva) and a convenient pedestrian cut-through directly to Park Avenue dining and shopping.

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

Improved! Positioned on a charming brick-lined street in historic Winter Park adjacent to Windsong, this custom-built residence pairs solid architectural craftsmanship with extensive modern upgrades. Refinished Mahoghany double doors open to 12-foot ceilings, soft curved archways and a thoughtful layout finished with travertine on the main level and reclaimed maple and beech hardwoods upstairs and in the primary suite. The expansive, open family room centers around a gorgeous gas fireplace and flows seamlessly into a true chef’s kitchen featuring a new marble tile backsplash, Rejuvenation drum chandelier, granite countertops, prep island, custom lighted cabinetry, a six-burner gas range with pot filler, double ovens with warming drawer and a Thermador French-door refrigerator. An adjoining butler’s pantry with wine fridge and wet bar connects directly to the formal dining room, complemented by a newly constructed dedicated wine room and a quiet main-level office or library. The first-floor primary suite offers a private retreat with detailed tray ceilings, dual walk-in closets, a jetted soaking tub, twin vanities and direct French-door access to the outdoor living area. Upstairs, three spacious bedrooms and two full baths including a private en-suite accompany a classic Juliet balcony overlooking the pretty front yard. Designed for effortless Florida living, the covered summer kitchen is perfect for relaxing with friends and watching football, featuring a built-in grill, custom copper hood and beverage fridge, while the second covered lanai is perfectly situated for a hot tub. Both look out over a private saltwater pool framed by maintence-free turf, lighting and a newly planted podocarpus privacy hedge. Recent capital improvements include new dual HVAC units, a tankless water heater, whole-home surge protection, central vacuum, smart-home automation for pool, security and irrigation, six new exterior fixtures, complete interior and exterior repainting, epoxy-coated garage floors, extensive kitchen renovations, refinished front entry doors and fully refreshed landscaping. Enjoy no HOA dues, seasonal neighborhood block gatherings and quick access to Lake Mizell, premier schools (Brookshire, WPHS, Park Maitland, Lake Highland, Geneva) and a convenient pedestrian cut-through directly to Park Avenue dining and shopping.

1398 Grove Terrace, Winter Park

$1,499,000

Photos coming soon. Experience timeless elegance and exceptional living in the heart of Winter Park! Nestled along a charming, quiet brick-lined street just moments from iconic Park Avenue, this beautifully designed custom residence offers the perfect combination of sophistication, comfort, and Florida indoor-outdoor living. Featuring 4 bedrooms, 3 full bathrooms, 2 half bathrooms, and 3,478 square feet of living space, this impressive home welcomes you with soaring 10-foot ceilings, rich Brazilian cherry hardwood floors, elegant architectural details, and an abundance of natural light. At the heart of the home, the gourmet kitchen is designed for both everyday living and effortless entertaining, featuring a spacious center island, natural wood cabinetry, premium cooking appliances, built-in refrigerator, and wine refrigerator. The kitchen flows seamlessly into the inviting family room, complete with a beautiful gas fireplace. The luxurious first-floor primary suite offers a peaceful retreat with generous walk-in closets, a spa-inspired bathroom, and French doors opening to the private screened pool and patio. Upstairs, additional bedrooms and a spacious bonus room provide flexibility for a home office, fitness studio, media room, or guest accommodations. Step outside to your own private oasis, where a sparkling pool, relaxing spa, mature landscaping, and inviting outdoor living spaces create an ideal setting for entertaining or unwinding year-round. Additional highlights include formal living and dining spaces, an attached two-car garage, abundant storage, and a desirable location with no HOA. Enjoy the best of the Winter Park lifestyle, with convenient access to Park Avenue's celebrated restaurants, boutique shopping, cafés, cultural attractions, parks, and nearby lakes. An exceptional opportunity to own a distinctive residence in one of Central Florida's most desirable communities. Schedule your private showing and discover everything this Winter Park home has!

4 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

Photos coming soon. Experience timeless elegance and exceptional living in the heart of Winter Park! Nestled along a charming, quiet brick-lined street just moments from iconic Park Avenue, this beautifully designed custom residence offers the perfect combination of sophistication, comfort, and Florida indoor-outdoor living. Featuring 4 bedrooms, 3 full bathrooms, 2 half bathrooms, and 3,478 square feet of living space, this impressive home welcomes you with soaring 10-foot ceilings, rich Brazilian cherry hardwood floors, elegant architectural details, and an abundance of natural light. At the heart of the home, the gourmet kitchen is designed for both everyday living and effortless entertaining, featuring a spacious center island, natural wood cabinetry, premium cooking appliances, built-in refrigerator, and wine refrigerator. The kitchen flows seamlessly into the inviting family room, complete with a beautiful gas fireplace. The luxurious first-floor primary suite offers a peaceful retreat with generous walk-in closets, a spa-inspired bathroom, and French doors opening to the private screened pool and patio. Upstairs, additional bedrooms and a spacious bonus room provide flexibility for a home office, fitness studio, media room, or guest accommodations. Step outside to your own private oasis, where a sparkling pool, relaxing spa, mature landscaping, and inviting outdoor living spaces create an ideal setting for entertaining or unwinding year-round. Additional highlights include formal living and dining spaces, an attached two-car garage, abundant storage, and a desirable location with no HOA. Enjoy the best of the Winter Park lifestyle, with convenient access to Park Avenue's celebrated restaurants, boutique shopping, cafés, cultural attractions, parks, and nearby lakes. An exceptional opportunity to own a distinctive residence in one of Central Florida's most desirable communities. Schedule your private showing and discover everything this Winter Park home has!

1350 Lyndale Boulevard, Winter Park

$5,950,000

Under Construction. Exceptional waterfront living meets European-inspired design in this new Vimaro Homes residence on Lake Sylvan. Positioned on an oversized Winter Park lot with 130 feet of water frontage, the home pairs timeless architecture, richly detailed interiors, and expansive outdoor living. Led by a husband-and-wife team originally from Europe, Vimaro Homes brings together her expertise in interior design and his in construction. Their hands-on approach brings a personal commitment to every selection and detail, prioritizing lasting quality, thoughtful design, and craftsmanship over the cost-driven formulas common in investment-built spec homes. A striking façade and tile roof establish an elegant arrival, complemented by a dual-entry driveway featuring a diamond-patterned composition of turf and concrete. An underground three-car garage preserves the architectural approach, while an elevator connects all three levels. Inside, a marble mosaic entry introduces intricate trim work and classic reeded crown molding, establishing the home’s enduring character. The spacious living room features a marble-wrapped fireplace, custom built-ins with LED up-lighting, and expansive sliding doors framing views of the pool and lake. The kitchen pairs marble countertops and custom inset cabinetry with Perrin & Rowe fixtures and Thermador appliances, including a paneled refrigerator. A substantial scullery with a prep kitchen and pantry supports entertaining, while the nearby dining room overlooks the water. The downstairs primary suite offers a private retreat with its own fireplace and an expansive, custom-fitted walk-in closet with a center island. The primary bath features Casablanca marble tile, dual vanities, Perrin & Rowe fixtures, and a spacious walk-in shower. Upstairs, four additional bedrooms each offer an ensuite bath and walk-in closet, alongside a bonus room, laundry room, and terrace. Throughout the home, natural stone, finely crafted cabinetry, and classic architectural details reflect the team’s European influences. Outdoors, a generous lanai with retractable screens and a full summer kitchen extends the living spaces toward Lake Sylvan. A three-tiered deck brings together a pool, spa, and sweeping water views, while expansive green space and a dock complete the waterfront setting. Set on a brick street moments from Park Avenue’s restaurants, boutiques, and cafés, this residence combines Winter Park’s distinctive character with an exceptional lakefront setting. Shaped by the personal vision and craftsmanship of Vimaro Homes, it offers a refined expression of waterfront living.

5 Beds ⋅ 6 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Under Construction. Exceptional waterfront living meets European-inspired design in this new Vimaro Homes residence on Lake Sylvan. Positioned on an oversized Winter Park lot with 130 feet of water frontage, the home pairs timeless architecture, richly detailed interiors, and expansive outdoor living. Led by a husband-and-wife team originally from Europe, Vimaro Homes brings together her expertise in interior design and his in construction. Their hands-on approach brings a personal commitment to every selection and detail, prioritizing lasting quality, thoughtful design, and craftsmanship over the cost-driven formulas common in investment-built spec homes. A striking façade and tile roof establish an elegant arrival, complemented by a dual-entry driveway featuring a diamond-patterned composition of turf and concrete. An underground three-car garage preserves the architectural approach, while an elevator connects all three levels. Inside, a marble mosaic entry introduces intricate trim work and classic reeded crown molding, establishing the home’s enduring character. The spacious living room features a marble-wrapped fireplace, custom built-ins with LED up-lighting, and expansive sliding doors framing views of the pool and lake. The kitchen pairs marble countertops and custom inset cabinetry with Perrin & Rowe fixtures and Thermador appliances, including a paneled refrigerator. A substantial scullery with a prep kitchen and pantry supports entertaining, while the nearby dining room overlooks the water. The downstairs primary suite offers a private retreat with its own fireplace and an expansive, custom-fitted walk-in closet with a center island. The primary bath features Casablanca marble tile, dual vanities, Perrin & Rowe fixtures, and a spacious walk-in shower. Upstairs, four additional bedrooms each offer an ensuite bath and walk-in closet, alongside a bonus room, laundry room, and terrace. Throughout the home, natural stone, finely crafted cabinetry, and classic architectural details reflect the team’s European influences. Outdoors, a generous lanai with retractable screens and a full summer kitchen extends the living spaces toward Lake Sylvan. A three-tiered deck brings together a pool, spa, and sweeping water views, while expansive green space and a dock complete the waterfront setting. Set on a brick street moments from Park Avenue’s restaurants, boutiques, and cafés, this residence combines Winter Park’s distinctive character with an exceptional lakefront setting. Shaped by the personal vision and craftsmanship of Vimaro Homes, it offers a refined expression of waterfront living.

1441 Grove Terrace, Winter Park

$1,425,000

Under Construction. Nestled on a quiet street on an oversized homesite in Winter Park, this stunning new construction home by David Weekley Homes blends timeless design with modern comfort. Featuring 4 spacious bedrooms and 4.5 beautifully appointed baths, the home offers an ideal layout for both everyday living and entertaining. A private study provides a perfect work-from-home retreat, while the dedicated media room invites movie nights and game-day gatherings. Upstairs, a versatile loft adds flexible living space for a playroom, lounge, or fitness area. Thoughtfully designed with high-quality finishes and abundant natural light, this home delivers exceptional craftsmanship in one of Central Florida’s most desirable neighborhoods—just minutes from top schools, parks, dining, and shopping.

4 Beds ⋅ 5 Baths ⋅ Kenilworth Estates SubDv. ⋅ 32792 Zip Code

Under Construction. Nestled on a quiet street on an oversized homesite in Winter Park, this stunning new construction home by David Weekley Homes blends timeless design with modern comfort. Featuring 4 spacious bedrooms and 4.5 beautifully appointed baths, the home offers an ideal layout for both everyday living and entertaining. A private study provides a perfect work-from-home retreat, while the dedicated media room invites movie nights and game-day gatherings. Upstairs, a versatile loft adds flexible living space for a playroom, lounge, or fitness area. Thoughtfully designed with high-quality finishes and abundant natural light, this home delivers exceptional craftsmanship in one of Central Florida’s most desirable neighborhoods—just minutes from top schools, parks, dining, and shopping.

2237 Woodcrest Drive, Winter Park

$1,379,900

Under Construction. NEW CONSTRUCTION! New photos coming soon! Photos of a similar model. Welcome to Winter Park Grove — Winter Park’s newest community by one of the area's finest builders. This stunning new farmhouse-inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant 2 story entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, an oversized island, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool & lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual sink vanity, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. Upstairs, a large bonus room with a closet offers versatility as a second living, game room and it can even be enclosed to create an additional bedroom. Two spacious bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. Photos are of a similar model, finishes may vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

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

Under Construction. NEW CONSTRUCTION! New photos coming soon! Photos of a similar model. Welcome to Winter Park Grove — Winter Park’s newest community by one of the area's finest builders. This stunning new farmhouse-inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant 2 story entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, an oversized island, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool & lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual sink vanity, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. Upstairs, a large bonus room with a closet offers versatility as a second living, game room and it can even be enclosed to create an additional bedroom. Two spacious bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. Photos are of a similar model, finishes may vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

1534 Miller Avenue, Winter Park

$849,900

Under Construction. Welcome to your NEW Home! This residence to-be-built is a rare single story home. This bright open floor-plan features a large great room open to the kitchen. Enjoy dining at the island and plenty of space to entertain, featuring stainless appliances, and an extra large walk-in pantry (6.8 x 7 ft) to meet all your storage needs. The Primary bedroom is located off of the main living with a spacious (10x 6.5 ft) walk in closet. The primary bath features double sinks and a separate shower and soaking tub as well as a private toilet room. All of the secondary bedrooms are generously sized with signifcant built-in closet space. The extra large laundry space gives ample additional storage. 2 Car garage. Summer Kitchen with a grill available to add-on. Don't wait, take this opportunity to make this pre-construction residence you perfect place to call home.

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

Under Construction. Welcome to your NEW Home! This residence to-be-built is a rare single story home. This bright open floor-plan features a large great room open to the kitchen. Enjoy dining at the island and plenty of space to entertain, featuring stainless appliances, and an extra large walk-in pantry (6.8 x 7 ft) to meet all your storage needs. The Primary bedroom is located off of the main living with a spacious (10x 6.5 ft) walk in closet. The primary bath features double sinks and a separate shower and soaking tub as well as a private toilet room. All of the secondary bedrooms are generously sized with signifcant built-in closet space. The extra large laundry space gives ample additional storage. 2 Car garage. Summer Kitchen with a grill available to add-on. Don't wait, take this opportunity to make this pre-construction residence you perfect place to call home.

2011 Harmon Avenue, Winter Park

$385,000

Move-In Ready & Priced to Sell! Nestled in a prime Winter Park location, this 3-bedroom, 2-bathroom completely renovated and upgraded single-story home delivers effortless living on an oversized lot. Designed with a sought-after split-bedroom layout, the light-filled interior showcases an upgraded kitchen with Stainless Steel appliances, new Quartz countertops and two completely refreshed bathrooms, one with a new tub. Fresh paint, new flooring, new doors, smooth ceilings, new window coverings, updated hardware, fixtures and fans leave nothing for a buyer to worry about. Major updates include a newer HVAC system and a roof replaced in 2015. Home was re-piped by Emerald Plumbing. The backyard awaits your imagination and offers a unique opportunity to design your own outdoor oasis, ideal for entertaining, building an outdoor kitchen or adding your dream pool. The long-time owner made a significant investment to upgrade this home and has pre-inspected it, offering buyers peace of mind with a full report ready for review. Enjoy convenient suburban living just minutes from Publix, Walmart, top-rated schools, Red Bug Lake Park and local dining. With easy highway access, you are under 30 minutes from UCF, Downtown Orlando, Universal Studios and the airport. Whether you are looking for a turnkey home or a high-demand investment property, this gem won’t last long.

3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code

Move-In Ready & Priced to Sell! Nestled in a prime Winter Park location, this 3-bedroom, 2-bathroom completely renovated and upgraded single-story home delivers effortless living on an oversized lot. Designed with a sought-after split-bedroom layout, the light-filled interior showcases an upgraded kitchen with Stainless Steel appliances, new Quartz countertops and two completely refreshed bathrooms, one with a new tub. Fresh paint, new flooring, new doors, smooth ceilings, new window coverings, updated hardware, fixtures and fans leave nothing for a buyer to worry about. Major updates include a newer HVAC system and a roof replaced in 2015. Home was re-piped by Emerald Plumbing. The backyard awaits your imagination and offers a unique opportunity to design your own outdoor oasis, ideal for entertaining, building an outdoor kitchen or adding your dream pool. The long-time owner made a significant investment to upgrade this home and has pre-inspected it, offering buyers peace of mind with a full report ready for review. Enjoy convenient suburban living just minutes from Publix, Walmart, top-rated schools, Red Bug Lake Park and local dining. With easy highway access, you are under 30 minutes from UCF, Downtown Orlando, Universal Studios and the airport. Whether you are looking for a turnkey home or a high-demand investment property, this gem won’t last long.

7361 Grand Avenue, Winter Park

$2,449,000

Under Construction. In the heart of Winter Park’s coveted Tree Streets, this stunning residence brings together impeccable finishes, a striking architectural presence, and a location that puts so much of daily life within easy reach. Opportunities to find new construction in this established neighborhood are becoming harder to come by, making this home an especially exciting offering. The front façade makes a memorable first impression, with beautiful curb appeal that carries naturally into the interiors. In the spacious living room, a stone-wrapped fireplace anchors the space, complemented by a built-in entertainment center and display shelving with soft LED underlighting. The kitchen is a standout. Calacatta quartz countertops and an intricate mosaic backsplash set an elegant tone, while a full suite of Thermador appliances, including a paneled refrigerator, brings substance to the beautiful design. A spacious pantry keeps everything tucked away, and a wine bar with a dedicated wine refrigerator makes hosting feel effortless. The primary suite offers a lovely sense of retreat. This spacious bedroom is complemented by a beautifully finished bath with marble mosaic tile, a freestanding tub, and a generous walk-in shower with a rain showerhead. An oversized closet adds the kind of everyday luxury that is just as valuable as the finishes themselves. A rare first-floor guest bedroom gives visitors a comfortable place of their own or offers a space for a dedicated office. Upstairs, three additional bedrooms, each with a walk-in closet, surround a loft that offers room for a second living area, movie nights, or a quiet place to unwind. The outdoor living is equally impressive, with a spacious covered lanai and full summer kitchen overlooking the pool and spa, a beautiful setting for dinners or a quiet afternoon at home. Surrounding green space gives the backyard a sense of openness and room to enjoy the Florida sunshine. With Phelps Park and the YMCA moments away, and Park Avenue’s restaurants and boutiques just a golf cart ride from home, the location is every bit as appealing as the residence itself. Beautifully finished and thoughtfully arranged, this is a chance to enjoy the ease of a brand-new home in a neighborhood whose charm has long been established.

5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Under Construction. In the heart of Winter Park’s coveted Tree Streets, this stunning residence brings together impeccable finishes, a striking architectural presence, and a location that puts so much of daily life within easy reach. Opportunities to find new construction in this established neighborhood are becoming harder to come by, making this home an especially exciting offering. The front façade makes a memorable first impression, with beautiful curb appeal that carries naturally into the interiors. In the spacious living room, a stone-wrapped fireplace anchors the space, complemented by a built-in entertainment center and display shelving with soft LED underlighting. The kitchen is a standout. Calacatta quartz countertops and an intricate mosaic backsplash set an elegant tone, while a full suite of Thermador appliances, including a paneled refrigerator, brings substance to the beautiful design. A spacious pantry keeps everything tucked away, and a wine bar with a dedicated wine refrigerator makes hosting feel effortless. The primary suite offers a lovely sense of retreat. This spacious bedroom is complemented by a beautifully finished bath with marble mosaic tile, a freestanding tub, and a generous walk-in shower with a rain showerhead. An oversized closet adds the kind of everyday luxury that is just as valuable as the finishes themselves. A rare first-floor guest bedroom gives visitors a comfortable place of their own or offers a space for a dedicated office. Upstairs, three additional bedrooms, each with a walk-in closet, surround a loft that offers room for a second living area, movie nights, or a quiet place to unwind. The outdoor living is equally impressive, with a spacious covered lanai and full summer kitchen overlooking the pool and spa, a beautiful setting for dinners or a quiet afternoon at home. Surrounding green space gives the backyard a sense of openness and room to enjoy the Florida sunshine. With Phelps Park and the YMCA moments away, and Park Avenue’s restaurants and boutiques just a golf cart ride from home, the location is every bit as appealing as the residence itself. Beautifully finished and thoughtfully arranged, this is a chance to enjoy the ease of a brand-new home in a neighborhood whose charm has long been established.

1441 Palm Avenue, Winter Park

$410,000

URBAN CONVENIENCE MEETS QUIET "OLD FLORIDA" CHARM! Rarely does a truly move-in-ready home hit the market in the heart of Seminole County Winter Park—especially one with no HOA, a massive private backyard, and an exceptional price point. Tucked away on a quiet, low-traffic dead-end street, this solid concrete-block ranch is the ultimate starter home or a turnkey addition to any high-performing investment portfolio. The exterior welcomes you with an extra-wide paver driveway, mature professional landscaping, and a charming paver front walkway and patio, while the fully fenced backyard offers an oversized outdoor living space complete with a patio for entertaining and a convenient storage shed. Step inside to discover a bright open-concept living, dining, and kitchen area enhanced by continuous luxury vinyl flooring flowing throughout. The chef’s kitchen is beautifully appointed with sleek granite countertops, solid wood cabinetry, stainless steel appliances, an eat-in island, and a practical closet-style pantry. Designed with a desirable split bedroom layout, the private primary suite boasts three closets and an ensuite bath with an updated vanity and custom tile shower, while two additional guest bedrooms and a fully updated guest bath sit on the opposite side of the home for optimal privacy. Additional conveniences include a spacious indoor laundry room and a front-lawn irrigation system, backed by peace-of-mind upgrades including a 2014 roof and a 2018 HVAC. Zoned for highly rated Seminole County schools and situated just moments from N Park Ave—while remaining centrally located 15 minutes from Downtown Orlando and 30 minutes from MCO Airport—opportunities at this price point and in this location do not last long. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code

URBAN CONVENIENCE MEETS QUIET "OLD FLORIDA" CHARM! Rarely does a truly move-in-ready home hit the market in the heart of Seminole County Winter Park—especially one with no HOA, a massive private backyard, and an exceptional price point. Tucked away on a quiet, low-traffic dead-end street, this solid concrete-block ranch is the ultimate starter home or a turnkey addition to any high-performing investment portfolio. The exterior welcomes you with an extra-wide paver driveway, mature professional landscaping, and a charming paver front walkway and patio, while the fully fenced backyard offers an oversized outdoor living space complete with a patio for entertaining and a convenient storage shed. Step inside to discover a bright open-concept living, dining, and kitchen area enhanced by continuous luxury vinyl flooring flowing throughout. The chef’s kitchen is beautifully appointed with sleek granite countertops, solid wood cabinetry, stainless steel appliances, an eat-in island, and a practical closet-style pantry. Designed with a desirable split bedroom layout, the private primary suite boasts three closets and an ensuite bath with an updated vanity and custom tile shower, while two additional guest bedrooms and a fully updated guest bath sit on the opposite side of the home for optimal privacy. Additional conveniences include a spacious indoor laundry room and a front-lawn irrigation system, backed by peace-of-mind upgrades including a 2014 roof and a 2018 HVAC. Zoned for highly rated Seminole County schools and situated just moments from N Park Ave—while remaining centrally located 15 minutes from Downtown Orlando and 30 minutes from MCO Airport—opportunities at this price point and in this location do not last long. Schedule your private showing today!

1935 Azalea Avenue, Winter Park

$225,000

**HIGHEST & BEST BY 6:00PM 11/2/26.**INVESTOR OPPORTUNITY IN WINTER PARK!** Discover the potential of 3462 Seagrape Drive, a single-story property featuring 3 bedrooms, 1 bathroom, and an additional flex room in the established Eastbrook neighborhood. Priced to sell, this property presents an opportunity for those looking to renovate, update, and add value. Inside, the home features a spacious living and dining room combination with vaulted ceilings and a functional layout ready for your vision. The additional flex room provides versatile space that could be used as a home office, hobby room, or bonus area. Outside, a covered and screened patio overlooks the generously sized backyard, where mature trees create a natural setting. A detached storage shed with double doors offers space for tools, lawn equipment, and outdoor essentials. The covered one-car carport and concrete driveway provide convenient parking. Situated in Winter Park's Eastbrook neighborhood, the property offers convenient access to Aloma Avenue, Semoran Boulevard, shopping, dining, local parks, and **schools, including Winter Park High School**. Downtown Winter Park's popular Park Avenue district is also within a short drive, offering boutiques, restaurants, and entertainment. With its established location, flexible layout, and renovation potential, 3462 Seagrape Drive offers the opportunity to renovate, reimagine, and bring your vision to life.

3 Beds ⋅ 1 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code

**HIGHEST & BEST BY 6:00PM 11/2/26.**INVESTOR OPPORTUNITY IN WINTER PARK!** Discover the potential of 3462 Seagrape Drive, a single-story property featuring 3 bedrooms, 1 bathroom, and an additional flex room in the established Eastbrook neighborhood. Priced to sell, this property presents an opportunity for those looking to renovate, update, and add value. Inside, the home features a spacious living and dining room combination with vaulted ceilings and a functional layout ready for your vision. The additional flex room provides versatile space that could be used as a home office, hobby room, or bonus area. Outside, a covered and screened patio overlooks the generously sized backyard, where mature trees create a natural setting. A detached storage shed with double doors offers space for tools, lawn equipment, and outdoor essentials. The covered one-car carport and concrete driveway provide convenient parking. Situated in Winter Park's Eastbrook neighborhood, the property offers convenient access to Aloma Avenue, Semoran Boulevard, shopping, dining, local parks, and **schools, including Winter Park High School**. Downtown Winter Park's popular Park Avenue district is also within a short drive, offering boutiques, restaurants, and entertainment. With its established location, flexible layout, and renovation potential, 3462 Seagrape Drive offers the opportunity to renovate, reimagine, and bring your vision to life.

3462 Seagrape Drive, Winter Park

$1,175,000

English cottage–inspired architecture, enchanting gardens and a setting directly across from Lake Sylvan introduce this exquisitely renovated Winter Park residence. Set among distinguished residences and substantial lakefront estates, the home occupies a corner lot along a charming brick street and offers three bedrooms, three full bathrooms and approximately 2,096 square feet of living space. Extensive improvements in recent years bring together exceptional finishes, thoughtful craftsmanship and substantial updates behind the walls. With interior design by New York City–based Paulette Pascarella, traditional architectural details find fresh expression through sophisticated materials and beautifully considered modern appointments. Expansive windows welcome natural light, while polished marble flooring in warm ivory tones extends throughout much of both levels. The kitchen features solid wood cabinetry, quartz countertops and a full-height backsplash, complemented by a Bertazzoni refrigerator, Bosch 800 Series gas range and Miele dishwasher. A separate study and sitting room has wood flooring and custom built-ins. With a full bathroom immediately adjacent, this versatile space presents potential for conversion into a fourth bedroom with an en-suite bath. Carefully selected details include Visual Comfort and Currey lighting, Buster + Punch and Baldwin hardware, and custom window treatments incorporating designer textiles and motorized shades from The Shade Store. Nine Marvin Ultimate windows with wood interiors, a VELUX skylight and a mahogany Craftsman front door further distinguish the renovation. A custom stair railing by Boris Petkoff Iron Works and millwork by Dunning Custom Carpentry add distinctive craftsmanship. All three bedrooms are upstairs, where the primary suite features soaring ceilings, treetop outlooks and an extensively fitted California Closets walk-in dressing room with custom cabinetry and soft-close dovetail drawers. Its beautifully appointed bathroom features Perrin + Rowe Georgian Era vanity and shower fixtures, reflecting the caliber of fittings selected throughout the home. Two additional bedrooms, one with an en-suite bathroom, provide flexibility for guests or a home office. Upstairs views of Lake Sylvan connect the interiors to their picturesque surroundings. Substantial improvements include whole-house repiping, electrical upgrades, a Rinnai tankless water heater and a whole-house water treatment system. The roof was replaced in August 2023. Outside, cottage gardens frame a welcoming entrance, while an intimate brick patio nestled within the garden and a quiet garden corner offer peaceful places for morning coffee or an afternoon outdoors. A private parking pad adds convenience. Beyond the garden, oak-shaded brick streets invite leisurely walks past beautiful homes and scenic views of Lakes Sylvan and Osceola. A small lakeside green space lies just down Harris Circle, with Crosby Wellness Center, AdventHealth and Park Avenue’s dining, boutiques and cultural attractions conveniently nearby. An inviting choice for a primary residence or Winter Park retreat.

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

English cottage–inspired architecture, enchanting gardens and a setting directly across from Lake Sylvan introduce this exquisitely renovated Winter Park residence. Set among distinguished residences and substantial lakefront estates, the home occupies a corner lot along a charming brick street and offers three bedrooms, three full bathrooms and approximately 2,096 square feet of living space. Extensive improvements in recent years bring together exceptional finishes, thoughtful craftsmanship and substantial updates behind the walls. With interior design by New York City–based Paulette Pascarella, traditional architectural details find fresh expression through sophisticated materials and beautifully considered modern appointments. Expansive windows welcome natural light, while polished marble flooring in warm ivory tones extends throughout much of both levels. The kitchen features solid wood cabinetry, quartz countertops and a full-height backsplash, complemented by a Bertazzoni refrigerator, Bosch 800 Series gas range and Miele dishwasher. A separate study and sitting room has wood flooring and custom built-ins. With a full bathroom immediately adjacent, this versatile space presents potential for conversion into a fourth bedroom with an en-suite bath. Carefully selected details include Visual Comfort and Currey lighting, Buster + Punch and Baldwin hardware, and custom window treatments incorporating designer textiles and motorized shades from The Shade Store. Nine Marvin Ultimate windows with wood interiors, a VELUX skylight and a mahogany Craftsman front door further distinguish the renovation. A custom stair railing by Boris Petkoff Iron Works and millwork by Dunning Custom Carpentry add distinctive craftsmanship. All three bedrooms are upstairs, where the primary suite features soaring ceilings, treetop outlooks and an extensively fitted California Closets walk-in dressing room with custom cabinetry and soft-close dovetail drawers. Its beautifully appointed bathroom features Perrin + Rowe Georgian Era vanity and shower fixtures, reflecting the caliber of fittings selected throughout the home. Two additional bedrooms, one with an en-suite bathroom, provide flexibility for guests or a home office. Upstairs views of Lake Sylvan connect the interiors to their picturesque surroundings. Substantial improvements include whole-house repiping, electrical upgrades, a Rinnai tankless water heater and a whole-house water treatment system. The roof was replaced in August 2023. Outside, cottage gardens frame a welcoming entrance, while an intimate brick patio nestled within the garden and a quiet garden corner offer peaceful places for morning coffee or an afternoon outdoors. A private parking pad adds convenience. Beyond the garden, oak-shaded brick streets invite leisurely walks past beautiful homes and scenic views of Lakes Sylvan and Osceola. A small lakeside green space lies just down Harris Circle, with Crosby Wellness Center, AdventHealth and Park Avenue’s dining, boutiques and cultural attractions conveniently nearby. An inviting choice for a primary residence or Winter Park retreat.

1500 Harris Circle, Winter Park

$415,000

Welcome to this beautifully updated 3-bedroom, 2-bath home with a 2-car garage, nestled in the highly desirable Eastbrook neighborhood of Winter Park! Light, bright, and inviting, this home offers an abundance of natural light through its numerous windows, creating a warm and welcoming atmosphere throughout. The updated kitchen features crisp white cabinetry, beautiful quartz countertops, and stainless steel appliances. Luxury vinyl plank flooring extends throughout most of the home, offering both style and easy maintenance. Both bathrooms have been tastefully updated, adding to the home's fresh, modern appeal. Step outside to the screened and covered patio, the perfect spot for morning coffee, outdoor dining, or simply relaxing while overlooking the generously sized, fully fenced backyard. There's plenty of room to entertain, garden, or enjoy the Florida sunshine! Major improvements provide added peace of mind, including a new roof (2019), replumbing (2022), new HVAC system (2022), and new double-pane windows and sliding glass door (2023). Both the interior and exterior were freshly painted in 2023, completing the home's move-in-ready appeal. Ideally situated in the established Eastbrook community, this home offers the charm of Winter Park living with convenient access to shopping, dining, parks, and major roadways. With its thoughtful updates, inviting living spaces, and wonderful outdoor setting, this is a home you won't want to miss!

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated 3-bedroom, 2-bath home with a 2-car garage, nestled in the highly desirable Eastbrook neighborhood of Winter Park! Light, bright, and inviting, this home offers an abundance of natural light through its numerous windows, creating a warm and welcoming atmosphere throughout. The updated kitchen features crisp white cabinetry, beautiful quartz countertops, and stainless steel appliances. Luxury vinyl plank flooring extends throughout most of the home, offering both style and easy maintenance. Both bathrooms have been tastefully updated, adding to the home's fresh, modern appeal. Step outside to the screened and covered patio, the perfect spot for morning coffee, outdoor dining, or simply relaxing while overlooking the generously sized, fully fenced backyard. There's plenty of room to entertain, garden, or enjoy the Florida sunshine! Major improvements provide added peace of mind, including a new roof (2019), replumbing (2022), new HVAC system (2022), and new double-pane windows and sliding glass door (2023). Both the interior and exterior were freshly painted in 2023, completing the home's move-in-ready appeal. Ideally situated in the established Eastbrook community, this home offers the charm of Winter Park living with convenient access to shopping, dining, parks, and major roadways. With its thoughtful updates, inviting living spaces, and wonderful outdoor setting, this is a home you won't want to miss!

2038 Ponderosa Avenue, Winter Park

$550,000

Welcome to 257 Lincolnshire Road, a 3-bedroom, 2-bath home offering 1,610 square feet of living space in the established Winter Park Pines neighborhood. Situated at the end of a cul-de-sac street, this single-story home sits on an expansive 0.58-acre lot, providing an inviting setting with room to bring your vision to life. Inside, a spacious living and dining layout features multiple gathering areas, large windows that welcome natural light, and a distinctive brick fireplace with wood-paneled detailing. The kitchen offers generous cabinet storage, a breakfast bar, and an open connection to the main living area. An attached two-car garage adds everyday convenience. Sliding glass doors open to a covered, screened-in patio overlooking the oversized backyard. With over 200 feet of rear property line, this expansive outdoor space offers remarkable flexibility for entertaining, gardening, recreation, or designing your own outdoor retreat. Mature trees and natural greenery create a welcoming backdrop with plenty of room to enjoy. Whether you envision renovating and personalizing the existing home or starting fresh by removing the current structure and building a new residence, this expansive property offers the flexibility to explore a variety of possibilities. Enjoy the appeal of an established neighborhood with the golf course just down the street and convenient access to Aloma Avenue. With its generous lot, cul-de-sac setting, and Winter Park location, this property is ready for your ideas.

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

Welcome to 257 Lincolnshire Road, a 3-bedroom, 2-bath home offering 1,610 square feet of living space in the established Winter Park Pines neighborhood. Situated at the end of a cul-de-sac street, this single-story home sits on an expansive 0.58-acre lot, providing an inviting setting with room to bring your vision to life. Inside, a spacious living and dining layout features multiple gathering areas, large windows that welcome natural light, and a distinctive brick fireplace with wood-paneled detailing. The kitchen offers generous cabinet storage, a breakfast bar, and an open connection to the main living area. An attached two-car garage adds everyday convenience. Sliding glass doors open to a covered, screened-in patio overlooking the oversized backyard. With over 200 feet of rear property line, this expansive outdoor space offers remarkable flexibility for entertaining, gardening, recreation, or designing your own outdoor retreat. Mature trees and natural greenery create a welcoming backdrop with plenty of room to enjoy. Whether you envision renovating and personalizing the existing home or starting fresh by removing the current structure and building a new residence, this expansive property offers the flexibility to explore a variety of possibilities. Enjoy the appeal of an established neighborhood with the golf course just down the street and convenient access to Aloma Avenue. With its generous lot, cul-de-sac setting, and Winter Park location, this property is ready for your ideas.

257 Lincolnshire Road, Winter Park

$450,000

Welcome to this beautifully renovated pool home featuring a rare and versatile double primary suite layout! Completely renovated in 2024, this 5-bedroom, 3-bathroom home offers 1,636 square feet of stylish, thoughtfully designed living space with modern finishes throughout. Light gray wood-look plank tile flooring and recessed lighting create a bright, cohesive feel. The contemporary kitchen showcases gray shaker-style cabinetry, sleek black granite countertops, a marble-look tile backsplash with black mosaic accents, stainless steel appliances, and a breakfast bar with seating for four. The first primary suite is privately positioned away from the additional bedrooms and features an ensuite bathroom with a marble-look tiled shower, decorative mosaic accents, multiple shower heads including a rain shower, a frameless glass enclosure, and a gray vanity topped with black granite. The second primary suite provides added flexibility for multigenerational living, extended guests, or a private retreat. Step outside to enjoy your own backyard oasis, complete with an in-ground pool, screened lanai, and fully fenced, spacious backyard with plenty of green space for relaxing, entertaining, and outdoor activities. Ideally located approximately 10 minutes from the restaurants and boutiques of Park Avenue, with convenient access to UCF, Full Sail University, Rollins College, major transportation routes, shopping, and dining. Orlando International Airport is approximately 25 minutes away. With its modern renovations, dual primary suites, and inviting outdoor living space, this home offers a unique combination of comfort, flexibility, and convenience! ROOF - 2024 HVAC - 2025 PLUMBING - 2026 ELECTRICAL - 2024

5 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully renovated pool home featuring a rare and versatile double primary suite layout! Completely renovated in 2024, this 5-bedroom, 3-bathroom home offers 1,636 square feet of stylish, thoughtfully designed living space with modern finishes throughout. Light gray wood-look plank tile flooring and recessed lighting create a bright, cohesive feel. The contemporary kitchen showcases gray shaker-style cabinetry, sleek black granite countertops, a marble-look tile backsplash with black mosaic accents, stainless steel appliances, and a breakfast bar with seating for four. The first primary suite is privately positioned away from the additional bedrooms and features an ensuite bathroom with a marble-look tiled shower, decorative mosaic accents, multiple shower heads including a rain shower, a frameless glass enclosure, and a gray vanity topped with black granite. The second primary suite provides added flexibility for multigenerational living, extended guests, or a private retreat. Step outside to enjoy your own backyard oasis, complete with an in-ground pool, screened lanai, and fully fenced, spacious backyard with plenty of green space for relaxing, entertaining, and outdoor activities. Ideally located approximately 10 minutes from the restaurants and boutiques of Park Avenue, with convenient access to UCF, Full Sail University, Rollins College, major transportation routes, shopping, and dining. Orlando International Airport is approximately 25 minutes away. With its modern renovations, dual primary suites, and inviting outdoor living space, this home offers a unique combination of comfort, flexibility, and convenience! ROOF - 2024 HVAC - 2025 PLUMBING - 2026 ELECTRICAL - 2024

1825 Chilean Lane, Winter Park

$5,695,000

Experience Winter Park lakefront living at 541 Virginia Drive, where timeless architecture, craftsmanship, and waterfront lifestyle come together. Set on approximately 130 feet of Lake Virginia frontage, this estate offers access to the Winter Park Chain of Lakes, a private dock with a covered electric boat lift, and grand water views toward Rollins College and historic Knowles Chapel. On a quiet Timberlane Shores cul-de-sac, this award-winning residence was built in 2008 by Farina & Sons. Recognized with an Aurora Award and Parade of Homes Grand Winner honors, the home blends historic Winter Park charm with modern luxury. Offering 4 bedrooms, 3.5 bathrooms, and 4,725 square feet of thoughtfully designed living space, every detail reflects quality and character. Inside, rich hardwood flooring, exposed wood beams, elegant coffered ceilings, and expansive Andersen windows and doors fill the home with natural light. The current owners have further elevated the residence with exquisite custom illuminated built-ins, architectural lighting, and beautifully enhanced living spaces that seamlessly blend traditional craftsmanship with contemporary elegance. At the heart of the home, the chef's kitchen features Caesarstone concrete countertops, a striking custom copper range hood, premium Sub-Zero and Viking appliances, and a generous walk-in pantry. A dedicated wine room and walk-in bar provide additional spaces for entertaining, while the thoughtfully designed floor plan offers a spacious first-floor primary suite with a spa-inspired bathroom and custom closets, along with two additional main-level bedrooms. A private outdoor shower just outside the primary suite offers a spa-like retreat. Upstairs, an impressive transformation has created an exceptional entertainment retreat featuring a completely redesigned custom bar, expansive bonus room, and beautifully appointed home office with captivating views across Lake Virginia. An additional bedroom with a private bathroom and kitchenette offers flexibility for guests or extended stays. The outdoor living experience is truly extraordinary. A magnificent covered lanai with graceful architectural arches and a gas fireplace overlooks the sparkling pool, relaxing hot tub, and beautifully landscaped waterfront grounds. Recently installed automated retractable screens surround the covered patio, allowing you to enjoy the outdoor living areas with added comfort at the touch of a button. Additional features include a UV pool treatment system, outdoor shower, and thoughtfully designed landscape lighting that brings the property to life after sunset. Just beyond the pool, approximately 130 feet of Lake Virginia shoreline opens the door to one of Central Florida's most sought-after lifestyles. Your private dock and covered powered boat lift make it effortless to spend afternoons cruising the Winter Park Chain of Lakes, exploring scenic canals, or simply enjoying the peaceful beauty of the water. Mature trees, lush landscaping, and spectacular lake views create an enchanting setting for both quiet mornings and unforgettable evenings. All of this is conveniently located just minutes from the boutique shopping, acclaimed restaurants, and cultural attractions of Winter Park's iconic Park Avenue. Beautiful homes can be found in many places, but the opportunity to enjoy this extraordinary Lake Virginia lifestyle is something truly special. Welcome home to 541 Virginia Drive.

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

Experience Winter Park lakefront living at 541 Virginia Drive, where timeless architecture, craftsmanship, and waterfront lifestyle come together. Set on approximately 130 feet of Lake Virginia frontage, this estate offers access to the Winter Park Chain of Lakes, a private dock with a covered electric boat lift, and grand water views toward Rollins College and historic Knowles Chapel. On a quiet Timberlane Shores cul-de-sac, this award-winning residence was built in 2008 by Farina & Sons. Recognized with an Aurora Award and Parade of Homes Grand Winner honors, the home blends historic Winter Park charm with modern luxury. Offering 4 bedrooms, 3.5 bathrooms, and 4,725 square feet of thoughtfully designed living space, every detail reflects quality and character. Inside, rich hardwood flooring, exposed wood beams, elegant coffered ceilings, and expansive Andersen windows and doors fill the home with natural light. The current owners have further elevated the residence with exquisite custom illuminated built-ins, architectural lighting, and beautifully enhanced living spaces that seamlessly blend traditional craftsmanship with contemporary elegance. At the heart of the home, the chef's kitchen features Caesarstone concrete countertops, a striking custom copper range hood, premium Sub-Zero and Viking appliances, and a generous walk-in pantry. A dedicated wine room and walk-in bar provide additional spaces for entertaining, while the thoughtfully designed floor plan offers a spacious first-floor primary suite with a spa-inspired bathroom and custom closets, along with two additional main-level bedrooms. A private outdoor shower just outside the primary suite offers a spa-like retreat. Upstairs, an impressive transformation has created an exceptional entertainment retreat featuring a completely redesigned custom bar, expansive bonus room, and beautifully appointed home office with captivating views across Lake Virginia. An additional bedroom with a private bathroom and kitchenette offers flexibility for guests or extended stays. The outdoor living experience is truly extraordinary. A magnificent covered lanai with graceful architectural arches and a gas fireplace overlooks the sparkling pool, relaxing hot tub, and beautifully landscaped waterfront grounds. Recently installed automated retractable screens surround the covered patio, allowing you to enjoy the outdoor living areas with added comfort at the touch of a button. Additional features include a UV pool treatment system, outdoor shower, and thoughtfully designed landscape lighting that brings the property to life after sunset. Just beyond the pool, approximately 130 feet of Lake Virginia shoreline opens the door to one of Central Florida's most sought-after lifestyles. Your private dock and covered powered boat lift make it effortless to spend afternoons cruising the Winter Park Chain of Lakes, exploring scenic canals, or simply enjoying the peaceful beauty of the water. Mature trees, lush landscaping, and spectacular lake views create an enchanting setting for both quiet mornings and unforgettable evenings. All of this is conveniently located just minutes from the boutique shopping, acclaimed restaurants, and cultural attractions of Winter Park's iconic Park Avenue. Beautiful homes can be found in many places, but the opportunity to enjoy this extraordinary Lake Virginia lifestyle is something truly special. Welcome home to 541 Virginia Drive.

541 Virginia Drive, Winter Park

$365,000

STOP THE SCROLL! ?? Your Dream Home Is Calling! ? Welcome to this beautifully updated 3-bedroom, 2-bath gem where style, comfort, and location come together! Enjoy tasteful updates, newer windows and doors, and a HUGE backyard ready for BBQs, pets, parties, and making memories! Nestled in a quiet friendly neighborhood with plenty of places to walk, you're just minutes from everything—including Full Sail University! Cute house. Big yard. Great location. What more could you want? This one deserves a spot at the top of your must-see list!

3 Beds ⋅ 2 Baths ⋅ Ridge High 1st Add SubDv. ⋅ 32792 Zip Code

STOP THE SCROLL! ?? Your Dream Home Is Calling! ? Welcome to this beautifully updated 3-bedroom, 2-bath gem where style, comfort, and location come together! Enjoy tasteful updates, newer windows and doors, and a HUGE backyard ready for BBQs, pets, parties, and making memories! Nestled in a quiet friendly neighborhood with plenty of places to walk, you're just minutes from everything—including Full Sail University! Cute house. Big yard. Great location. What more could you want? This one deserves a spot at the top of your must-see list!

2168 Ridge Drive, Winter Park

$1,625,000

Historic Winter Park charm with modern updates, close to N Park Avenue. Set on a picturesque, tree-lined street, this thoughtfully renovated home puts you minutes from Winter Park's restaurants, sidewalk cafés, boutique shops, art galleries, Central Park, and year-round festivals. You get the character of an established historic neighborhood with the comforts of modern living. Set back amid mature landscaping, the home greets you with a charming front porch and an elegant entry with marble floors, arched windows, and beautiful architectural details. Inside, spacious rooms feature rich hardwood floors, crown molding, wainscoting, and plantation shutters. The updated kitchen offers bright cabinetry, stone countertops, a generous island, stainless steel appliances, and a gas range, all opening to a living area with a classic fireplace and custom built-ins. An exceptionally spacious flex room lined with custom cabinetry and shelving works beautifully as a home office, library, or creative studio. The primary suite includes a beautifully remodeled bath with a freestanding soaking tub, oversized glass-enclosed shower, dual vanities, and a customized walk-in closet. Generously sized secondary bedrooms add flexibility for family, guests, or a second workspace. Outside, a private fenced backyard shaded by mature trees features a brick-paver patio made for outdoor dining or quiet relaxation. A rear-access garage adds convenience without disrupting the home's charming streetscape. Timeless character, extensive modern updates, and an exceptional location near the heart of Winter Park. Come enjoy the distinctive lifestyle that makes this community so desirable. Schedule your private showing today.

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

Historic Winter Park charm with modern updates, close to N Park Avenue. Set on a picturesque, tree-lined street, this thoughtfully renovated home puts you minutes from Winter Park's restaurants, sidewalk cafés, boutique shops, art galleries, Central Park, and year-round festivals. You get the character of an established historic neighborhood with the comforts of modern living. Set back amid mature landscaping, the home greets you with a charming front porch and an elegant entry with marble floors, arched windows, and beautiful architectural details. Inside, spacious rooms feature rich hardwood floors, crown molding, wainscoting, and plantation shutters. The updated kitchen offers bright cabinetry, stone countertops, a generous island, stainless steel appliances, and a gas range, all opening to a living area with a classic fireplace and custom built-ins. An exceptionally spacious flex room lined with custom cabinetry and shelving works beautifully as a home office, library, or creative studio. The primary suite includes a beautifully remodeled bath with a freestanding soaking tub, oversized glass-enclosed shower, dual vanities, and a customized walk-in closet. Generously sized secondary bedrooms add flexibility for family, guests, or a second workspace. Outside, a private fenced backyard shaded by mature trees features a brick-paver patio made for outdoor dining or quiet relaxation. A rear-access garage adds convenience without disrupting the home's charming streetscape. Timeless character, extensive modern updates, and an exceptional location near the heart of Winter Park. Come enjoy the distinctive lifestyle that makes this community so desirable. Schedule your private showing today.

345 Beloit Avenue, Winter Park

$375,000

Welcome to 1830 Gladiolas Drive, a beautiful 3 bedroom, 2 bathroom home in Winter Park’s Garden Lake Estates community. This move-in ready home features a 2023 AC, a 2022 water heater, a 2020 roof, and a brand new freshly painted interior. Inside, the spacious open living and kitchen area is the heart of the home. The thoughtful layout keeps everyone connected, whether you’re cooking, hosting friends, or settling in for a quiet evening. Natural flow between the spaces makes the home feel open and welcoming. The primary suite is a private retreat. It’s generously sized and has a large walk-in closet, so you have plenty of room for your wardrobe and a calm place to start and end your day. Outside, the expansive rear patio extends your living space into the Florida outdoors. It’s ready for morning coffee, weekend barbecues, or dinner under the stars. Beyond it, the big backyard gives you room to play, garden, or add the features you’ve been dreaming of. Functional, inviting, and close to everything in Winter Park, this home is ready for its next chapter with several major updates already completed. This home is a great opportunity for someone looking to add their own personal touch.

3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

Welcome to 1830 Gladiolas Drive, a beautiful 3 bedroom, 2 bathroom home in Winter Park’s Garden Lake Estates community. This move-in ready home features a 2023 AC, a 2022 water heater, a 2020 roof, and a brand new freshly painted interior. Inside, the spacious open living and kitchen area is the heart of the home. The thoughtful layout keeps everyone connected, whether you’re cooking, hosting friends, or settling in for a quiet evening. Natural flow between the spaces makes the home feel open and welcoming. The primary suite is a private retreat. It’s generously sized and has a large walk-in closet, so you have plenty of room for your wardrobe and a calm place to start and end your day. Outside, the expansive rear patio extends your living space into the Florida outdoors. It’s ready for morning coffee, weekend barbecues, or dinner under the stars. Beyond it, the big backyard gives you room to play, garden, or add the features you’ve been dreaming of. Functional, inviting, and close to everything in Winter Park, this home is ready for its next chapter with several major updates already completed. This home is a great opportunity for someone looking to add their own personal touch.

1830 Gladiolas Drive, Winter Park

1021 Princess Gate Boulevard, Winter Park

$410,000

Virtually Staged. Welcome to this 3-bedroom, 2-bath pool home in the established Howell Estates neighborhood of Winter Park! Situated on a spacious 0.31-acre lot, this single-story residence offers 1,318 square feet of living space with a split-bedroom layout and a combination of tile and luxury vinyl flooring. The living room features built-in cabinetry with a granite countertop, while the kitchen offers stone countertops, a tile backsplash, and a closet pantry. The primary suite includes dual closets and a private bathroom with a walk-in shower. Sliding glass doors from the dining area open to a covered lanai and screened-in pool, creating an inviting setting for outdoor relaxation and entertaining. The spacious, fenced backyard offers additional room to enjoy the outdoors. Other highlights include a brand-new water heater, a 2018 roof, a 2024 HVAC system, and no HOA fees. Conveniently located near Howell Branch Road and Semoran Boulevard, the property provides access to shopping, dining, parks, and everyday essentials throughout the Winter Park area. With its private pool, generous lot size, and convenient location, this home offers a wonderful opportunity to enjoy Florida living. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ Howell Estates Rep SubDv. ⋅ 32792 Zip Code

Virtually Staged. Welcome to this 3-bedroom, 2-bath pool home in the established Howell Estates neighborhood of Winter Park! Situated on a spacious 0.31-acre lot, this single-story residence offers 1,318 square feet of living space with a split-bedroom layout and a combination of tile and luxury vinyl flooring. The living room features built-in cabinetry with a granite countertop, while the kitchen offers stone countertops, a tile backsplash, and a closet pantry. The primary suite includes dual closets and a private bathroom with a walk-in shower. Sliding glass doors from the dining area open to a covered lanai and screened-in pool, creating an inviting setting for outdoor relaxation and entertaining. The spacious, fenced backyard offers additional room to enjoy the outdoors. Other highlights include a brand-new water heater, a 2018 roof, a 2024 HVAC system, and no HOA fees. Conveniently located near Howell Branch Road and Semoran Boulevard, the property provides access to shopping, dining, parks, and everyday essentials throughout the Winter Park area. With its private pool, generous lot size, and convenient location, this home offers a wonderful opportunity to enjoy Florida living. Schedule your private showing today!

1021 Princess Gate Boulevard, Winter Park

$1,190,000

New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This split-plan three-bedroom and 2.5-bath home has over 4,880 total square feet in the main home and 1,944 total square feet in the detached in-law/office unit under roof. Constructed with solid poured concrete block and 1-inch insulation, this remarkable residence was designed to withstand the test of time while delivering modern luxury and comfort. A rare feature, the home includes two reinforced safe rooms built with rebar-reinforced solid poured concrete walls and 12-inch concrete ceilings, along with a built-in, concrete-bolted safe. Additional security enhancements include a full alarm system and security spotlights. Designed for everyday living and entertaining, the property is equipped with a full-house 22-kilowatt generator, a buried 500-gallon propane tank, propane gas range and outdoor grill, two tankless water heaters, whole-house water softening and filtration systems, EV charging capability and energy-efficient construction resulting in remarkably low utility costs. The well-appointed kitchen features a solid wood cabinetry, quartz countertops, a kitchen, butler pantry, coffee bar and laundry room, Verona gas range, Frigidaire Professional French-door refrigerator, KitchenAid dishwasher, convenient under-counter outlets and the kitchen island has lighted shelves. Additional highlights include plantation shutters throughout, wine cellar, climate-controlled storage attic, granite in baths, custom garage cabinetry, epoxy-finished garage floors, hurricane-impact windows in the office/apartment, Pet Turf in the entire backyard with no maintenance necessary and a striking 35-foot flagpole. Combining superior craftsmanship, advanced infrastructure and thoughtful upgrades rarely found in today's market, this extraordinary property presents a unique opportunity to own a one-of-a-kind residence. Total heated square footage includes heated/cooled space to use as garage, workshop, and/or utility room in the detached structure.

4 Beds ⋅ 4 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code

New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This split-plan three-bedroom and 2.5-bath home has over 4,880 total square feet in the main home and 1,944 total square feet in the detached in-law/office unit under roof. Constructed with solid poured concrete block and 1-inch insulation, this remarkable residence was designed to withstand the test of time while delivering modern luxury and comfort. A rare feature, the home includes two reinforced safe rooms built with rebar-reinforced solid poured concrete walls and 12-inch concrete ceilings, along with a built-in, concrete-bolted safe. Additional security enhancements include a full alarm system and security spotlights. Designed for everyday living and entertaining, the property is equipped with a full-house 22-kilowatt generator, a buried 500-gallon propane tank, propane gas range and outdoor grill, two tankless water heaters, whole-house water softening and filtration systems, EV charging capability and energy-efficient construction resulting in remarkably low utility costs. The well-appointed kitchen features a solid wood cabinetry, quartz countertops, a kitchen, butler pantry, coffee bar and laundry room, Verona gas range, Frigidaire Professional French-door refrigerator, KitchenAid dishwasher, convenient under-counter outlets and the kitchen island has lighted shelves. Additional highlights include plantation shutters throughout, wine cellar, climate-controlled storage attic, granite in baths, custom garage cabinetry, epoxy-finished garage floors, hurricane-impact windows in the office/apartment, Pet Turf in the entire backyard with no maintenance necessary and a striking 35-foot flagpole. Combining superior craftsmanship, advanced infrastructure and thoughtful upgrades rarely found in today's market, this extraordinary property presents a unique opportunity to own a one-of-a-kind residence. Total heated square footage includes heated/cooled space to use as garage, workshop, and/or utility room in the detached structure.

1940 Magnolia Avenue, Winter Park

$5,995,000

Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live in every day and will feel just as right decades from now. Set on nearly half an acre in the highly desirable Vias of Winter Park, this fully renovated, turnkey home is modern European design at its most elegant and understated, with bespoke cabinetry & built-ins in every room and rare natural stone throughout. It offers five bedrooms, five full baths, a half bath, and has been curated with the care of a private collection. A sculptural curved staircase greets you in the foyer, and wood floors carry through the main level. The living room rises beneath vaulted ceilings, centered on a gas fireplace wrapped in Sequoia quartzite, with a wall of sliding glass doors opening to the pool so gatherings drift outdoors without a second thought. In the kitchen, rare leathered Naica quartzite forms the waterfall island, countertops, & backsplash, and custom cabinetry rises floor to ceiling. Appliances include a Wolf gas range with pot filler, Sub-Zero refrigerator, & two Miele dishwashers, plus a prep sink, concealed outlets, & push-to-open, soft-close drawers. To one side, a pantry/butler’s passage with matching cabinetry also houses the laundry. At the front of the home, a bright formal dining room & eat-in area complete the space. Just off the eat-in area, a large turf side courtyard offers a low-maintenance space where kids & pets can play within view of the kitchen. The main-level primary suite features two walk-in closets & a double-sided wood-burning fireplace shared with the private office. The spa-inspired bath showcases leathered Taj Mahal quartzite with integrated dual sinks, an extra-large soaking tub for two, & a walk-in shower, all with Graff fixtures. The office opens to the pool and is outfitted with floor-to-ceiling shelving, cabinetry, & file drawers, versatile enough to become a dressing room. The whiskey lounge with custom wet bar is sized for a game room or second office. A powder room completes the main floor. Upstairs, custom cabinetry lines the loft & hallway, offering storage at every turn. To the left, two bedrooms share an elegant bath with dual sinks and a separate tub & shower, and a single door closes them off creating an optional, private two-bedroom suite. To the right, two additional bedrooms each enjoy an en suite bath. Every bedroom is finished with built-in closets. A separate upstairs wing houses the generously sized media room, with state-of-the-art surround sound & extensive hidden storage. Outdoors, a weathered marble pool deck surrounds the saltwater pool, framed by grounds created by Signature Landscape. The garden pavilion with its own fireplace is one of the home’s most special spaces, joined by a summer kitchen with stone counters & wall, a natural gas grill, & a sink, plus a pool bath. Additional features include a three-car side-entry garage with epoxy floors, EV charger capability, & ample storage, along with Lutron lighting on the main level, Toto toilets throughout, water filtration, natural gas, a whole-home generator, & three Trane HVAC systems. The Winter Park Racquet Club, Interlachen Country Club, the shops & dining of Park Avenue, and the Winter Park 9 golf course are all within walking distance. Refined, move-in ready, and crafted without compromise, 1200 Via Salerno awaits its next owner.

5 Beds ⋅ 6 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code

Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live in every day and will feel just as right decades from now. Set on nearly half an acre in the highly desirable Vias of Winter Park, this fully renovated, turnkey home is modern European design at its most elegant and understated, with bespoke cabinetry & built-ins in every room and rare natural stone throughout. It offers five bedrooms, five full baths, a half bath, and has been curated with the care of a private collection. A sculptural curved staircase greets you in the foyer, and wood floors carry through the main level. The living room rises beneath vaulted ceilings, centered on a gas fireplace wrapped in Sequoia quartzite, with a wall of sliding glass doors opening to the pool so gatherings drift outdoors without a second thought. In the kitchen, rare leathered Naica quartzite forms the waterfall island, countertops, & backsplash, and custom cabinetry rises floor to ceiling. Appliances include a Wolf gas range with pot filler, Sub-Zero refrigerator, & two Miele dishwashers, plus a prep sink, concealed outlets, & push-to-open, soft-close drawers. To one side, a pantry/butler’s passage with matching cabinetry also houses the laundry. At the front of the home, a bright formal dining room & eat-in area complete the space. Just off the eat-in area, a large turf side courtyard offers a low-maintenance space where kids & pets can play within view of the kitchen. The main-level primary suite features two walk-in closets & a double-sided wood-burning fireplace shared with the private office. The spa-inspired bath showcases leathered Taj Mahal quartzite with integrated dual sinks, an extra-large soaking tub for two, & a walk-in shower, all with Graff fixtures. The office opens to the pool and is outfitted with floor-to-ceiling shelving, cabinetry, & file drawers, versatile enough to become a dressing room. The whiskey lounge with custom wet bar is sized for a game room or second office. A powder room completes the main floor. Upstairs, custom cabinetry lines the loft & hallway, offering storage at every turn. To the left, two bedrooms share an elegant bath with dual sinks and a separate tub & shower, and a single door closes them off creating an optional, private two-bedroom suite. To the right, two additional bedrooms each enjoy an en suite bath. Every bedroom is finished with built-in closets. A separate upstairs wing houses the generously sized media room, with state-of-the-art surround sound & extensive hidden storage. Outdoors, a weathered marble pool deck surrounds the saltwater pool, framed by grounds created by Signature Landscape. The garden pavilion with its own fireplace is one of the home’s most special spaces, joined by a summer kitchen with stone counters & wall, a natural gas grill, & a sink, plus a pool bath. Additional features include a three-car side-entry garage with epoxy floors, EV charger capability, & ample storage, along with Lutron lighting on the main level, Toto toilets throughout, water filtration, natural gas, a whole-home generator, & three Trane HVAC systems. The Winter Park Racquet Club, Interlachen Country Club, the shops & dining of Park Avenue, and the Winter Park 9 golf course are all within walking distance. Refined, move-in ready, and crafted without compromise, 1200 Via Salerno awaits its next owner.

1200 Via Salerno, Winter Park

$1,050,000

Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of established Winter Park living in this inviting single-story home, situated on a beautifully landscaped 0.36-acre lot in the sought-after 32789 ZIP code. Spacious living areas, abundant natural light, and two inviting fireplaces, including a fireplace in the living room and a distinctive stone fireplace in the primary suite, create a warm and welcoming atmosphere. Step outside to your private swimming pool, surrounded by mature landscaping, offering the perfect setting for relaxing or entertaining. Additional features include a tankless water heater, updated pool equipment, and access to Waterbridge neighborhood tennis courts. An exceptional Winter Park location. Enjoy convenient proximity to AdventHealth Winter Park Hospital, the Winter Park VA Clinic, and Winter Park High School, along with easy access to downtown Winter Park's iconic Park Avenue, renowned restaurants, boutique shopping, Rollins College, Mead Botanical Garden, and downtown Orlando. Combining valuable improvements, single-story convenience, private pool living, and an established neighborhood setting, 1735 Demetree Drive offers the character, comfort, and lifestyle that make Winter Park, Florida, such a desirable place to call home.

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

Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of established Winter Park living in this inviting single-story home, situated on a beautifully landscaped 0.36-acre lot in the sought-after 32789 ZIP code. Spacious living areas, abundant natural light, and two inviting fireplaces, including a fireplace in the living room and a distinctive stone fireplace in the primary suite, create a warm and welcoming atmosphere. Step outside to your private swimming pool, surrounded by mature landscaping, offering the perfect setting for relaxing or entertaining. Additional features include a tankless water heater, updated pool equipment, and access to Waterbridge neighborhood tennis courts. An exceptional Winter Park location. Enjoy convenient proximity to AdventHealth Winter Park Hospital, the Winter Park VA Clinic, and Winter Park High School, along with easy access to downtown Winter Park's iconic Park Avenue, renowned restaurants, boutique shopping, Rollins College, Mead Botanical Garden, and downtown Orlando. Combining valuable improvements, single-story convenience, private pool living, and an established neighborhood setting, 1735 Demetree Drive offers the character, comfort, and lifestyle that make Winter Park, Florida, such a desirable place to call home.

1735 Demetree Drive, Winter Park

$419,900

Private in-ground pool on a 9,000+ sq ft lot in Winter Park, with no HOA. This 4 bed, 2 bath home has 1,427 sq ft of updated living space and an open floor plan with hardwood and vinyl floors throughout. The kitchen was remodeled in 2021 and comes with all appliances, including the refrigerator, range, dishwasher, and microwave. The big-ticket items are already done: roof replaced in 2022, A/C in 2019, plumbing updated in 2021, and a new main electrical panel in 2026. The first-floor primary suite has a walk-in closet, and the other three bedrooms give you room for guests, a home office, or a gym. Outside you get a covered carport, a private entrance, and a large backyard built around the pool. Just minutes from Winter Park dining and shopping, with Lakemont Elementary nearby. Schedule your private showing today.

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code

Private in-ground pool on a 9,000+ sq ft lot in Winter Park, with no HOA. This 4 bed, 2 bath home has 1,427 sq ft of updated living space and an open floor plan with hardwood and vinyl floors throughout. The kitchen was remodeled in 2021 and comes with all appliances, including the refrigerator, range, dishwasher, and microwave. The big-ticket items are already done: roof replaced in 2022, A/C in 2019, plumbing updated in 2021, and a new main electrical panel in 2026. The first-floor primary suite has a walk-in closet, and the other three bedrooms give you room for guests, a home office, or a gym. Outside you get a covered carport, a private entrance, and a large backyard built around the pool. Just minutes from Winter Park dining and shopping, with Lakemont Elementary nearby. Schedule your private showing today.

603 Carnation Drive, Winter Park

$985,000

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigned from top to bottom, this exceptional residence offers a bright, open feel with multiple living spaces perfect for everyday living and entertaining. The light-filled kitchen features quartz countertops, stainless steel appliances, and a custom backsplash, creating a stylish and functional space for cooking and gathering. Spacious family and game rooms provide plenty of room to relax and entertain, while a sun-filled bonus room offers endless possibilities as a home office, playroom, fitness room, or creative space. Two bedrooms on the first floor provide flexibility for guests, a private office, or multigenerational living. Upstairs, the beautifully redesigned primary suite serves as a private retreat, complete with a gorgeous en-suite bathroom featuring a walk-in shower and soaking tub. Two additional bedrooms and a full bathroom complete the second floor, offering comfortable accommodations and room for everyone. Step outside to enjoy the expansive 0.34-acre lot tucked away on a peaceful cul-de-sac, with plenty of space for outdoor entertaining, play, and relaxation. The oversized detached garage offers 500+ additional square feet of versatile space, ideal for hobbies, projects, a workshop, or extra storage. With no HOA restrictions, you’ll have the freedom to make the property your own. The location is just as impressive, with Lake Killarney just steps away and Park Avenue and Winter Park Village only a short drive away for premier shopping, dining, and entertainment. Convenient access to I-4 makes commuting and exploring Central Florida a breeze. Combining thoughtful renovations, flexible living spaces, an oversized lot, and an unbeatable Winter Park location, this home is a rare opportunity to enjoy the best of Florida living. Schedule your private showing today!

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

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigned from top to bottom, this exceptional residence offers a bright, open feel with multiple living spaces perfect for everyday living and entertaining. The light-filled kitchen features quartz countertops, stainless steel appliances, and a custom backsplash, creating a stylish and functional space for cooking and gathering. Spacious family and game rooms provide plenty of room to relax and entertain, while a sun-filled bonus room offers endless possibilities as a home office, playroom, fitness room, or creative space. Two bedrooms on the first floor provide flexibility for guests, a private office, or multigenerational living. Upstairs, the beautifully redesigned primary suite serves as a private retreat, complete with a gorgeous en-suite bathroom featuring a walk-in shower and soaking tub. Two additional bedrooms and a full bathroom complete the second floor, offering comfortable accommodations and room for everyone. Step outside to enjoy the expansive 0.34-acre lot tucked away on a peaceful cul-de-sac, with plenty of space for outdoor entertaining, play, and relaxation. The oversized detached garage offers 500+ additional square feet of versatile space, ideal for hobbies, projects, a workshop, or extra storage. With no HOA restrictions, you’ll have the freedom to make the property your own. The location is just as impressive, with Lake Killarney just steps away and Park Avenue and Winter Park Village only a short drive away for premier shopping, dining, and entertainment. Convenient access to I-4 makes commuting and exploring Central Florida a breeze. Combining thoughtful renovations, flexible living spaces, an oversized lot, and an unbeatable Winter Park location, this home is a rare opportunity to enjoy the best of Florida living. Schedule your private showing today!

2330 Westminster Ct., Winter Park

$509,999

Welcome to 808 Densmore Drive, a beautifully updated 3-bedroom, 2-bathroom pool home tucked into the established Winter Park Estates neighborhood! Blending modern farmhouse charm with thoughtful upgrades, this home offers 1,460 square feet of inviting living space designed for both everyday comfort and entertaining. Step inside to a bright, open floor plan where the spacious living and dining areas flow effortlessly into the kitchen, complete with quartz countertops, stainless steel appliances, a built-in microwave, tile backsplash, and a window overlooking the outdoors. On the opposite side of the home, you'll find three comfortable bedrooms and two beautifully updated bathrooms, offering a practical layout with plenty of privacy. An oversized interior laundry room and enclosed porch provide additional functional space. Outside is where this home truly shines! The private backyard features a sparkling in-ground pool, a newly installed paver patio (2025), and a brand-new fence (2026), creating an inviting setting for weekend gatherings, outdoor dining, or relaxing in the Florida sunshine. Recent improvements also include a new irrigation system and control panel (2026), updated pool filtration equipment (2026), and a water heater replaced approximately three years ago. Beyond the property, enjoy a prime Winter Park location just minutes from Cady Way Trail, Winter Park Pines Golf Course, Rollins College, and the shopping, dining, and charm of Park Avenue. With its updated interiors, private pool, and convenient access to everything Winter Park has to offer, 808 Densmore Drive is ready to welcome you home!

3 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code

Welcome to 808 Densmore Drive, a beautifully updated 3-bedroom, 2-bathroom pool home tucked into the established Winter Park Estates neighborhood! Blending modern farmhouse charm with thoughtful upgrades, this home offers 1,460 square feet of inviting living space designed for both everyday comfort and entertaining. Step inside to a bright, open floor plan where the spacious living and dining areas flow effortlessly into the kitchen, complete with quartz countertops, stainless steel appliances, a built-in microwave, tile backsplash, and a window overlooking the outdoors. On the opposite side of the home, you'll find three comfortable bedrooms and two beautifully updated bathrooms, offering a practical layout with plenty of privacy. An oversized interior laundry room and enclosed porch provide additional functional space. Outside is where this home truly shines! The private backyard features a sparkling in-ground pool, a newly installed paver patio (2025), and a brand-new fence (2026), creating an inviting setting for weekend gatherings, outdoor dining, or relaxing in the Florida sunshine. Recent improvements also include a new irrigation system and control panel (2026), updated pool filtration equipment (2026), and a water heater replaced approximately three years ago. Beyond the property, enjoy a prime Winter Park location just minutes from Cady Way Trail, Winter Park Pines Golf Course, Rollins College, and the shopping, dining, and charm of Park Avenue. With its updated interiors, private pool, and convenient access to everything Winter Park has to offer, 808 Densmore Drive is ready to welcome you home!

808 Densmore Drive, Winter Park

$699,900

Enjoy bright, inviting living and your own screened pool retreat in Winter Park! This 3-bedroom, 2-bath home offers 1,666 square feet with vaulted ceilings, abundant natural light, and plantation shutters. The spacious family room features laminate flooring and a wood-burning fireplace, creating a welcoming place to gather. The updated kitchen offers stainless steel appliances, ample drawer storage, a pullout pantry, and a sunny dinette with sliding doors to the outdoor living area. Multiple access points throughout the home connect to the screened pool enclosure, where a recently resurfaced pool and covered patio provide space for relaxing and entertaining. The primary suite features a walk-in closet and an en-suite bath with dual sinks and a separate shower. Two additional bedrooms offer flexibility for guests or a home office, while the second full bath includes a bathtub. An attached two-car garage provides laundry space, extensive cabinetry, and pull-down attic access. All appliances are included, adding convenience to this inviting Winter Park home.

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

Enjoy bright, inviting living and your own screened pool retreat in Winter Park! This 3-bedroom, 2-bath home offers 1,666 square feet with vaulted ceilings, abundant natural light, and plantation shutters. The spacious family room features laminate flooring and a wood-burning fireplace, creating a welcoming place to gather. The updated kitchen offers stainless steel appliances, ample drawer storage, a pullout pantry, and a sunny dinette with sliding doors to the outdoor living area. Multiple access points throughout the home connect to the screened pool enclosure, where a recently resurfaced pool and covered patio provide space for relaxing and entertaining. The primary suite features a walk-in closet and an en-suite bath with dual sinks and a separate shower. Two additional bedrooms offer flexibility for guests or a home office, while the second full bath includes a bathtub. An attached two-car garage provides laundry space, extensive cabinetry, and pull-down attic access. All appliances are included, adding convenience to this inviting Winter Park home.

1884 Jessica Court, Winter Park

$4,500,000

Brand new construction (2023) on a beautifully sized .29± acre lot in the heart of Winter Park. This 5BR/5.5BA estate offers an open-concept layout with high ceilings, abundant natural light, and premium finishes throughout. Every bedroom features its own en-suite bath. Resort-style pool and putting green anchor the outdoor living space, perfect for Florida's year-round lifestyle. Detached garage offers flexible storage, workshop space, plus room for a private home gym. Minutes from Park Avenue's shops, dining, and top-rated schools. Top quality construction and unbeatable location. Schedule your private showing today.

5 Beds ⋅ 6 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code

Brand new construction (2023) on a beautifully sized .29± acre lot in the heart of Winter Park. This 5BR/5.5BA estate offers an open-concept layout with high ceilings, abundant natural light, and premium finishes throughout. Every bedroom features its own en-suite bath. Resort-style pool and putting green anchor the outdoor living space, perfect for Florida's year-round lifestyle. Detached garage offers flexible storage, workshop space, plus room for a private home gym. Minutes from Park Avenue's shops, dining, and top-rated schools. Top quality construction and unbeatable location. Schedule your private showing today.

1631 Hillcrest Avenue, Winter Park

$3,195,000

1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed stone, a stately brick entry, and striking black-framed windows define its European-inspired architecture in Winter Park’s coveted Kenilworth Shores. Brand-new and awaiting its first owner, this expansive custom residence offers over 4,300 square feet of timeless character and bespoke craftsmanship. Inside, natural light moves across wide-plank engineered white oak floors. Grand entertaining spaces meet intimate rooms. Architectural symmetry defines the great room, where a soaring fluted terrazzo fireplace is framed by custom cabinetry and brass picture lights. Expansive glass opens to the lanai, while a sitting room features a custom bar with brass mesh cabinetry, illuminated shelving, glazed tile, and wine refrigeration. The kitchen is a masterpiece, and you'll know it the moment you walk in. A Taj Mahal quartzite island commands the room, framed by floor-to-ceiling bespoke cabinetry, illuminated reeded glass, and a sculptural fluted hood. Sweeping waterfall edges meet a custom fluted wood base. A 48-inch Viking gas range, double ovens, and separate refrigerator and freezer columns complete the kitchen. Beyond, a windowed butler’s pantry offers quartzite countertops, illuminated shelving, and beverage refrigeration. Opening to the pool, the dining room invites memorable dinners that linger long after the last guest should have left. And then there's the first-floor primary suite—where luxury becomes personal. Vaulted ceilings with stained oak beams bring warmth and architectural character, while the bathroom is a destination in itself. Brass-inlaid marble floors, lilac-veined stone, a quartzite double vanity, and makeup station introduce a spectacular wet room with four rainfall showerheads, two handheld showers, and a sculptural fluted soaking tub. An oversized, fully customized walk-in closet features built-in cabinetry and elegant glass-front displays. Just off the foyer, the library is a room you'll fall in love with. Color-drenched walls, a stained oak-plank ceiling, custom built-ins, and brass-lit shelving create an intimate retreat, enclosed in glass with doors to a secluded side patio. The mudroom, plum-cabinetry laundry, and plaster-inspired powder bath complete the level. Upstairs, a light-filled loft opens to an uncovered terrace with checkerboard stone flooring, made for sunset conversations beneath the stars. Three bedrooms each feature an en-suite bath and custom closet. A jewel-box powder bath and vaulted bonus room, ideal for a cinema or game lounge, complete the level. Outside, a covered lanai with stained tongue-and-groove ceiling features a summer kitchen in whitewashed brick, fluted cabinetry, and leathered granite. French-pattern Talya leathered stone frames the PebbleTec pool, tanning ledge, inset spa, and calming waterfall—a setting made for sunlit afternoons, entertaining, and memorable evenings. Custom-built by Structure Redevelopment, LLC, this residence reflects a passion for distinctive architecture, superior craftsmanship, and uncompromising detail. Among Kenilworth Shores' distinguished residences and lakefront estates, it places you moments from Park Avenue’s restaurants, boutiques, and cafés, Rollins College, and the Chain of Lakes. Schedule your private showing today.

4 Beds ⋅ 6 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed stone, a stately brick entry, and striking black-framed windows define its European-inspired architecture in Winter Park’s coveted Kenilworth Shores. Brand-new and awaiting its first owner, this expansive custom residence offers over 4,300 square feet of timeless character and bespoke craftsmanship. Inside, natural light moves across wide-plank engineered white oak floors. Grand entertaining spaces meet intimate rooms. Architectural symmetry defines the great room, where a soaring fluted terrazzo fireplace is framed by custom cabinetry and brass picture lights. Expansive glass opens to the lanai, while a sitting room features a custom bar with brass mesh cabinetry, illuminated shelving, glazed tile, and wine refrigeration. The kitchen is a masterpiece, and you'll know it the moment you walk in. A Taj Mahal quartzite island commands the room, framed by floor-to-ceiling bespoke cabinetry, illuminated reeded glass, and a sculptural fluted hood. Sweeping waterfall edges meet a custom fluted wood base. A 48-inch Viking gas range, double ovens, and separate refrigerator and freezer columns complete the kitchen. Beyond, a windowed butler’s pantry offers quartzite countertops, illuminated shelving, and beverage refrigeration. Opening to the pool, the dining room invites memorable dinners that linger long after the last guest should have left. And then there's the first-floor primary suite—where luxury becomes personal. Vaulted ceilings with stained oak beams bring warmth and architectural character, while the bathroom is a destination in itself. Brass-inlaid marble floors, lilac-veined stone, a quartzite double vanity, and makeup station introduce a spectacular wet room with four rainfall showerheads, two handheld showers, and a sculptural fluted soaking tub. An oversized, fully customized walk-in closet features built-in cabinetry and elegant glass-front displays. Just off the foyer, the library is a room you'll fall in love with. Color-drenched walls, a stained oak-plank ceiling, custom built-ins, and brass-lit shelving create an intimate retreat, enclosed in glass with doors to a secluded side patio. The mudroom, plum-cabinetry laundry, and plaster-inspired powder bath complete the level. Upstairs, a light-filled loft opens to an uncovered terrace with checkerboard stone flooring, made for sunset conversations beneath the stars. Three bedrooms each feature an en-suite bath and custom closet. A jewel-box powder bath and vaulted bonus room, ideal for a cinema or game lounge, complete the level. Outside, a covered lanai with stained tongue-and-groove ceiling features a summer kitchen in whitewashed brick, fluted cabinetry, and leathered granite. French-pattern Talya leathered stone frames the PebbleTec pool, tanning ledge, inset spa, and calming waterfall—a setting made for sunlit afternoons, entertaining, and memorable evenings. Custom-built by Structure Redevelopment, LLC, this residence reflects a passion for distinctive architecture, superior craftsmanship, and uncompromising detail. Among Kenilworth Shores' distinguished residences and lakefront estates, it places you moments from Park Avenue’s restaurants, boutiques, and cafés, Rollins College, and the Chain of Lakes. Schedule your private showing today.

1825 Whitehall Drive, Winter Park

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