Pinecrestmanagement.com Search Results

$3,750,000

Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in one special property. Set behind a private gated entrance on approximately 4.3 total acres, with roughly half of the property consisting of dry land and the balance extending into Lake Howell, this remarkable estate offers a rare combination of privacy, space, and direct lake access, yet remains just minutes from the charm of Park Avenue, Interlachen Country Club, shopping, dining, and everything Winter Park has to offer. Lake Howell provides a spectacular backdrop for everyday living and entertaining, with opportunities for boating, fishing, watersports, sunset cruises, and unforgettable days on the water. The property features its own private boat ramp, boathouse, and boat dock, making lake life exceptionally convenient. The grounds are designed for both grand entertaining and relaxed family living. A massive detached barn offers an incredible flexible space for private events, parties, gatherings, game nights, or simply creating your own ultimate entertainment venue. Fully air conditioned and featuring high ceilings, the barn provides room for additional vehicles, RVs, boats, recreational equipment, and more. It also includes a private gym and bathroom, making it a versatile addition to the property. For RV enthusiasts, the property also features a full 50 amp RV hookup, providing convenient power access for a recreational vehicle or guests. A separate four-car detached garage with workshop provides substantial storage and workspace. A generator adds another level of convenience and peace of mind. The expansive fenced grounds offer plenty of room for family, pets, recreation, and outdoor activities, including a large playset and a firepit with comfortable seating the perfect setting for cool evenings, roasting marshmallows, sharing stories, and making memories together. The recently updated pool area is designed to feel like your own private resort. Enjoy the covered lanai, outdoor kitchen, pool, and stunning lake views, along with a gas fireplace that creates an inviting atmosphere for evening entertaining. The outdoor kitchen is a chef’s dream, making it easy to host everything from casual family gatherings to unforgettable waterfront celebrations. Inside, the home was thoughtfully renovated in 2016 and offers just over 3,377 square feet under air, with approximately 7,758 total square feet. Beautiful wood flooring, tile, and carpeted bedrooms create a comfortable blend of style and functionality. The Florida room provides the perfect place to relax, take in the lake views, and enjoy the natural beauty surrounding the home. The upgraded kitchen features stainless steel appliances and a Thermador range, while the spacious executive office provides an ideal work-from-home environment or private study. The residence offers four bedrooms and three bathrooms, providing generous accommodations for family and guests. With multiple indoor and outdoor gathering spaces, extraordinary storage, recreational amenities, and direct access to Lake Howell, this property is much more than a home it is a private lifestyle estate. Whether you're looking for a peaceful waterfront sanctuary, a place to entertain on a grand scale, a family compound, or simply a rare piece of Winter Park property with exceptional lake access, this property delivers an unparalleled opportunity.

4 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 32792 Zip Code

Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in one special property. Set behind a private gated entrance on approximately 4.3 total acres, with roughly half of the property consisting of dry land and the balance extending into Lake Howell, this remarkable estate offers a rare combination of privacy, space, and direct lake access, yet remains just minutes from the charm of Park Avenue, Interlachen Country Club, shopping, dining, and everything Winter Park has to offer. Lake Howell provides a spectacular backdrop for everyday living and entertaining, with opportunities for boating, fishing, watersports, sunset cruises, and unforgettable days on the water. The property features its own private boat ramp, boathouse, and boat dock, making lake life exceptionally convenient. The grounds are designed for both grand entertaining and relaxed family living. A massive detached barn offers an incredible flexible space for private events, parties, gatherings, game nights, or simply creating your own ultimate entertainment venue. Fully air conditioned and featuring high ceilings, the barn provides room for additional vehicles, RVs, boats, recreational equipment, and more. It also includes a private gym and bathroom, making it a versatile addition to the property. For RV enthusiasts, the property also features a full 50 amp RV hookup, providing convenient power access for a recreational vehicle or guests. A separate four-car detached garage with workshop provides substantial storage and workspace. A generator adds another level of convenience and peace of mind. The expansive fenced grounds offer plenty of room for family, pets, recreation, and outdoor activities, including a large playset and a firepit with comfortable seating the perfect setting for cool evenings, roasting marshmallows, sharing stories, and making memories together. The recently updated pool area is designed to feel like your own private resort. Enjoy the covered lanai, outdoor kitchen, pool, and stunning lake views, along with a gas fireplace that creates an inviting atmosphere for evening entertaining. The outdoor kitchen is a chef’s dream, making it easy to host everything from casual family gatherings to unforgettable waterfront celebrations. Inside, the home was thoughtfully renovated in 2016 and offers just over 3,377 square feet under air, with approximately 7,758 total square feet. Beautiful wood flooring, tile, and carpeted bedrooms create a comfortable blend of style and functionality. The Florida room provides the perfect place to relax, take in the lake views, and enjoy the natural beauty surrounding the home. The upgraded kitchen features stainless steel appliances and a Thermador range, while the spacious executive office provides an ideal work-from-home environment or private study. The residence offers four bedrooms and three bathrooms, providing generous accommodations for family and guests. With multiple indoor and outdoor gathering spaces, extraordinary storage, recreational amenities, and direct access to Lake Howell, this property is much more than a home it is a private lifestyle estate. Whether you're looking for a peaceful waterfront sanctuary, a place to entertain on a grand scale, a family compound, or simply a rare piece of Winter Park property with exceptional lake access, this property delivers an unparalleled opportunity.

2622 Lake Howell Lane, Winter Park

$699,000

Virtually Staged. Zoned for Fantastic Winter Park Schools, this 4 bed, 2 bath recently renovated abode is waiting for you. Located on a quiet, tree-lined street, you can walk to highly rated Brookshire Elem and Winter Park High. The open-plan living space has beautiful travertine tile floors flowing through the kitchen, dining room, and living room. Renovated in 2026, the kitchen offers quartz counter tops, new appliances, under cabinet lighting, custom tile backsplash, and pendant lights. Flowing from the kitchen to the dining room and through to the living room, this open floor plan is sure to please. Double French doors open from the sunny living room to the spacious backyard. The oversized two-car garage and laundry room are just off the kitchen. Travertine continues down the hall, while all 4 bedrooms have newly installed wood flooring (2024). The primary bedroom has a renovated ensuite (2026) with enlarged walk-in shower, custom tile, new fixtures, and new quartz topped vanity. All 4 bedrooms have window shutters and new ceiling fans, and the renovated hall bath (2025) offers new marble topped double sink vanity, new mirrors, and tub/shower tile surround. Out back, the grassy backyard with new fencing and St Augustine sod (2025) offers plenty of room for kids and pets to play or even a future pool addition. Located just 3 miles to Rollins College and the Park Ave shopping and dining district, this prime location offers other, even closer, benefits. Cady Way Park is 2 blocks away with a community pool, pickleball courts, tennis courts, picnic tables, and access to the Cady Way Bike Trail. NEW HVAC 2024, Roof 2015, updated electrical box 2014, and house re-piped with CPVC 2009. Come check out this charming move-in ready Winter Park house and make it your own home.

4 Beds ⋅ 2 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code

Virtually Staged. Zoned for Fantastic Winter Park Schools, this 4 bed, 2 bath recently renovated abode is waiting for you. Located on a quiet, tree-lined street, you can walk to highly rated Brookshire Elem and Winter Park High. The open-plan living space has beautiful travertine tile floors flowing through the kitchen, dining room, and living room. Renovated in 2026, the kitchen offers quartz counter tops, new appliances, under cabinet lighting, custom tile backsplash, and pendant lights. Flowing from the kitchen to the dining room and through to the living room, this open floor plan is sure to please. Double French doors open from the sunny living room to the spacious backyard. The oversized two-car garage and laundry room are just off the kitchen. Travertine continues down the hall, while all 4 bedrooms have newly installed wood flooring (2024). The primary bedroom has a renovated ensuite (2026) with enlarged walk-in shower, custom tile, new fixtures, and new quartz topped vanity. All 4 bedrooms have window shutters and new ceiling fans, and the renovated hall bath (2025) offers new marble topped double sink vanity, new mirrors, and tub/shower tile surround. Out back, the grassy backyard with new fencing and St Augustine sod (2025) offers plenty of room for kids and pets to play or even a future pool addition. Located just 3 miles to Rollins College and the Park Ave shopping and dining district, this prime location offers other, even closer, benefits. Cady Way Park is 2 blocks away with a community pool, pickleball courts, tennis courts, picnic tables, and access to the Cady Way Bike Trail. NEW HVAC 2024, Roof 2015, updated electrical box 2014, and house re-piped with CPVC 2009. Come check out this charming move-in ready Winter Park house and make it your own home.

2260 Coldstream Drive, Winter Park

$5,999,990

Virtually Staged. AN ARCHITECTURAL STATEMENT IN ONE OF WINTER PARK'S MOST COVETED LOCATIONS. Set on a prominent corner lot within exclusive Via Tuscany, this extraordinary new-construction residence by Developer & Builder Group represents far more than exceptional modern design. Its distinction lies equally in what you see and in what you don't see, the extraordinary level of construction, engineering, materials, and craftsmanship behind every detail. Built with reinforced concrete, steel, and iron framing and incorporating exceptionally high construction specifications, the residence was created with an uncompromising commitment to structural integrity, durability, and long-term quality. From its substantial structural components to its impact-resistant glass and carefully sourced materials, the home reflects a philosophy rarely found in residential construction: build beautifully, but build exceptionally well. Offering approximately 4,636 square feet of heated living space and 5,260 total square feet, the residence features 4 bedrooms, 4.5 bathrooms, a private pool, and an attached two-car garage. Expansive floor-to-ceiling impact-resistant Techno Glass walls define the architecture, bringing abundant natural light into the interiors while creating a striking connection between indoor and outdoor living. At the center of the home is a dramatic 16-foot custom Costa One-Tree solid steel installation a true architectural work of art and one of the many elements created specifically for this residence. The same uncompromising approach continues throughout the interiors. Imported Italian porcelain flooring, sophisticated lighting fixtures imported from Greece, and carefully selected European finishes elevate every space. The gourmet kitchen features one-inch-thick Italian quartz countertops, imported Italian cabinetry, an extended entertaining island, premium Wolf appliances, and a Sub-Zero refrigerator. Two luxurious primary suites, one on each level provide exceptional flexibility and privacy, each complemented by a beautifully appointed bath and custom walk-in closet. Private balconies crafted with exquisite boat wood create intimate outdoor retreats, while the private pool completes the home's sophisticated indoor-outdoor lifestyle. The setting is equally exceptional. Via Tuscany offers a coveted Winter Park address near Interlachen Country Club and only minutes from Park Avenue's renowned dining, boutiques, museums, and cultural attractions, with convenient access to Downtown Orlando. This is a residence for the buyer who understands that true luxury is not defined by finishes alone. It is defined by the quality of the materials, the integrity of the construction, the precision of the craftsmanship, and the attention given to what lies behind the walls as much as what is visible within them. RESILIENT BY DESIGN. EXCEPTIONAL BY CONSTRUCTION. REFINED IN EVERY DETAIL.

4 Beds ⋅ 5 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. AN ARCHITECTURAL STATEMENT IN ONE OF WINTER PARK'S MOST COVETED LOCATIONS. Set on a prominent corner lot within exclusive Via Tuscany, this extraordinary new-construction residence by Developer & Builder Group represents far more than exceptional modern design. Its distinction lies equally in what you see and in what you don't see, the extraordinary level of construction, engineering, materials, and craftsmanship behind every detail. Built with reinforced concrete, steel, and iron framing and incorporating exceptionally high construction specifications, the residence was created with an uncompromising commitment to structural integrity, durability, and long-term quality. From its substantial structural components to its impact-resistant glass and carefully sourced materials, the home reflects a philosophy rarely found in residential construction: build beautifully, but build exceptionally well. Offering approximately 4,636 square feet of heated living space and 5,260 total square feet, the residence features 4 bedrooms, 4.5 bathrooms, a private pool, and an attached two-car garage. Expansive floor-to-ceiling impact-resistant Techno Glass walls define the architecture, bringing abundant natural light into the interiors while creating a striking connection between indoor and outdoor living. At the center of the home is a dramatic 16-foot custom Costa One-Tree solid steel installation a true architectural work of art and one of the many elements created specifically for this residence. The same uncompromising approach continues throughout the interiors. Imported Italian porcelain flooring, sophisticated lighting fixtures imported from Greece, and carefully selected European finishes elevate every space. The gourmet kitchen features one-inch-thick Italian quartz countertops, imported Italian cabinetry, an extended entertaining island, premium Wolf appliances, and a Sub-Zero refrigerator. Two luxurious primary suites, one on each level provide exceptional flexibility and privacy, each complemented by a beautifully appointed bath and custom walk-in closet. Private balconies crafted with exquisite boat wood create intimate outdoor retreats, while the private pool completes the home's sophisticated indoor-outdoor lifestyle. The setting is equally exceptional. Via Tuscany offers a coveted Winter Park address near Interlachen Country Club and only minutes from Park Avenue's renowned dining, boutiques, museums, and cultural attractions, with convenient access to Downtown Orlando. This is a residence for the buyer who understands that true luxury is not defined by finishes alone. It is defined by the quality of the materials, the integrity of the construction, the precision of the craftsmanship, and the attention given to what lies behind the walls as much as what is visible within them. RESILIENT BY DESIGN. EXCEPTIONAL BY CONSTRUCTION. REFINED IN EVERY DETAIL.

2661 Via Tuscany, Winter Park

$1,395,000

Welcome to 2873 Old Castle Drive, an exceptional property located within the sought-after gated community of Bear Gully Pointe in Winter Park. Nestled along the shores of Bear Lake, a 137- acre spring-fed lake, this stunning estate-like property sits on more than half an acre and is surrounded by lush landscaping, mature trees and beautifully maintained grounds. From the moment you arrive, the long, newly paved driveway sets the tone for what awaits. Meticulously maintained, this impressive home offers 4 bedrooms, 4 full bathrooms, a dedicated office and a spacious upstairs loft/bonus room. The dramatic entry features soaring ceilings, expansive windows and sliding glass doors that draw your attention to the pool and picturesque backyard. The formal dining room, accented by coffered ceilings, flows seamlessly into the beautifully appointed kitchen through a wet bar and wine closet. Completely reimagined down to the studs in 2016, the kitchen features gorgeous marble countertops, custom cabinetry with built-in drawers, a brand-new gas cooktop, double wall ovens, Sub-Zero refrigerator, generous breakfast nook and a large picture window overlooking the pool. The kitchen opens directly to the spacious family room, where soaring ceilings, floor- to-ceiling windows, a gas fireplace and custom built-in cabinetry create an inviting gathering space. A secondary bedroom and full bathroom are conveniently located just off the family room. The expansive downstairs primary suite is a true retreat, featuring tall ceilings, abundant windows and a French door providing direct access to the pool and lanai. Completely remodeled in 2019, the luxurious primary bath offers two separate vanities with dual sinks, a spacious shower with dual shower heads, a beautiful soaking tub and a custom walk-in closet. Just beyond the primary suite is a dedicated office and convenient pool bath. Upstairs, a separate living area provides exceptional flexibility with a generous loft/bonus room, two spacious bedrooms and a full bath featuring dual sinks, a soaking tub and separate shower. Designed with entertaining in mind, the home’s indoor and outdoor spaces blend effortlessly together. The heated pool and spa are surrounded by a covered, screened lanai and a lush backyard oasis complete with mature trees and charming walking paths—creating a private setting for relaxing or entertaining. Bear Gully Pointe offers sidewalks throughout the community, a tennis court, playground and a brand-new gazebo overlooking Bear Lake. Ideally located just minutes from downtown Winter Park, Trinity Preparatory School, Winter Springs and Oviedo. Additional updates include a 2021 roof, 2022 gas water heater, 2024 re-pipe, 2016 pool resurfacing, 2025 driveway, 2022 exterior paint and hardwood flooring downstairs added in 2013.

4 Beds ⋅ 4 Baths ⋅ Bear Gully Pointe SubDv. ⋅ 32792 Zip Code

Welcome to 2873 Old Castle Drive, an exceptional property located within the sought-after gated community of Bear Gully Pointe in Winter Park. Nestled along the shores of Bear Lake, a 137- acre spring-fed lake, this stunning estate-like property sits on more than half an acre and is surrounded by lush landscaping, mature trees and beautifully maintained grounds. From the moment you arrive, the long, newly paved driveway sets the tone for what awaits. Meticulously maintained, this impressive home offers 4 bedrooms, 4 full bathrooms, a dedicated office and a spacious upstairs loft/bonus room. The dramatic entry features soaring ceilings, expansive windows and sliding glass doors that draw your attention to the pool and picturesque backyard. The formal dining room, accented by coffered ceilings, flows seamlessly into the beautifully appointed kitchen through a wet bar and wine closet. Completely reimagined down to the studs in 2016, the kitchen features gorgeous marble countertops, custom cabinetry with built-in drawers, a brand-new gas cooktop, double wall ovens, Sub-Zero refrigerator, generous breakfast nook and a large picture window overlooking the pool. The kitchen opens directly to the spacious family room, where soaring ceilings, floor- to-ceiling windows, a gas fireplace and custom built-in cabinetry create an inviting gathering space. A secondary bedroom and full bathroom are conveniently located just off the family room. The expansive downstairs primary suite is a true retreat, featuring tall ceilings, abundant windows and a French door providing direct access to the pool and lanai. Completely remodeled in 2019, the luxurious primary bath offers two separate vanities with dual sinks, a spacious shower with dual shower heads, a beautiful soaking tub and a custom walk-in closet. Just beyond the primary suite is a dedicated office and convenient pool bath. Upstairs, a separate living area provides exceptional flexibility with a generous loft/bonus room, two spacious bedrooms and a full bath featuring dual sinks, a soaking tub and separate shower. Designed with entertaining in mind, the home’s indoor and outdoor spaces blend effortlessly together. The heated pool and spa are surrounded by a covered, screened lanai and a lush backyard oasis complete with mature trees and charming walking paths—creating a private setting for relaxing or entertaining. Bear Gully Pointe offers sidewalks throughout the community, a tennis court, playground and a brand-new gazebo overlooking Bear Lake. Ideally located just minutes from downtown Winter Park, Trinity Preparatory School, Winter Springs and Oviedo. Additional updates include a 2021 roof, 2022 gas water heater, 2024 re-pipe, 2016 pool resurfacing, 2025 driveway, 2022 exterior paint and hardwood flooring downstairs added in 2013.

2873 Old Castle Drive, Winter Park

$360,000

Great investment opportunity in Winter Park. 4 bedroom 2.5 bathroom. Large covered patio overlooks huge completely fenced back yard. New roof 2025, HVAC system 2020, water heater 2024 and upgraded electric panel re-piping of water system with Pex in 2010. Terrazzo flooring through most of the home. Excellent Seminole County neighborhood located just minutes to Downtown Winter Park, City of Orlando, Orlando International Airport, UCF & Full Sail Universities, Rollins College, Banking, Shopping & Winter Park Hospital. Within 1 hour of area attractions, Atlantic Coast Beaches, Cap Canaveral.

4 Beds ⋅ 3 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code

Great investment opportunity in Winter Park. 4 bedroom 2.5 bathroom. Large covered patio overlooks huge completely fenced back yard. New roof 2025, HVAC system 2020, water heater 2024 and upgraded electric panel re-piping of water system with Pex in 2010. Terrazzo flooring through most of the home. Excellent Seminole County neighborhood located just minutes to Downtown Winter Park, City of Orlando, Orlando International Airport, UCF & Full Sail Universities, Rollins College, Banking, Shopping & Winter Park Hospital. Within 1 hour of area attractions, Atlantic Coast Beaches, Cap Canaveral.

2122 Ridge Drive, Winter Park

$1,350,000

Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Orlando. Offering nearly 3,000 square feet of thoughtfully designed living space, this 4-bedroom, 4-bath home combines contemporary architecture, abundant natural light, and elevated finishes in one of Central Florida’s most sought-after locations. Oversized windows and an open-concept layout create a bright, seamless connection between the living, dining, and kitchen spaces—equally suited for everyday living and entertaining. At the heart of the home, the gourmet kitchen features premium stainless steel appliances, custom cabinetry, designer backsplash and lighting, and an oversized island with dramatic waterfall-edge quartz countertops and generous seating. The thoughtfully designed floor plan includes a first-floor guest suite and full bath, providing privacy and flexibility for overnight guests, multigenerational living, or a private home office. Upstairs, the spacious primary retreat features a spa-inspired bath with dual vanities, soaking tub, oversized walk-in shower, and a generous walk-in closet enhanced with a custom organization system. Two additional bedroom suites complete the second level. Outside, the fully fenced backyard and covered lanai with summer kitchen create an inviting extension of the home’s living space—perfect for outdoor dining and entertaining year-round. Additional highlights include designer LED lighting, abundant storage, a two-car garage, manicured landscaping, and no HOA. Located near shopping, dining, highly rated schools, Park Avenue, and the best of Winter Park and Orlando, 1320 Orchid Avenue offers the rare opportunity to enjoy newer construction, modern design, and an exceptional location without sacrificing space or privacy. Schedule your private showing today.

4 Beds ⋅ 4 Baths ⋅ Elizabeth Heights Sub SubDv. ⋅ 32789 Zip Code

Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Orlando. Offering nearly 3,000 square feet of thoughtfully designed living space, this 4-bedroom, 4-bath home combines contemporary architecture, abundant natural light, and elevated finishes in one of Central Florida’s most sought-after locations. Oversized windows and an open-concept layout create a bright, seamless connection between the living, dining, and kitchen spaces—equally suited for everyday living and entertaining. At the heart of the home, the gourmet kitchen features premium stainless steel appliances, custom cabinetry, designer backsplash and lighting, and an oversized island with dramatic waterfall-edge quartz countertops and generous seating. The thoughtfully designed floor plan includes a first-floor guest suite and full bath, providing privacy and flexibility for overnight guests, multigenerational living, or a private home office. Upstairs, the spacious primary retreat features a spa-inspired bath with dual vanities, soaking tub, oversized walk-in shower, and a generous walk-in closet enhanced with a custom organization system. Two additional bedroom suites complete the second level. Outside, the fully fenced backyard and covered lanai with summer kitchen create an inviting extension of the home’s living space—perfect for outdoor dining and entertaining year-round. Additional highlights include designer LED lighting, abundant storage, a two-car garage, manicured landscaping, and no HOA. Located near shopping, dining, highly rated schools, Park Avenue, and the best of Winter Park and Orlando, 1320 Orchid Avenue offers the rare opportunity to enjoy newer construction, modern design, and an exceptional location without sacrificing space or privacy. Schedule your private showing today.

1320 Orchid Avenue, Winter Park

$495,000

UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, and NO HOA, tucked into the established Wrenwood neighborhood of Winter Park. From the thoughtfully updated interior to the backyard designed for Florida living, this home offers the space, flexibility, and location you've been looking for. Step inside to a bright and inviting interior featuring new LVP flooring throughout, a split-bedroom floor plan, and multiple living and dining spaces that provide plenty of room to spread out, gather, and entertain. The kitchen features abundant cabinetry and counter space, stone countertops, a built-in oven and cooktop, and a window overlooking the backyard. Custom epoxy flooring in the kitchen and entry adds durability and a unique finishing touch. The primary suite is one of the home's standout spaces, featuring a beautifully remodeled bathroom with a double vanity and an oversized glass-enclosed shower, along with a custom-built closet with shelving and organization designed to maximize storage and functionality. But the backyard may be where you'll want to spend most of your time. Step outside to a private in-ground pool, covered screened patio, fenced backyard, and an expanded pool deck with additional pavers, creating multiple spaces to lounge, entertain, dine outdoors, or simply enjoy the Florida sunshine. There's even green space beyond the pool, giving the backyard a more open feel than you might expect from a pool home. The home also offers important improvements already completed for you, including a roof replaced in 2019, re-pipe completed in 2013, and HVAC system replaced in 2018/2019. A professionally installed security system and security cameras add another layer of functionality. The location ties it all together. Situated in Winter Park's Wrenwood neighborhood, 3020 Nicholson Drive puts you within easy reach of some of Central Florida's favorite destinations, including Park Avenue, Winter Park Village, and Baldwin Park, with shopping, dining, entertainment, and everyday conveniences nearby. Convenient access to SR 436 and the 408 also makes it easy to reach Downtown Orlando and destinations throughout Central Florida.

4 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code

UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, and NO HOA, tucked into the established Wrenwood neighborhood of Winter Park. From the thoughtfully updated interior to the backyard designed for Florida living, this home offers the space, flexibility, and location you've been looking for. Step inside to a bright and inviting interior featuring new LVP flooring throughout, a split-bedroom floor plan, and multiple living and dining spaces that provide plenty of room to spread out, gather, and entertain. The kitchen features abundant cabinetry and counter space, stone countertops, a built-in oven and cooktop, and a window overlooking the backyard. Custom epoxy flooring in the kitchen and entry adds durability and a unique finishing touch. The primary suite is one of the home's standout spaces, featuring a beautifully remodeled bathroom with a double vanity and an oversized glass-enclosed shower, along with a custom-built closet with shelving and organization designed to maximize storage and functionality. But the backyard may be where you'll want to spend most of your time. Step outside to a private in-ground pool, covered screened patio, fenced backyard, and an expanded pool deck with additional pavers, creating multiple spaces to lounge, entertain, dine outdoors, or simply enjoy the Florida sunshine. There's even green space beyond the pool, giving the backyard a more open feel than you might expect from a pool home. The home also offers important improvements already completed for you, including a roof replaced in 2019, re-pipe completed in 2013, and HVAC system replaced in 2018/2019. A professionally installed security system and security cameras add another layer of functionality. The location ties it all together. Situated in Winter Park's Wrenwood neighborhood, 3020 Nicholson Drive puts you within easy reach of some of Central Florida's favorite destinations, including Park Avenue, Winter Park Village, and Baldwin Park, with shopping, dining, entertainment, and everyday conveniences nearby. Convenient access to SR 436 and the 408 also makes it easy to reach Downtown Orlando and destinations throughout Central Florida.

3020 Nicholson Drive, Winter Park

$739,777

Welcome to Lake Waunatta Woods, where neighbors become family. It is rare to find an exclusive, tight-knit community where neighbors look out for one another, and friendships feel more like family. This charming enclave of homes is a sanctuary of warmth, connection, and tranquility in a well-established Winter Park neighborhood. At the heart of this exceptional community is a beautifully renovated one-story residence, thoughtfully designed and built by its owners with a modern flair. From the moment you arrive, you are greeted by an elegant neutral palette, charming architectural windows and a beautifully pavered driveway leading to the stately four-pane glass front door. Step inside to soaring ceilings, art niches, elegant and an abundance of natural light that creates a warm and inviting atmosphere. To the right of the entry, the formal living room offers versatility and could easily serve as a home office, library, or additional gathering space. The heart of the home is the extraordinary chef's kitchen, beautifully appointed with custom Dovetail Gray cabinetry, oak cabinetry accented with ebony pulls, stacked white subway tile backsplash, farmhouse sink, wine cooler, state-of-the-art appliance package and a spectacular 10-foot island topped with luxurious white quartzite accented by subtle veining. This stunning kitchen flows effortlessly into the family room, creating an ideal space for everyday living and entertaining. Luxury plank flooring, neutral earth tones, and a dramatic wood-burning fireplace surrounded by natural floor-to-ceiling stone add warmth and character, while the abundance of natural light brings the beauty of the outdoors inside. The primary suite is a private retreat styled in a calming ivory palette, with wood floors, beautifully dressed windows and double doors opening directly to the poolside. The primary bath offers a distinctive custom vanity with a charming wooden treasure-chest design and a luxurious walk-in shower finished with stacked white subway tile, sitting bench and multiple shower heads for the ultimate in comfort and relaxation. Each bedroom is thoughtfully equipped with a California Closet system. Two additional generously sized bedrooms and a beautifully updated shared bath complete the one-story floor plan, offering flexibility for every lifestyle. This home has been lovingly maintained and thoughtfully refreshed, with major systems and improvements recently completed, including Andersen windows in 2024, roof in 2024, renovated baths in 2023, blown attic insulation in 2023, water heater in 2025, pool resurfacing in 2021, new salt system in 2026, and a Trane variable-speed air-conditioning system with UV light purification. The fully fenced PVC backyard provides a private setting surrounded by peaceful wooded views and beautifully landscaped grounds featuring Blue Bamboo, Foxtail trees, flower beds, and decorative river rock. Step outside to your own private backyard retreat, complete with a sparkling saltwater swimming pool and generous space for outdoor entertaining, relaxing, and enjoying the Florida lifestyle. A separate detached office/den adds exceptional versatility, featuring electricity, soundproofing and internet connectivity, making it ideal for a private home office, gym, playroom, studio, or creative space. The European-style pergola is equipped with power for lighting and a unique roof and gutter removal system and was thoughtfully designed for outdoor living space.

4 Beds ⋅ 2 Baths ⋅ Lake Waunatta Woods SubDv. ⋅ 32792 Zip Code

Welcome to Lake Waunatta Woods, where neighbors become family. It is rare to find an exclusive, tight-knit community where neighbors look out for one another, and friendships feel more like family. This charming enclave of homes is a sanctuary of warmth, connection, and tranquility in a well-established Winter Park neighborhood. At the heart of this exceptional community is a beautifully renovated one-story residence, thoughtfully designed and built by its owners with a modern flair. From the moment you arrive, you are greeted by an elegant neutral palette, charming architectural windows and a beautifully pavered driveway leading to the stately four-pane glass front door. Step inside to soaring ceilings, art niches, elegant and an abundance of natural light that creates a warm and inviting atmosphere. To the right of the entry, the formal living room offers versatility and could easily serve as a home office, library, or additional gathering space. The heart of the home is the extraordinary chef's kitchen, beautifully appointed with custom Dovetail Gray cabinetry, oak cabinetry accented with ebony pulls, stacked white subway tile backsplash, farmhouse sink, wine cooler, state-of-the-art appliance package and a spectacular 10-foot island topped with luxurious white quartzite accented by subtle veining. This stunning kitchen flows effortlessly into the family room, creating an ideal space for everyday living and entertaining. Luxury plank flooring, neutral earth tones, and a dramatic wood-burning fireplace surrounded by natural floor-to-ceiling stone add warmth and character, while the abundance of natural light brings the beauty of the outdoors inside. The primary suite is a private retreat styled in a calming ivory palette, with wood floors, beautifully dressed windows and double doors opening directly to the poolside. The primary bath offers a distinctive custom vanity with a charming wooden treasure-chest design and a luxurious walk-in shower finished with stacked white subway tile, sitting bench and multiple shower heads for the ultimate in comfort and relaxation. Each bedroom is thoughtfully equipped with a California Closet system. Two additional generously sized bedrooms and a beautifully updated shared bath complete the one-story floor plan, offering flexibility for every lifestyle. This home has been lovingly maintained and thoughtfully refreshed, with major systems and improvements recently completed, including Andersen windows in 2024, roof in 2024, renovated baths in 2023, blown attic insulation in 2023, water heater in 2025, pool resurfacing in 2021, new salt system in 2026, and a Trane variable-speed air-conditioning system with UV light purification. The fully fenced PVC backyard provides a private setting surrounded by peaceful wooded views and beautifully landscaped grounds featuring Blue Bamboo, Foxtail trees, flower beds, and decorative river rock. Step outside to your own private backyard retreat, complete with a sparkling saltwater swimming pool and generous space for outdoor entertaining, relaxing, and enjoying the Florida lifestyle. A separate detached office/den adds exceptional versatility, featuring electricity, soundproofing and internet connectivity, making it ideal for a private home office, gym, playroom, studio, or creative space. The European-style pergola is equipped with power for lighting and a unique roof and gutter removal system and was thoughtfully designed for outdoor living space.

4039 Cool Water Court, Winter Park

$700,000

This exceptional homesite on Arbor Ridge sits in one of Winter Park's most prestigious and tightly held residential pockets—where elegant estates, mature canopy trees, and enduring property values define the neighborhood. Perfectly positioned, and ready for your vision, the lot places you just two blocks from the Winter Park YMCA and half a mile from highly regarded Lakemont Elementary. The combination of privacy, convenience, and top-tier location ensures a strong demand for a custom residence of distinction. Surrounded by new construction and the graceful shade of established trees, the property offers the ideal canvas for a high-end home that honors the neighborhood’s timeless character while delivering the refined finishes and modern living today’s discerning buyers expect. This is more than a lot—it’s a prime development opportunity in a location that rarely becomes available. Create the legacy residence that belongs here.

4 Beds ⋅ 3 Baths ⋅ Conwill Ests SubDv. ⋅ 32789 Zip Code

This exceptional homesite on Arbor Ridge sits in one of Winter Park's most prestigious and tightly held residential pockets—where elegant estates, mature canopy trees, and enduring property values define the neighborhood. Perfectly positioned, and ready for your vision, the lot places you just two blocks from the Winter Park YMCA and half a mile from highly regarded Lakemont Elementary. The combination of privacy, convenience, and top-tier location ensures a strong demand for a custom residence of distinction. Surrounded by new construction and the graceful shade of established trees, the property offers the ideal canvas for a high-end home that honors the neighborhood’s timeless character while delivering the refined finishes and modern living today’s discerning buyers expect. This is more than a lot—it’s a prime development opportunity in a location that rarely becomes available. Create the legacy residence that belongs here.

1592 Arbor Park Drive, Winter Park

$1,900,000

Set along a charming, tree-lined street in Winter Park, this stunning new construction home brings together modern farmhouse character, thoughtfully designed interiors, and an exceptional outdoor living experience. Inside, a dedicated home office just off the entry provides a private and convenient workspace. Beyond, the main living area serves as the heart of the home, where a custom entertainment wall with built-in LED underlighting and an electric fireplace creates a striking focal point. Pocketing sliders open completely to the covered lanai, extending the living space outdoors and creating an effortless setting for entertaining. The kitchen is equally impressive, featuring Taj Mahal quartzite countertops, abundant cabinetry, a full suite of Thermador appliances, and a walk-in pantry. A spacious formal dining area provides plenty of room for larger gatherings while remaining connected to the main living spaces. The primary suite offers a private retreat with his and hers walk-in closets and a beautifully appointed spa-inspired bath. Dual vanities, a freestanding soaking tub, and an oversized walk-in shower create a space designed for both luxury and functionality. Upstairs, a generous bonus room provides flexibility for an additional lounge, media room, or playroom, while a conveniently located laundry room adds to the home’s thoughtful layout. Outside is where this residence truly distinguishes itself. The backyard is centered around a spacious pool with a water feature, creating a private setting for relaxing and entertaining. An expansive covered lanai provides a seamless extension of the interior living areas, while a detached cabana with a full summer kitchen and built-in grill creates a destination of its own overlooking the pool. The location is every bit as compelling. Just a short golf cart ride from Park Avenue, the boutiques, acclaimed restaurants, cafés, and energy of downtown Winter Park are always within easy reach. Phelps Park, Interlachen Country Club, and the YMCA are also just minutes away. With an exceptional outdoor living experience, and a location that places the best of Winter Park close at hand, this home delivers the lifestyle so many come to Winter Park to find.

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

Set along a charming, tree-lined street in Winter Park, this stunning new construction home brings together modern farmhouse character, thoughtfully designed interiors, and an exceptional outdoor living experience. Inside, a dedicated home office just off the entry provides a private and convenient workspace. Beyond, the main living area serves as the heart of the home, where a custom entertainment wall with built-in LED underlighting and an electric fireplace creates a striking focal point. Pocketing sliders open completely to the covered lanai, extending the living space outdoors and creating an effortless setting for entertaining. The kitchen is equally impressive, featuring Taj Mahal quartzite countertops, abundant cabinetry, a full suite of Thermador appliances, and a walk-in pantry. A spacious formal dining area provides plenty of room for larger gatherings while remaining connected to the main living spaces. The primary suite offers a private retreat with his and hers walk-in closets and a beautifully appointed spa-inspired bath. Dual vanities, a freestanding soaking tub, and an oversized walk-in shower create a space designed for both luxury and functionality. Upstairs, a generous bonus room provides flexibility for an additional lounge, media room, or playroom, while a conveniently located laundry room adds to the home’s thoughtful layout. Outside is where this residence truly distinguishes itself. The backyard is centered around a spacious pool with a water feature, creating a private setting for relaxing and entertaining. An expansive covered lanai provides a seamless extension of the interior living areas, while a detached cabana with a full summer kitchen and built-in grill creates a destination of its own overlooking the pool. The location is every bit as compelling. Just a short golf cart ride from Park Avenue, the boutiques, acclaimed restaurants, cafés, and energy of downtown Winter Park are always within easy reach. Phelps Park, Interlachen Country Club, and the YMCA are also just minutes away. With an exceptional outdoor living experience, and a location that places the best of Winter Park close at hand, this home delivers the lifestyle so many come to Winter Park to find.

1702 Arbor Park Drive, Winter Park

$549,000

Welcome to this beautifully updated 4-bedroom, 2-bath pool home located in the highly desirable Winter Woods community of Winter Park. From the moment you step inside, you’ll appreciate the bright, open-concept floor plan, abundant natural light, and plantation shutters that complement the home’s expansive windows. The spacious living area flows seamlessly into the beautifully appointed kitchen, featuring a large center island with breakfast bar seating, stainless steel appliances, ample cabinetry, and a distinctive herringbone tile backsplash. Just off the kitchen, the dining area provides an inviting space for both everyday meals and entertaining. The private primary suite offers an ensuite bath and sliding glass doors that open directly to the pool deck, creating an effortless connection between indoor and outdoor living. A desirable split-bedroom floor plan places the three additional bedrooms and full guest bath on the opposite side of the home, offering added privacy. The laundry room provides convenient direct access to the two-car garage. Step outside to an expansive screened-in patio spanning the rear of the home and overlooking the private pool. Surrounded by tropical landscaping, this backyard retreat offers the perfect setting for entertaining, relaxing poolside, or enjoying Florida living year-round. The home has been thoughtfully maintained and updated, with improvements including a saltwater pool system (2019), asphalt shingle roof (2020), new sewer line from the home to the street and whole-home repipe (2021), kitchen and bathroom renovations (2021), new pool equipment (2023), and a new A/C system (2023). Ideally situated in Winter Park, this home offers convenient access to Downtown Winter Park, Downtown Orlando, shopping, dining, medical facilities, and major roadways. With its combination of thoughtful updates, flexible living spaces, private pool, and sought-after location, this Winter Woods home offers an exceptional opportunity to enjoy the best of Central Florida living. Schedule your private showing today.

4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 03 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated 4-bedroom, 2-bath pool home located in the highly desirable Winter Woods community of Winter Park. From the moment you step inside, you’ll appreciate the bright, open-concept floor plan, abundant natural light, and plantation shutters that complement the home’s expansive windows. The spacious living area flows seamlessly into the beautifully appointed kitchen, featuring a large center island with breakfast bar seating, stainless steel appliances, ample cabinetry, and a distinctive herringbone tile backsplash. Just off the kitchen, the dining area provides an inviting space for both everyday meals and entertaining. The private primary suite offers an ensuite bath and sliding glass doors that open directly to the pool deck, creating an effortless connection between indoor and outdoor living. A desirable split-bedroom floor plan places the three additional bedrooms and full guest bath on the opposite side of the home, offering added privacy. The laundry room provides convenient direct access to the two-car garage. Step outside to an expansive screened-in patio spanning the rear of the home and overlooking the private pool. Surrounded by tropical landscaping, this backyard retreat offers the perfect setting for entertaining, relaxing poolside, or enjoying Florida living year-round. The home has been thoughtfully maintained and updated, with improvements including a saltwater pool system (2019), asphalt shingle roof (2020), new sewer line from the home to the street and whole-home repipe (2021), kitchen and bathroom renovations (2021), new pool equipment (2023), and a new A/C system (2023). Ideally situated in Winter Park, this home offers convenient access to Downtown Winter Park, Downtown Orlando, shopping, dining, medical facilities, and major roadways. With its combination of thoughtful updates, flexible living spaces, private pool, and sought-after location, this Winter Woods home offers an exceptional opportunity to enjoy the best of Central Florida living. Schedule your private showing today.

2211 King Richards Court, Winter Park

$1,824,000

Under contract-accepting backup offers. Timeless charm meets thoughtful investment in the heart of Park Grove, Winter Park's most coveted enclave. Set on one of the neighborhood's largest lots beneath a canopy of mature oaks, this home offers something increasingly rare this close to Park Avenue: room to breathe, inside and out. Behind that charm is a home that has been genuinely looked after. A new roof in 2021, a complete replumb in 2023, and new air conditioning in 2025 mean the unglamorous work is finished. There is nothing here waiting on you. Move in, unpack, and simply enjoy it. Out front, a newly remodeled courtyard sets the tone. It is a gracious welcome and an unexpectedly versatile entertaining space, equally suited to morning coffee, an evening glass of wine, or a gathering that spills comfortably outdoors. Inside, the floor plan rewards daily living. Generous proportions, abundant natural light, and storage of a kind that simply is not built anymore, with closets throughout that are uncommonly deep and plentiful. The kitchen is anchored by custom cabinetry, thoughtfully designed and beautifully executed, while handsome built-ins and a wine refrigerator remain with the home. Two recently remodeled guest bathrooms carry the same restraint, finished in a timeless, traditional style that flows seamlessly with the rest of the home rather than competing with it. The primary suite is a genuine retreat, opening to a private sitting room that has served as both a nursery and a home office over the years and stands ready to become whatever the next chapter requires: a study, a reading room, a nursery once again, or a quiet place to close the door on the day. Beyond the back doors, the grounds unfold deep and green, framed by established landscaping and shaded by mature oaks. The rear of the property faces west, so evening light spills generously across the patio and the lawn beyond. There is ample room to add the pool of your dreams, an increasingly uncommon luxury on lots of this size so near the heart of Winter Park. Park Grove itself needs little introduction. Treasured for its oversized lots and unusually wide, oak-lined streets, the neighborhood delivers the quiet residential character that draws one to Winter Park in the first place, with an enviable position moments from the shops, restaurants and galleries of Park Avenue and effortless access to I-4, downtown Orlando and the airport. Homes here rarely come available, and for good reason.

4 Beds ⋅ 4 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Timeless charm meets thoughtful investment in the heart of Park Grove, Winter Park's most coveted enclave. Set on one of the neighborhood's largest lots beneath a canopy of mature oaks, this home offers something increasingly rare this close to Park Avenue: room to breathe, inside and out. Behind that charm is a home that has been genuinely looked after. A new roof in 2021, a complete replumb in 2023, and new air conditioning in 2025 mean the unglamorous work is finished. There is nothing here waiting on you. Move in, unpack, and simply enjoy it. Out front, a newly remodeled courtyard sets the tone. It is a gracious welcome and an unexpectedly versatile entertaining space, equally suited to morning coffee, an evening glass of wine, or a gathering that spills comfortably outdoors. Inside, the floor plan rewards daily living. Generous proportions, abundant natural light, and storage of a kind that simply is not built anymore, with closets throughout that are uncommonly deep and plentiful. The kitchen is anchored by custom cabinetry, thoughtfully designed and beautifully executed, while handsome built-ins and a wine refrigerator remain with the home. Two recently remodeled guest bathrooms carry the same restraint, finished in a timeless, traditional style that flows seamlessly with the rest of the home rather than competing with it. The primary suite is a genuine retreat, opening to a private sitting room that has served as both a nursery and a home office over the years and stands ready to become whatever the next chapter requires: a study, a reading room, a nursery once again, or a quiet place to close the door on the day. Beyond the back doors, the grounds unfold deep and green, framed by established landscaping and shaded by mature oaks. The rear of the property faces west, so evening light spills generously across the patio and the lawn beyond. There is ample room to add the pool of your dreams, an increasingly uncommon luxury on lots of this size so near the heart of Winter Park. Park Grove itself needs little introduction. Treasured for its oversized lots and unusually wide, oak-lined streets, the neighborhood delivers the quiet residential character that draws one to Winter Park in the first place, with an enviable position moments from the shops, restaurants and galleries of Park Avenue and effortless access to I-4, downtown Orlando and the airport. Homes here rarely come available, and for good reason.

631 Williams Drive, Winter Park

$995,999

Exceptional Winter Park Opportunity with In-Law Suite & Income Potential Discover the opportunity to own a versatile property in one of Central Florida’s most desirable locations. 471 Holt Ave. in Winter Park offers buyers something increasingly valuable: flexibility. With a private in-law suite, this property presents an exciting opportunity for multigenerational living, a guest suite, home office, or potential rental income. For homeowners, the additional living space provides the freedom to accommodate family members or guests while maintaining privacy and separation. For investors, the configuration creates the potential to generate supplemental income, subject to applicable local regulations and requirements. The property’s location adds to its appeal, placing you near Winter Park’s renowned dining, shopping, parks, cultural attractions, and vibrant community amenities. Also, just a short distance to Rollins College! Whether you’re looking to offset your mortgage, create an additional income stream, or simply secure a property with adaptable living options, this home offers a compelling combination of lifestyle and investment potential. Opportunities with this level of flexibility are hard to find. Live in the main residence, utilize the suite for family or guests, or explore its income-producing potential. 471 Holt Ave. offers the versatility today’s buyers are looking for and the potential long-term value investors appreciate. Don’t miss the opportunity to make this flexible Winter Park property your next home or investment.

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

Exceptional Winter Park Opportunity with In-Law Suite & Income Potential Discover the opportunity to own a versatile property in one of Central Florida’s most desirable locations. 471 Holt Ave. in Winter Park offers buyers something increasingly valuable: flexibility. With a private in-law suite, this property presents an exciting opportunity for multigenerational living, a guest suite, home office, or potential rental income. For homeowners, the additional living space provides the freedom to accommodate family members or guests while maintaining privacy and separation. For investors, the configuration creates the potential to generate supplemental income, subject to applicable local regulations and requirements. The property’s location adds to its appeal, placing you near Winter Park’s renowned dining, shopping, parks, cultural attractions, and vibrant community amenities. Also, just a short distance to Rollins College! Whether you’re looking to offset your mortgage, create an additional income stream, or simply secure a property with adaptable living options, this home offers a compelling combination of lifestyle and investment potential. Opportunities with this level of flexibility are hard to find. Live in the main residence, utilize the suite for family or guests, or explore its income-producing potential. 471 Holt Ave. offers the versatility today’s buyers are looking for and the potential long-term value investors appreciate. Don’t miss the opportunity to make this flexible Winter Park property your next home or investment.

471 Holt Avenue, Winter Park

$1,598,000

Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed by renowned architect Gary Hancock. From the impressive curb appeal and graceful archways to the carefully selected finishes throughout, every part of this home was designed with purpose. The result is a residence that feels sophisticated and distinctive while remaining remarkably comfortable for everyday living. Striking from the moment you arrive, the home features beautiful archways, balanced architectural lines, and a timeless exterior that immediately sets it apart. Step inside to an open, light-filled floor plan with 10-foot ceilings, expansive windows, level 5 drywall, and designer lighting throughout.An open floor plan creates an easy flow between the main living spaces, with a fireplace anchoring the living room and the adjoining dining area opening directly to the outdoor entertaining space. At the center of the home is a Italian-inspired chef’s kitchen featuring custom cabinetry, designer countertops, a paneled refrigerator, and premium induction range.The primary suite offers a private retreat with a spacious bath complete with a freestanding soaking tub, oversized walk-in shower, and a large walk-in closet. Each secondary bedroom is generously sized and includes its own en-suite bath, providing privacy and convenience for family and guests, while the bonus room and additional storage provide added flexibility. The outdoor spaces are an extension of the home, with a covered patio, fully equipped summer kitchen, sparkling pool, and expansive backyard offering plenty of room for both entertaining and relaxing. Perfectly positioned in Winter Park, this home offers easy access to Park Avenue, exceptional dining and shopping, top-rated schools, and virtually everything you need just minutes from your front door. A rare opportunity to own a custom-designed home with exceptional architecture, quality construction, and a prime Winter Park location—all at an exceptional value.

4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed by renowned architect Gary Hancock. From the impressive curb appeal and graceful archways to the carefully selected finishes throughout, every part of this home was designed with purpose. The result is a residence that feels sophisticated and distinctive while remaining remarkably comfortable for everyday living. Striking from the moment you arrive, the home features beautiful archways, balanced architectural lines, and a timeless exterior that immediately sets it apart. Step inside to an open, light-filled floor plan with 10-foot ceilings, expansive windows, level 5 drywall, and designer lighting throughout.An open floor plan creates an easy flow between the main living spaces, with a fireplace anchoring the living room and the adjoining dining area opening directly to the outdoor entertaining space. At the center of the home is a Italian-inspired chef’s kitchen featuring custom cabinetry, designer countertops, a paneled refrigerator, and premium induction range.The primary suite offers a private retreat with a spacious bath complete with a freestanding soaking tub, oversized walk-in shower, and a large walk-in closet. Each secondary bedroom is generously sized and includes its own en-suite bath, providing privacy and convenience for family and guests, while the bonus room and additional storage provide added flexibility. The outdoor spaces are an extension of the home, with a covered patio, fully equipped summer kitchen, sparkling pool, and expansive backyard offering plenty of room for both entertaining and relaxing. Perfectly positioned in Winter Park, this home offers easy access to Park Avenue, exceptional dining and shopping, top-rated schools, and virtually everything you need just minutes from your front door. A rare opportunity to own a custom-designed home with exceptional architecture, quality construction, and a prime Winter Park location—all at an exceptional value.

2430 Chantilly Avenue, Winter Park

$1,795,000

Under contract-accepting backup offers. Nestled along one of Winter Park's picturesque brick streets, this beautifully appointed four-bedroom, three-and-one-half-bath residence combines timeless charm with modern luxury in an exceptional location. Thoughtfully designed with an open-concept floor plan, the home offers seamless everyday living and effortless entertaining. At the heart of the home is the beautifully updated chef's kitchen overlooking the spacious living room. Premium Thermador appliances include an impressive eight-burner range featuring six gas burners and two induction burners, a separate steam oven, a built-in microwave and a three-tower refrigeration system with refrigerator, freezer and wine refrigeration. A generous breakfast nook provides abundant seating for casual dining, while the adjacent formal dining room offers versatility and is currently utilized as a private home office. The inviting living room is filled with natural light and features French doors that open to the covered lanai, creating an ideal indoor-outdoor living experience. The first-floor primary suite serves as a peaceful retreat with a spacious walk-in closet, two sets of blackout window treatments, a luxurious spa-inspired bath featuring a glass-enclosed shower and separate soaking tub and private access to the lanai and pool area. Completing the first floor are a convenient built-in workspace, a separate laundry room and a stylish powder bath. A graceful staircase leads to the second level, where you'll find three additional bedrooms, including one with an ensuite bath, along with a generous family room that provides the perfect gathering space for family and guests. Expansive windows throughout the home fill every room with abundant natural light, creating a bright and welcoming atmosphere. Outside, the covered lanai features remote-controlled retractable screens, including an integrated pet door, allowing the space to be fully enclosed for year-round enjoyment. The sparkling saltwater pool with a tranquil waterfall feature is surrounded by a beautifully landscaped, fully fenced backyard, offering exceptional privacy and a true backyard oasis. Additional features include LeafGuard-protected rain gutters, new exterior paint completed in July 2026 and a spacious two-car garage. Ideally located, this exceptional home is just an easy bike ride to the renowned boutiques, restaurants, coffee shops and Central Park along Park Avenue, as well as the popular weekly Winter Park Farmers' Market. Offering luxurious finishes, thoughtful design and an unbeatable location, this is a wonderful opportunity to enjoy the very best of Winter Park living.

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

Under contract-accepting backup offers. Nestled along one of Winter Park's picturesque brick streets, this beautifully appointed four-bedroom, three-and-one-half-bath residence combines timeless charm with modern luxury in an exceptional location. Thoughtfully designed with an open-concept floor plan, the home offers seamless everyday living and effortless entertaining. At the heart of the home is the beautifully updated chef's kitchen overlooking the spacious living room. Premium Thermador appliances include an impressive eight-burner range featuring six gas burners and two induction burners, a separate steam oven, a built-in microwave and a three-tower refrigeration system with refrigerator, freezer and wine refrigeration. A generous breakfast nook provides abundant seating for casual dining, while the adjacent formal dining room offers versatility and is currently utilized as a private home office. The inviting living room is filled with natural light and features French doors that open to the covered lanai, creating an ideal indoor-outdoor living experience. The first-floor primary suite serves as a peaceful retreat with a spacious walk-in closet, two sets of blackout window treatments, a luxurious spa-inspired bath featuring a glass-enclosed shower and separate soaking tub and private access to the lanai and pool area. Completing the first floor are a convenient built-in workspace, a separate laundry room and a stylish powder bath. A graceful staircase leads to the second level, where you'll find three additional bedrooms, including one with an ensuite bath, along with a generous family room that provides the perfect gathering space for family and guests. Expansive windows throughout the home fill every room with abundant natural light, creating a bright and welcoming atmosphere. Outside, the covered lanai features remote-controlled retractable screens, including an integrated pet door, allowing the space to be fully enclosed for year-round enjoyment. The sparkling saltwater pool with a tranquil waterfall feature is surrounded by a beautifully landscaped, fully fenced backyard, offering exceptional privacy and a true backyard oasis. Additional features include LeafGuard-protected rain gutters, new exterior paint completed in July 2026 and a spacious two-car garage. Ideally located, this exceptional home is just an easy bike ride to the renowned boutiques, restaurants, coffee shops and Central Park along Park Avenue, as well as the popular weekly Winter Park Farmers' Market. Offering luxurious finishes, thoughtful design and an unbeatable location, this is a wonderful opportunity to enjoy the very best of Winter Park living.

1230 Sunset Drive, Winter Park

$1,829,000

Under Construction. LUXURY NEW CONSTRUCTION IN WINTER PARK'S HIGHLY SOUGHT-AFTER TREE STREETS! Welcome to 1550 Palm Avenue, a thoughtfully designed new residence by LUIH Luxury Homes offering 4 bedrooms, 3.5 bathrooms, 2,706 square feet of living space, a 2-car garage and private pool, all set along a charming BRICK STREET in one of Winter Park's most desirable neighborhoods. Contemporary architecture, refined finishes and an intelligently planned layout come together to create a home that feels as functional as it is beautiful. A standout feature of the design is the unique placement of the DOWNSTAIRS PRIMARY SUITE, thoughtfully positioned so it does not interrupt the impressive rear living space. This allows the FAMILY ROOM, DINING AREA AND KITCHEN to extend across the back of the home in one expansive, open-concept setting, creating exceptional sightlines and a seamless connection to the pool and backyard. Large windows and doors bring natural light into the living areas while enhancing the indoor-outdoor relationship that makes this true Luxury Florida living. The main-level primary suite provides a peaceful retreat apart from the home's central gathering spaces, while three additional bedrooms provide flexibility for a variety of uses, including guest accommodations or a home office. Throughout the residence, clean architectural lines, thoughtfully designed spaces and contemporary finishes create an elegant yet comfortable atmosphere ideal for everyday living and entertaining. Outside, the PRIVATE POOL and backyard become a natural extension of the home's living space, easily enjoyed from the expansive rear entertaining areas. The 7,561-square-foot homesite provides an exceptional setting for a brand-new residence while maintaining the character and established surroundings that make the Tree Streets so special. And the location is difficult to beat. Enjoy the charm of living on a brick street while remaining convenient to Downtown Winter Park, Park Avenue, shopping, dining, recreation and major roadways. NEW CONSTRUCTION opportunities in this established Winter Park neighborhood are limited, making 1550 Palm Avenue an exceptional opportunity to enjoy modern design and amenities in a location known for its character and enduring appeal. Renderings are artistic interpretations. Features and finishes may vary from final construction.

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace 2nd Add SubDv. ⋅ 32789 Zip Code

Under Construction. LUXURY NEW CONSTRUCTION IN WINTER PARK'S HIGHLY SOUGHT-AFTER TREE STREETS! Welcome to 1550 Palm Avenue, a thoughtfully designed new residence by LUIH Luxury Homes offering 4 bedrooms, 3.5 bathrooms, 2,706 square feet of living space, a 2-car garage and private pool, all set along a charming BRICK STREET in one of Winter Park's most desirable neighborhoods. Contemporary architecture, refined finishes and an intelligently planned layout come together to create a home that feels as functional as it is beautiful. A standout feature of the design is the unique placement of the DOWNSTAIRS PRIMARY SUITE, thoughtfully positioned so it does not interrupt the impressive rear living space. This allows the FAMILY ROOM, DINING AREA AND KITCHEN to extend across the back of the home in one expansive, open-concept setting, creating exceptional sightlines and a seamless connection to the pool and backyard. Large windows and doors bring natural light into the living areas while enhancing the indoor-outdoor relationship that makes this true Luxury Florida living. The main-level primary suite provides a peaceful retreat apart from the home's central gathering spaces, while three additional bedrooms provide flexibility for a variety of uses, including guest accommodations or a home office. Throughout the residence, clean architectural lines, thoughtfully designed spaces and contemporary finishes create an elegant yet comfortable atmosphere ideal for everyday living and entertaining. Outside, the PRIVATE POOL and backyard become a natural extension of the home's living space, easily enjoyed from the expansive rear entertaining areas. The 7,561-square-foot homesite provides an exceptional setting for a brand-new residence while maintaining the character and established surroundings that make the Tree Streets so special. And the location is difficult to beat. Enjoy the charm of living on a brick street while remaining convenient to Downtown Winter Park, Park Avenue, shopping, dining, recreation and major roadways. NEW CONSTRUCTION opportunities in this established Winter Park neighborhood are limited, making 1550 Palm Avenue an exceptional opportunity to enjoy modern design and amenities in a location known for its character and enduring appeal. Renderings are artistic interpretations. Features and finishes may vary from final construction.

1550 Palm Avenue, Winter Park

$3,600,000

Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with exceptional attention to detail, the home offers clean, contemporary interiors balanced by beautiful architectural elements, and abundant natural light. The main level offers two bedrooms and three full bathrooms, including a primary suite with a versatile bonus room behind French doors—perfect for a private office, gym, or additional bedroom. The ensuite features two walk-in closets, a double sink vanity, a large rainfall shower, and a soaking tub. The open-concept floorplan features a beautifully appointed kitchen with high-end appliances and custom cabinetry, flowing seamlessly with the dining area and the spacious living room, where a gas fireplace creates a welcoming gathering space. Architectural light wood ceiling beams, plantation shutters, and expansive glass sliders frame beautiful views of the outdoor living area. Upstairs, two additional bedrooms each feature private ensuite baths and balconies, complemented by a kitchenette and additional living space. This flexible layout is ideal for multigenerational living, guests, live-in staff, or simply creating a private retreat within the home. Designed for effortless indoor-outdoor living, the entire downstairs opens to a private backyard oasis featuring a sparkling saltwater pool, lush bamboo backdrop, summer kitchen, gas fireplace, and outdoor shower. The covered lanai is equipped with automatic screens, creating an inviting and comfortable space to enjoy the outdoors year-round. Beyond its sophisticated design, the home offers exceptional functionality, including an oversized two-car garage pre-wired for EV charging, whole-home surround sound, hurricane-impact windows, a whole-house Generac generator, indoor built-in sprinkler system, dual laundry rooms, and enhanced insulation for exceptional peace and quiet. The entire first floor is completely wheelchair accessible. Tastefully furnished and offered with all furnishings, this exceptional residence presents a rare combination of refined design, thoughtful functionality, and classic Winter Park charm. Ideally located just one mile from Park Avenue and minutes from Winter Park’s renowned restaurants, shops, hospitals, schools, and scenic Lake Osceola, this is a home designed for both elevated living and everyday comfort.

4 Beds ⋅ 5 Baths ⋅ Detmar Terrace Winter Park SubDv. ⋅ 32789 Zip Code

Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with exceptional attention to detail, the home offers clean, contemporary interiors balanced by beautiful architectural elements, and abundant natural light. The main level offers two bedrooms and three full bathrooms, including a primary suite with a versatile bonus room behind French doors—perfect for a private office, gym, or additional bedroom. The ensuite features two walk-in closets, a double sink vanity, a large rainfall shower, and a soaking tub. The open-concept floorplan features a beautifully appointed kitchen with high-end appliances and custom cabinetry, flowing seamlessly with the dining area and the spacious living room, where a gas fireplace creates a welcoming gathering space. Architectural light wood ceiling beams, plantation shutters, and expansive glass sliders frame beautiful views of the outdoor living area. Upstairs, two additional bedrooms each feature private ensuite baths and balconies, complemented by a kitchenette and additional living space. This flexible layout is ideal for multigenerational living, guests, live-in staff, or simply creating a private retreat within the home. Designed for effortless indoor-outdoor living, the entire downstairs opens to a private backyard oasis featuring a sparkling saltwater pool, lush bamboo backdrop, summer kitchen, gas fireplace, and outdoor shower. The covered lanai is equipped with automatic screens, creating an inviting and comfortable space to enjoy the outdoors year-round. Beyond its sophisticated design, the home offers exceptional functionality, including an oversized two-car garage pre-wired for EV charging, whole-home surround sound, hurricane-impact windows, a whole-house Generac generator, indoor built-in sprinkler system, dual laundry rooms, and enhanced insulation for exceptional peace and quiet. The entire first floor is completely wheelchair accessible. Tastefully furnished and offered with all furnishings, this exceptional residence presents a rare combination of refined design, thoughtful functionality, and classic Winter Park charm. Ideally located just one mile from Park Avenue and minutes from Winter Park’s renowned restaurants, shops, hospitals, schools, and scenic Lake Osceola, this is a home designed for both elevated living and everyday comfort.

276 Detmar Drive, Winter Park

$660,000

This "Investment Opportunity" duplex is centrally located on a quiet, tree lined, brick street, close to shopping, restaurants, downtown Winter Park, Rollins College & Mead Gardens. It has a total of 4 bedrooms, 2 full baths & 2 half baths. Each unit has 2 bedrooms with a Jack & Jill bath, and 1 half bath. Live in one side while a tenant lives in the other.

4 Beds ⋅ 4 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code

This "Investment Opportunity" duplex is centrally located on a quiet, tree lined, brick street, close to shopping, restaurants, downtown Winter Park, Rollins College & Mead Gardens. It has a total of 4 bedrooms, 2 full baths & 2 half baths. Each unit has 2 bedrooms with a Jack & Jill bath, and 1 half bath. Live in one side while a tenant lives in the other.

1016 Aragon Avenue, Winter Park

$660,000

This "Investment Opportunity" Duplex is centrally located on a quiet tree lined, brick street, close to shopping, restaurants, downtown Winter Park, Rollins College & Mead Gardens. It has a total of 4 Bedrooms, 2 full baths & 2 half baths. Each unit has 2 bedrooms with a Jack & Jill bath, and 1 half bath. Live in one side while a tenant (now occupied) lives in the other.

4 Beds ⋅ 4 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code

This "Investment Opportunity" Duplex is centrally located on a quiet tree lined, brick street, close to shopping, restaurants, downtown Winter Park, Rollins College & Mead Gardens. It has a total of 4 Bedrooms, 2 full baths & 2 half baths. Each unit has 2 bedrooms with a Jack & Jill bath, and 1 half bath. Live in one side while a tenant (now occupied) lives in the other.

1016 Aragon Avenue, Winter Park

$600,000

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

4 Beds ⋅ 2 Baths ⋅ Arrowhead Cove SubDv. ⋅ 32792 Zip Code

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

7525 Lodge Pole Trail, Winter Park

$664,900

Welcome to 2333 Westminster Court, a stunningly reimagined residence that perfectly captures the effortless elegance of Winter Park living. A thoughtful and meticulous renovation in 2020 offers piece of mind showcasing a new roof, HVAC, plumbing, and a new septic tank. Step inside to find a bright, cohesive interior featuring modern flooring and a chef-inspired kitchen outfitted with sleek appliances and contemporary finishes. The open layout flows seamlessly to the outdoors, where your own private oasis awaits. The backyard was elevated in 2025 with a brand-new travertine paver deck surrounding a tropical-style pool, creating a resort-like atmosphere perfect for weekend lounging or evening gatherings under the stars. Situated in one of the most sought-after pockets of the area, you are just moments away from the scenic beauty of Lake Killarney and the vibrant energy of Park Avenue. Whether you’re looking for high-end shopping, acclaimed dining in Winter Park and Maitland, or a quick coffee at a local bistro, everything that makes this community so special is right at your fingertips. This is more than just a house; it’s a turn-key lifestyle in the heart of it all. Schedule your private viewing today.

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

Welcome to 2333 Westminster Court, a stunningly reimagined residence that perfectly captures the effortless elegance of Winter Park living. A thoughtful and meticulous renovation in 2020 offers piece of mind showcasing a new roof, HVAC, plumbing, and a new septic tank. Step inside to find a bright, cohesive interior featuring modern flooring and a chef-inspired kitchen outfitted with sleek appliances and contemporary finishes. The open layout flows seamlessly to the outdoors, where your own private oasis awaits. The backyard was elevated in 2025 with a brand-new travertine paver deck surrounding a tropical-style pool, creating a resort-like atmosphere perfect for weekend lounging or evening gatherings under the stars. Situated in one of the most sought-after pockets of the area, you are just moments away from the scenic beauty of Lake Killarney and the vibrant energy of Park Avenue. Whether you’re looking for high-end shopping, acclaimed dining in Winter Park and Maitland, or a quick coffee at a local bistro, everything that makes this community so special is right at your fingertips. This is more than just a house; it’s a turn-key lifestyle in the heart of it all. Schedule your private viewing today.

2333 Westminster Court, Winter Park

$689,900

Welcome to this beautifully maintained four-bedroom, three-bathroom home offering over 2,000 square feet of thoughtfully designed living space in desirable Winter Park community. Overlooking the 9th fairway of Winter Park Pines Golf Course, this home offers a picturesque golf course setting and a peaceful backdrop for everyday living. The split-bedroom floor plan provides both privacy and versatility, while the formal living and dining rooms create inviting spaces for entertaining. Light-toned wood and tile flooring flow throughout, complemented by crown molding, recessed lighting, and a wood-burning fireplace that adds warmth and character. The contemporary kitchen features honey-oak cabinetry, granite countertops, stainless steel appliances, a breakfast nook, and a center island with seating for two. The spacious primary suite is privately positioned from the secondary bedrooms and offers a generous walk-in closet and an impressive ensuite bathroom featuring floor-to-ceiling slate tile, an espresso-colored contemporary double vanity with glass vessel sinks, and a walk-in slate tile shower. Ideal for family or guests, a convenient Jack and Jill bathroom serves two bedrooms while the hall bathroom is directly adjacent to the fourth bedroom. A dedicated laundry room/mud room with built in shelving includes the washer and dryer. French doors open to the spacious screened lanai, where the scenic 9th fairway views take center stage. New screening was installed in 2021, creating an ideal setting for morning coffee, al fresco dining, or relaxing while enjoying the beautifully maintained golf course landscape. The quarter-acre lot also features lemon and Japanese blueberry trees, while the two-car garage offers built-in shelving and an updated garage door and mechanicals. Beyond the property, enjoy convenient access to the Cady Way Trail, Cady Way pool, playground, and tennis/pickleball courts, as well as nearby UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center. Orlando International Airport is approximately 20 minutes away. Zoned for top-rated Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines comfortable living, desirable amenities, and spectacular golf course views in a sought-after Winter Park location. ROOF - 2024 HVAC - 2024 ELECTRICAL - 2015

4 Beds ⋅ 3 Baths ⋅ Golfside Sec 03 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained four-bedroom, three-bathroom home offering over 2,000 square feet of thoughtfully designed living space in desirable Winter Park community. Overlooking the 9th fairway of Winter Park Pines Golf Course, this home offers a picturesque golf course setting and a peaceful backdrop for everyday living. The split-bedroom floor plan provides both privacy and versatility, while the formal living and dining rooms create inviting spaces for entertaining. Light-toned wood and tile flooring flow throughout, complemented by crown molding, recessed lighting, and a wood-burning fireplace that adds warmth and character. The contemporary kitchen features honey-oak cabinetry, granite countertops, stainless steel appliances, a breakfast nook, and a center island with seating for two. The spacious primary suite is privately positioned from the secondary bedrooms and offers a generous walk-in closet and an impressive ensuite bathroom featuring floor-to-ceiling slate tile, an espresso-colored contemporary double vanity with glass vessel sinks, and a walk-in slate tile shower. Ideal for family or guests, a convenient Jack and Jill bathroom serves two bedrooms while the hall bathroom is directly adjacent to the fourth bedroom. A dedicated laundry room/mud room with built in shelving includes the washer and dryer. French doors open to the spacious screened lanai, where the scenic 9th fairway views take center stage. New screening was installed in 2021, creating an ideal setting for morning coffee, al fresco dining, or relaxing while enjoying the beautifully maintained golf course landscape. The quarter-acre lot also features lemon and Japanese blueberry trees, while the two-car garage offers built-in shelving and an updated garage door and mechanicals. Beyond the property, enjoy convenient access to the Cady Way Trail, Cady Way pool, playground, and tennis/pickleball courts, as well as nearby UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center. Orlando International Airport is approximately 20 minutes away. Zoned for top-rated Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines comfortable living, desirable amenities, and spectacular golf course views in a sought-after Winter Park location. ROOF - 2024 HVAC - 2024 ELECTRICAL - 2015

943 Fairway Drive, Winter Park

$450,000

The one you’ve been waiting for! This beautifully redesigned home offers 4 bedrooms, 2 bathrooms, and nearly 1,700 square feet of thoughtfully curated living space. Manchester offers both style and peace of mind with major upgrades including a 2026 A/C, 2024 roof, 2026 windows, Brand new privacy fence, 2026 garage door, and 2026 electrical panel. At the heart of the home is a stunning designer kitchen featuring custom wood cabinetry, Taj Mahal countertops, a dedicated coffee bar, and an open layout designed for both entertaining and everyday living. Every space has been intentionally designed to be as functional as it is beautiful, with a split floor plan, custom bathrooms, and ample storage throughout. The private primary suite is thoughtfully positioned on its own side of the home and features a walk-in closet and en-suite bathroom. Situated on an oversized lot, the spacious backyard offers plenty of room for entertaining, playing, and making memories. With beautiful finishes, extensive upgrades, and zoning for A-rated schools, Manchester is one you won’t want to miss. Come see it before it’s gone!

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

The one you’ve been waiting for! This beautifully redesigned home offers 4 bedrooms, 2 bathrooms, and nearly 1,700 square feet of thoughtfully curated living space. Manchester offers both style and peace of mind with major upgrades including a 2026 A/C, 2024 roof, 2026 windows, Brand new privacy fence, 2026 garage door, and 2026 electrical panel. At the heart of the home is a stunning designer kitchen featuring custom wood cabinetry, Taj Mahal countertops, a dedicated coffee bar, and an open layout designed for both entertaining and everyday living. Every space has been intentionally designed to be as functional as it is beautiful, with a split floor plan, custom bathrooms, and ample storage throughout. The private primary suite is thoughtfully positioned on its own side of the home and features a walk-in closet and en-suite bathroom. Situated on an oversized lot, the spacious backyard offers plenty of room for entertaining, playing, and making memories. With beautiful finishes, extensive upgrades, and zoning for A-rated schools, Manchester is one you won’t want to miss. Come see it before it’s gone!

1011 Manchester Circle, Winter Park

$745,000

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

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

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

1287 Verdant Glade Place, Winter Park

$419,000

Virtually Staged. Modern design , open concept layout , sleek quartz counter top , all new appliances, new luxury vinyl plank flooring, new lanai upgrade. This beautiful 4 bedroom and 2 full bath is situated on a 8,250 square feet lot, which was newly fenced in 2024 which gives a sense of privacy and spaciousness. As you exit the interior through the French door into the lanai . There is two detached shed for your storage convenience. This beautiful done home was renovated in ,2024 with lot of upgrades and it is situated in desirable winter Park , which is close proximity to shopping, downtown ,highways , airport , universities( U.C.F) etc. No H.O.A fees ,the open concept layout gives this home a sense of comfort , convenience , spaciousness and a pleasant and relaxing ambiance. The home is move in ready and the front yard is ready for your customized landscape.Be the lucky one to own this home.Roof was redone in February/2020.

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 2nd Rep SubDv. ⋅ 32792 Zip Code

Virtually Staged. Modern design , open concept layout , sleek quartz counter top , all new appliances, new luxury vinyl plank flooring, new lanai upgrade. This beautiful 4 bedroom and 2 full bath is situated on a 8,250 square feet lot, which was newly fenced in 2024 which gives a sense of privacy and spaciousness. As you exit the interior through the French door into the lanai . There is two detached shed for your storage convenience. This beautiful done home was renovated in ,2024 with lot of upgrades and it is situated in desirable winter Park , which is close proximity to shopping, downtown ,highways , airport , universities( U.C.F) etc. No H.O.A fees ,the open concept layout gives this home a sense of comfort , convenience , spaciousness and a pleasant and relaxing ambiance. The home is move in ready and the front yard is ready for your customized landscape.Be the lucky one to own this home.Roof was redone in February/2020.

1842 Puritan Avenue, Winter Park

$550,000

Modern Ranch Gem on a Corner Lot | 4 Bed | 2 Bath | 2,126 Sq Ft | Screened Pool | No HOA | Winter Park, FL Welcome to this beautiful 4-bedroom, 2-bathroom ranch-style home in Winter Park Estates! Situated on a desirable corner lot with no HOA, this spacious 2,126-square-foot home offers flexibility, comfort, and plenty of room to enjoy Florida living. The inviting floor plan features a huge bonus room, perfect for a media room, home office, playroom, gym, or additional living space. The updated kitchen offers a fresh, modern feel while maintaining a practical layout. Step outside to your screened-in pool and spacious outdoor area, ideal for relaxing, entertaining, and enjoying the Florida sunshine year-round. With four bedrooms, two full bathrooms, a generous bonus room, a corner lot, and no HOA restrictions, this home offers an exceptional combination of space and convenience in Winter Park. You will be close to charming downtown shops, restaurants, parks, and easy access to Orlando amenities, all while enjoying a quiet residential setting. A must-see for buyers looking for a move-in-ready home with room to live, work, and entertain!

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

Modern Ranch Gem on a Corner Lot | 4 Bed | 2 Bath | 2,126 Sq Ft | Screened Pool | No HOA | Winter Park, FL Welcome to this beautiful 4-bedroom, 2-bathroom ranch-style home in Winter Park Estates! Situated on a desirable corner lot with no HOA, this spacious 2,126-square-foot home offers flexibility, comfort, and plenty of room to enjoy Florida living. The inviting floor plan features a huge bonus room, perfect for a media room, home office, playroom, gym, or additional living space. The updated kitchen offers a fresh, modern feel while maintaining a practical layout. Step outside to your screened-in pool and spacious outdoor area, ideal for relaxing, entertaining, and enjoying the Florida sunshine year-round. With four bedrooms, two full bathrooms, a generous bonus room, a corner lot, and no HOA restrictions, this home offers an exceptional combination of space and convenience in Winter Park. You will be close to charming downtown shops, restaurants, parks, and easy access to Orlando amenities, all while enjoying a quiet residential setting. A must-see for buyers looking for a move-in-ready home with room to live, work, and entertain!

2641 Carvell Court, Winter Park

$765,000

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

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

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

1246 Verdant Glade Place, Winter Park

$520,000

Florida living at its best! Welcome to this beautifully appointed single-story home, ideally situated on a quiet roundabout and offering the perfect blend of comfortable living and standout outdoor space. Inside, you’ll find a stylish modern kitchen featuring QUARTZ COUNTERTOPS, sleek cabinetry, STAINLESS STEEL APPLIANCES, and a beautiful backsplash, complemented by luxury vinyl flooring and plush carpet throughout. With 2 FULL BATHROOMS, a 2-CAR GARAGE, and convenient one-level living, this home is both functional and inviting. Step outside to your OVERSIZED, FENCED BACKYARD, where a SCREENED-IN POOL AND COVERED PORCH create an ideal setting for relaxing, entertaining, and enjoying the Florida sunshine year-round. Thoughtfully updated and designed for easy living, this home offers the space, features, and outdoor lifestyle you’ve been looking for!

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 13 SubDv. ⋅ 32792 Zip Code

Florida living at its best! Welcome to this beautifully appointed single-story home, ideally situated on a quiet roundabout and offering the perfect blend of comfortable living and standout outdoor space. Inside, you’ll find a stylish modern kitchen featuring QUARTZ COUNTERTOPS, sleek cabinetry, STAINLESS STEEL APPLIANCES, and a beautiful backsplash, complemented by luxury vinyl flooring and plush carpet throughout. With 2 FULL BATHROOMS, a 2-CAR GARAGE, and convenient one-level living, this home is both functional and inviting. Step outside to your OVERSIZED, FENCED BACKYARD, where a SCREENED-IN POOL AND COVERED PORCH create an ideal setting for relaxing, entertaining, and enjoying the Florida sunshine year-round. Thoughtfully updated and designed for easy living, this home offers the space, features, and outdoor lifestyle you’ve been looking for!

1905 Bonanza Ct, Winter Park

$499,000

Income Producing Duplex in Winter Park, Florida! Great investment opportunity in a desirable location! This duplex features two 2-bedroom, 1-bath units, each approximately 600 square feet, with private entrances, central AC, and a private screened patio area. Both units are currently leased, providing established rental income and long-term occupancy. Each unit offers a spacious living area and a functional kitchen, with a shared laundry room equipped with a washer and dryer for added convenience. Both units include a full bath with updated showers. Enjoy all of Downtown Winter Park, including the shops and restaurants along Park Avenue, Winter Park Village, and an abundance of entertainment and recreational options such as Mead Botanical Garden, Winter Park Tennis Center, Winter Park Golf Course, and much more. The property also offers easy access to major highways and is just minutes from Rollins College. Don't miss this opportunity to own an income-producing property in one of Central Florida's most desirable areas with no HOA. Pictures were taken prior to occupancy.

4 Beds ⋅ 2 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Income Producing Duplex in Winter Park, Florida! Great investment opportunity in a desirable location! This duplex features two 2-bedroom, 1-bath units, each approximately 600 square feet, with private entrances, central AC, and a private screened patio area. Both units are currently leased, providing established rental income and long-term occupancy. Each unit offers a spacious living area and a functional kitchen, with a shared laundry room equipped with a washer and dryer for added convenience. Both units include a full bath with updated showers. Enjoy all of Downtown Winter Park, including the shops and restaurants along Park Avenue, Winter Park Village, and an abundance of entertainment and recreational options such as Mead Botanical Garden, Winter Park Tennis Center, Winter Park Golf Course, and much more. The property also offers easy access to major highways and is just minutes from Rollins College. Don't miss this opportunity to own an income-producing property in one of Central Florida's most desirable areas with no HOA. Pictures were taken prior to occupancy.

2183 Crandon Avenue, Winter Park

$770,000

Virtually Staged. Welcome to one of the most uniquely positioned homes in the highly sought-after gated community of Hawk’s Crest. This former Meritage model home sits on a premium corner lot just steps from the clubhouse and resort-style amenities, and is one of the few corner homes in the community permitted to have a private fenced backyard. With more than 2,100 square feet of thoughtfully designed, energy-efficient living space, the home showcases an impressive collection of upgrades and finishes selected to highlight the best Hawk’s Crest has to offer. From the moment you enter, high ceilings and an inviting entryway set the tone. As a former model, the home features upgraded interior doors, cabinetry, baseboards, bathroom vanities, and custom details throughout. The expansive kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinetry, granite countertops, double ovens, a walk-in pantry, stainless steel appliances, and a large center island with pendant lighting overlooking the living and dining spaces. The spacious owner’s suite offers a true retreat with an oversized walk-in closet and en-suite bath featuring dual vanities and a walk-in shower. Three additional bedrooms, two full bathrooms, and a generous laundry room with a utility sink and custom built-in drop zone provide plenty of space, storage, and everyday functionality. Outside, the covered lanai opens to a private fenced backyard surrounded by lush landscaping and complete with a fire pit, an ideal setting for entertaining, pets, or simply enjoying the outdoors. Hawk’s Crest residents enjoy an impressive collection of amenities including a resort-style pool, clubhouse, fitness center, splash pad, playgrounds, dog park, virtual guard gate, and access to Lake Howell. Former model home. Rare fenced corner lot. Extensive upgrades. And one of the shortest walks to the clubhouse in the entire community. This is an opportunity that truly stands apart in Hawk’s Crest.

4 Beds ⋅ 3 Baths ⋅ Preserve At Hawks Crest SubDv. ⋅ 32792 Zip Code

Virtually Staged. Welcome to one of the most uniquely positioned homes in the highly sought-after gated community of Hawk’s Crest. This former Meritage model home sits on a premium corner lot just steps from the clubhouse and resort-style amenities, and is one of the few corner homes in the community permitted to have a private fenced backyard. With more than 2,100 square feet of thoughtfully designed, energy-efficient living space, the home showcases an impressive collection of upgrades and finishes selected to highlight the best Hawk’s Crest has to offer. From the moment you enter, high ceilings and an inviting entryway set the tone. As a former model, the home features upgraded interior doors, cabinetry, baseboards, bathroom vanities, and custom details throughout. The expansive kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinetry, granite countertops, double ovens, a walk-in pantry, stainless steel appliances, and a large center island with pendant lighting overlooking the living and dining spaces. The spacious owner’s suite offers a true retreat with an oversized walk-in closet and en-suite bath featuring dual vanities and a walk-in shower. Three additional bedrooms, two full bathrooms, and a generous laundry room with a utility sink and custom built-in drop zone provide plenty of space, storage, and everyday functionality. Outside, the covered lanai opens to a private fenced backyard surrounded by lush landscaping and complete with a fire pit, an ideal setting for entertaining, pets, or simply enjoying the outdoors. Hawk’s Crest residents enjoy an impressive collection of amenities including a resort-style pool, clubhouse, fitness center, splash pad, playgrounds, dog park, virtual guard gate, and access to Lake Howell. Former model home. Rare fenced corner lot. Extensive upgrades. And one of the shortest walks to the clubhouse in the entire community. This is an opportunity that truly stands apart in Hawk’s Crest.

2286 Marsh Sedge Lane, Winter Park