Homesinorlando.forsale Search Results

$2,699,000

Under contract-accepting backup offers. Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV - creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.

4 Beds ⋅ 6 Baths ⋅ Windsong Lakeside Sec 02 43/71 SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV - creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.

1529 Holts Grove Circle, Winter Park

$1,810,000

Stunning Mediterranean Pool Home by M. Lahr Custom Homes in one of the sought-after neighborhoods of Winter Park.

5 Beds ⋅ 5 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

Stunning Mediterranean Pool Home by M. Lahr Custom Homes in one of the sought-after neighborhoods of Winter Park.

1710 Oneco Avenue, Winter Park

$3,100,000

Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

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

Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

141 Glenridge Way, Winter Park

$2,490,000

Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot, providing modern functionality, Old World charm, and an unmatched lifestyle. The main residence spans over 3,600+ SF with 4 bedrooms, 4 bathrooms, and an attached 2-car garage. Across the brick driveway is a detached, fully-equipped 700+ SF studio apartment (5th bedroom suite) located above an additional 2-car garage, and an air-conditioned outdoor bar. With two dwellings, a 4-car garage, and an expansive outdoor entertaining space on a ½ acre lot, this home is a true private compound. Notable updates include newer HVAC systems (2020 & 2025), a new tankless gas water heater (2024), a fully renovated laundry room with new LG stackable washer/dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more... Ask for the $400K list of improvements! Enter the main residence to a family room that stretches 30 feet wide, with 12-foot ceilings, a gas fireplace, and multiple French doors lining the rear wall to showcase the brick-paver pool deck and lush, fenced-in backyard oasis, and southern exposure that invites natural light all morning and afternoon. The expansive family room is open to the kitchen, making this home ideal for entertaining. The kitchen perfectly balances charm and function, with a NEW Sub-Zero refrigerator, natural gas Wolf range, 2 Miele dishwashers, a copper-topped island that offers room for prep, serving, or seating, and a spacious dinette area with pool views. Behind the kitchen sits a dining room and adjacent den (currently used as a library/office) for more living/dining flexibility. A side entrance opens to a covered side porch overlooking a generous side yard framed by tall Podocarpus hedges... ideal for pets, a fabulous garden, or future expanded parking. A 1st floor rear bedroom wing presents 3 bedrooms & 3 full baths. Privately positioned upstairs, the expansive primary suite offers a quiet retreat, highlighted by a recent luxury bathroom renovation with elegant custom finishes including a large glass shower with 3 showerheads, 2 separate vanities, a Toto washlet, and tons of cabinetry for linen storage. French doors from both the bedroom and bath open to a covered balcony overlooking the backyard and pool, while 3 custom walk-in closets create a true dressing room experience, or the perfect opportunity to turn excess space into an office or special hobby room. Designed for entertaining, the outdoor living is equally impressive, with a sprawling lawn surrounding the large saltwater pool and an expansive paver patio for lounging and dining. A covered, air-conditioned bar is designed with custom cabinetry, exquisite lighting, a copper sink, dishwasher, wine fridge, and beverage fridge...all secured by an electronic storm shutter. The extended bar seamlessly serves the adjacent tent-covered lounge area, complete with a natural gas grill, pool bath, and outdoor shower. Above the detached 2-car garage is the studio apartment with a private entry, along with a full kitchen and bath, making it ideal for extended stays or flexible living arrangements. Located just minutes from the vibrant Park Avenue, this distinctive Winter Park compound is a one-of-a-kind property!

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

Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot, providing modern functionality, Old World charm, and an unmatched lifestyle. The main residence spans over 3,600+ SF with 4 bedrooms, 4 bathrooms, and an attached 2-car garage. Across the brick driveway is a detached, fully-equipped 700+ SF studio apartment (5th bedroom suite) located above an additional 2-car garage, and an air-conditioned outdoor bar. With two dwellings, a 4-car garage, and an expansive outdoor entertaining space on a ½ acre lot, this home is a true private compound. Notable updates include newer HVAC systems (2020 & 2025), a new tankless gas water heater (2024), a fully renovated laundry room with new LG stackable washer/dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more... Ask for the $400K list of improvements! Enter the main residence to a family room that stretches 30 feet wide, with 12-foot ceilings, a gas fireplace, and multiple French doors lining the rear wall to showcase the brick-paver pool deck and lush, fenced-in backyard oasis, and southern exposure that invites natural light all morning and afternoon. The expansive family room is open to the kitchen, making this home ideal for entertaining. The kitchen perfectly balances charm and function, with a NEW Sub-Zero refrigerator, natural gas Wolf range, 2 Miele dishwashers, a copper-topped island that offers room for prep, serving, or seating, and a spacious dinette area with pool views. Behind the kitchen sits a dining room and adjacent den (currently used as a library/office) for more living/dining flexibility. A side entrance opens to a covered side porch overlooking a generous side yard framed by tall Podocarpus hedges... ideal for pets, a fabulous garden, or future expanded parking. A 1st floor rear bedroom wing presents 3 bedrooms & 3 full baths. Privately positioned upstairs, the expansive primary suite offers a quiet retreat, highlighted by a recent luxury bathroom renovation with elegant custom finishes including a large glass shower with 3 showerheads, 2 separate vanities, a Toto washlet, and tons of cabinetry for linen storage. French doors from both the bedroom and bath open to a covered balcony overlooking the backyard and pool, while 3 custom walk-in closets create a true dressing room experience, or the perfect opportunity to turn excess space into an office or special hobby room. Designed for entertaining, the outdoor living is equally impressive, with a sprawling lawn surrounding the large saltwater pool and an expansive paver patio for lounging and dining. A covered, air-conditioned bar is designed with custom cabinetry, exquisite lighting, a copper sink, dishwasher, wine fridge, and beverage fridge...all secured by an electronic storm shutter. The extended bar seamlessly serves the adjacent tent-covered lounge area, complete with a natural gas grill, pool bath, and outdoor shower. Above the detached 2-car garage is the studio apartment with a private entry, along with a full kitchen and bath, making it ideal for extended stays or flexible living arrangements. Located just minutes from the vibrant Park Avenue, this distinctive Winter Park compound is a one-of-a-kind property!

1300 Mayfield Avenue, Winter Park

$3,675,000

JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKET Proudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods. Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas. While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration. The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout. The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional. The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision. Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers. A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering. Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level. This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.

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

JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKET Proudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods. Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas. While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration. The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout. The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional. The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision. Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers. A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering. Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level. This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.

150 Dana Way, Winter Park

$3,755,000

Experience the art of luxury living just steps from the boutiques, cafés & celebrated dining of Park Avenue, Winter Park Village, Rollins College & the iconic Winter Park Art Festival. This beautifully crafted custom one-story pool home built in 2024 blends elegant design with an effortless, modern lifestyle. THIS HOME RECEIVED THE 2025 ARDA GRAND AWARD FOR CUSTOM HOME (built). A thoughtful quad split bedroom layout offers 4 bedrooms & 4.5 baths, including a serene primary suite with Hunter Douglas automated light filtering/light blocking shades. The primary suite includes a spectacular custom walk-in closet featuring an island, 36 drawers, built-in benches, dual hampers, a safe, locking jewelry drawers & display shelving. The ensuite bath provides a spa-like retreat. Additionally, two guest suites also enjoy private ensuite baths & large walk-in closets. The showpiece chef’s kitchen is designed for both culinary mastery & entertaining, featuring Dura Supreme cabinetry, a 60" Wolf dual fuel range with griddle, pot filler, 36" Sub Zero Designer Column refrigerator, Sub Zero freezer drawers, two Bosch dishwashers, Wolf microwave drawer, Revati dual tier 57" sink with custom inserts for colander, cutting board & strainer & dual automatic faucets. Dramatic 15-foot waterfall island with Dekton countertops & matching backsplash. A hidden scullery adds even more function with a French door refrigerator, sink, pantry shelving, Dekton counters & floating LED-lit shelves. The stylish wet bar includes white oak floating shelves with LED lighting, Dekton countertops & backsplash, a glass rinser, Scotsman gourmet ice machine & Thermador refrigerator drawers. Dining room has a climate-controlled wine cellar that holds up to 240 bottles. Enjoy picking lemons, limes & oranges from your own mature trees for juicing or garnishes. The expansive family room impresses with six LED-lit floating shelves, a 60" linear gas fireplace & an extraordinary 52 feet of 10-foot-tall sliding stacking patio doors that create seamless indoor-outdoor flow. Step outside to a resort-style outdoor kitchen & living area, complete with a Dekton waterfall countertop, Perlick refrigerator drawers & kegerator, 48" DCS grill with rotisserie & 2 side burners, pizza oven, Ruvati sink with ice chest, bar-height island seating, three 60" Minka Aire remote control fans, outdoor electric fireplace & retractable screens. The app-controlled pool features water elements, bubblers, two ledge loungers with umbrella holder/end table/ice chest & a 9-seat hot tub. Custom closets are found throughout the home, including the media room with built-in Queen Murphy bed & closet & a dedicated exercise room with closet or potential fifth bedroom. Large office filled with natural sunlight. The laundry room includes custom cabinetry with built-ins for pet bowls & bed & a fold-out ironing board. Additional features include Visual Comfort lighting, Guardian security system, Trane home automation, Quantum Fiber, built-in speakers throughout the main living areas & outdoor kitchen, living room & pool, Emtek hardware, PGT casement windows & 8" white oak hardwood floors. The sellers will also provide a one-year home warranty for added benefit. This home delivers a refined, fun & effortless luxury lifestyle in one of Winter Park’s most coveted locations—where every detail is designed to impress. Finding a one-story, almost-new home on a large lot in Winter Park is like finding a rare gem!

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

Experience the art of luxury living just steps from the boutiques, cafés & celebrated dining of Park Avenue, Winter Park Village, Rollins College & the iconic Winter Park Art Festival. This beautifully crafted custom one-story pool home built in 2024 blends elegant design with an effortless, modern lifestyle. THIS HOME RECEIVED THE 2025 ARDA GRAND AWARD FOR CUSTOM HOME (built). A thoughtful quad split bedroom layout offers 4 bedrooms & 4.5 baths, including a serene primary suite with Hunter Douglas automated light filtering/light blocking shades. The primary suite includes a spectacular custom walk-in closet featuring an island, 36 drawers, built-in benches, dual hampers, a safe, locking jewelry drawers & display shelving. The ensuite bath provides a spa-like retreat. Additionally, two guest suites also enjoy private ensuite baths & large walk-in closets. The showpiece chef’s kitchen is designed for both culinary mastery & entertaining, featuring Dura Supreme cabinetry, a 60" Wolf dual fuel range with griddle, pot filler, 36" Sub Zero Designer Column refrigerator, Sub Zero freezer drawers, two Bosch dishwashers, Wolf microwave drawer, Revati dual tier 57" sink with custom inserts for colander, cutting board & strainer & dual automatic faucets. Dramatic 15-foot waterfall island with Dekton countertops & matching backsplash. A hidden scullery adds even more function with a French door refrigerator, sink, pantry shelving, Dekton counters & floating LED-lit shelves. The stylish wet bar includes white oak floating shelves with LED lighting, Dekton countertops & backsplash, a glass rinser, Scotsman gourmet ice machine & Thermador refrigerator drawers. Dining room has a climate-controlled wine cellar that holds up to 240 bottles. Enjoy picking lemons, limes & oranges from your own mature trees for juicing or garnishes. The expansive family room impresses with six LED-lit floating shelves, a 60" linear gas fireplace & an extraordinary 52 feet of 10-foot-tall sliding stacking patio doors that create seamless indoor-outdoor flow. Step outside to a resort-style outdoor kitchen & living area, complete with a Dekton waterfall countertop, Perlick refrigerator drawers & kegerator, 48" DCS grill with rotisserie & 2 side burners, pizza oven, Ruvati sink with ice chest, bar-height island seating, three 60" Minka Aire remote control fans, outdoor electric fireplace & retractable screens. The app-controlled pool features water elements, bubblers, two ledge loungers with umbrella holder/end table/ice chest & a 9-seat hot tub. Custom closets are found throughout the home, including the media room with built-in Queen Murphy bed & closet & a dedicated exercise room with closet or potential fifth bedroom. Large office filled with natural sunlight. The laundry room includes custom cabinetry with built-ins for pet bowls & bed & a fold-out ironing board. Additional features include Visual Comfort lighting, Guardian security system, Trane home automation, Quantum Fiber, built-in speakers throughout the main living areas & outdoor kitchen, living room & pool, Emtek hardware, PGT casement windows & 8" white oak hardwood floors. The sellers will also provide a one-year home warranty for added benefit. This home delivers a refined, fun & effortless luxury lifestyle in one of Winter Park’s most coveted locations—where every detail is designed to impress. Finding a one-story, almost-new home on a large lot in Winter Park is like finding a rare gem!

1117 Kenwood Avenue, Winter Park

$1,250,000

Under contract-accepting backup offers. Discover Orwin Manor, one of Winter Park’s established neighborhoods centrally located within an easy distance to the Orange Avenue WP corridor and minutes to downtown Orlando. Transitional architecture with modern leaning influences, this home is designed for ease of living. This four-bedroom 3.5-bath home stretches across nearly 3,200 square feet and features open kitchen to dining and living spaces that all blend into a covered porch to backyard retreat. The kitchen is the center of the home with custom double-stacked cabinetry to ceiling, upgraded appliances, large pantry with barn door, center island with bar seating, and full granite slab backsplash and counters add to the artistry of the kitchen. Ceilings are upgraded throughout with floating box details with ambient lighting that gently wash the ceilings and colors can be changed as you wish. Dining and living spaces are generous, and lined with transom windows for privacy and natural light that creates a beautiful backdrop to gather and entertain in. Invisible back doors fully open to the lanai and slide into the wall, staying hidden, an elegant upgrade. Covered porch with tongue and groove ceiling overlooks saltwater pool with hot tub and spillway. Professionally landscaped includes a turfed putting green for the golf enthusiast. Additional main floor flex space can be additional living or home office. Secondary bedrooms are upstairs with generous bonus space and laundry. First-floor primary suite is light and bright, with coffered ceilings and a large walk-in closet. Primary bath is neutrally appointed with dual floating vanities with vessel sinks, a soaking tub, and walk-in shower with seamless glass. A transom window provides privacy and a glow of sunshine and warmth. Lots of seller upgrades. This property is turnkey. Orwin Manor is a special neighborhood blending historic homes with new builds and great neighborhood park to go to. It is also a strategic location, minutes to Park Avenue in Winter Park, known for its upscale dining, elevated cafés and luxury local shopping, also a short distance to Orange Avenue corridor in WP featuring Foxtail Coffee & Buttermilk Bakery and more, and minutes to the Mills district, Advent Health on Rollins as well as major roadways. Great schools, zoned for Edgewater High, known for its magnet program and close to Lake Highland and many other private school options.

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

Under contract-accepting backup offers. Discover Orwin Manor, one of Winter Park’s established neighborhoods centrally located within an easy distance to the Orange Avenue WP corridor and minutes to downtown Orlando. Transitional architecture with modern leaning influences, this home is designed for ease of living. This four-bedroom 3.5-bath home stretches across nearly 3,200 square feet and features open kitchen to dining and living spaces that all blend into a covered porch to backyard retreat. The kitchen is the center of the home with custom double-stacked cabinetry to ceiling, upgraded appliances, large pantry with barn door, center island with bar seating, and full granite slab backsplash and counters add to the artistry of the kitchen. Ceilings are upgraded throughout with floating box details with ambient lighting that gently wash the ceilings and colors can be changed as you wish. Dining and living spaces are generous, and lined with transom windows for privacy and natural light that creates a beautiful backdrop to gather and entertain in. Invisible back doors fully open to the lanai and slide into the wall, staying hidden, an elegant upgrade. Covered porch with tongue and groove ceiling overlooks saltwater pool with hot tub and spillway. Professionally landscaped includes a turfed putting green for the golf enthusiast. Additional main floor flex space can be additional living or home office. Secondary bedrooms are upstairs with generous bonus space and laundry. First-floor primary suite is light and bright, with coffered ceilings and a large walk-in closet. Primary bath is neutrally appointed with dual floating vanities with vessel sinks, a soaking tub, and walk-in shower with seamless glass. A transom window provides privacy and a glow of sunshine and warmth. Lots of seller upgrades. This property is turnkey. Orwin Manor is a special neighborhood blending historic homes with new builds and great neighborhood park to go to. It is also a strategic location, minutes to Park Avenue in Winter Park, known for its upscale dining, elevated cafés and luxury local shopping, also a short distance to Orange Avenue corridor in WP featuring Foxtail Coffee & Buttermilk Bakery and more, and minutes to the Mills district, Advent Health on Rollins as well as major roadways. Great schools, zoned for Edgewater High, known for its magnet program and close to Lake Highland and many other private school options.

1649 Harmon Avenue, Winter Park

$1,688,750

Presenting 1705 Elizabeths Walk for the first time since original construction, an exceptional custom residence located in the highly sought-after Windsong community of Winter Park. Perfectly positioned on a beautifully landscaped .34-acre lot, this elegant 5-bedroom, 5-bathroom estate offers nearly 4,000 square feet of refined living space designed for both comfortable living and sophisticated entertaining. From the moment you enter, you’re greeted by soaring volume ceilings, rich architectural details, and an abundance of natural light that create an inviting and luxurious atmosphere. The thoughtfully designed floor plan features formal living and dining spaces, a spacious family room, upstairs family room and loft, bonus room, and a chef-inspired kitchen with an island, breakfast bar, and large pantry, seamlessly connecting the home’s main gathering areas. The private primary suite on the main level serves as a tranquil retreat, complete with a spa-inspired bathroom featuring dual vanities, a soaking tub, and a separate walk-in shower. Additional bedrooms provide generous space for family and guests, while flexible living areas allow for a home office, library, or game room. Step outside to enjoy the Florida lifestyle with beautifully landscaped grounds and a huge outdoor living area, complete with an exterior gas fireplace for those chilly winter days, and ideal for relaxing or entertaining. Located within the prestigious Windsong neighborhood, residents enjoy access to community amenities including parks, playgrounds, boat dock and rental, and resort-style pools, all just minutes from Park Avenue’s world-class dining, shopping, and cultural attractions. Zoned for top-rated Winter Park schools, this remarkable home offers the perfect blend of luxury, comfort, and location in one of Central Florida’s most desirable communities.

5 Beds ⋅ 5 Baths ⋅ Windsong Elizabeths Walk SubDv. ⋅ 32789 Zip Code

Presenting 1705 Elizabeths Walk for the first time since original construction, an exceptional custom residence located in the highly sought-after Windsong community of Winter Park. Perfectly positioned on a beautifully landscaped .34-acre lot, this elegant 5-bedroom, 5-bathroom estate offers nearly 4,000 square feet of refined living space designed for both comfortable living and sophisticated entertaining. From the moment you enter, you’re greeted by soaring volume ceilings, rich architectural details, and an abundance of natural light that create an inviting and luxurious atmosphere. The thoughtfully designed floor plan features formal living and dining spaces, a spacious family room, upstairs family room and loft, bonus room, and a chef-inspired kitchen with an island, breakfast bar, and large pantry, seamlessly connecting the home’s main gathering areas. The private primary suite on the main level serves as a tranquil retreat, complete with a spa-inspired bathroom featuring dual vanities, a soaking tub, and a separate walk-in shower. Additional bedrooms provide generous space for family and guests, while flexible living areas allow for a home office, library, or game room. Step outside to enjoy the Florida lifestyle with beautifully landscaped grounds and a huge outdoor living area, complete with an exterior gas fireplace for those chilly winter days, and ideal for relaxing or entertaining. Located within the prestigious Windsong neighborhood, residents enjoy access to community amenities including parks, playgrounds, boat dock and rental, and resort-style pools, all just minutes from Park Avenue’s world-class dining, shopping, and cultural attractions. Zoned for top-rated Winter Park schools, this remarkable home offers the perfect blend of luxury, comfort, and location in one of Central Florida’s most desirable communities.

1705 Elizabeths Walk, Winter Park

$1,675,000

Welcome to a one-of-a-kind opportunity inside the Winter Park city limits, where timeless character, meaningful updates, and an exceptional lifestyle and location come together in a perfect blend! Set on a beautifully landscaped 0.27-acre lot along Winter Park’s iconic tree lined, brick paved streets, this custom 5-bedroom, 4.5-bathroom residence with an office, a gym and attached in-law suite offers 3,851 square feet of living space, remarkable flexibility, and the kind of charm that simply cannot be replicated. Buyers will also appreciate the peace of mind that comes with major recent updates, including a metal roof installed in 2017, two HVAC units replaced in 2026, a third HVAC unit replaced in 2022, and two water heaters installed in 2025. The pool was resurfaced in 2025, the exterior and interior of the home was painted in 2025, & the house has also been completely re-plumbed! From the moment you arrive, the home makes a lasting impression with its large brick front porch, circular driveway, mature landscaping, detached oversized 2 car garage, and classic architectural presence. Large windows and thoughtfully designed living spaces fill the home with natural light, while hardwood floors, custom built-ins, plantation shutters, fireplaces, and refined traditional details create a warm and inviting feel throughout. This is the perfect blend of classic Winter Park charm and functional modern updates. The floor plan offers both elegance and versatility. In addition to five bedrooms, the home features an office space that can also serve as a formal living room, library, or flex space depending on your needs. The spacious family room is anchored by one of the home’s two wood burning fireplaces and opens beautifully to the outdoor living area, creating an easy flow for both everyday living and entertaining. The kitchen offers granite countertops, custom cabinetry, abundant counter space, a large island, and lots of natural light. It is open, functional, and well positioned at the heart of the home, allowing the next owner to enjoy it as is or make it their own. The primary suite is generously sized, featuring its own fireplace, an oversized bathroom with large walk-in shower, extensive vanity space, and a huge custom closet. One of the most special features of this home is the attached in-law suite, with its own separate entrance while still remaining accessible from the main home. Complete with a living room, bedroom, full bathroom, and kitchenette, this apartment style space offers exceptional flexibility for multigenerational living, live in family, guests, or even potential income producing use. Outside, the screened pool and spa area is a true highlight. Beautifully integrated into the architecture of the home, this private outdoor setting offers a covered lanai, lush tropical landscaping, and a peaceful courtyard style feel that makes it easy to relax, entertain, and enjoy Florida living year-round. The large paver driveway and detached garage create an impressive amount of parking and enhance the home’s unique layout and curb appeal. All of this is located less than 1.5 miles from Rollins College, Park Avenue, downtown Winter Park, public access to the Winter Park Chain of Lakes, and all the dining, shopping, boating, and everyday convenience that make this area so desirable. This is more than just a home. It is a rare chance to enjoy the Winter Park lifestyle in a custom home full of character, flexibility, and lasting value.

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

Welcome to a one-of-a-kind opportunity inside the Winter Park city limits, where timeless character, meaningful updates, and an exceptional lifestyle and location come together in a perfect blend! Set on a beautifully landscaped 0.27-acre lot along Winter Park’s iconic tree lined, brick paved streets, this custom 5-bedroom, 4.5-bathroom residence with an office, a gym and attached in-law suite offers 3,851 square feet of living space, remarkable flexibility, and the kind of charm that simply cannot be replicated. Buyers will also appreciate the peace of mind that comes with major recent updates, including a metal roof installed in 2017, two HVAC units replaced in 2026, a third HVAC unit replaced in 2022, and two water heaters installed in 2025. The pool was resurfaced in 2025, the exterior and interior of the home was painted in 2025, & the house has also been completely re-plumbed! From the moment you arrive, the home makes a lasting impression with its large brick front porch, circular driveway, mature landscaping, detached oversized 2 car garage, and classic architectural presence. Large windows and thoughtfully designed living spaces fill the home with natural light, while hardwood floors, custom built-ins, plantation shutters, fireplaces, and refined traditional details create a warm and inviting feel throughout. This is the perfect blend of classic Winter Park charm and functional modern updates. The floor plan offers both elegance and versatility. In addition to five bedrooms, the home features an office space that can also serve as a formal living room, library, or flex space depending on your needs. The spacious family room is anchored by one of the home’s two wood burning fireplaces and opens beautifully to the outdoor living area, creating an easy flow for both everyday living and entertaining. The kitchen offers granite countertops, custom cabinetry, abundant counter space, a large island, and lots of natural light. It is open, functional, and well positioned at the heart of the home, allowing the next owner to enjoy it as is or make it their own. The primary suite is generously sized, featuring its own fireplace, an oversized bathroom with large walk-in shower, extensive vanity space, and a huge custom closet. One of the most special features of this home is the attached in-law suite, with its own separate entrance while still remaining accessible from the main home. Complete with a living room, bedroom, full bathroom, and kitchenette, this apartment style space offers exceptional flexibility for multigenerational living, live in family, guests, or even potential income producing use. Outside, the screened pool and spa area is a true highlight. Beautifully integrated into the architecture of the home, this private outdoor setting offers a covered lanai, lush tropical landscaping, and a peaceful courtyard style feel that makes it easy to relax, entertain, and enjoy Florida living year-round. The large paver driveway and detached garage create an impressive amount of parking and enhance the home’s unique layout and curb appeal. All of this is located less than 1.5 miles from Rollins College, Park Avenue, downtown Winter Park, public access to the Winter Park Chain of Lakes, and all the dining, shopping, boating, and everyday convenience that make this area so desirable. This is more than just a home. It is a rare chance to enjoy the Winter Park lifestyle in a custom home full of character, flexibility, and lasting value.

1560 Woodland Avenue, Winter Park

$2,200,000

Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s exclusive Chain of Lakes-Lake Virginia, Lake Mizell, Lake Osceola, Lake Maitland, Lake Nina, and Lake Minnehaha. Morning sunrises and golden afternoon sunsets create unforgettable moments to enjoy privately or share with family and friends. Built in 2008, this exceptional home welcomes you with a stunning rotunda accented by stained glass panels, setting the tone for the refined design found throughout. Vaulted recessed ceilings enhance the open floor plan, filling the home with natural light and architectural elegance. Thoughtfully curated details and custom finishes are showcased in every space. Offering approximately 5,051 square feet, the home features four spacious bedrooms, each with its own en suite bathroom. The owner’s suite is a private retreat with picturesque canal views and luxurious built-in features. The spa-inspired owner’s bath includes dual vanities, designer textiles, strategic lighting, expansive walk-in closets, a steam shower with dual stations and multiple shower heads, a Jacuzzi tub, bidet, linen storage,and a private water closet. Designed for effortless entertaining, the gourmet chef’s kitchen is both functional and beautiful. Highlights include an oversized working island, high-top bar seating,Thermador gas range,Thermadore double ovens,Thermadore refrigerator, wine cooler, hidden lighted walk-in pantry and multiple prep areas. The kitchen flows seamlessly into the formal dining room and the expansive great room, which showcases floor-to-ceiling views of the lushly landscaped backyard, paver patio and serene Venetian Canal water view. A stunning library with floor-to-ceiling canal views features a custom gas fireplace and built-in shelving, perfect for displaying books and treasured collections. The first floor features a convenient half bath adjacent to the laundry room, along with a lovely powder room ideal for guests. Upstairs, a striking staircase leads to three additional bedrooms and two bathrooms. One bedroom room has a private en-suite bathroom and the other bedrooms share an adjoining en- suite bath. There are two oversized, versatile gathering spaces complete with a built-in wet bar and beverage refrigerator. A spacious living area overlooks the canal and opens to an upper-level lanai-ideal for outdoor entertaining. This level also includes a home theater and flexible space suitable for an additional bedroom, office, or recreation room. Location is unmatched. Situated in the heart of Winter Park, this home offers easy access to both Winter Park and Maitland amenities. Enjoy Park Avenue dining, shopping, art festivals, farmers markets, outdoor concerts, scenic walking and biking trails, and beautiful green spaces. Zoned for top rated OCPS schools: Dommerich Elementary, Maitland Middle School, and Winter Park High School. This remarkable Winter Park Canal home combines timeless style, exceptional craftsmanship, private dock access, Venetian Canal frontage, and direct connection to the Winter Park Chain of Lakes-all in one of Central Florida’s most sought-after locations.

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

Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s exclusive Chain of Lakes-Lake Virginia, Lake Mizell, Lake Osceola, Lake Maitland, Lake Nina, and Lake Minnehaha. Morning sunrises and golden afternoon sunsets create unforgettable moments to enjoy privately or share with family and friends. Built in 2008, this exceptional home welcomes you with a stunning rotunda accented by stained glass panels, setting the tone for the refined design found throughout. Vaulted recessed ceilings enhance the open floor plan, filling the home with natural light and architectural elegance. Thoughtfully curated details and custom finishes are showcased in every space. Offering approximately 5,051 square feet, the home features four spacious bedrooms, each with its own en suite bathroom. The owner’s suite is a private retreat with picturesque canal views and luxurious built-in features. The spa-inspired owner’s bath includes dual vanities, designer textiles, strategic lighting, expansive walk-in closets, a steam shower with dual stations and multiple shower heads, a Jacuzzi tub, bidet, linen storage,and a private water closet. Designed for effortless entertaining, the gourmet chef’s kitchen is both functional and beautiful. Highlights include an oversized working island, high-top bar seating,Thermador gas range,Thermadore double ovens,Thermadore refrigerator, wine cooler, hidden lighted walk-in pantry and multiple prep areas. The kitchen flows seamlessly into the formal dining room and the expansive great room, which showcases floor-to-ceiling views of the lushly landscaped backyard, paver patio and serene Venetian Canal water view. A stunning library with floor-to-ceiling canal views features a custom gas fireplace and built-in shelving, perfect for displaying books and treasured collections. The first floor features a convenient half bath adjacent to the laundry room, along with a lovely powder room ideal for guests. Upstairs, a striking staircase leads to three additional bedrooms and two bathrooms. One bedroom room has a private en-suite bathroom and the other bedrooms share an adjoining en- suite bath. There are two oversized, versatile gathering spaces complete with a built-in wet bar and beverage refrigerator. A spacious living area overlooks the canal and opens to an upper-level lanai-ideal for outdoor entertaining. This level also includes a home theater and flexible space suitable for an additional bedroom, office, or recreation room. Location is unmatched. Situated in the heart of Winter Park, this home offers easy access to both Winter Park and Maitland amenities. Enjoy Park Avenue dining, shopping, art festivals, farmers markets, outdoor concerts, scenic walking and biking trails, and beautiful green spaces. Zoned for top rated OCPS schools: Dommerich Elementary, Maitland Middle School, and Winter Park High School. This remarkable Winter Park Canal home combines timeless style, exceptional craftsmanship, private dock access, Venetian Canal frontage, and direct connection to the Winter Park Chain of Lakes-all in one of Central Florida’s most sought-after locations.

2550 Venetian Way, Winter Park

$3,000,000

Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park Avenue. Inside, rich hardwood floors run throughout the living spaces, complemented by Restoration Hardware lighting that brings a refined, cohesive feel to every room. The welcoming foyer opens to a gracious formal living room with a gas fireplace and custom built-ins, an elegant yet comfortable space for entertaining or relaxing. Just beyond, the formal dining room is well proportioned for hosting holiday gatherings and dinner parties with ease. The heart of the home is the expansive chef’s kitchen, thoughtfully designed for everyday living and effortless entertaining. An oversized island anchors the space, topped with Carrara marble counters and offering generous seating. A dual Wolf oven with six-burner range plus French cooktop, custom cabinetry, walk-in pantry, and a butler’s pantry complete with under-counter wine refrigerator provide beauty and functionality. A spacious breakfast room filled with natural light overlooks the backyard and flows seamlessly into the family room. Here, a gas fireplace, custom built-ins and three sets of French doors create a warm focal point while inviting in the outdoors. The first-floor primary suite serves as a private retreat, featuring large windows with tranquil views of the pool and direct access to the covered lanai. Dual walk-in closets provide ample storage, and the spa-like primary bath is finished in Carrara marble, offering a large soaking tub and an expansive glass-enclosed shower with dual shower heads. Two powder baths, one thoughtfully designed as a pool bath, along with one of two laundry rooms complete the main level. Upstairs, four additional bedrooms and a dedicated office provide generous space for family and guests. Two of the bedrooms feature private en-suite baths, while the remaining two share a well-appointed Jack & Jill bath. One of these rooms is arranged as a bonus lounge, offering flexibility to serve as a fifth bedroom, media room or additional gathering space if desired. The thoughtful second-floor layout easily adapts to a variety of lifestyle needs, whether accommodating guests, growing families or multi-generational living. A secondary laundry room upstairs adds an added layer of everyday convenience. Outdoor living is equally impressive. The spacious covered lanai with summer kitchen overlooks the saltwater, heated pool and spa, creating an extension of the interior living space. Brick paver flooring continues from the lanai to the open patio, offering multiple areas for lounging, dining and entertaining beneath the Florida sky. Ideally in a desirable location and zoned for sought-after Audubon Park K-8, 2040 Randall Circle offers timeless style, thoughtful design and seamless indoor-outdoor living in one of the area’s charming neighborhoods.

5 Beds ⋅ 6 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park Avenue. Inside, rich hardwood floors run throughout the living spaces, complemented by Restoration Hardware lighting that brings a refined, cohesive feel to every room. The welcoming foyer opens to a gracious formal living room with a gas fireplace and custom built-ins, an elegant yet comfortable space for entertaining or relaxing. Just beyond, the formal dining room is well proportioned for hosting holiday gatherings and dinner parties with ease. The heart of the home is the expansive chef’s kitchen, thoughtfully designed for everyday living and effortless entertaining. An oversized island anchors the space, topped with Carrara marble counters and offering generous seating. A dual Wolf oven with six-burner range plus French cooktop, custom cabinetry, walk-in pantry, and a butler’s pantry complete with under-counter wine refrigerator provide beauty and functionality. A spacious breakfast room filled with natural light overlooks the backyard and flows seamlessly into the family room. Here, a gas fireplace, custom built-ins and three sets of French doors create a warm focal point while inviting in the outdoors. The first-floor primary suite serves as a private retreat, featuring large windows with tranquil views of the pool and direct access to the covered lanai. Dual walk-in closets provide ample storage, and the spa-like primary bath is finished in Carrara marble, offering a large soaking tub and an expansive glass-enclosed shower with dual shower heads. Two powder baths, one thoughtfully designed as a pool bath, along with one of two laundry rooms complete the main level. Upstairs, four additional bedrooms and a dedicated office provide generous space for family and guests. Two of the bedrooms feature private en-suite baths, while the remaining two share a well-appointed Jack & Jill bath. One of these rooms is arranged as a bonus lounge, offering flexibility to serve as a fifth bedroom, media room or additional gathering space if desired. The thoughtful second-floor layout easily adapts to a variety of lifestyle needs, whether accommodating guests, growing families or multi-generational living. A secondary laundry room upstairs adds an added layer of everyday convenience. Outdoor living is equally impressive. The spacious covered lanai with summer kitchen overlooks the saltwater, heated pool and spa, creating an extension of the interior living space. Brick paver flooring continues from the lanai to the open patio, offering multiple areas for lounging, dining and entertaining beneath the Florida sky. Ideally in a desirable location and zoned for sought-after Audubon Park K-8, 2040 Randall Circle offers timeless style, thoughtful design and seamless indoor-outdoor living in one of the area’s charming neighborhoods.

2040 Randall Circle, Winter Park

$1,649,000

PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated everyday living, this exceptional 5-bedroom, 3.5-bath residence (currently configured as 4 bedrooms + dedicated office) offers a level of quality that simply cannot be replicated at this price point. Just minutes from Park Avenue, Audubon Park, dining, shopping, and top Winter Park amenities, the location is as compelling as the home itself. This residence delivers the rare combination of TIMELESS ARCHITECTURE + MODERN CONSTRUCTION. Built using INSULATED CONCRETE FORM (ICF) CONSTRUCTION, the home offers exceptional durability, energy efficiency, and a remarkably quiet interior—creating a true retreat from outside noise and Florida heat. Average summer utility bills are approximately $185/month. The exterior was freshly repainted in 2023, further enhancing the home’s curb appeal and long-term maintenance appeal. The floor plan was intentionally designed for real life. The FIRST-FLOOR PRIMARY SUITE serves as a private retreat with an attached office, custom walk-in closet with hidden under-stair storage, and a spa-like bath featuring dual sinks, marble vanity, freestanding cast iron soaking tub, marble floors, and an oversized walk-in shower with dual shower heads. A separate downstairs office easily functions as a fifth bedroom if desired. At the center of the home, the chef’s kitchen was built to perform as beautifully as it looks with MARBLE COUNTERTOPS, WALNUT ISLAND, GE CAFÉ GAS RANGE, BOSCH DISHWASHER, BRAND-NEW SAMSUNG REFRIGERATOR, and an oversized walk-in pantry/butler’s pantry. The adjacent living room is equally impressive with extensive custom built-ins, gas fireplace, library shelving, surround sound wiring, and French doors opening seamlessly to outdoor entertaining spaces. Designed with entertaining in mind, the outdoor spaces feel like an extension of the home with a spacious river rock patio, covered breezeway with tongue-and-groove ceiling, natural gas hookup for grilling, detached rear-entry two-car garage, circular front drive, and additional rear parking—an uncommon luxury in this highly sought-after location. Upstairs, soaring ceilings frame a large bonus/playroom alongside three additional bedrooms and two baths, including a Jack-and-Jill layout. A climate-controlled attic space under AC offers valuable bonus storage not included in the home’s stated square footage. Additional upgrades include NATURAL GAS (range, fireplace, dryer & grill), TANKLESS WATER HEATERS, CAT 6 ETHERNET WIRING, QUANTUM FIBER READINESS, and LOW-E DOUBLE PANE WINDOWS. Every inch of this home was intentionally designed with longevity, comfort, and function in mind. Try building this level of fully custom home in Winter Park today—on this timeline, with these finishes, this infrastructure, and this location—at this price point. It’s nearly impossible. Homes of this caliber rarely become available, especially PRICED BELOW APPRAISAL. Schedule your private showing and experience firsthand what makes this Winter Park home so exceptional.

5 Beds ⋅ 4 Baths ⋅ Parklando #3 SubDv. ⋅ 32789 Zip Code

PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated everyday living, this exceptional 5-bedroom, 3.5-bath residence (currently configured as 4 bedrooms + dedicated office) offers a level of quality that simply cannot be replicated at this price point. Just minutes from Park Avenue, Audubon Park, dining, shopping, and top Winter Park amenities, the location is as compelling as the home itself. This residence delivers the rare combination of TIMELESS ARCHITECTURE + MODERN CONSTRUCTION. Built using INSULATED CONCRETE FORM (ICF) CONSTRUCTION, the home offers exceptional durability, energy efficiency, and a remarkably quiet interior—creating a true retreat from outside noise and Florida heat. Average summer utility bills are approximately $185/month. The exterior was freshly repainted in 2023, further enhancing the home’s curb appeal and long-term maintenance appeal. The floor plan was intentionally designed for real life. The FIRST-FLOOR PRIMARY SUITE serves as a private retreat with an attached office, custom walk-in closet with hidden under-stair storage, and a spa-like bath featuring dual sinks, marble vanity, freestanding cast iron soaking tub, marble floors, and an oversized walk-in shower with dual shower heads. A separate downstairs office easily functions as a fifth bedroom if desired. At the center of the home, the chef’s kitchen was built to perform as beautifully as it looks with MARBLE COUNTERTOPS, WALNUT ISLAND, GE CAFÉ GAS RANGE, BOSCH DISHWASHER, BRAND-NEW SAMSUNG REFRIGERATOR, and an oversized walk-in pantry/butler’s pantry. The adjacent living room is equally impressive with extensive custom built-ins, gas fireplace, library shelving, surround sound wiring, and French doors opening seamlessly to outdoor entertaining spaces. Designed with entertaining in mind, the outdoor spaces feel like an extension of the home with a spacious river rock patio, covered breezeway with tongue-and-groove ceiling, natural gas hookup for grilling, detached rear-entry two-car garage, circular front drive, and additional rear parking—an uncommon luxury in this highly sought-after location. Upstairs, soaring ceilings frame a large bonus/playroom alongside three additional bedrooms and two baths, including a Jack-and-Jill layout. A climate-controlled attic space under AC offers valuable bonus storage not included in the home’s stated square footage. Additional upgrades include NATURAL GAS (range, fireplace, dryer & grill), TANKLESS WATER HEATERS, CAT 6 ETHERNET WIRING, QUANTUM FIBER READINESS, and LOW-E DOUBLE PANE WINDOWS. Every inch of this home was intentionally designed with longevity, comfort, and function in mind. Try building this level of fully custom home in Winter Park today—on this timeline, with these finishes, this infrastructure, and this location—at this price point. It’s nearly impossible. Homes of this caliber rarely become available, especially PRICED BELOW APPRAISAL. Schedule your private showing and experience firsthand what makes this Winter Park home so exceptional.

2501 Winter Park Road, Winter Park

$1,900,000

Move-in ready and tucked into a desirable Winter Park setting, this home offers a rare blend of privacy, functionality, and elevated everyday living. For buyers relocating or purchasing a second home, this property eliminates the typical friction points of contractor timelines, uncertain updates, and drawn-out closings. Instead new homeowner gets a clean, turnkey experience in one of Winter Park’s most desirable areas. Inside, the heart of the home is a beautifully designed chef’s kitchen, built for both serious cooking and effortless entertaining, with high-end appliances, generous prep space, and seamless flow into the main living areas. The primary suite serves as a true retreat, featuring a spacious ensuite bath and a layout designed for comfort and quiet. Natural light, clean finishes, and intentional design choices throughout create a calm, polished environment that supports both relaxation and hosting. With both front and rear driveway access, the property provides a unique sense of separation and ease—ideal for discreet entry, guest flow, and a more flexible approach to daily life. Outdoor spaces are designed for privacy and ease, offering a more intimate setting without the demands of a larger property. Well-maintained and thoughtfully updated, the home allows for immediate enjoyment while still offering flexibility to personalize over time. Located just minutes from Winter Park’s dining, shopping, and top-rated schools, this property delivers a refined lifestyle with practical advantages of privacy, flexibility, and a layout that simply works. Easy to show, easy to love, easy to make your own!

4 Beds ⋅ 3 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Move-in ready and tucked into a desirable Winter Park setting, this home offers a rare blend of privacy, functionality, and elevated everyday living. For buyers relocating or purchasing a second home, this property eliminates the typical friction points of contractor timelines, uncertain updates, and drawn-out closings. Instead new homeowner gets a clean, turnkey experience in one of Winter Park’s most desirable areas. Inside, the heart of the home is a beautifully designed chef’s kitchen, built for both serious cooking and effortless entertaining, with high-end appliances, generous prep space, and seamless flow into the main living areas. The primary suite serves as a true retreat, featuring a spacious ensuite bath and a layout designed for comfort and quiet. Natural light, clean finishes, and intentional design choices throughout create a calm, polished environment that supports both relaxation and hosting. With both front and rear driveway access, the property provides a unique sense of separation and ease—ideal for discreet entry, guest flow, and a more flexible approach to daily life. Outdoor spaces are designed for privacy and ease, offering a more intimate setting without the demands of a larger property. Well-maintained and thoughtfully updated, the home allows for immediate enjoyment while still offering flexibility to personalize over time. Located just minutes from Winter Park’s dining, shopping, and top-rated schools, this property delivers a refined lifestyle with practical advantages of privacy, flexibility, and a layout that simply works. Easy to show, easy to love, easy to make your own!

1760 Alabama Drive, Winter Park

$6,900,000

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

6 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

1260 Alabama Drive, Winter Park

$3,278,530

Located in the desirable heart of the Via's, this single story home with a transitional interior in Sicilian Shores is a meticulously renovated Winter Park charmer. Nestled quietly on an almost 1/2 acre corner lot, this beautiful home is walking distance to the Winter Park Racquet Club and easy proximity to Park Avenue and Interlachen Country Club. Complete with a gracious master bedroom adjacent to an eloquent sitting room and walk in closet, a secondary master sized bedroom, two beautiful guest bedrooms, en suite bathrooms for all bedrooms, and half bath, this floor plan is the perfect design for any living configuration. With the exception of one guest bathroom, the entire home has been redone with wood look tile from Italy throughout and a plethora of custom upgrades and style features. An elegantly appointed kitchen, laundry, tiled and screened porch (with added gas fireplace and television), stunning master bath, built-ins, and large gas burning fireplace in living room are among the many special features of this stunning single story residence. With plenty of natural light and well-maintained landscaping, 700 Pinetree is perfectly appointed for Winter Park living at its finest. Exterior includes fenced dog run with turf, gated back yard, pool, lighting, sprinkler system, pavers, and mature privacy landscaping. Appliances include GE Cafe and Sub Zero. Natural gas, LED lighting throughout, and custom electronics in fourth bedroom turned media space. California closet in a true master suite with freestanding tub and plenty of storage, high volume and tray ceilings, skylights, integrated home generator, and a six year old roof add to the appeal of this stunning corner property. Elegance, privacy, and sophistication, combined with quality finishes and touches makes this home a true gem!

4 Beds ⋅ 5 Baths ⋅ Sicilian Shores SubDv. ⋅ 32789 Zip Code

Located in the desirable heart of the Via's, this single story home with a transitional interior in Sicilian Shores is a meticulously renovated Winter Park charmer. Nestled quietly on an almost 1/2 acre corner lot, this beautiful home is walking distance to the Winter Park Racquet Club and easy proximity to Park Avenue and Interlachen Country Club. Complete with a gracious master bedroom adjacent to an eloquent sitting room and walk in closet, a secondary master sized bedroom, two beautiful guest bedrooms, en suite bathrooms for all bedrooms, and half bath, this floor plan is the perfect design for any living configuration. With the exception of one guest bathroom, the entire home has been redone with wood look tile from Italy throughout and a plethora of custom upgrades and style features. An elegantly appointed kitchen, laundry, tiled and screened porch (with added gas fireplace and television), stunning master bath, built-ins, and large gas burning fireplace in living room are among the many special features of this stunning single story residence. With plenty of natural light and well-maintained landscaping, 700 Pinetree is perfectly appointed for Winter Park living at its finest. Exterior includes fenced dog run with turf, gated back yard, pool, lighting, sprinkler system, pavers, and mature privacy landscaping. Appliances include GE Cafe and Sub Zero. Natural gas, LED lighting throughout, and custom electronics in fourth bedroom turned media space. California closet in a true master suite with freestanding tub and plenty of storage, high volume and tray ceilings, skylights, integrated home generator, and a six year old roof add to the appeal of this stunning corner property. Elegance, privacy, and sophistication, combined with quality finishes and touches makes this home a true gem!

700 Pinetree Road, Winter Park

$1,400,000

Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main house has a flexible floor plan that includes four bedrooms and four and one half baths, a sunroom ideal for home office, formal dining room, oversized family room and charming sitting area with fireplace. The kitchen is a chef's delight with six burner gas range, large center island, plentiful l space for gatherings and a separate breakfast room. Other notable features include gleaming wood floors, double pane windows offering abundant natural light, adorable laundry room/mud room. French doors from many rooms open to a classic front porch that is a perfect place for relaxing and enjoying picturesque grounds with towering oaks. Step outside to a private heated pool. Detached garage includes Tesla charging station. This gated compound situated on .42 acres is one block from Lake Osceola and a easy walk to Park Avenue.

4 Beds ⋅ 6 Baths ⋅ Osceola Shores Sec 1 SubDv. ⋅ 32789 Zip Code

Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main house has a flexible floor plan that includes four bedrooms and four and one half baths, a sunroom ideal for home office, formal dining room, oversized family room and charming sitting area with fireplace. The kitchen is a chef's delight with six burner gas range, large center island, plentiful l space for gatherings and a separate breakfast room. Other notable features include gleaming wood floors, double pane windows offering abundant natural light, adorable laundry room/mud room. French doors from many rooms open to a classic front porch that is a perfect place for relaxing and enjoying picturesque grounds with towering oaks. Step outside to a private heated pool. Detached garage includes Tesla charging station. This gated compound situated on .42 acres is one block from Lake Osceola and a easy walk to Park Avenue.

234 Detmar Drive, Winter Park

$2,750,000

Repositioned at $2,850,000, 151 Oakwood Way is one of the strongest newer luxury opportunities under $3M in Winter Park. Built by LunDev Custom Homes in 2023, this 4,129-square-foot residence sits on a quiet brick street in Charmont and offers a private pool, spa, covered lanai, summer kitchen, automatic screens, and a rare under-$700/sf position for newer luxury construction in 32789. Inside, the home features wide-plank wood flooring, high ceilings, quartz surfaces, Thermador appliances, custom built-ins, a wet bar, walk-in closets, and an open kitchen, dining, and living layout filled with natural light. The main living areas connect directly to the outdoor entertaining space, creating the indoor-outdoor flow buyers want in Winter Park. The floor plan includes 4 bedrooms, 4.5 baths, a main-level primary suite, generous secondary spaces, and a large flex room that can function as an office, family room, media room, game room, or future guest suite, with plumbing already in place. Set on a landscaped 0.26-acre lot with no HOA shown publicly, 151 Oakwood offers a compelling combination in 32789: newer LunDev construction, private pool, outdoor kitchen, brick-street setting, and a sub-$3M position close to Winter Park, Baldwin Park, Audubon Park, and Park Avenue.

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

Repositioned at $2,850,000, 151 Oakwood Way is one of the strongest newer luxury opportunities under $3M in Winter Park. Built by LunDev Custom Homes in 2023, this 4,129-square-foot residence sits on a quiet brick street in Charmont and offers a private pool, spa, covered lanai, summer kitchen, automatic screens, and a rare under-$700/sf position for newer luxury construction in 32789. Inside, the home features wide-plank wood flooring, high ceilings, quartz surfaces, Thermador appliances, custom built-ins, a wet bar, walk-in closets, and an open kitchen, dining, and living layout filled with natural light. The main living areas connect directly to the outdoor entertaining space, creating the indoor-outdoor flow buyers want in Winter Park. The floor plan includes 4 bedrooms, 4.5 baths, a main-level primary suite, generous secondary spaces, and a large flex room that can function as an office, family room, media room, game room, or future guest suite, with plumbing already in place. Set on a landscaped 0.26-acre lot with no HOA shown publicly, 151 Oakwood offers a compelling combination in 32789: newer LunDev construction, private pool, outdoor kitchen, brick-street setting, and a sub-$3M position close to Winter Park, Baldwin Park, Audubon Park, and Park Avenue.

151 Oakwood Way, Winter Park

$599,900

TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch welcomes you into the living room with a fireplace. A front room currently used as a formal parlor or sitting room doubles as the third bedroom, also ideal for entertaining or reading. Two additional bedrooms and full baths are located down the hall. The dining room sits just off the main living space, with French doors opening into the hallway. The kitchen is positioned toward the back of the home with a tucked away laundry closet. Accessed by an interior staircase off the kitchen, the HIGHLIGHT of the home is the handcrafted upstairs loft with design in a class of itself. Currently used as an exquisite billiards room and library, this flexible space can serve as a library, office, or creative retreat, and features a balcony with views of Lake Killarney. Additional features include 42-inch kitchen cabinets, stone countertops, a roof replaced in 2018, AC replaced in 2019. Wind mitigation passed April 2024, septic pumped October 2025, and on top of it all, no HOA! Conveniently located minutes from Downtown Winter Park, Park Avenue, Rollins College, and just minutes from I-4, this is a truly unique property offering craftsmanship and character rarely found today.

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

TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch welcomes you into the living room with a fireplace. A front room currently used as a formal parlor or sitting room doubles as the third bedroom, also ideal for entertaining or reading. Two additional bedrooms and full baths are located down the hall. The dining room sits just off the main living space, with French doors opening into the hallway. The kitchen is positioned toward the back of the home with a tucked away laundry closet. Accessed by an interior staircase off the kitchen, the HIGHLIGHT of the home is the handcrafted upstairs loft with design in a class of itself. Currently used as an exquisite billiards room and library, this flexible space can serve as a library, office, or creative retreat, and features a balcony with views of Lake Killarney. Additional features include 42-inch kitchen cabinets, stone countertops, a roof replaced in 2018, AC replaced in 2019. Wind mitigation passed April 2024, septic pumped October 2025, and on top of it all, no HOA! Conveniently located minutes from Downtown Winter Park, Park Avenue, Rollins College, and just minutes from I-4, this is a truly unique property offering craftsmanship and character rarely found today.

1951 Staunton Avenue, Winter Park

$1,050,000

Welcome to 831 & 833 Huntington Court, a rarely available duplex tucked away on a quiet cul-de-sac in one of Winter Park’s most walkable and desirable locations. Just minutes from Park Avenue, local lakes, dining, shopping, and entertainment, this property offers the perfect blend of privacy, convenience, and long-term value. Both properties are beautifully landscaped and have pavered driveways offering plenty of parking for the residents and their guests. Each thoughtfully designed unit lives like a single-family home. Both sides feature private, fully fenced yards complete with patios ideal for outdoor dining or relaxing, as well as access to a shared saltwater pool. Additional amenities include two storage sheds, one for pool equipment and another for general storage. Inside, each property welcomes you directly into the living room, which flows naturally into the updated kitchen. In addition to the living room, each unit offers a flexible downstairs room that can be used as a sitting area, separate dining space, home office, or additional living area, allowing the home to adapt to a variety of lifestyles. Each unit offers a functional and inviting layout with one bedroom and full bathroom downstairs, and two bedrooms with a full bathroom upstairs. The downstairs features tile flooring throughout, an updated kitchen with granite countertops, stylish backsplash, stainless steel appliances, under-cabinet lighting, and a breakfast bar with overhang seating. Indoor laundry and ample cabinetry are conveniently located near the kitchen, and generous closet space can be found throughout both homes. Upstairs, you’ll find two comfortable bedrooms with newer carpet and a shared bathroom, creating a private and peaceful retreat. Each unit features a front porch with a portico to the one car garage. Lovingly maintained over the years, this duplex offers exceptional privacy, great walkability, and versatile use. It's ideal as a long-term rental investment, or for an owner-occupant looking to live in one unit while enjoying income from the other. It's truly a special opportunity in the heart of Winter Park.

6 Beds ⋅ 4 Baths ⋅ Huntington Court SubDv. ⋅ 32789 Zip Code

Welcome to 831 & 833 Huntington Court, a rarely available duplex tucked away on a quiet cul-de-sac in one of Winter Park’s most walkable and desirable locations. Just minutes from Park Avenue, local lakes, dining, shopping, and entertainment, this property offers the perfect blend of privacy, convenience, and long-term value. Both properties are beautifully landscaped and have pavered driveways offering plenty of parking for the residents and their guests. Each thoughtfully designed unit lives like a single-family home. Both sides feature private, fully fenced yards complete with patios ideal for outdoor dining or relaxing, as well as access to a shared saltwater pool. Additional amenities include two storage sheds, one for pool equipment and another for general storage. Inside, each property welcomes you directly into the living room, which flows naturally into the updated kitchen. In addition to the living room, each unit offers a flexible downstairs room that can be used as a sitting area, separate dining space, home office, or additional living area, allowing the home to adapt to a variety of lifestyles. Each unit offers a functional and inviting layout with one bedroom and full bathroom downstairs, and two bedrooms with a full bathroom upstairs. The downstairs features tile flooring throughout, an updated kitchen with granite countertops, stylish backsplash, stainless steel appliances, under-cabinet lighting, and a breakfast bar with overhang seating. Indoor laundry and ample cabinetry are conveniently located near the kitchen, and generous closet space can be found throughout both homes. Upstairs, you’ll find two comfortable bedrooms with newer carpet and a shared bathroom, creating a private and peaceful retreat. Each unit features a front porch with a portico to the one car garage. Lovingly maintained over the years, this duplex offers exceptional privacy, great walkability, and versatile use. It's ideal as a long-term rental investment, or for an owner-occupant looking to live in one unit while enjoying income from the other. It's truly a special opportunity in the heart of Winter Park.

831/833 Huntington Court, Winter Park

$669,000

Well-maintained and beautifully upgraded, this exceptional home is located in the highly desirable Dubsdread Heights neighborhood of Winter Park. Offering 4 bedrooms and 2.5 baths (with the 4th bedroom downstairs currently used as an office/den), every detail of this residence has been thoughtfully enhanced. Recent major upgrades include a new roof (2024), new HVAC systems (2024/2025), and upgraded flooring throughout. The gourmet open kitchen features solid cabinetry, a tile backsplash, NEW French Door Refrigerator and an oversized island that flows seamlessly into the inviting family room, highlighted by a stunning gas fireplace. Architectural details abound, including framed windows, 8-foot solid core doors, custom crown molding, and a triple set of French doors that enhance the home’s character and charm. The oversized primary suite is a true retreat, featuring a spa-like bath with an extra-large double vanity, walk-in closet, jetted tub, spacious shower with steamer, and a private covered Juliet balcony. A large downstairs office/study/den with French doors offers flexibility for work or additional living space. The pavered driveway leads to a detached, oversized 2-car garage with air conditioning and an insulated garage door. Outdoors, the backyard is a private oasis with brand-new vinyl fencing and a generous covered patio—perfect for relaxing or entertaining. Ideally located near Dubsdread Golf Course and just minutes from I-4, Winter Park, and College Park shopping, dining, and professional services, this home offers luxury, comfort, and convenience in one exceptional package. Fireplace has never been operated nor is a propane tank on site.

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

Well-maintained and beautifully upgraded, this exceptional home is located in the highly desirable Dubsdread Heights neighborhood of Winter Park. Offering 4 bedrooms and 2.5 baths (with the 4th bedroom downstairs currently used as an office/den), every detail of this residence has been thoughtfully enhanced. Recent major upgrades include a new roof (2024), new HVAC systems (2024/2025), and upgraded flooring throughout. The gourmet open kitchen features solid cabinetry, a tile backsplash, NEW French Door Refrigerator and an oversized island that flows seamlessly into the inviting family room, highlighted by a stunning gas fireplace. Architectural details abound, including framed windows, 8-foot solid core doors, custom crown molding, and a triple set of French doors that enhance the home’s character and charm. The oversized primary suite is a true retreat, featuring a spa-like bath with an extra-large double vanity, walk-in closet, jetted tub, spacious shower with steamer, and a private covered Juliet balcony. A large downstairs office/study/den with French doors offers flexibility for work or additional living space. The pavered driveway leads to a detached, oversized 2-car garage with air conditioning and an insulated garage door. Outdoors, the backyard is a private oasis with brand-new vinyl fencing and a generous covered patio—perfect for relaxing or entertaining. Ideally located near Dubsdread Golf Course and just minutes from I-4, Winter Park, and College Park shopping, dining, and professional services, this home offers luxury, comfort, and convenience in one exceptional package. Fireplace has never been operated nor is a propane tank on site.

681 Overspin Drive, Winter Park

$13,000,000

Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

6 Beds ⋅ 9 Baths ⋅ --- SubDv. ⋅ 32789 Zip Code

Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

2203 Via Tuscany, Winter Park

$640,000

This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a dedicated study. A large screened-in front porch adds to the home’s classic charm and provides the perfect space to relax and unwind. Tucked away in the rear of the property there is both flexibility and income potential: a stylish studio office and a spacious one-bedroom unit complete with its own living area and separate loft. This property is ideal for investors, multi-generational living, or owner-occupants seeking strong rental returns. Located closely to beautiful Lake Killarney and conveniently situated near highways, restaurants, and shopping, this property combines charm, location, and income potential in one exceptional offering.

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

This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a dedicated study. A large screened-in front porch adds to the home’s classic charm and provides the perfect space to relax and unwind. Tucked away in the rear of the property there is both flexibility and income potential: a stylish studio office and a spacious one-bedroom unit complete with its own living area and separate loft. This property is ideal for investors, multi-generational living, or owner-occupants seeking strong rental returns. Located closely to beautiful Lake Killarney and conveniently situated near highways, restaurants, and shopping, this property combines charm, location, and income potential in one exceptional offering.

352 Cambridge Boulevard, Winter Park

$1,650,000

PRICE IMPROVEMENT! This exceptional custom residence, built by Meridian Homes and designed by Zero Latitude, offers a rare combination of thoughtful architecture, high-end finishes, and modern functionality. Interior design by Lauren Ayers Interiors sets a refined tone throughout, complemented by curated details such as Rifle Paper wallpaper, accent walls, and wide-plank hardwood flooring by Britannia Flooring. The home features five bedrooms, five full baths, and two half baths, including a first-floor primary suite with a spacious walk-in closet and a spa-inspired bathroom showcasing upgraded imported tile and a large walk-in shower. The main level also includes a powder room, laundry room, a private home office with doors, and a guest suite—ideal for multigenerational living or overnight guests. At the center of the home is a chef’s kitchen with an abundance of custom white cabinetry by Monarch Kitchens and Bath, paired with a striking oversized blue island with seating for four plus additional space for a dining table. Premium appliances include a Wolf oven, GE Café double oven/microwave, refrigerator, and beverage fridge, along with a Thermador dishwasher. The kitchen flows seamlessly into the family room, which features an electric fireplace and custom built-ins, creating an inviting space for everyday living and entertaining. Upstairs, three additional bedrooms each offer private baths featuring custom cabinetry, fixtures, and tile, along with generous closet space, plus a versatile bonus area-ideal as a second family room or media space. Outdoor living is equally impressive. A covered rear lanai overlooks a heated saltwater pool and hot tub, complemented by a summer kitchen with a high-end built-in, vented gas grill, sink, and under-counter refrigerator. An outdoor shower and pool-half-bath complete this resort-style setting. Additional highlights include: floor-to-ceiling imported tile in every bathroom, Custom wrought iron stair railings, Custom wood plantation shutters on all windows, an Automatic driveway gate, a Built-in surround sound system, and a “Control4” whole-house smart system with integrated security, as well as a 2-car garage. This meticulously designed home delivers uncompromising quality, comfort, and convenience in a warm, quiet setting, making it ideal for both everyday living and entertaining. Ideally located in the heart of Winter Park, close to the area's top-rated schools, parks, the YMCA, the boutiques and restaurants on Park Ave, and also minutes from Rollins College and downtown Orlando. Do not miss this opportunity to live in this sophisticated, luxurious home. Schedule your private appointment today.

5 Beds ⋅ 7 Baths ⋅ Orange Grove Sub SubDv. ⋅ 32789 Zip Code

PRICE IMPROVEMENT! This exceptional custom residence, built by Meridian Homes and designed by Zero Latitude, offers a rare combination of thoughtful architecture, high-end finishes, and modern functionality. Interior design by Lauren Ayers Interiors sets a refined tone throughout, complemented by curated details such as Rifle Paper wallpaper, accent walls, and wide-plank hardwood flooring by Britannia Flooring. The home features five bedrooms, five full baths, and two half baths, including a first-floor primary suite with a spacious walk-in closet and a spa-inspired bathroom showcasing upgraded imported tile and a large walk-in shower. The main level also includes a powder room, laundry room, a private home office with doors, and a guest suite—ideal for multigenerational living or overnight guests. At the center of the home is a chef’s kitchen with an abundance of custom white cabinetry by Monarch Kitchens and Bath, paired with a striking oversized blue island with seating for four plus additional space for a dining table. Premium appliances include a Wolf oven, GE Café double oven/microwave, refrigerator, and beverage fridge, along with a Thermador dishwasher. The kitchen flows seamlessly into the family room, which features an electric fireplace and custom built-ins, creating an inviting space for everyday living and entertaining. Upstairs, three additional bedrooms each offer private baths featuring custom cabinetry, fixtures, and tile, along with generous closet space, plus a versatile bonus area-ideal as a second family room or media space. Outdoor living is equally impressive. A covered rear lanai overlooks a heated saltwater pool and hot tub, complemented by a summer kitchen with a high-end built-in, vented gas grill, sink, and under-counter refrigerator. An outdoor shower and pool-half-bath complete this resort-style setting. Additional highlights include: floor-to-ceiling imported tile in every bathroom, Custom wrought iron stair railings, Custom wood plantation shutters on all windows, an Automatic driveway gate, a Built-in surround sound system, and a “Control4” whole-house smart system with integrated security, as well as a 2-car garage. This meticulously designed home delivers uncompromising quality, comfort, and convenience in a warm, quiet setting, making it ideal for both everyday living and entertaining. Ideally located in the heart of Winter Park, close to the area's top-rated schools, parks, the YMCA, the boutiques and restaurants on Park Ave, and also minutes from Rollins College and downtown Orlando. Do not miss this opportunity to live in this sophisticated, luxurious home. Schedule your private appointment today.

1861 Taylor Avenue, Winter Park

$2,010,000

Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than ¾ of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed by beautiful wood floors and versatile spaces to the left that can serve as a formal living room, dining room, office, or playroom. Continue into the impressive family room, featuring vaulted ceilings, skylights, and a wood-burning fireplace, creating a light-filled and inviting atmosphere. To the right wing of the home are four bedrooms and two bathrooms, including the primary suite. One secondary bedroom connects to the primary, making it ideal for a nursery, home office, or sitting room. The spacious primary retreat offers large walk-in closets, dual vanities, a soaking tub, separate shower, and French doors that open directly to the pool and backyard oasis. The kitchen, located just off the family room, features travertine flooring and flows seamlessly into a huge pantry, oversized laundry room, drop zone, and a second primary suite with ensuite bath—perfect for guests or multigenerational living. Outside, the home has been meticulously maintained, showcasing a new roof (2023), exterior paint (2018), pavered circular driveway, well, and lush tropical landscaping that enhances the home’s curb appeal. Additional features include a three-car side-entry garage, pool heater, designer lighting, engineered hardwood floors, and crown molding throughout. Located within the highly sought-after Winter Park School District (Audubon K-8 and Winter Park High School) and just minutes from Park Avenue, Central Park, Rollins College, SunRail, the Winter Park Farmer’s Market, and world-class shopping and dining. Schedule your private showing today—this exceptional home won’t last long!

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

Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than ¾ of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed by beautiful wood floors and versatile spaces to the left that can serve as a formal living room, dining room, office, or playroom. Continue into the impressive family room, featuring vaulted ceilings, skylights, and a wood-burning fireplace, creating a light-filled and inviting atmosphere. To the right wing of the home are four bedrooms and two bathrooms, including the primary suite. One secondary bedroom connects to the primary, making it ideal for a nursery, home office, or sitting room. The spacious primary retreat offers large walk-in closets, dual vanities, a soaking tub, separate shower, and French doors that open directly to the pool and backyard oasis. The kitchen, located just off the family room, features travertine flooring and flows seamlessly into a huge pantry, oversized laundry room, drop zone, and a second primary suite with ensuite bath—perfect for guests or multigenerational living. Outside, the home has been meticulously maintained, showcasing a new roof (2023), exterior paint (2018), pavered circular driveway, well, and lush tropical landscaping that enhances the home’s curb appeal. Additional features include a three-car side-entry garage, pool heater, designer lighting, engineered hardwood floors, and crown molding throughout. Located within the highly sought-after Winter Park School District (Audubon K-8 and Winter Park High School) and just minutes from Park Avenue, Central Park, Rollins College, SunRail, the Winter Park Farmer’s Market, and world-class shopping and dining. Schedule your private showing today—this exceptional home won’t last long!

1711 Barcelona Way, Winter Park

$3,800,000

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

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

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

637 N Park Avenue, Winter Park

$2,100,000

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

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

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

2503 Versailles Avenue, Winter Park

$895,000

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

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

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

1802 Arbor Park Drive, Winter Park

$2,000,000

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

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

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

1624 Barcelona Way, Winter Park

$1,690,000

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

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

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

1630 Chestnut Avenue, Winter Park

$1,850,000

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

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

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

419 W Morse Boulevard, Winter Park