Search Results: Single Family Homes in Winter Park for Sale

1120 PRESERVE POINT DRIVE
WINTER PARK FL 32789

Residential / Single Family Residence

7 Bed  ·  9 Bath  ·  2 Half Baths  ·  11,255 SqFt  ·  $1,057/SqFt

Days on Market: 1

County: Orange
Complex/CommunityName: WINDSONG
Legal Subdivision Name: WINDSONG-PRESERVE POINT
Year built: 2009
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 1.63

Nestled within the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean Estate is a true private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm, and privacy that is rarely found in Winter Park. The home features 7 spacious bedrooms and 9 full and 2 half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating, and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for ... Read more....»

2661 VIA TUSCANY
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  1 Half Bath  ·  4,564 SqFt  ·  $2,410/SqFt

Days on Market: 45

County: Orange
Legal Subdivision Name: WINTER PARK
Year built: 2024
Garage: Yes 2 vehicles
Private Pool: Yes

Introducing a stunning modern European-style home, blending contemporary design with timeless elegance. This property offers luxurious finishes, open-concept living spaces, Located in the heart of Historic Winter Park, Florida, this exceptional property offers top-of-the-line amenities, perfect for those who appreciate Luxury living. Features:• 4,564 sq ft of living space • 4 Bedrooms, 4 Bathrooms, 1 Half Bath • Custom Built CostaRica One Tree Solid Piece – A 16-foot tall, one-of-a-kind steel masterpiece featured prominently in the design • Italian Porcelain Floors throughout • All-Glass Windows with impact-resistant, top-of-the-line glass by Techno Glass• Chef’s Kitchen featuring: • Custom 1-inch thick Italian ... Read more....»

1400 ALABAMA DRIVE
WINTER PARK FL 32789

Residential / Single Family Residence

5 Bed  ·  5 Bath  ·  4 Half Baths  ·  7,916 SqFt  ·  $878/SqFt

Days on Market: 171

County: Orange
Legal Subdivision Name: J KRONENBERGER SUB
Year built: 1996
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes

Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland - the largest of the Winter Park Chain of Lakes. A timeless Neoclassical Italian home that exudes luxury and sophistication. Built by Charles Clayton. Designed by Marc Michaels. The main house boasts over 7,100 sf with 4 bedrooms, 4 full bathrooms, and 3 half bathrooms. The detached Guest House/In-Law is approx. 500 sf, with 1 bedroom, 1 bathroom, two closets, and a wet bar. The detached Catering Room with half (pool) bath is approx. 350 sf with an additional refrigerator, wall-to-wall built-in ... Read more....»

541 VIRGINIA DRIVE
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  1 Half Bath  ·  4,725 SqFt  ·  $1,323/SqFt

Days on Market: 3

County: Orange
Legal Subdivision Name: TIMBERLANE SHORES
Year built: 2008
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes

Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers the perfect blend of luxury and tranquility. With 4 bedrooms, 3.5 baths, and a generous 4,725 sq ft of living space, this home is an Aurora and Parade of Homes Grand Winner and boasts 130 ft of lakefront frontage on the serene Lake Virginia. As you approach this stunning property, you'll find it situated on a quiet cul-de-sac, ensuring peace and privacy. Step into the backyard oasis, where a lanai with a ... Read more....»

210 CHELTON CIRCLE
WINTER PARK FL 32789

Residential / Single Family Residence

5 Bed  ·  5 Bath  ·  1 Half Bath  ·  5,264 SqFt  ·  $1,082/SqFt

Days on Market: 105

County: Orange
Legal Subdivision Name: FOREST HILLS
Year built: 2024
Garage: Yes 3 vehicles
Private Pool: Yes

This gorgeous, new-construction FG Schaub custom home is the epitome of stunning contemporary design by architect, Michael Weinrich. As you enter this sprawling residence, with views of both Lake Sue and Lake Chelton you'll be greeted by exquisite tile work with brass inlays, wood floors, drop down ceiling, crown molding, wainscoting and natural light that pulls the outside living in. The first floor was meticulously designed with your Owner’s suite, an additional en suite bedroom with walk in closet, large laundry room with full size washer and dryer and an abundance of cabinet and counter space, an eye catching drop ... Read more....»

2228 AZALEA PLACE
WINTER PARK FL 32789

Residential / Single Family Residence

5 Bed  ·  5 Bath  ·  1 Half Bath  ·  5,072 SqFt  ·  $1,065/SqFt

Days on Market: 38

County: Orange
Legal Subdivision Name: MAITLAND SHORES FIRST ADD
Year built: 2008
Garage: Yes 3 vehicles
Private Pool: Yes

Gorgeous Winter Park home beautifully curated with designer details and recently featured in June’s “Orange Appeal” and was the 2022 Mystery Home Tour selected by Council of 101 for the Orlando Museum of Art. This elegant transitional French Provincial residence is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This designer home has been significantly enhanced inside and out by the current owner and is in “brand new condition.” The home features 5,100 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 ... Read more....»

2161 SHARON ROAD
WINTER PARK FL 32789

Residential / Single Family Residence

5 Bed  ·  6 Bath  ·  1 Half Bath  ·  6,338 SqFt  ·  $787/SqFt

Days on Market: 1

County: Orange
Legal Subdivision Name: TUSCANIA
Year built: 2023
Garage: Yes 4 vehicles
Private Pool: Yes

Nestled in the esteemed The Vias area and near the WPRC, resides a home signifying the essence of sophistication and luxury. Situated on a secluded street, it occupies an approximately 0.58-acre lot with an expansive backyard landscape that is truly captivating. This exquisite home encompasses five bedrooms and six-and-a-half bathrooms with a four-car garage. An indomitable presence is seen in its immense and grand pivoting iron door which directs you to a double-height foyer and great room separated by a glass-railing catwalk. The property boasts exclusive features like a formal dining room endowed with a glass-encased wine display as well ... Read more....»

571 LAKE FRONT BOULEVARD
WINTER PARK FL 32789

Residential / Single Family Residence

7 Bed  ·  5 Bath  ·  5,500 SqFt  ·  $764/SqFt

Days on Market: 157

County: Orange
Legal Subdivision Name: LORDS SUB
Year built: 1967
Garage: Yes 3 vehicles
Waterfront: Yes

Pre-Construction. To be built. Welcome to Winter Park lakefront living at its finest. In the heart of Winter Park, this new construction residence promises to be a masterpiece of luxury and modern living. Spanning over 5,500 square feet, this magnificent lakefront residence offers an unparalleled lifestyle with breathtaking panoramic sunset views. Tolaris Homes, an esteemed custom builder in Central Florida with over 45 years of expertise, will guide you from conceptualization to realization of your dream home. Designed to capture the essence of serene lakeside living, the home is ideally positioned to provide scenic vistas of the water and the ... Read more....»

1751 GLENCOE ROAD
WINTER PARK FL 32789

Residential / Single Family Residence

5 Bed  ·  5 Bath  ·  1 Half Bath  ·  4,520 SqFt  ·  $907/SqFt

Days on Market: 17

County: Orange
Legal Subdivision Name: FOREST HILLS
Year built: 2025
Garage: Yes 2 vehicles
Private Pool: Yes

Under Construction. Exquisite new construction residence nestled in the heart of Winter Park, walking distance to Park Ave. This luxurious home boasts over 4,000 square feet of meticulously designed living space, offering an unparalleled blend of elegance and modern sophistication. Upon entering, you are greeted by soaring two-story ceilings that create a grand and inviting atmosphere. The home features 5 spacious bedrooms and 5 1/2 beautifully appointed bathrooms, each showcasing high-end finishes that exemplify luxury living. The gourmet kitchen is a chef's dream, equipped with top-of-the-line appliances and elegant cabinetry, seamlessly flowing into the open-concept living and dining areas, perfect ... Read more....»

1341 COLLEGE POINT
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  1 Half Bath  ·  4,279 SqFt  ·  $934/SqFt

Days on Market: 59

County: Orange
Legal Subdivision Name: VIRGINIA HEIGHTS
Year built: 2005
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes

This custom lakefront home on Winter Park's Chain of Lakes offers stunning views of Lake Virginia and is in the historic Virginia Heights neighborhood, just a short walk from Rollins College and downtown Park Avenue. Facing north, it provides picturesque sunrise views over the lake, highlighting Rollins College and its chapel. Lovingly maintained and improved over time, the 4279 square feet does not include an additional 310 square foot finished bonus room with separate HVAC, perfect for game room or office. Upon entering, you are greeted by lake views and a foyer that leads to separate formal living and dining ... Read more....»

850 GEORGIA AVENUE
WINTER PARK FL 32789

Residential / Single Family Residence

3 Bed  ·  5 Bath  ·  1 Half Bath  ·  4,627 SqFt  ·  $854/SqFt

Days on Market: 100
Cumulative Days on Market: 112

County: Orange
Legal Subdivision Name: WINTER PARK
Year built: 1987
Garage: Yes 3 vehicles
Private Pool: Yes

Welcome to an exquisite 3-bedroom, 5.5-bath plus office pool home in the heart of Winter Park. Set back 150 feet from the picturesque brick street, this stunning residence offers unparalleled privacy and elegance, exuding sophistication from the moment you arrive. Stately double-front doors open into a grand foyer with direct views of the beautiful pool and meticulously landscaped backyard. Step inside to discover a magnificent custom concrete and iron staircase that sets the tone for the remarkable craftsmanship throughout the home. The spacious open kitchen overlooks the family room and breakfast area, providing seamless access to the covered lanai. Outfitted ... Read more....»

1391 RICHMOND ROAD
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  5 Bath  ·  1 Half Bath  ·  4,635 SqFt  ·  $840/SqFt

Days on Market: 66

County: Orange
Legal Subdivision Name: VIRGINIA HEIGHTS
Year built: 2001
Garage: Yes 2 vehicles
Waterfront: Yes

Welcome to 1391 Richmond Road—a true work of art and a surreal living experience now on the market. The most discerning buyer will fall in love with the optimal location, an unusually private lot right in the heart of Winter Park, a short stroll to Park Avenue along the stunning shores of Lake Virginia. This handcrafted Georgian style home, designed to emulate New York City townhouse living was masterfully crafted on a magical lot abundant with pristine natural vegetation. Enjoy the Florida lifestyle with frontage on Howell Creek…kayak or paddleboard amongst incredible wildlife to the Winter Park Chain of Lakes. ... Read more....»

2550 VENETIAN WAY
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  2 Half Baths  ·  4,875 SqFt  ·  $677/SqFt

Days on Market: 57
Cumulative Days on Market: 58

County: Orange
Legal Subdivision Name: MAITLAND SHORES FIRST ADD
Year built: 2008
Garage: Yes 2 vehicles
Waterfront: Yes

"The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic and renowned city of Winter Park, accessing the Maitland/Winter Park CHAIN OF LAKES! This custom modern/contemporary 2008 build, derives it's over 4800 sq/ft of essence and uniqueness by fusing vibrant colors and eloquence with high-end home features and artistic details. Upon entry, visitors are greeted by a gorgeous rotunda accented with stained glass panels and vaulted, recessed ceilings. With 4 bedrooms, 3 full baths, and 2 half baths, this split ... Read more....»

1730 WINCHESTER DRIVE
WINTER PARK FL 32789

Residential / Single Family Residence

5 Bed  ·  5 Bath  ·  1 Half Bath  ·  4,080 SqFt  ·  $808/SqFt

Days on Market: 105

County: Orange
Legal Subdivision Name: TIMBERLANE SHORES
Year built: 2024
Garage: Yes 2 vehicles
Private Pool: Yes

Under Construction. Welcome to this exquisite 5-bedroom, 5.5-bathroom home built by Lundev, perfectly situated in the highly sought-after Timberlane Shores neighborhood of Winter Park. Spanning 4,080 square feet, this property offers the ultimate blend of luxury and comfort. Thoughtfully designed for both entertaining and everyday living, this home features high-end finishes and top-quality craftsmanship throughout. Upon entering, you're greeted by a charming front porch with a cozy fireplace, setting the tone for the warmth and elegance that continues inside. This inviting outdoor space is perfect for relaxing with a morning coffee or enjoying cool evenings with friends and family. Step inside ... Read more....»

1900 W FAWSETT ROAD
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  1 Half Bath  ·  4,600 SqFt  ·  $707/SqFt

Days on Market: 76

County: Orange
Legal Subdivision Name: FOREST HILLS
Year built: 1969
Garage: Yes 2 vehicles
Waterfront: Yes
Lot Size (in acres): 1.10

Discover this exquisite lakefront property located in the heart of Winter Park! Nestled on over an acre with more than 125 feet of water frontage, this home offers breathtaking views and absolutely stunning sunsets. As you step through the front door, you’re greeted by captivating lake views that flow from front to back. The spacious foyer leads to a charming living room, complete with a brick wood-burning fireplace. This area seamlessly transitions into the Florida room, an entertainer’s paradise featuring a wet bar, seating area and pool table, with easy access to a full bathroom that is equipped with a ... Read more....»

884 AUDUBON LANE
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  2,995 SqFt  ·  $1,000/SqFt

Days on Market: 7

County: Orange
Legal Subdivision Name: POINT MIZELL REP
Year built: 1947
Garage: Yes 2 vehicles
Waterfront: Yes

Discover an extraordinary opportunity to own a one-story lakefront retreat on the picturesque Lake Mizell, part of the coveted Winter Park Chain of Lakes. This stunning 4-bedroom, 4-bath home, completely remodeled in 2020, offers nearly 3,000 square feet of thoughtfully designed living space on a tranquil, half-acre lot. The tri-split floor plan ensures privacy and functionality, with walls of glass sliders and expansive picture windows that flood the home with natural light and showcase breathtaking lake views. Gleaming hardwood floors flow throughout, complementing the modern updates and timeless charm of this exceptional residence. The spacious primary suite is a serene ... Read more....»

1010 N PENNSYLVANIA AVENUE
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  1 Half Bath  ·  4,074 SqFt  ·  $650/SqFt

Days on Market: 62

County: Orange
Legal Subdivision Name: TANTUMS ADDITIONS TO WINTER PARK
Year built: 2017
Garage: Yes 2 vehicles
Private Pool: Yes

New price is $150K below a November 2024 appraisal! Home has been pre-inspected; seller is willing to share the 4PT Report as well as the appraisal. Located in the heart of Winter Park's downtown corridor, 1010 N Pennsylvania Ave offers a luxurious Mediterranean-inspired design with so many modern upgrades, all just steps from Park Avenue’s shops, Winter Park Village, and Whole Foods Market. This stunning home, set on a prime lot adjacent to the Winter Park Golf Course, provides the perfect balance of privacy and convenience. Upon entering through custom double front doors, you’re greeted by an impressive foyer ... Read more....»

1000 VIA TUSCANY OAKS WAY
WINTER PARK FL 32789

Residential / Single Family Residence

5 Bed  ·  3 Bath  ·  2 Half Baths  ·  4,002 SqFt  ·  $649/SqFt

County: Orange
Legal Subdivision Name: VIA TUSCANY OAKS 47/75
Year built: 2003
Garage: Yes 3 vehicles
Private Pool: Yes

Nestled in the exclusive, sought-after cul-de-sac of Via Tuscany Oaks, this estate offers a rare opportunity to own a premier piece of Winter Park real estate. Situated among only six other distinguished homes and surrounded by a meticulously landscaped central park, this property perfectly blends privacy, elegance, and an unmatched location. The chef’s kitchen is a masterpiece of both design and functionality, featuring custom copper sinks, exquisite marble countertops, and custom cabinetry—an ideal space for both intimate meals and large gatherings. Step outside to find an entertainer’s dream: a custom-built summer kitchen complete with a grill, wet bar, refrigerator, and kegerator. ... Read more....»

1506 CHESTNUT AVE.
WINTER PARK FL 32789

Residential / Single Family Residence

5 Bed  ·  4 Bath  ·  2 Half Baths  ·  3,545 SqFt  ·  $704/SqFt

New Listing!!! 

County: Orange
Legal Subdivision Name: LAKE KNOWLES TERRACE
Year built: 2021
Garage: Yes 2 vehicles
Private Pool: Yes

Nestled in one of Winter Parks most coveted neighborhoods, this exquisite Bates Custom Homes house is a 3-year-old modern farmhouse that offers the perfect blend of style, luxury, and comfort. With 5 spacious bedrooms, a creative hub, and 4.5 beautifully appointed bathrooms, this home is designed for both relaxed living and elegant entertaining. The Primary suite is located downstairs and boast large windows and a spa- like bathroom with dual vanities, a soaking tub, a walk in shower, and a custom walk in closet. The additional four bedrooms are located upstairs. The heart of the home is the ... Read more....»

2412 CHANTILLY AVENUE
WINTER PARK FL 32789

Residential / Single Family Residence

5 Bed  ·  6 Bath  ·  1 Half Bath  ·  4,500 SqFt  ·  $554/SqFt

Days on Market: 216
Cumulative Days on Market: 268

County: Orange
Legal Subdivision Name: WINTER PARK VILLAGE
Year built: 2024
Garage: Yes 3 vehicles
Private Pool: Yes

Welcome to the sophistication and contemporary masterpiece developed by DaVinci Development. This exceptional residence features five spacious bedrooms, six and a half bathrooms, and 4,500 square feet of meticulously designed living space. Nestled within the exclusive enclave of Winter Park, this new construction opportunity redefines opulent living. The architectural marvel boasts a unique contemporary design, seamlessly integrating form and function. From the moment you arrive, the striking facade captivates with sleek lines and 10 foot ceilings on both levels of the home. Inside, natural light floods the open-concept living spaces, creating an inviting atmosphere that is both luxurious and welcoming. Entertain with ... Read more....»

2522 LAFAYETTE AVENUE
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  1 Half Bath  ·  3,399 SqFt  ·  $706/SqFt

Days on Market: 78

County: Orange
Legal Subdivision Name: WINTER PARK VILLAGE
Year built: 2022
Garage: Yes 2 vehicles
Private Pool: Yes

This exquisite, custom-designed residence blends impeccable architectural details with unparalleled craftsmanship, in the highly sought Winter Park Village. With Pella windows and natural stone accents throughout, this home showcases a Poggenpohl gourmet kitchen featuring Wolf and Sub-Zero appliances, cascading countertops, and natural hardwood floors. A unique double primary suite layout offers two luxurious primary bedrooms, each with its own expansive executive powder room. The upper suite opens onto a private outdoor terrace, perfect for enjoying views of the lush outdoor oasis, which includes a heated luxury pool and spa, completed by an outdoor summer kitchen featuring Miele appliances. This home ... Read more....»

1522 LAKE KNOWLES CIRCLE
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  1 Half Bath  ·  4,144 SqFt  ·  $573/SqFt

New Listing!!!  Days on Market: 1

County: Orange
Legal Subdivision Name: LAKE KNOWLES TERRACE
Year built: 2000
Garage: Yes 2 vehicles
Private Pool: Yes

Welcome to this charming one owner home nestled on the shores of Lake Knowles in the heart of Winter Park, located in one of the most sought-after neighborhoods. This home truly has it all and is just steps from Winter Park Racquet Club and minutes to Winter Park’s Interlachen Country Club as well as coveted Park Avenue, that features many restaurants and shops. This 4-bedroom, 3.5 bath pool home has amazing curb appeal with incredible landscaping as well as unique features throughout that will make you never want to leave. From the minute you park, the car to the first ... Read more....»

1032 EARLY AVENUE
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  2,894 SqFt  ·  $795/SqFt

Days on Market: 18

County: Orange
Legal Subdivision Name: N/A
Year built: 1999
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 5.15

Discover your own slice of paradise on this extraordinary property spanning nearly five acres, perfectly nestled between two serene lakes in Winter Park. Offering unmatched privacy and tranquility, this retreat is ideal for those who value seclusion, natural beauty, and convenience—all within city limits, yet feeling a world away. With motorized boats allowed on both lakes, you can spend afternoons cruising, water skiing, tubing, or simply enjoying the water. A newly constructed custom dock, located just behind the home, ensures your boating experience is effortless and enjoyable. From the moment you arrive, the journey begins with a picturesque 1,000-foot gravel driveway ... Read more....»

2234 VIA LUNA
WINTER PARK FL 32789

Residential / Single Family Residence

6 Bed  ·  3 Bath  ·  1 Half Bath  ·  3,554 SqFt  ·  $616/SqFt

Days on Market: 203

County: Orange
Legal Subdivision Name: TUSCANY TERRACE
Year built: 1998
Garage: Yes 2 vehicles
Private Pool: Yes

One or more photo(s) has been virtually staged. Newly Renovated Partially Furnished Home in the Beautiful Via’s of Winter Park! Designed and built by Groninger Custom Homes. Privately located on a large wrap around corner lot. It is meticulously maintained with eye-catching curb appeal with mature magnolia trees and beautiful landscaping with newly installed lighting to illuminate at night. This stunning 6 bedroom and 3.5 bath home boasts over 3,554 SF of comfortable living space and offers high ceilings, arched entries, and luxury vinyl flooring throughout the main floor. Upon entering the expansive foyer, to the right is a den/office ... Read more....»

2260 MULBRY DRIVE
WINTER PARK FL 32789

Residential / Single Family Residence

5 Bed  ·  4 Bath  ·  3,246 SqFt  ·  $616/SqFt

Days on Market: 1

County: Orange
Legal Subdivision Name: LAKE FOREST PARK
Year built: 2025
Garage: Yes 2 vehicles

Pre-Construction. To be built. Your Dream Home Is Ready To Be Built! Pre-Construction Opportunity! Build-to-Suit! Build your custom dream home with renowned Konkol Homes in one of Central Florida’s most desirable areas! This nearly 1/4-acre lot is perfectly situated near Baldwin Park, East End Market, Audubon Park K-8, Rollins College, and Advent Health. The stunning Transitional Modern design features 3,246 sq. ft. of living space, offering 5 bedrooms, 4 baths, and a loft. The first-floor primary and guest suites provide convenience and privacy, while the Chef’s Kitchen flows seamlessly into the oversized Gathering Room in this open-concept design. The second ... Read more....»

1970 LAUREL ROAD
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  1 Half Bath  ·  3,440 SqFt  ·  $581/SqFt

Days on Market: 17

County: Orange
Legal Subdivision Name: CHARMONT
Year built: 2015
Garage: Yes 2 vehicles
Private Pool: Yes

JUST LISTED – STUNNING, CONTEMPORARY ESTATE IN THE HEART OF WINTER PARK! Custom-built by award-winning builder LunDev, this masterful residence offers 4 bedrooms, 3.5 baths, 3,440 SF, and defining features which blend indoor and outdoor living seamlessly together. Large, open spaces are complimented by beautiful engineered wood floors, stone accent wall(s), an abundance of natural light, and the perfect blend of modern and sophisticated finishes. The chef’s kitchen is trimmed with gorgeous maple cabinetry, Quartz counters, and a large island. High-end Bosch appliances, including a 35” French door refrigerator, gas cooktop and built-in oven(s), create the dream space for the ... Read more....»

1451 LYNDALE BOULEVARD
WINTER PARK FL 32789

Residential / Single Family Residence

6 Bed  ·  4 Bath  ·  3,853 SqFt  ·  $519/SqFt

Days on Market: 83

County: Orange
Legal Subdivision Name: DIXIE TERRACE
Year built: 2012
Garage: Yes 2 vehicles
Private Pool: Yes

**Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the pinnacle of sophisticated living. Boasting 6 total bedrooms, 4 bathrooms, including a detached 2-bedroom guest house, this property seamlessly blends modern amenities with timeless charm. As you step through the grand entrance, you are immediately greeted by a stunning foyer adorned ... Read more....»

1340 CHESTNUT AVENUE
WINTER PARK FL 32789

Residential / Single Family Residence

6 Bed  ·  5 Bath  ·  1 Half Bath  ·  4,182 SqFt  ·  $473/SqFt

Days on Market: 266

County: Orange
Legal Subdivision Name: LAKE KNOWLES TERRACE
Year built: 1963
Garage: Yes 2 vehicles
Private Pool: Yes

Amazing contemporary home in the heart of Winter Park. This home was fully remodeled in 2023 and in 2018 was added the second floor...New LED lights all around... This residence showcases impeccable craftsmanship and thoughtful design, ensuring a comfortable and stylish living experience. Upon entering, you'll be greeted by an inviting foyer that leads you into the heart of the home. The main level features an open-concept layout, allowing for effortless flow and an abundance of natural light. The spacious living area is perfect for entertaining guests or relaxing with loved ones. The kitchen exudes modern sophistication with its sleek ... Read more....»

1764 ELIZABETHS WALK
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  4 Bath  ·  3,989 SqFt  ·  $476/SqFt

Days on Market: 137
Cumulative Days on Market: 299

County: Orange
Legal Subdivision Name: WINDSONG ELIZABETHS WALK
Year built: 2012
Garage: Yes 2 vehicles
Private Pool: Yes

WINDSONG - Welcome to an Unparalleled Mediterranean Retreat in Exclusive Winter Park! Step into this incomparable custom home, boasting just under 4,000 square feet of luxurious living space, and discover a haven of ultimate privacy. Nestled on a serene cul-de-sac, this meticulously designed residence promises a lifestyle of tranquility and sophistication. As you enter through the grand wrought iron door, you are greeted by an impressive foyer adorned with soaring high ceilings, elegant wood beams, and graceful travertine flooring that extends throughout the home. The newly painted interior adds a fresh, contemporary touch. The first-floor primary bedroom retreat exudes luxury with its gleaming ... Read more....»

1781 GOODRICH AVENUE
WINTER PARK FL 32789

Residential / Single Family Residence

4 Bed  ·  3 Bath  ·  1 Half Bath  ·  2,701 SqFt  ·  $666/SqFt

Days on Market: 60

County: Orange
Legal Subdivision Name: SYLVAN HEIGHTS
Year built: 2024
Garage: Yes 2 vehicles
Private Pool: Yes

Introducing an exquisite Modern English Cottage by Floridian Custom Homes. This pool home offers just over 2,700 s/f with 4 bedrooms and 3 1/2 bathrooms of luxury living. Step inside and discover the European influence in both classic design and luxury selections. Level 4 drywall, soft arches, vaulted ceilings, custom scissor beams, 1-3/4" solid core doors with Emtek hardware—just to name a few. The Andersen window and door package is oversized, filling the space with natural warmth and light. Downstairs offers a strategic office/bedroom option at the front of the house with an adjacent half bath featuring a European wall-mounted toilet. ... Read more....»