Homes In Miami Florida Real Estate
Homes In Miami Florida Real Estate

Winter Park Luxury Homes, Winter Park Luxury Real Estate For Sale


(192) PROPERTIES

$6,990,000

1360 ALABAMA DR - WINTER PARK, FL

1360 ALABAMA DR WINTER PARK, FL 32789
7 Beds 11 Baths Square Ft: 10600
Single Family - MLS#: O5541737
Community: j kronenberger sub Subdivision: j kronenberger sub

NEW PRICE! Stunning Mediterranean Lakefront Estate. Across from the secret gardens of Kraft Azalea Park sits this palatial 1-acre compound with over 10,000 SF of luxurious living space, private tennis court, resort-style pool, and more! Offering formal living areas, gourmet chefs kitchen, open great room, his and her home offices, elevator, 12-person home theater, billiard room, and six guest suites, each with a private en suite, and a separate guest apartment with kitchen, this home leaves nothing…

$6,745,000

1016 GENIUS - WINTER PARK, FL

1016 GENIUS WINTER PARK, FL 32789
6 Beds 9 Baths Square Ft: 10314
Single Family - MLS#: O5496008
Community: windsong ests sec 1 Subdivision: windsong ests sec 1

Incredible 2-acre Modern Mediterranean lakefront estate on hidden peninsula between Lake Mizell & Virginia on the 6-lake chain of lakes Enjoy both picturesque sunrises & sunsets with Rollins College chapel and downtown Orlando illuminated in the evening. This property is on a private street with only 2 other lakefront homes and the only gated lakefront street in all of Winter Park! This award-winning home was designed by Bernie Johnson and Master Custom Builder, Rial Jones with exceptional attention…

$4,950,000

115 PALMER - WINTER PARK, FL

115 PALMER WINTER PARK, FL 32789
4 Beds 5 Baths Square Ft: 9838
Single Family - MLS#: O5564470
Community: macdonald robert dhu pk Subdivision: macdonald robert dhu pk

Stunning lakefront estate in premier location close to Park Ave Situated on 1.5 acres with 280 of lake frontage on Lake Maitland 6 lake chain of lakes. Enjoy lake views from almost every room including the grand master suite, formal living room with wood burning fireplace, elegant entry and kitchen that leads to sunroom. The spacious backyard with pristine landscaping features resort style pool, outdoor shower, multiple lanai areas & private boat house.

$3,500,000

2170 W FAWSETT - WINTER PARK, FL

2170 W FAWSETT WINTER PARK, FL 32789
5 Beds 7 Baths Square Ft: 6589
Single Family - MLS#: O5714430
Community: forest hills Subdivision: forest hills

Featured in the Orlando Museum of Art Antiques Magazine and selected for the Winter Park Garden Tour. This spectacular Tudor-style residence boasts serene Lake Sue views. Offering a kitchen and family room combo, gorgeous views can be enjoyed from the dining, formal living and downstairs master bedroom. The home has a spacious kitchen and 4 bedrooms with en-suites and sitting rooms. Crafted with meticulous attention to detail, there are hand-hewn antique wood floor beams in the master and pecky…

$3,499,000

2742 LAKE HOWELL - WINTER PARK, FL

2742 LAKE HOWELL WINTER PARK, FL 32792
6 Beds 8 Baths Square Ft: 7666
Single Family - MLS#: O5706509
Community: schauders lake howell estate Subdivision: schauders lake howell estate

One of Winter Parks most prestigious lakefront estates that allows horses. Enter into the grand two-story foyer with the grand double staircase, you are immediately greeted by the picturesque lake views. This spacious lakefront home has soaring ceilings, den/office and formal living and dining rooms and a three-car garage. The newly updated chefs kitchen has solid wood white cabinets and quartz countertops and is equipped with top-of-the-line Thermador appliances and Sub-Zero refrigeration in the…

$3,250,000

740 PALMER - WINTER PARK, FL

740 PALMER WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 4810
Single Family - MLS#: O5509686
Community: osceola place Subdivision: osceola place

Never before on the market this is a rare opportunity to own a piece of Winter Park History! Gorgeous 1955 Gamble Rogers home with double waterfrontage (155 on Lake Osceola, 235 on the Venetian Canal). Amazing architecture, both inside and out. Grand foyer with spiral staircase. Formal living areas with panoramic views of the majestic oaks and lake. Double master suites, one upstairs and one down. Room for an expansive, gourmet kitchen. Oversized bedrooms, each with full bath. Walk out balconies…

$3,250,000

541 VIRGINIA - WINTER PARK, FL

541 VIRGINIA WINTER PARK, FL 32789
4 Beds 4 Baths Square Ft: 4057
Single Family - MLS#: O5532667
Community: timberlane shores Subdivision: timberlane shores

Casa Fiera Vista ~ Rare opportunity to own an Elegant Custom Lakefront Estate located on the Winter Park Chain of Lakes. This home is an Aurora and Parade of Homes Grand Winner! The attention to detail, workmanship and quality is unapparelled. Designed by Architects-Lucia Kassik & Monday, Grant Gribble Interiors, Landscape Architect- Frank Joseph Brooks and built by Victor Farina. 130 feet of lakefront on Lake Virginia -Sunrise and Sunsets overlooking Rollins and the tranquil Knowles Chapel. The…

$2,995,000

2049 VENETIAN - WINTER PARK, FL

2049 VENETIAN WINTER PARK, FL 32789
5 Beds 9 Baths Square Ft: 7631
Single Family - MLS#: O5552108
Community: n/a Subdivision: n/a

JUST REDUCED by $455,000! Priced to sell its the lowest $/SF on the Winter Park Chain of Lakes!!! Come see this unbelievably gorgeous lakefront estate home in Winter Park. Located on the quiet side of Lake Maitland, this 5 bedroom, 7,600 SF home features formal living areas, a home office, downstairs master and guest suite, upstairs bonus room, a game room with a temperature controlled wine chateau, heated pool, a private boathouse, and 4-car garage. Beautiful travertine and wood floors flow throughout…

$2,995,000

511 W CANTON - WINTER PARK, FL

511 W CANTON WINTER PARK, FL 32789
5 Beds 7 Baths Square Ft: 8910
Single Family - MLS#: O5536500
Community: winter park Subdivision: winter park

Step into this dramatic Mid-Century Modern home and youll never want to leave. Enjoy the perfection of the glass porcelain floors and dramatic windows, as you overlook the spectacular courtyard from every room. Entertain large parties simply with the spacious and commercial grade kitchen, grand family and living rooms, and resort-like courtyard. Display art, cars, or RVs in the oversized heated and air-conditioned garage space with over 20 ft. of ceiling height (with space for 19 cars). And, with…

$2,950,000

440 HENKEL - WINTER PARK, FL

440 HENKEL WINTER PARK, FL 32789
5 Beds 8 Baths Square Ft: 6025
Single Family - MLS#: O5473303
Community: thomas m henkels Subdivision: thomas m henkels

Come enjoy Florida living at its best with this gorgeous Craftsman style home, featuring approximately an acre of land and 200 on Lake Mizell. Impeccably designed, with attention to every detail, this stunning four bedroom home offers four full baths, three half-baths, a detached one bedroom + living quarters guest house, a home fitness center, boathouse & more! The Chefs kitchen includes state-of-the-art Viking appliances, a gas range, custom wood cabinetry, a breakfast nook with built-in seating,…

$2,695,000

699 OSCEOLA - WINTER PARK, FL

699 OSCEOLA WINTER PARK, FL 32789
5 Beds 4 Baths Square Ft: 5409
Single Family - MLS#: O5559096
Community: winter park Subdivision: winter park

This authentic 5 Bedroom Spanish Mediterranean Lakefront Estate is now available in Winter Park, Florida. Woven into the history of Winter Park, the home is comfortably updated to todays standards, yet expresss the character, warmth, and architecture of the 1930s. The unique very setting offers privacy, quiet seclusion, and clear expansive gorgeous views throughout the entire home of Lake Osceola. Exceptional attention was focused on interior & exterior details, finishes & unique fixtures. The outdoor…

$2,600,000

1000 ANCHORAGE - WINTER PARK, FL

1000 ANCHORAGE WINTER PARK, FL 32789
6 Beds 6 Baths Square Ft: 6378
Single Family - MLS#: O5570431
Community: anchorage estates Subdivision: anchorage estates

Gorgeous, one-of-a-kind French estate, in Olde Winter Park! 3-blocks from Park Avenue, Walk to the Winter Park Golf Course, boutique shops, award-winning restaurants & more. Immaculate interior boasts over 6,300 SF of luxurious living with high-end custom details throughout. From the French inspired copper dome entrance to the grand foyer & elegant staircase, marble/onyx flooring, & 5 layers of crown moldings, the flawless attention to detail is evident in every room of the home including the formal…

$2,600,000

531 LAKE FRONT - WINTER PARK, FL

531 LAKE FRONT WINTER PARK, FL 32789
4 Beds 6 Baths Square Ft: 5374
Single Family - MLS#: O5565630
Community: lords sub Subdivision: lords sub

Gorgeous Mediterranean style estate in the heart of Winter Park. Situated on Lake Killarney, this custom residence has character and style. A spiral staircase constructed of travertine and oak wooded stairs greets you with grand style. Off the foyer you will find the main office that has custom wood cabinetry and a coffered style ceiling made of solid oak. Off the main living area, you will find your formal dining room with tray ceiling architecture and crown molding. Chef style kitchen, granite…

$2,590,000

720 PALMER - WINTER PARK, FL

720 PALMER WINTER PARK, FL 32789
3 Beds 4 Baths Square Ft: 3242
Single Family - MLS#: T3106529
Community: osceola place Subdivision: osceola place

Home located on a beautiful .93 acre Lakefront Lot on Lake Osceola within walking distance of downtown Winter Park.

$2,507,896

521 VIRGINIA - WINTER PARK, FL

521 VIRGINIA WINTER PARK, FL 32789
3 Beds 4 Baths Square Ft: 3808
Single Family - MLS#: T3111029
Community: lake virginia pt rep Subdivision: lake virginia pt rep

Casa Bella Vista is a beautiful home, beautiful lake, beautiful neighborhood, and beautiful city. Most residents that live on Lake Virginia have lived here for decades and some are multi-generational. Great schools, safe environment and a quite secluded neighborhood. The house is directly across from Rollins College and downtown Winter Park, a beautiful city-scape both day and night. * 3 bedrooms, 2 full baths and 2 half baths. * Large living room/TV room. * Fabulous sun room with wood burning fireplace.…

$2,500,000

750 PINETREE - WINTER PARK, FL

750 PINETREE WINTER PARK, FL 32789
5 Beds 7 Baths Square Ft: 4780
Single Family - MLS#: O5567355
Community: sicilian shores rep 02 Subdivision: sicilian shores rep 02

Exquisitely crafted with meticulous attention to detail, this magnificent residence is situated in the heart of the exclusive Winter Park Vias on a rare oversized lot (nearly half acre) across the street from Lake Maitland and a short stroll to the WP Park Racquet Club. Showcasing the finest finishes, this custom-built home boasts 5 bedrooms, 5-and-2 half baths plus 2 outdoor showers. An entertainers delight, the transitional open floor plan highlights both formal and casual living, ideal for entertaining…

$2,499,978

4078 SCARLET IRIS - WINTER PARK, FL

4078 SCARLET IRIS WINTER PARK, FL 32792
4 Beds 6 Baths Square Ft: 9011
Single Family - MLS#: O5526618
Community: bear gully pointe Subdivision: bear gully pointe

Exclusive LAKEFRONT home in Bear Gully Point. This majestic home rests on private Bear Gully Lake. Home was constructed by the original owner who was a private home builder for over 30 years, so this home has every option imaginable. Every option was hand picked and crafted to rest on just over acre with fantastic views and designed to have views lake from practically every room in the house. Features include 4 fire places, 30 foot ceilings, 4 wet bars, over 2000 square feet music/game room with…

$2,475,000

1860 SUMMERLAND - WINTER PARK, FL

1860 SUMMERLAND WINTER PARK, FL 32789
5 Beds 6 Baths Square Ft: 5022
Single Family - MLS#: O5557186
Community: green oaks rep Subdivision: green oaks rep

Welcome home to this exquisite waterfront property with connecting guest cottage offering privacy on all sides. Its full of light with morning sunrise views of the Isle of Sicily on Lake Maitland in Winter Park. Enter THE PRIVACY OF a long driveway surrounded by gardens arriving to a spacious French Provencal styled home, guest quarters and four bay garage. This elegant styled home is perfect for small or large scale indoor or outdoor entertaining. The main house offers lake views in almost every…

$2,360,000

251 W FAWSETT - WINTER PARK, FL

251 W FAWSETT WINTER PARK, FL 32789
4 Beds 6 Baths Square Ft: 4400
Single Family - MLS#: O5717304
Community: forest hills Subdivision: forest hills

Pre-construction. To be built. This waterfront property boasts stunning panoramic views of beautiful Lake Sue! Nestled into the heart of Winter Park on a beautiful brick-lined street, this lot is available to build your custom home with master builder FG Schaub Custom Homes. Use the plans already in the works, or you can fully customize to fit your needs. Just over 1/4 of an acre, this property boasts 88 feet of lake frontage, a boat dock, and beautiful live oaks. Just minutes from the Florida Hospital,…

$2,350,000

1760 VIA VENETIA - WINTER PARK, FL

1760 VIA VENETIA WINTER PARK, FL 32789
4 Beds 6 Baths Square Ft: 6242
Single Family - MLS#: O5716286
Community: sicilian shores rep 02 Subdivision: sicilian shores rep 02

Absolutely stunning, four bedroom pool home in the Vias! Located on an impressive 0.43 acre lot, in the heart of one of Winter Parks most sought-after neighborhoods this executive estate features gorgeous finishes, beautiful hardwood floors, oversized living areas for entertainment, a downstairs master bedroom, a billiard room and more. The chef inspired kitchen was custom designed and showcases solid wood cabinetry, granite and Caesarstone countertops, Thermador appliances, elevated ceilings, and…

$2,250,000

1619 LOOKOUT LANDING - WINTER PARK, FL

1619 LOOKOUT LANDING WINTER PARK, FL 32789
5 Beds 7 Baths Square Ft: 7316
Single Family - MLS#: O5719228
Community: windsong lookout landing 43/79 Subdivision: windsong lookout landing 43/79

Expect to be impressed! This custom Windsong estate hasnt left any detail out. With over 7000 sq ft, this home offers 5 full bedroom suites plus an office, game room and a full theater that seats eight. The gourmet kitchen is a chefs dream with a 6 burner Wolf gas range, beautiful wood island, two sinks and a hidden walk-in pantry. Step out off of the family room, living room or dining room onto a covered lanai with a summer kitchen and gorgeous stone flooring and amazing lake views. The main floor…

$2,249,000

940 OLD ENGLAND - WINTER PARK, FL

940 OLD ENGLAND WINTER PARK, FL 32789
4 Beds 5 Baths Square Ft: 4949
Single Family - MLS#: O5554384
Community: dyer susan resub Subdivision: dyer susan resub

STUNNING DOWNTOWN WINTER PARK CHARACTER HOME beautifully updated and renovated on .97 acres of prime land. Originally built in the 1930s this remarkable home has elegant craftsmanship throughout such as hand hewn beams and vaulted ceiling in the 27 ft long great room, plaster walls, four fireplaces and wood floors. The sellers added a luxurious pool, a new garage with attached large guest cottage with living/dining room, kitchen and spacious upstairs master and a downstairs artist studio with separate…

$1,999,995

1799 LAKE BERRY - WINTER PARK, FL

1799 LAKE BERRY WINTER PARK, FL 32789
5 Beds 4 Baths Square Ft: 4575
Single Family - MLS#: O5707473
Community: waterbridge Subdivision: waterbridge

Welcome to this amazing Spanish Mediterranean home on Lake Berry in Winter Park! Nestled on a huge lot overlooking a 76 acre private ski lake that is perfect for boating, fishing, paddle boarding, and much more. Stunningly finished with travertine stone, exotic Brazilian cherry wood, porcelain tile, and has five-bedrooms, four baths and an oversized four car garage! Amazing elevated lake views on first floor as well as a thirty-six-foot-long covered lanai with retractable screens for quiet evenings…

$1,995,000

1712 LOOKOUT LANDING - WINTER PARK, FL

1712 LOOKOUT LANDING WINTER PARK, FL 32789
5 Beds 7 Baths Square Ft: 5179
Single Family - MLS#: O5706832
Community: windsong lookout landing 43/79 Subdivision: windsong lookout landing 43/79

Gorgeous five bedroom, five bath and 2 half baths transitional custom home located in prestigious Windsong! This beautiful 5,179 sq. ft. custom home built by Parkland Homes has the finest details and finishes throughout. The open floor plan offers beautiful hardwood floors, vaulted and wood beamed ceilings. The first level features the master suite with custom designed his and hers walk-in closets, a separate guest suite, formal dining room, and laundry room and wine room. The second level has three…

$1,995,000

471 SYLVAN - WINTER PARK, FL

471 SYLVAN WINTER PARK, FL 32789
5 Beds 6 Baths Square Ft: 6204
Single Family - MLS#: O5570851
Community: osceola or lakeview deed Subdivision: osceola or lakeview deed

Magnificent Spanish Estate in the heart of Winter Park. This 5 bedroom, 6 bath home has great curb appeal with immaculate landscaping and quality finishes throughout the interior, such as high ceilings, detailed craftsmanship, and the finest tile and millwork. Beautiful arched entry doors welcome you into this exceptional home, as you enter into an entrance hall with formal dining room on your left and formal living room in front. This well appointed space also includes wine and liquor storage.…

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