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

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


(114) PROPERTIES

$7,500,000

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

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 to be desired.…

$5,750,000

115 PALMER - WINTER PARK, FL

115 PALMER WINTER PARK, FL 32789
4 Beds 5 Baths Square Ft: 9838
Single Family - MLS#: O5547897
Community: macdonald robert dhu pk Subdivision: macdonald robert dhu pk

Location Location Location! This is your opportunity to own this stunning Winter Park Estate just a short and beautiful walk to Park Avenue and everything it has to offer. The majestic residence sits on 1.5 acres and has over 280on the enchanting Winter Park chain of lakes (Lake Maitland)The home boasts gorgeous lake views from most rooms, a lovely sprawling private master suite, formal living with a wood burning fireplace, elegant entrance, great kitchen for entertaining guest who want to see the…

$4,950,000

1212 N PARK - WINTER PARK, FL

1212 N PARK WINTER PARK, FL 32789
5 Beds 6 Baths Square Ft: 4681
Single Family - MLS#: O5544700
Community: twelve oaks Subdivision: twelve oaks

Called Winter Parks finest location, Twelve Oaks peninsula, is a unique and truly exceptional opportunity in the heart of Winter Park! A quiet, private drive leads to this stately custom-built waterfront estate which is available for the first time. Surrounded by the tranquil waters of the largest lake on the Chain of Lakes, Lake Maitland, this home offers a total of 254 feet water frontage, custom woodwork throughout and almost every room in the house takes advantage of gorgeous panoramic lake…

$4,850,000

1941 LEGION - WINTER PARK, FL

1941 LEGION WINTER PARK, FL 32789
6 Beds 9 Baths Square Ft: 10493
Single Family - MLS#: O5484879
Community: green oaks rep 02 Subdivision: green oaks rep 02

LUXURIOUS LAKE MAITLAND ESTATE! This Winter Park Chain of Lakes Custom 5 car garage home has panoramic views of Lk. Maitland w/ 175 of water frontage on 1.09 acres. This magnificient home has it ALL & Below Appraisal!! The living & entertaining areas are spacious & elegant, w/ sweeping views of the lake from almost every room. High end finishes in the main house include French doors, central vacuum, custom built-ins, surround sound, security camera, wine cellar, gas fireplaces, & extensive detailed…

$3,995,000

1316 GREEN COVE - WINTER PARK, FL

1316 GREEN COVE WINTER PARK, FL 32789
6 Beds 7 Baths Square Ft: 6763
Single Family - MLS#: O5549098
Community: camwood Subdivision: camwood

Stunning 6 Bedroom, 6.5 Bath Lakefront Estate on Lake Maitland. Located in one of Winter Parks premier communities, youre less than 1 mile away from Park Avenue and all of the award-winning restaurants and charming boutique shops. Redesigned in 2017, this magnificent home now features a one-of-a-kind master retreat with breathtaking water views, a custom floor to ceiling marble bath, and an expansive dressing room/closet that is sure to impress. Enter the home through the grand foyer and be greeted…

$3,499,000

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…

$3,450,000

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

Unbelievably gorgeous lakefront estate home in Winter Park! Located on the quiet lagoon 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 the home, complimented by extensive millwork and crown moldings, 4 gas fireplaces, high ceilings, and…

$3,450,000

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…

$3,200,000

1637 CHASE LANDING - WINTER PARK, FL

1637 CHASE LANDING WINTER PARK, FL 32789
5 Beds 6 Baths Square Ft: 6272
Single Family - MLS#: O5522419
Community: windsong preserve point 43/76 Subdivision: windsong preserve point 43/76

Huge price reduction!! This amazing 2 story lakefront home is located in Winter Parks exclusive Windsong Preserve Point neighborhood and features stunning views of Lake Berry. The house was extensively renovated in 2008-2009. Enjoy the Florida luxury lifestyle while relaxing in your private pool and spa or entertain your friends and family with a full outdoor kitchen and huge patio area. The large covered dock has a motorized lift thats perfect for your boat, jet ski, fishing or you can simply enjoy…

$3,195,000

975 GREENTREE - WINTER PARK, FL

975 GREENTREE WINTER PARK, FL 32789
4 Beds 5 Baths Square Ft: 5731
Single Family - MLS#: O5557598
Community: acreage & unrec Subdivision: acreage & unrec

Elegant Charleston style lakefront residence in secluded setting on premier Lake Osceola overlooking an absolutely gorgeous, tranquil cove! Sophisticated home where the attention to detail, character and quality in craftsmanship with this home is outstanding Located on a quiet treelined dead end street walking distance or a short boat ride across the lake to downtown Winter Park! Flexible open, yet warm traditional interiors with spacious rooms, high ceilings, extensive moldings, gorgeous heart…

$3,190,000

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,…

$2,995,000

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…

$2,975,000

181 VIRGINIA - WINTER PARK, FL

181 VIRGINIA WINTER PARK, FL 32789
4 Beds 4 Baths Square Ft: 4908
Single Family - MLS#: O5500763
Community: ellno willo Subdivision: ellno willo

This is the first time in almost 50 years this amazing Mediterranean lakefront estate has been available for purchase. Located just blocks from Park Avenue on the shores of Lake Virginia you can enjoy panoramic views across the lake at Rollins College. Originally built in 1928, this home has been lovingly maintained, enhanced, and updated over the years all while maintaining the original charm. Nestled on over 3/4 acre with more than 150 of lakefront, this is one of Winter Parks premier lakefront…

$2,895,000

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…

$2,795,000

1740 VIA VENETIA - WINTER PARK, FL

1740 VIA VENETIA WINTER PARK, FL 32789
5 Beds 8 Baths Square Ft: 5862
Single Family - MLS#: O5538382
Community: sicilian shores rep 02 Subdivision: sicilian shores rep 02

Breathtaking contemporary pool home in the heart of the Vias. This newly constructed home sits high over the street on an oversized lot and has all the modern amenities and conveniences that todays market demands. Another masterpiece built by FG Schaub Custom Homes. Enter into a large foyer hallway accented with glass railings, barn doors, and large porcelain tile floors.. Interior features include very open floor plan allowing flexibility in how to design your interior spaces to fit your lifestyle.…

$2,625,000

1260 ALABAMA - WINTER PARK, FL

1260 ALABAMA WINTER PARK, FL 32789
4 Beds 6 Baths Square Ft: 6026
Single Family - MLS#: O5511707
Community: kronenberger j Subdivision: kronenberger j

Elegant canal front Estate on Chain of Lakes recently completely remodeled & tastefully enhanced with modern transitional interiors... Premier setting walking distance to Park Avenue on an oversized lot... Magnificent, lushly landscaped grounds and private boat house property on canal near entrance to Lake Maitland... No detail or expense has been spared in this well executed & artfully designed renovation. Home is extremely well built with masonry walls, plus brick and solid stone surround accents.…

$2,495,000

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…

$2,490,000

888 MAYFIELD - WINTER PARK, FL

888 MAYFIELD WINTER PARK, FL 32789
6 Beds 8 Baths Square Ft: 5099
Single Family - MLS#: O5556141
Community: kronenberger j Subdivision: kronenberger j

This stunning 6 bdm/8 ba Mediterranean plus office is the epitome of timeless elegance. The luxurious estates master craftsmanship located on the brick paved streets of Olde Winter Park, impresses with its high end finishes and the meticulous attention to detail. A grand entrance, sweeping staircase and perfectly manicured grounds, all welcome you as you enter. A well-appointed kitchen has a 6-burner Dacor stove, double ovens and warming drawer, plus 2 Bocsh dishwashers, huge island with sink, will…

$2,325,000

150 W ROCKWOOD - WINTER PARK, FL

150 W ROCKWOOD WINTER PARK, FL 32789
4 Beds 5 Baths Square Ft: 5082
Single Family - MLS#: O5528444
Community: forest hills Subdivision: forest hills

Stunning Custom French Country Estate. Built in 2015 and featured in Parade of Homes, this magnificent eco-friendly home features 4 bedrooms, 5 full baths and a luxurious interior that highlights high-end finishes and a modern layout. Step into the home through the column-lined courtyard and into the grand foyer where your eyes will immediately be drawn to the masterful spiral staircase with wrought-iron detailing. To the left and right of the foyer entry are the formal living and dining rooms.…

$2,260,000

521 VIRGINIA - WINTER PARK, FL

521 VIRGINIA WINTER PARK, FL 32789
3 Beds 4 Baths Square Ft: 3900
Single Family - MLS#: O5526187
Community: lake virginia pt rep Subdivision: lake virginia pt rep

LAKEFRONT ONE STORY ESTATE HOME ON LAKE VIRGINIA! Last sale over 30 years ago. This home has been beautifully maintained and renovated throughout the years. The home boasts 3900 SF of living areawith large rooms appointed with crown molding, wood floors, plantation shutters, porcelain tile, french doors and stunning lake views including Rollins College and Chapel. Additions include large den with vaulted tongue/groove ceilings & custom built - ins, large covered lanai area for outdoor entertaining.…

$2,199,000

302 GENIUS - WINTER PARK, FL

302 GENIUS WINTER PARK, FL 32789
5 Beds 7 Baths Square Ft: 6607
Single Family - MLS#: O5521671
Community: windsong lakeside sec 02 43/71 Subdivision: windsong lakeside sec 02 43/71

Beautiful Windsong Community, 5 Bedrooms with 5 full baths and 2 half. Hardwood floors, gourmet kitchen overlooking pool with summer kitchen.

$2,195,000

2025 SUMMERLAND - WINTER PARK, FL

2025 SUMMERLAND WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 4400
Single Family - MLS#: O5546563
Community: green oaks rep 02 Subdivision: green oaks rep 02

Secluded premier lakefront property on quiet cove on Lake Maitland chain of lakes... terrific lakefront price point with so little opportunity in this price range including expansive lake frontage to enjoy picturesque sunset views... home is in excellent condition and very well maintained with spacious flexible floor plan... split plan with 5 bedroom suites, large bonus/flex room, open island kitchen to gathering room, bright-open home with tall windows and French doors, quality construction, extensive…

$2,095,000

410 LAKEWOOD - WINTER PARK, FL

410 LAKEWOOD WINTER PARK, FL 32789
5 Beds 7 Baths Square Ft: 5036
Single Family - MLS#: O5533080
Community: osceola shores sec 03 Subdivision: osceola shores sec 03

Selling as lot only. Lakefront property with 100 feet of frontage on Lake Osceola on the Winter Park chain of lakes. A rare opportunity to build your dream home on this fantastic lot located on a quiet cul-de-sac street! Walking distance to Park Avenue and Rollins College.

$1,999,500

1203 PRESERVE POINT - WINTER PARK, FL

1203 PRESERVE POINT WINTER PARK, FL 32789
5 Beds 5 Baths Square Ft: 5856
Single Family - MLS#: O5491592
Community: windsong lookout landing 43/79 Subdivision: windsong lookout landing 43/79

Stunning Custom-built Cahill home in Windsongs Preserve Point! Enjoy beautiful views of Lake Virginia from the privacy of your 2nd floor verandah and outdoor living area. Inside youll be impressed by each and every custom detail that went into this home. From luxurious, high-end finishes that include vaulted coffered ceilings, beautiful hardwood and stone floors, detailed moldings, and more to the thoughtfully designed floorplan that includes one-story living and a gentlemans study. The homes great…

$1,999,000

1134 BELLA LAGO - WINTER PARK, FL

1134 BELLA LAGO WINTER PARK, FL 32792
5 Beds 8 Baths Square Ft: 6955
Single Family - MLS#: O5520448
Community: lake howell Subdivision: lake howell

Price just SLASHED 200k!!! Make a point to see this MAGNIFICENT custom home! Almost 7k sq ft of beauty and elegance with close to 200 ft of frontage on Lake Howell!Completely renovated in 2004 AND almost 2k sq ft, and a second floor with balcony, added as an additional master suite/Mother-in-law suite in 2015 (elevator and/or stair access from main home). Below this beautiful 2nd master suite (with den/library, and zen/meditation room) is an over-sized 3-car garage and an additional storage room…

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