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

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


(150) 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.…

$6,795,000

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

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…

$4,895,000

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…

$4,595,000

147 VIRGINIA - WINTER PARK, FL

147 VIRGINIA WINTER PARK, FL 32789
5 Beds 8 Baths Square Ft: 7224
Single Family - MLS#: O5493376
Community: the ellno willo Subdivision: the ellno willo

One of Winter Parks most premier and timeless traditional lakefront estates elevated on apprx. 1.5 acres and 200 of lake frontage on Lake Virginia walking distance to Rollins College and famed Park Avenue... The home was originally built in 1925, but the current owners completely renovated and expanded the home in 2010. There are spacious living spaces & high ceilings in the main home includes 4 bedrooms/5 baths, library, formal living and dining rooms, and family room. There is a detached guest…

$4,200,000

935 GREENTREE - WINTER PARK, FL

935 GREENTREE WINTER PARK, FL 32789
3 Beds 5 Baths Square Ft: 4975
Single Family - MLS#: O5544810
Community: palmer avenue lakeside Subdivision: palmer avenue lakeside

Stunning Georgian-style lakefront estate in the heart of Olde Winter Park. Quietly tucked away, along the north shore of Lake Osceola, sits this breathtaking home, shaded by moss-draped oak trees. Designed by Architect Michael Smith and built by Posada Custom Homes, this 3 Bedroom, 5 Bath manor exudes sophistication and welcomes its residents and guests with timeless elegance around every corner. Custom detailing found throughout the home exemplifies just how much consideration went into the design…

$3,500,000

2150 VIA TUSCANY - WINTER PARK, FL

2150 VIA TUSCANY WINTER PARK, FL 32789
7 Beds 10 Baths Square Ft: 7670
Single Family - MLS#: O5398109
Community: adair place Subdivision: adair place

Timeless perfection encompasses every room of this stunning Winter Park estate. Custom built by Charles Clayton, this seven bedroom, seven bath home exudes character and charm throughout and includes features so seldom found in todays homes including brick laid floors, wood beam ceilings, formal living and dining rooms, three brick fireplaces, a gourmet kitchen that opens to the family room, downstairs master retreat, home office, movie theater, upstairs game room, a detached in-law suite, and a…

$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

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…

$3,295,000

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…

$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!! Seller is motivated and willing to consider all offers. 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…

$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…

$2,995,000

472 HENKEL - WINTER PARK, FL

472 HENKEL WINTER PARK, FL 32789
4 Beds 7 Baths Square Ft: 4686
Single Family - MLS#: O5517710
Community: thomas m henkels add Subdivision: thomas m henkels add

Just completed 2017 new contemporary lakefront masterpiece on Chain of Lakes and convenient walking distance to downtown Winter Park / Park Ave and Alfond Inn! Approx 5,000sf of air conditioned living area with bright - wide open floor plan, clean lines, neutral designer interiors , 108 architectural ceilings, expansive picturesque windows/doors thru-out, 10 Casablanca folding LaCantina doors, 4 bedroom suites w/ Master down, 2nd level spacious media/flex room w/ private terrace overlooking tranquil…

$2,895,000

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.…

$2,795,000

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.…

$2,450,000

1204 N PARK - WINTER PARK, FL

1204 N PARK WINTER PARK, FL 32789
2 Beds 2 Baths Square Ft: 1202
Single Family - MLS#: O5494384
Community: twelve oaks Subdivision: twelve oaks

Extremely unique opportunity: For the first time in almost 20 years, this one of a kind property on chain of lakes located in the Twelve Oaks peninsula and walking distance to downtown Park Avenue is available... This unprecedented property is on a spacious lot with boathouse and frontage on Lake Maitland, this unique property is the ultimate private retreat... Luxurious outdoor living with magnificent landscaping and lighting... plenty of room to expand/customize home or design & build new construction…

$2,350,000

660 VIA LUGANO - WINTER PARK, FL

660 VIA LUGANO WINTER PARK, FL 32789
4 Beds 5 Baths Square Ft: 3712
Single Family - MLS#: O5442203
Community: sicilian shores Subdivision: sicilian shores

Premier setting for this New Orleans style home on Lake Maitland in the heart of the Vias! Spectacular views from almost every room in the home with southern exposure that provides bright light all day... Multiple covered porches with extensive French doors. Gorgeous olde world heart of pine hardwood floors and high ceilings with spacious rooms throughout. Expansive white chefs island kitchen equipped with farmhouse sink, Carrera marble countertops, and custom cabinets. Large upstairs master retreat…

$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.…

$2,295,000

1619 LOOKOUT LANDING - WINTER PARK, FL

1619 LOOKOUT LANDING WINTER PARK, FL 32789
5 Beds 7 Baths Square Ft: 7450
Single Family - MLS#: O5522701
Community: windsong lookout landing 43/79 Subdivision: windsong lookout landing 43/79

Custom Windsong Estate Home....Exceptional attention to detail Over 7,000 sf of living area & apprx 10,000 sf under roof, this home offers a masterfully designed floor plan, 5 bedroom suites, media rm, library, game room & other flexible spaces Features include custom painted ceilings, Venetian plaster, custom millwork, travertine & Brazilian flooring with exquisite detail Gourmet kitchen features custom ebony wood island, as well as breakfast bar seating, commercial grade natural gas appliances…

$2,280,000

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.…

$2,275,000

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…

$2,250,000

531 LAKE FRONT - WINTER PARK, FL

531 LAKE FRONT WINTER PARK, FL 32789
4 Beds 6 Baths Square Ft: 5194
Single Family - MLS#: O5541750
Community: lords sub Subdivision: lords sub

Must see Video and photography of this Stunning Villa Paradise Home!!! Luxury lifestyle living with the best commute and most convenient location in Central Florida/Old Winter Park. This custom built home is truly workmans quality from Grand-Entry to doorknobs to breathtaking panorama view of Lake Killarney. Take a walk or drive a bike to most prestige shopping plazas and tons of dinning and luxe restaurant, boutiques, Winter Parks famous Park Avenue and farmers market. Enjoy your cold beverage…

$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.

$2,150,000

1560 OAKHURST - WINTER PARK, FL

1560 OAKHURST WINTER PARK, FL 32789
5 Beds 7 Baths Square Ft: 5296
Single Family - MLS#: O5537909
Community: comstock park Subdivision: comstock park

New Rex-Tibbs Construction on beautiful brick street in premier Winter Park location Modern style home with standing seam metal roof, extensive large picture windows, european styling, clean lines and bright-open interiors Transitional neutral colors with spacious Master suite as well as private entry guest suite both on the 1st floor 3 bedroom suites and 2 bonus/media rooms upstairs. Wonderful island kitchen with top grade Sub Zero/Wolf appliances, wine cooler, natural gas service, fireplace, built-ins,…

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