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Find Homes For Sale in Winter Park FL. Search Winter Park Real Estate Listings including Winter Park Bank Owned Homes & Winter Park Short Sales. Find exclusive Winter Park Luxury homes for sale here not seen on any other Florida Real Estate listings site.



See more properties for sale below


MLS #O4989010 | Winter Park Lake view, Park-like views, Waterview Lakefront, Waterfront Single Family 5 Bedrooms / 6.5 Bathrooms Pool Spanish For Sale Twelve Oaks 1220 N PARK AVE
Winter Park, FL 32789
ROLLOVER TO VIEW 12 PHOTOS
$20,000,000.00
($1,676.00/sqft)
Winter Park Single Family For Sale
5 beds, 5 baths, 3 half baths, 11931 living sqft

Casa del mondo - house of the world. imagine the look of an italian mediterranean mansion set in a hawaiian rain forest on the shores of a tahitian lagoon but instead its a 1.5 ac gated estate on lake maitland in the heart of winter park. 14,931sf. ...
Top Features: for sale , Lakefront, Waterfront , Lake view, Park-like views, Waterview Has a pool , Subdivision: Twelve Oaks , Lot SQFT: 153291sqft , Built in  2003 , Style: Spanish
MLS #O4949379 | Winter Park Lake access, Waterview Lakefront, Waterfront Single Family 5 Bedrooms / 7 Bathrooms Pool Spanish For Sale Winter Park Old Town 420 N INTERLACHEN AVE
Winter Park, FL 32789
ROLLOVER TO VIEW 10 PHOTOS
$6,995,000.00
($744.00/sqft)
Winter Park Single Family For Sale
5 beds, 7 baths, 9399 living sqft

Price reduced $505,000.00 since 12/2/09 | Welcome to the Premier home on the Winter Park chain of lakes. Constructed in 1938 in the Italianate style and updated in 1989, this home has the grace of the old combined with the functionality of the new. There are spaces for everyone in the ...
Top Features: for sale , Lakefront, Waterfront , Lake access, Waterview Has a pool , Subdivision: Winter Park Old Town , Lot SQFT: 84096sqft , Built in  1938 , Style: Spanish
MLS #S4669799 | Winter Park Lake access, Lake view, Waterview Lakefront, Waterfront Single Family 7 Bedrooms / 9 Bathrooms Pool Victorian For Sale Chain Of Lakes 240 TRISMEN TERR
Winter Park, FL 32789
ROLLOVER TO VIEW 12 PHOTOS
$6,600,000.00
($825.00/sqft)
Winter Park Single Family For Sale
7 beds, 8 baths, 2 half baths, 8000 living sqft

This lake front estate home is located off the beautiful lake osceola and will truly take your breath away! take your boat for a spin or simply enjoy the beauty from your master bedroom window or widows tower on the roof of your home. play a ...
Top Features: for sale , Lakefront, Waterfront , Lake access, Lake view, Waterview Has a pool , Subdivision: Chain Of Lakes , Lot SQFT: 61323sqft , Built in  1901 , Style: Victorian
MLS #O4992176 | Winter Park Lake access Lakefront, Waterfront Single Family 4 Bedrooms / 5 Bathrooms For Sale Isle Of Sicily 3 ISLE OF SICILY
Winter Park, FL 32789
ROLLOVER TO VIEW 12 PHOTOS
$5,500,000.00
($730.00/sqft)
Winter Park Single Family For Sale
4 beds, 4 baths, 2 half baths, 7531 living sqft

Four Winds, the site of James Gamble Rogers' 1929 home on the Isle of Sicily, is available for purchase. This magnificent French Provencial Normandy style home underwent major renovation and additions in 1987 and 1993, and is situated on ...
Top Features: for sale , Lakefront, Waterfront , Lake access , Subdivision: Isle Of Sicily , Lot SQFT: 52799sqft , Built in  1932
MLS #O4978340 | Winter Park Lakefront, Waterfront Single Family 6 Bedrooms / 7.5 Bathrooms Pool For Sale Windsong Ests Sec 2
Winter Park, FL 32789
ROLLOVER TO VIEW 12 PHOTOS
$5,350,000.00
($618.00/sqft)
Winter Park Single Family For Sale
6 beds, 7 baths, 1 half baths, 8653 living sqft

Exquisite luxury yet warm and livable. This privately gated home is surrounded by water on 3 sides and located in the exclusive Estates section of Windsong.From the Brazilian Cherry floors to the Travertine pool deck,every detail has been hand ...
Top Features: for sale , Lakefront, Waterfront Has a pool , Subdivision: Windsong Ests Sec 2 , Lot SQFT: 47345sqft , Built in  2003 , Maint Fees: $632.00
MLS #O4954715 | Winter Park Lakefront, Waterfront Single Family 5 Bedrooms / 5.5 Bathrooms Pool Traditional For Sale Winter Park 1250 N PARK AVE
Winter Park, FL 32789
ROLLOVER TO VIEW 10 PHOTOS
$5,300,000.00
($646.00/sqft)
Winter Park Single Family For Sale
5 beds, 5 baths, 1 half baths, 8207 living sqft

Exquisite lake front home situated on 157 ft on the shores of Lake Maitland in the heart of Olde Winter Park. Exclusive Winter Park chain of lakes. Amazing 1.5 acre lot is meticulously manicured. This gated estate custom built by Charles Clayton ...
Top Features: for sale , Lakefront, Waterfront Has a pool , Subdivision: Winter Park , Lot SQFT: 201229sqft , Built in  2001 , Style: Traditional
MLS #O4922532 | Winter Park Lakefront, Waterfront Single Family 6 Bedrooms / 7.5 Bathrooms Pool For Sale Windsong Preserve Point 1136 PRESERVE POINT DR
Winter Park, FL 32789
ROLLOVER TO VIEW 10 PHOTOS
$4,995,000.00
($468.00/sqft)
Winter Park Single Family For Sale
6 beds, 6 baths, 3 half baths, 10662 living sqft

Chateau Sur Le Lac...Breathtaking French style estate in desirable Windsong of Winter Park. With six bedrooms, 6 full and 3 half baths, this home is unique in design and detail. Gourmet kitchen with oversized breakfast room, family room, upstairs ...
Top Features: for sale , Lakefront, Waterfront Has a pool , Subdivision: Windsong Preserve Point , Lot SQFT: 67988sqft , Built in  2008 , Maint Fees: $662.00
MLS #O4977457 | Winter Park Lake access, Lake view, Waterview Lakefront, Waterfront Single Family 4 Bedrooms / 4.5 Bathrooms Pool Traditional For Sale Macdonald Robert Dhu Pk 115 PALMER AVE
Winter Park, FL 32789
ROLLOVER TO VIEW 12 PHOTOS
$4,500,000.00
($500.00/sqft)
Winter Park Single Family For Sale
4 beds, 4 baths, 1 half baths, 9007 living sqft

Price reduced $1,000,000.00 since 4/25/10 | Lake Maitland Winter Park Estate in a premier location - walk to Park Ave. The residence is situated on 1.5 acres with approx. 280' on the water. New custom slate roof, pavered back porch area, several AC units have been replaced, new windows ...
Top Features: for sale , Lakefront, Waterfront , Lake access, Lake view, Waterview Has a pool , Subdivision: Macdonald Robert Dhu Pk , Lot SQFT: 56484sqft , Built in  1989 , Style: Traditional
MLS #O4954703 | Winter Park Condotown Home 5 Bedrooms / 4.5 Bathrooms Pool Spanish For Sale Residences Condo 300 S INTERLACHEN AVE Unit: 604
Winter Park, FL 32789
ROLLOVER TO VIEW 10 PHOTOS
$4,300,000.00
($745.00/sqft)
Winter Park Condotown Home For Sale
5 beds, 4 baths, 1 half baths, 5770 living sqft

Ultimate in luxury living in downtown Winter Park, Florida! This stunning five bedroom, four and one half-bath two-story Penthouse condominium combines lock-and-leave convenience with the privacy of single family living. Professionally designed ...
Top Features: for sale Has a pool , Subdivision: Residences Condo , Built in  2005 , Style: Spanish , Maint Fees: $4,670.00
MLS #O4987220 | Winter Park Lake access, Lake view, Waterview Lakefront, Waterfront Single Family 4 Bedrooms / 4.5 Bathrooms Traditional For Sale Winter Park 490 E WEBSTER AVE
Winter Park, FL 32789
ROLLOVER TO VIEW 12 PHOTOS
$4,250,000.00
($855.00/sqft)
Winter Park Single Family For Sale
4 beds, 4 baths, 1 half baths, 4971 living sqft

Classic and Beautiful Gamble Rogers. This Winter Park direct lakefront Lake Osceola home has been lovingly restored and enlarged. Gracefully situated on almost an acre of lawn & meticulous landscaping this character home offers spectacular ...
Top Features: for sale , Lakefront, Waterfront , Lake access, Lake view, Waterview , Subdivision: Winter Park , Lot SQFT: 39055sqft , Built in  1930 , Style: Traditional



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