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Orlando Condo ManiaBrowse by City > WINTER PARK Condos For Sale
Located just northeast of downtown Orlando, Winter Park is an historic neighborhood with cobblestone, tree-lined streets, an array of mansions and is one of the most expensive places to live in the city. Visit the spendy boutiques on Park Avenue, take a leisurely cruise on the Winter Park Scenic Boat Ride or stroll the Saturday Farmer's Market in the restored train depot.
The condo homes in Winter Park come in a variety of styles but you won't find any high rises. If you enjoy a traditional, urban feel check out the Douglas Grand, just off Central Park. This three-story luxury community of condo flats offers open concept floor plans, stainless steel appliances and top quality finish. Walk to Park Ave.
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New Listings in WINTER PARK
MLS # List Date List Price Beds Baths Sq Ft Community G5112476 2026-05-17 $425,000 3 3 1907 GRAYSON SQUARE O6408516 2026-05-16 $259,900 2 2 1026 CHATEAUX DU LAC O6403591 2026-05-14 $4,295,000 3 5 4231 PARK HILL O6407259 2026-05-12 $410,000 2 3 1428 KILLARNEY BAY O6406448 2026-05-09 $175,000 2 2 990 HIDDEN OAKS
Recent WINTER PARK Blog Posts
Condos on Lake Osceola in Winter Park
Lakefront condos in Winter Park can be found at these condos on Lake Osceola.
WINTER PARK Categories
Winter Park Luxury Condos
Winter Park's luxury condos are often mid-rise communities close to the Park Avenue restaurants, boutiques and Lake Oceola.
WINTER PARK Market Reports
Communities for this City
Featured Communities
HIDDEN OAKS
8 Listings
$169,500 to $229,000
COLONIES
7 Listings
$89,900 to $165,000
WATERFALL COVE
7 Listings
$109,000 to $205,000
STRATFORD
6 Listings
$144,000 to $220,000
CEDARWOOD VILLAGE
5 Listings
$265,000 to $295,000
LAKESIDE MANOR
5 Listings
$164,900 to $224,999
Browse WINTER PARK Condos For Sale by Community
Community Active Listings Price Range ALOMA TRAILS 1 Listing Priced at $390,000 CEDARWOOD VILLAGE 5 Listings Priced from: $265,000 to $295,000 CHATEAUX DU LAC 3 Listings Priced from: $259,500 to $262,000 CLOISTERS 4 Listings Priced from: $879,000 to $1,950,000 COLONIES 7 Listings Priced from: $89,900 to $165,000 DOUGLAS GRAND No Active Listings FOUR SEASONS 1 Listing Priced at $170,000 GOLDENROD VILLAS 4 Listings Priced from: $219,900 to $250,000 GOLFSIDE VILLAS 1 Listing Priced at $122,990 GRAYSON SQUARE 3 Listings Priced from: $425,000 to $465,000 HIDDEN OAKS 8 Listings Priced from: $169,500 to $229,000 KILLARNEY BAY 3 Listings Priced from: $325,000 to $495,000 LAKE KILLARNEY 1 Listing Priced at $298,000 LAKE VIRGINIA No Active Listings LAKESIDE MANOR 5 Listings Priced from: $164,900 to $224,999 LAZY OAKS 1 Listing Priced at $285,000 MONDRIAN 1 Listing Priced at $1,099,000 PARK HILL 1 Listing Priced at $4,295,000 PARKVIEW VILLAGE 5 Listings Priced from: $149,000 to $205,000 QUARTERS AT WINTER PARK 1 Listing Priced at $595,000 SANDLEWOOD CREEK 1 Listing Priced at $314,000 STRATFORD 6 Listings Priced from: $144,000 to $220,000 SWOOPE PARK 1 Listing Priced at $695,000 THE LANDMARK No Active Listings THE RESIDENCES No Active Listings VILLA SIENA No Active Listings VILLAGE AT WHISPERWOOD 1 Listing Priced at $236,800 VILLAS OF CASSELBERRY 1 Listing Priced at $419,900 WATERFALL COVE 7 Listings Priced from: $109,000 to $205,000 WHISPERING WATERS 4 Listings Priced from: $289,900 to $2,075,000 WHISPERWOOD 4 Listings Priced from: $189,999 to $250,000 WINTER PARK VILLAS 1 Listing Priced at $199,900 WINTER PARK WOODS 3 Listings Priced from: $99,000 to $150,000 WRENWOOD 3 Listings Priced from: $179,000 to $209,900
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Information Deemed Reliable But Not Guaranteed. The information being provided is for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This information, including square footage, while not guaranteed, has been acquired from sources believed to be reliable.
Last Updated: 2026-05-19 03:09:29