Winter Springs, FL Subdivisions & Condo Buildings
Winter Springs is built around dozens of established neighborhoods clustered along the Tuscawilla corridor and the older grid near SR 434, giving buyers a mix of mature tree-canopy streets and newer construction. Oak Forest is the largest and most active community in the city, with more listings moving through it at any given time than any other subdivision, making it a useful benchmark for pricing and inventory. Golf-course living remains a strong draw here, with Tuskawilla Crossings, Chelsea Parc at Tuscawilla, and Arrowhead at Tuscawilla representing the resale-only side of that market, while communities such as Hickory Grove, Jesups Reserve, Barclay Reserve, and Cypress Club reflect the newer townhome and single-family construction filled in around them over the past several years. For buyers wanting a lock-and-leave lifestyle without age restrictions, Baytree Village and Tuscany Place offer condo living, while Hacienda Village is the city's dedicated 55+ active adult community. Older, character-filled sections like North Orlando Terrace and Highlands sit alongside newer builds like Deersong and The Seasons, giving the city genuine range from entry-level resale to executive new construction. Altogether, Winter Springs subdivisions serve a broad cross-section of move-up families, golf and lake-lifestyle buyers, and retirees, with pricing that spans from modest condo communities to million-dollar estate sections of Tuscawilla.
Arrowhead at Tuscawilla
2 homes sold in the past year ranging from $1,250,000 to $1,300,000.
Barclay Reserve
There are currently 2 townhouses from $325,000 to $339,900 for sale.
Barrington Estates
There are currently 4 single-family homes from $650,000 to $699,900 for sale.
Casa Park Villas
There are currently 7 townhouses from $219,900 to $256,000 and 1 single-family home at $255,000 for sale.
Chelsea Parc at Tuscawilla
There are currently 1 townhouse at $344,900 and 3 single-family homes from $424,900 to $486,900 for sale.
Chestnut Estates
There is currently 1 single-family home at $665,000 for sale.
Country Club Village
There are currently 6 single-family homes from $309,777 to $545,000 for sale.
Cypress Club
There are currently 2 townhouses from $199,000 to $205,000 for sale.
Deersong
There are currently 4 single-family homes from $242,000 to $285,000 for sale.
Eagles Watch
There are currently 2 single-family homes from $475,000 to $479,000 for sale.
Forrest Creek Estates
There are currently 2 single-family homes from $499,000 to $660,000 for sale.
Georgetowne
There are currently 3 single-family homes from $385,000 to $550,000 for sale.
Glen Eagle
There are currently 2 single-family homes from $835,000 to $995,000 for sale.
Greenbriar
There are currently 2 single-family homes from $360,000 to $429,900 for sale.
Greenspointe
There are currently 2 single-family homes from $340,000 to $374,400 for sale.
Harbor Winds
There are currently 2 townhouses from $329,000 to $335,000 for sale.
Heritage Park
There are currently 2 townhouses from $289,000 to $289,900 for sale.
Hickory Grove
There are currently 10 townhouses from $386,990 to $514,990 for sale.
Highland Village
There are currently 2 single-family homes from $324,900 to $350,000 for sale.
Highlands
There are currently 5 single-family homes from $344,000 to $485,000, 1 townhouse at $299,990 and 1 condo at $270,000 for sale.
Hollowbrook
There are currently 2 single-family homes from $449,000 to $525,000 for sale.
Indian Ridge
There are currently 2 condos from $145,000 to $178,900 for sale.
Jesups Landing
There are currently 3 townhouses from $365,000 to $405,000 for sale.
Jesups Reserve
There are currently 4 townhouses from $321,000 to $387,500 for sale.
Mount Greenwood
There are currently 2 townhouses from $244,000 to $275,000 and 1 single-family home at $349,000 for sale.
North Orlando Terrace
There are currently 5 single-family homes from $260,000 to $345,000 for sale.
Oak Forest
There are currently 15 single-family homes from $375,000 to $569,999 for sale.
Seminole Crossing Townhomes
There are currently 2 townhouses from $455,000 to $457,393 for sale.
Seville Chase
There are currently 3 single-family homes from $639,900 to $925,000 for sale.
The Landings at Parkstone
2 homes sold in the past year ranging from $399,500 to $435,000.
The Seasons
There are currently 4 single-family homes from $284,000 to $349,900 for sale.
Tuskawilla Crossings
There are currently 3 single-family homes from $489,000 to $529,900 for sale.
Wedgewood
There are currently 2 single-family homes from $419,900 to $440,000 for sale.
Winding Hollow
There are currently 4 single-family homes from $550,000 to $785,000 for sale.
Winter Springs Village
10 homes sold in the past year ranging from $410,000 to $762,500.
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