Winter Garden's resale and new-build market spans 171 subdivisions and condo buildings, ranging from established in-town neighborhoods to master-planned communities still building out west of downtown. Waterleigh stands out as the largest active community by listing volume, anchoring the Hamlin corridor alongside neighboring sections like Hamlin Meadows at Hamlin and Avalon Woods. Buyers wanting new construction have plenty to choose from, with 75 communities still building, including Storey Grove, Esplanade at McKinnon Groves, and the Ovation collection of neighborhoods such as Westhaven at Ovation, Serenade at Ovation, and Harvest at Ovation. For buyers 55 and older, Del Webb Oasis is the city's dedicated active adult community. Older, resale-only pockets like Deer Island, Foxcrest, and Tuscany round out the inventory with no current new-home activity, giving the market a genuine mix of mature tree-lined streets and fresh subdivisions still under development. Condo buyers aren't left out either, with options at The Grove Resort and Spa and Southern Pines. Overall, Winter Garden's subdivisions serve a broad range of move-up families, downtown-adjacent lifestyle buyers, and retirees, spanning entry-level condos into the multimillion-dollar lakefront estate segment.
There are currently 4 townhouses from $394,000 to $454,990 and 19 single-family homes from $487,500 to $874,000 for sale.
There are currently 2 single-family homes from $509,900 to $599,000 for sale.
There are currently 1 land listing at $299,000 and 3 single-family homes from $499,900 to $620,000 for sale.
There are currently 2 single-family homes from $1,339,000 to $1,999,000 for sale.
3 homes sold in the past year ranging from $1,190,500 to $1,910,500.
5 homes sold in the past year ranging from $620,000 to $895,000.
There are currently no homes for sale in Avalon Ridge.
There are currently 34 single-family homes from $579,820 to $1,016,060 for sale.
There are currently 2 single-family homes from $529,900 to $649,900 for sale.
There are currently 3 single-family homes from $669,000 to $1,089,000 for sale.
There is currently 1 single-family home at $600,000 for sale.
There are currently 4 single-family homes from $640,000 to $1,060,000 for sale.
There are currently 4 single-family homes from $699,000 to $1,499,990 for sale.
There are currently 1 single-family home at $649,999 and 1 multi-unit property at $699,000 for sale.
There are currently 2 single-family homes from $595,000 to $820,000 for sale.
There is currently 1 single-family home at $1,360,000 for sale.
There are currently 3 single-family homes from $650,000 to $810,000 for sale.
3 homes sold in the past year ranging from $485,000 to $520,000.
There are currently no homes for sale in Country Trail Estates.
There are currently 4 single-family homes from $552,275 to $800,000 for sale.
There are currently 2 single-family homes from $449,500 to $1,150,000 for sale.
There are currently 3 townhouses from $307,000 to $325,000 for sale.
There are currently 2 single-family homes from $380,000 to $410,000 for sale.
There is currently 1 single-family home at $1,495,000 for sale.
There are currently 2 single-family homes from $620,000 to $645,000 for sale.
There are currently 13 single-family homes from $392,500 to $967,500 for sale.
There are currently 2 single-family homes from $334,000 to $825,000 and 1 multi-unit property at $825,000 for sale.
There are currently 2 single-family homes from $425,000 to $525,000 for sale.
2 homes sold in the past year ranging from $395,000 to $435,000.
There are currently 2 single-family homes from $545,000 to $735,000 for sale.
There are currently 5 single-family homes from $435,000 to $879,900 and 3 townhouses from $435,070 to $510,000 for sale.
There are currently 14 single-family homes from $400,000 to $925,000 for sale.
There are currently 2 single-family homes from $693,000 to $1,159,825 for sale.
There are currently 2 single-family homes from $450,000 to $570,000 for sale.
There are currently 2 single-family homes from $414,990 to $485,000 for sale.
There are currently 2 single-family homes from $541,999 to $589,900 for sale.
There are currently 2 single-family homes from $425,000 to $565,000 for sale.
There are currently 6 single-family homes from $790,000 to $899,000 for sale.
There is currently 1 single-family home at $599,000 for sale.
There are currently 2 townhouses from $375,000 to $400,000 and 2 single-family homes from $473,000 to $859,990 for sale.
There are currently 44 single-family homes from $510,880 to $909,990 and 3 townhouses from $449,990 to $473,797 for sale.
There are currently 6 single-family homes from $539,900 to $859,000 and 3 townhouses from $394,500 to $485,000 for sale.
There are currently 3 townhouses from $434,990 to $461,190 for sale.
There are currently 26 single-family homes from $530,000 to $833,771, 1 townhouse at $449,000 and 1 condo at $227,900 for sale.
There are currently 3 townhouses from $394,000 to $439,900 and 9 single-family homes from $559,000 to $1,325,000 for sale.
4 homes sold in the past year ranging from $485,000 to $735,000.
There are currently 2 townhouses from $410,000 to $473,000 and 2 single-family homes from $924,900 to $1,999,999 for sale.
There are currently 13 single-family homes from $464,900 to $599,000 for sale.
There are currently 3 single-family homes from $465,000 to $649,900 and 2 townhouses from $465,000 to $469,900 for sale.
There are currently 4 single-family homes from $635,000 to $825,000 for sale.
There are currently 20 single-family homes from $499,900 to $4,300,000 and 11 townhouses from $329,000 to $488,000 for sale.
There is currently 1 single-family home at $2,300,000 for sale.
There is currently 1 single-family home at $699,900 for sale.
There are currently 3 single-family homes from $568,990 to $1,129,900 for sale.
There are currently 3 land listings from $975,000 to $2,470,000 and 4 single-family homes from $1,150,000 to $2,790,000 for sale.
There are currently 2 single-family homes from $849,988 to $925,000 for sale.
There are currently 4 single-family homes from $543,000 to $708,900 for sale.
There are currently 2 single-family homes from $1,200,000 to $1,399,999 for sale.
There are currently 8 single-family homes from $559,990 to $929,990 for sale.
There are currently 5 single-family homes from $535,000 to $2,985,000 for sale.
There are currently 5 single-family homes from $450,000 to $1,675,000 for sale.
There are currently 4 townhouses from $604,580 to $697,240 and 3 single-family homes from $899,760 to $1,157,190 for sale.
There are currently 2 single-family homes from $619,000 to $695,000 for sale.
There are currently 2 single-family homes from $640,738 to $685,000 for sale.
There are currently 3 single-family homes from $329,900 to $579,000 and 1 land listing at $389,000 for sale.
There is currently 1 single-family home at $709,900 for sale.
There are currently 4 single-family homes from $595,000 to $648,500 for sale.
There are currently 3 townhouses from $455,000 to $475,000 for sale.
There are currently 3 single-family homes from $570,000 to $625,000 for sale.
There are currently 18 single-family homes from $649,000 to $1,350,000 and 1 townhouse at $410,000 for sale.
There is currently 1 single-family home at $445,000 for sale.
There are currently 1 land listing at $535,000 and 1 single-family home at $1,899,999 for sale.
There are currently 10 single-family homes from $789,000 to $2,495,000 for sale.
7 homes sold in the past year ranging from $392,500 to $606,000.
There are currently 2 single-family homes from $399,900 to $489,000 for sale.
There are currently 7 single-family homes from $519,995 to $910,000 and 1 townhouse at $355,000 for sale.
There are currently 8 single-family homes from $563,000 to $1,085,669 and 1 townhouse at $440,000 for sale.
There are currently 3 single-family homes from $869,000 to $999,000 for sale.
There are currently 4 single-family homes from $525,000 to $1,200,000 for sale.
There is currently 1 single-family home at $325,000 for sale.
There are currently 6 townhouses from $785,000 to $1,095,000 for sale.
There are currently 10 townhouses from $478,990 to $530,000 for sale.
There are currently 2 townhouses from $399,900 to $410,000 for sale.
There are currently 2 single-family homes from $575,000 to $614,900 for sale.
There are currently 4 single-family homes from $685,000 to $2,250,000 for sale.
There are currently 11 single-family homes from $498,900 to $778,531 and 7 townhouses from $419,990 to $456,496 for sale.
There are currently 8 single-family homes from $519,090 to $925,000 and 6 townhouses from $433,190 to $495,090 for sale.
There is currently 1 single-family home at $515,000 for sale.
There are currently 3 single-family homes from $505,125 to $580,495 for sale.
There are currently 13 condos from $204,900 to $325,000 for sale.
There are currently 6 single-family homes from $359,900 to $507,000 for sale.
There are currently 18 single-family homes from $435,000 to $915,000 and 14 townhouses from $389,900 to $498,000 for sale.
There are currently 3 single-family homes from $519,000 to $779,000 and 1 townhouse at $434,900 for sale.
There are currently 1 townhouse at $389,900 and 1 single-family home at $584,900 for sale.
There is currently 1 single-family home at $989,000 for sale.
There is currently 1 single-family home at $3,799,000 for sale.
There are currently 14 condos from $169,000 to $399,000 for sale.
There is currently 1 single-family home at $579,000 for sale.
5 homes sold in the past year ranging from $645,000 to $1,350,000.
9 homes sold in the past year ranging from $695,000 to $935,000.
There is currently 1 single-family home at $789,000 for sale.
There is currently 1 single-family home at $534,000 for sale.
4 homes sold in the past year ranging from $434,000 to $512,000.
There are currently 2 townhouses from $379,000 to $384,900 and 4 condos from $299,900 to $335,000 for sale.
There are currently 2 single-family homes from $560,000 to $589,000 for sale.
There are currently 6 single-family homes from $749,000 to $1,699,900 for sale.
There is currently 1 single-family home at $665,000 for sale.
There are currently 3 single-family homes from $774,000 to $925,000 for sale.
There are currently 2 townhouses from $165,000 to $218,000 for sale.
There are currently 2 townhouses from $460,000 to $525,000 for sale.
There are currently 49 single-family homes from $469,500 to $1,499,000 and 11 townhouses from $389,000 to $502,500 for sale.
There are currently 14 single-family homes from $435,800 to $1,150,000 and 2 townhouses from $429,900 to $529,000 for sale.
There are currently 10 single-family homes from $515,000 to $2,575,000 for sale.
There are currently 3 single-family homes from $650,000 to $729,000 for sale.
There are currently 13 single-family homes from $537,000 to $929,000 and 14 townhouses from $411,995 to $615,000 for sale.
There are currently 2 single-family homes from $585,000 to $750,000 for sale.
There are currently 3 townhouses from $189,000 to $295,000 for sale.
There are currently 9 single-family homes from $514,000 to $1,160,000 for sale.
There are currently 2 single-family homes from $800,000 to $829,500 for sale.
There are currently 5 single-family homes from $848,270 to $1,219,170 for sale.
There are currently 2 single-family homes from $680,000 to $749,995 for sale.
There are currently 4 single-family homes from $699,000 to $729,900 for sale.
There are currently 2 single-family homes from $765,000 to $790,000 for sale.
There is currently 1 single-family home at $619,999 for sale.
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