Windermere's real estate market spans 116 subdivisions and condo communities, ranging from established resale-only enclaves to newer neighborhoods still building out. Keenes Pointe stands out as the largest active community by listing count, and it anchors a market that also includes prestige, gated addresses like Isleworth, known for its lakefront estates and celebrity residents. Newer growth areas such as Windermere Trails, Ashlin Park, and Westside Village continue to see new construction, while older lakefront neighborhoods around Lake Butler and Lake Down, including Lake Butler Estates and Lake Down Estates, trade almost entirely on resale, with limited turnover and long-held properties. Townhome and villa buyers gravitate toward communities like Carrington, Lake Reams Townhomes, and Preston Square for lower-maintenance living closer to town. Windermere does not currently offer age-restricted 55+ communities, so its subdivisions serve a broad mix of families and move-up buyers rather than retirees. Overall, this is a market built for buyers who want space, water access, and top-tier schools, with price points running from entry-level townhomes into the multimillion-dollar range for lakefront estates in gated, amenity-rich communities.
There is currently 1 single-family home at $5,999,000 for sale.
There are currently 5 single-family homes from $589,000 to $755,000 and 2 townhouses from $410,000 to $445,000 for sale.
There are currently 2 single-family homes from $2,800,000 to $2,995,000 for sale.
There are currently 6 single-family homes from $349,900 to $745,000 for sale.
There are currently 4 single-family homes from $751,400 to $1,750,000 for sale.
There are currently 5 single-family homes from $1,395,000 to $5,390,000 for sale.
There are currently 5 single-family homes from $2,899,000 to $3,990,000 for sale.
There are currently 4 single-family homes from $2,299,000 to $15,500,000 and 3 land listings from $3,100,000 to $8,695,000 for sale.
There are currently 2 single-family homes from $850,000 to $6,800,000 for sale.
There are currently 4 single-family homes from $540,000 to $880,000 for sale.
There are currently 2 townhouses from $399,000 to $449,900 and 2 single-family homes from $673,000 to $780,000 for sale.
There are currently 2 single-family homes from $565,000 to $629,900 for sale.
There are currently 2 single-family homes from $1,985,000 to $2,170,000 for sale.
There are currently 2 single-family homes from $2,090,000 to $2,450,000 for sale.
There are currently 2 single-family homes from $1,169,900 to $1,347,000 for sale.
There is currently 1 single-family home at $11,900,000 for sale.
There are currently 2 single-family homes from $879,000 to $995,000 for sale.
There is currently 1 single-family home at $1,375,000 for sale.
There are currently 26 single-family homes from $2,800,000 to $19,500,000 and 1 land listing at $2,000,000 for sale.
There are currently 31 single-family homes from $940,000 to $15,900,000 for sale.
4 homes sold in the past year ranging from $1,375,000 to $2,925,000.
There are currently 6 townhouses from $399,800 to $449,000 and 2 single-family homes from $1,200,000 to $1,870,000 for sale.
There are currently 4 single-family homes from $900,000 to $3,000,000 for sale.
There are currently 5 townhouses from $556,256 to $641,681 for sale.
There are currently 2 single-family homes from $1,139,000 to $1,500,000 for sale.
2 homes sold in the past year ranging from $1,685,000 to $1,800,000.
There is currently 1 single-family home at $2,500,000 for sale.
There are currently 2 single-family homes from $1,399,900 to $1,595,000 for sale.
3 homes sold in the past year ranging from $3,100,000 to $6,000,000.
There are currently 2 single-family homes from $975,000 to $2,275,000 for sale.
There is currently 1 single-family home at $3,100,000 for sale.
There is currently 1 single-family home at $5,500,000 for sale.
There are currently 7 townhouses from $360,000 to $410,000 for sale.
There are currently 10 single-family homes from $555,000 to $759,000 and 6 townhouses from $349,000 to $380,000 for sale.
There are currently 9 single-family homes from $505,000 to $750,000 for sale.
There are currently 6 condos from $295,000 to $327,000 for sale.
There are currently no homes for sale in Lakeside Village Townhomes.
There is currently 1 single-family home at $990,000 for sale.
There are currently 2 townhouses from $409,900 to $415,000 for sale.
There is currently 1 single-family home at $850,000 for sale.
3 homes sold in the past year ranging from $315,000 to $407,500.
There are currently 2 single-family homes from $3,350,000 to $3,950,000 for sale.
There are currently 2 townhouses from $330,000 to $400,000 for sale.
There is currently 1 single-family home at $1,289,000 for sale.
There are currently 6 single-family homes from $979,990 to $1,305,990 for sale.
There is currently 1 single-family home at $809,500 for sale.
There are currently 2 townhouses from $444,900 to $475,000 and 1 single-family home at $575,000 for sale.
There are currently 4 single-family homes from $645,000 to $750,000 for sale.
There are currently 2 single-family homes from $1,275,000 to $1,900,000 and 1 land listing at $1,000,000 for sale.
There are currently 6 single-family homes from $1,100,000 to $1,795,000 for sale.
2 homes sold in the past year ranging from $1,365,000 to $1,650,000.
There are currently 1 single-family home at $2,542,000 and 1 land listing at $875,000 for sale.
There are currently 7 single-family homes from $539,900 to $945,000 for sale.
There are currently 2 townhouses from $375,000 to $379,000 for sale.
2 homes sold in the past year ranging from $1,000,000 to $1,700,000.
There is currently 1 single-family home at $625,000 for sale.
There are currently 3 single-family homes from $2,950,000 to $4,995,000 for sale.
There are currently 2 townhouses from $375,000 to $405,000 for sale.
There are currently 3 single-family homes from $1,318,000 to $1,500,000 for sale.
6 homes sold in the past year ranging from $620,000 to $986,000.
There is currently 1 single-family home at $1,488,000 for sale.
There are currently 5 single-family homes from $625,000 to $769,000 and 3 townhouses from $444,900 to $510,000 for sale.
There is currently 1 single-family home at $2,150,000 for sale.
There are currently 3 single-family homes from $1,575,000 to $2,600,000 for sale.
There are currently 2 single-family homes from $740,000 to $969,000 for sale.
There are currently 7 single-family homes from $499,990 to $1,300,000 for sale.
There are currently 2 single-family homes from $799,000 to $1,100,000 for sale.
There are currently 2 single-family homes from $520,000 to $610,000 and 2 townhouses from $354,900 to $399,000 for sale.
There are currently 4 single-family homes from $899,000 to $1,179,000 for sale.
There are currently 5 single-family homes from $679,000 to $1,479,000 for sale.
2 homes sold in the past year ranging from $1,120,000 to $1,210,000.
There are currently 5 single-family homes from $775,000 to $1,396,000 for sale.
There are currently 3 single-family homes from $520,000 to $1,590,000 for sale.
There is currently 1 single-family home at $1,150,000 for sale.
There are currently 4 single-family homes from $675,000 to $999,999 and 3 townhouses from $440,000 to $485,000 for sale.
There are currently 2 single-family homes from $639,000 to $775,000 for sale.
There are currently 14 single-family homes from $470,000 to $1,350,000 and 2 townhouses from $438,000 to $475,000 for sale.
There are currently 2 single-family homes from $1,375,000 to $1,395,000 for sale.
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