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Windermere is located in Orange County, 14 miles southwest of Downtown Orlando. Surrounded by the Butler Chain of Lakes, it provides its residents with beautiful water views and gorgeous landscapes. Use our custom search tool to view all homes for sale under $400k in Windermere. Click here to return to the list of surrounding towns and cities in the Orlando area or here for the list in the Kissimmee area. Have questions? Contact us here or schedule your FREE consultation here.


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  1. Photo of 8863 Newmarket Drive, Windermere, FL 34786 (MLS # O6259448)
    $390,000
    Photo of 8863 Newmarket Drive, Windermere, FL 34786 (MLS # O6259448)
    Photo of 8863 Newmarket Drive, Windermere, FL 34786 (MLS # O6259448)
    31
     
    8863 Newmarket Drive, Windermere, FL
    8863 Newmarket Drive
    Windermere, FL
    • 2 Beds
    • 3 Baths
    • 1,375 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  2. Photo of 11564 Mizzon Drive #309, Windermere, FL 34786 (MLS # G5089293)
    $325,000
    Photo of 11564 Mizzon Drive #309, Windermere, FL 34786 (MLS # G5089293)
    Photo of 11564 Mizzon Drive #309, Windermere, FL 34786 (MLS # G5089293)
    11564 Mizzon Drive #309, Windermere, FL
    11564 Mizzon Drive #309
    Windermere, FL
    • 2 Beds
    • 2 Baths
    • 1,161 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  3. Photo of 8265 Maritime Flag Street #S, Windermere, FL 34786 (MLS # O6251830)
    $369,900
    Photo of 8265 Maritime Flag Street #S, Windermere, FL 34786 (MLS # O6251830)
    Photo of 8265 Maritime Flag Street #S, Windermere, FL 34786 (MLS # O6251830)
    8265 Maritime Flag Street #S, Windermere, FL
    8265 Maritime Flag Street #S
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,644 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  4. Photo of 8150 Serenity Spring Drive, Windermere, FL 34786 (MLS # S5114884)
    $347,900
    Photo of 8150 Serenity Spring Drive, Windermere, FL 34786 (MLS # S5114884)
    Photo of 8150 Serenity Spring Drive, Windermere, FL 34786 (MLS # S5114884)
    8150 Serenity Spring Drive, Windermere, FL
    8150 Serenity Spring Drive
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,512 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  5. Photo of 12662 Langstaff Drive, Windermere, FL 34786 (MLS # O6252727)
    $365,000
    Photo of 12662 Langstaff Drive, Windermere, FL 34786 (MLS # O6252727)
    Photo of 12662 Langstaff Drive, Windermere, FL 34786 (MLS # O6252727)
    12662 Langstaff Drive, Windermere, FL
    12662 Langstaff Drive
    Windermere, FL
    • 2 Beds
    • 3 Baths
    • 1,110 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  6. Photo of 11565 Mizzon Drive #804, Windermere, FL 34786 (MLS # O6252549)
    $315,000
    Photo of 11565 Mizzon Drive #804, Windermere, FL 34786 (MLS # O6252549)
    Photo of 11565 Mizzon Drive #804, Windermere, FL 34786 (MLS # O6252549)
    32
     
    11565 Mizzon Drive #804, Windermere, FL
    11565 Mizzon Drive #804
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,455 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  7. Photo of 11562 Amidship Lane #106, Windermere, FL 34786 (MLS # O6250300)
    $339,000
    Photo of 11562 Amidship Lane #106, Windermere, FL 34786 (MLS # O6250300)
    Photo of 11562 Amidship Lane #106, Windermere, FL 34786 (MLS # O6250300)
    11562 Amidship Lane #106, Windermere, FL
    11562 Amidship Lane #106
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,455 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  8. Photo of 8259 Maritime Flag Street #6, Windermere, FL 34786 (MLS # O6246667)
    $345,000
    Photo of 8259 Maritime Flag Street #6, Windermere, FL 34786 (MLS # O6246667)
    Photo of 8259 Maritime Flag Street #6, Windermere, FL 34786 (MLS # O6246667)
    38
     
    8259 Maritime Flag Street #6, Windermere, FL
    8259 Maritime Flag Street #6
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,460 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  9. Photo of 11434 Jasper Kay Terrace #306, Windermere, FL 34786 (MLS # O6245281)
    $365,000
    Photo of 11434 Jasper Kay Terrace #306, Windermere, FL 34786 (MLS # O6245281)
    Photo of 11434 Jasper Kay Terrace #306, Windermere, FL 34786 (MLS # O6245281)
    15
     
    11434 Jasper Kay Terrace #306, Windermere, FL
    11434 Jasper Kay Terrace #306
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,455 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  10. Photo of 8156 Boat Hook Loop #305, Windermere, FL 34786 (MLS # O6220652)
    $315,000
    Photo of 8156 Boat Hook Loop #305, Windermere, FL 34786 (MLS # O6220652)
    Photo of 8156 Boat Hook Loop #305, Windermere, FL 34786 (MLS # O6220652)
    8156 Boat Hook Loop #305, Windermere, FL
    8156 Boat Hook Loop #305
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,332 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  11. Photo of 8156 Boat Hook Loop #614, Windermere, FL 34786 (MLS # S5100831)
    $330,000
    Photo of 8156 Boat Hook Loop #614, Windermere, FL 34786 (MLS # S5100831)
    Photo of 8156 Boat Hook Loop #614, Windermere, FL 34786 (MLS # S5100831)
    8156 Boat Hook Loop #614, Windermere, FL
    8156 Boat Hook Loop #614
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,455 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  12. Photo of 11562 Amidship Lane #105, Windermere, FL 34786 (MLS # O6167293)
    $345,000
    Photo of 11562 Amidship Lane #105, Windermere, FL 34786 (MLS # O6167293)
    Photo of 11562 Amidship Lane #105, Windermere, FL 34786 (MLS # O6167293)
    23
     
    11562 Amidship Lane #105, Windermere, FL
    11562 Amidship Lane #105
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,332 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
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