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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 pool homes for sale above $600k 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 12507 Overstreet Road, Windermere, FL 34786 (MLS # O6264872)
    $780,000
    Photo of 12507 Overstreet Road, Windermere, FL 34786 (MLS # O6264872)
    Photo of 12507 Overstreet Road, Windermere, FL 34786 (MLS # O6264872)
    12507 Overstreet Road, Windermere, FL
    12507 Overstreet Road
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,768 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  2. Photo of 8961 Lookout Pointe Drive, Windermere, FL 34786 (MLS # S5117255)
    $1,150,000
    Photo of 8961 Lookout Pointe Drive, Windermere, FL 34786 (MLS # S5117255)
    Photo of 8961 Lookout Pointe Drive, Windermere, FL 34786 (MLS # S5117255)
    8961 Lookout Pointe Drive, Windermere, FL
    8961 Lookout Pointe Drive
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 4,050 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
  3. Photo of 1295 Estancia Woods Loop, Windermere, FL 34786 (MLS # O6263134)
    $1,595,000
    Photo of 1295 Estancia Woods Loop, Windermere, FL 34786 (MLS # O6263134)
    Photo of 1295 Estancia Woods Loop, Windermere, FL 34786 (MLS # O6263134)
    1295 Estancia Woods Loop, Windermere, FL
    1295 Estancia Woods Loop
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 4,098 Home (sqft)
    • 5 Baths
    • 13,940 Lot (sqft)
  4. Photo of 12540 Park Avenue, Windermere, FL 34786 (MLS # O6265036)
    $4,650,000
    Photo of 12540 Park Avenue, Windermere, FL 34786 (MLS # O6265036)
    Photo of 12540 Park Avenue, Windermere, FL 34786 (MLS # O6265036)
    12540 Park Avenue, Windermere, FL
    12540 Park Avenue
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 7,736 Home (sqft)
    • 7 Baths
    • 43,560 Lot (sqft)
  5. Photo of 109 E 12th Avenue, Windermere, FL 34786 (MLS # O6264634)
    $1,439,000
    Photo of 109 E 12th Avenue, Windermere, FL 34786 (MLS # O6264634)
    Photo of 109 E 12th Avenue, Windermere, FL 34786 (MLS # O6264634)
    109 E 12th Avenue, Windermere, FL
    109 E 12th Avenue
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,791 Home (sqft)
    • 4 Baths
    • 12,633 Lot (sqft)
  6. Photo of 9343 Tibet Pointe Circle, Windermere, FL 34786 (MLS # O6264629)
    $8,790,000
    Photo of 9343 Tibet Pointe Circle, Windermere, FL 34786 (MLS # O6264629)
    Photo of 9343 Tibet Pointe Circle, Windermere, FL 34786 (MLS # O6264629)
    100
     
    9343 Tibet Pointe Circle, Windermere, FL
    9343 Tibet Pointe Circle
    Windermere, FL
    • 8 Beds
    • 10 Baths
    • 8,362 Home (sqft)
    • 10 Baths
    • 1.54 Lot (ac)
  7. Photo of 9301 Tibet Pointe Circle, Windermere, FL 34786 (MLS # O6263524)
    $6,500,000
    Photo of 9301 Tibet Pointe Circle, Windermere, FL 34786 (MLS # O6263524)
    Photo of 9301 Tibet Pointe Circle, Windermere, FL 34786 (MLS # O6263524)
    9301 Tibet Pointe Circle, Windermere, FL
    9301 Tibet Pointe Circle
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 7,405 Home (sqft)
    • 7 Baths
    • 2.40 Lot (ac)
  8. Photo of 1913 Westover Reserve Boulevard, Windermere, FL 34786 (MLS # O6263447)
    $899,000
    Photo of 1913 Westover Reserve Boulevard, Windermere, FL 34786 (MLS # O6263447)
    Photo of 1913 Westover Reserve Boulevard, Windermere, FL 34786 (MLS # O6263447)
    42
     
    1913 Westover Reserve Boulevard, Windermere, FL
    1913 Westover Reserve Boulevard
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,656 Home (sqft)
    • 3 Baths
    • 11,326 Lot (sqft)
  9. Photo of 6326 Swanson Street, Windermere, FL 34786 (MLS # O6264310)
    $1,250,000
    Photo of 6326 Swanson Street, Windermere, FL 34786 (MLS # O6264310)
    Photo of 6326 Swanson Street, Windermere, FL 34786 (MLS # O6264310)
    6326 Swanson Street, Windermere, FL
    6326 Swanson Street
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,295 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  10. Photo of 9111 Outlook Rock Trail, Windermere, FL 34786 (MLS # S5116911)
    $1,130,000
    Photo of 9111 Outlook Rock Trail, Windermere, FL 34786 (MLS # S5116911)
    Photo of 9111 Outlook Rock Trail, Windermere, FL 34786 (MLS # S5116911)
    9111 Outlook Rock Trail, Windermere, FL
    9111 Outlook Rock Trail
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 4,070 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
  11. Photo of 9664 Weatherstone Court, Windermere, FL 34786 (MLS # O6263072)
    $2,899,999
    Photo of 9664 Weatherstone Court, Windermere, FL 34786 (MLS # O6263072)
    Photo of 9664 Weatherstone Court, Windermere, FL 34786 (MLS # O6263072)
    9664 Weatherstone Court, Windermere, FL
    9664 Weatherstone Court
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 6,200 Home (sqft)
    • 7 Baths
    • 1.74 Lot (ac)
  12. Photo of 1140 Kelso Boulevard, Windermere, FL 34786 (MLS # O6263154)
    $2,650,000
    Photo of 1140 Kelso Boulevard, Windermere, FL 34786 (MLS # O6263154)
    Photo of 1140 Kelso Boulevard, Windermere, FL 34786 (MLS # O6263154)
    1140 Kelso Boulevard, Windermere, FL
    1140 Kelso Boulevard
    Windermere, FL
    • 6 Beds
    • 6 Baths
    • 6,003 Home (sqft)
    • 6 Baths
    • 1.19 Lot (ac)
  13. Photo of 2812 Marquesas Court, Windermere, FL 34786 (MLS # O6262787)
    $3,150,000
    Photo of 2812 Marquesas Court, Windermere, FL 34786 (MLS # O6262787)
    Photo of 2812 Marquesas Court, Windermere, FL 34786 (MLS # O6262787)
    2812 Marquesas Court, Windermere, FL
    2812 Marquesas Court
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 5,624 Home (sqft)
    • 5 Baths
    • 1.36 Lot (ac)
  14. Photo of 1003 Oakdale Street, Windermere, FL 34786 (MLS # O6261656)
    $2,999,999
    Photo of 1003 Oakdale Street, Windermere, FL 34786 (MLS # O6261656)
    Photo of 1003 Oakdale Street, Windermere, FL 34786 (MLS # O6261656)
    1003 Oakdale Street, Windermere, FL
    1003 Oakdale Street
    Windermere, FL
    • 6 Beds
    • 6 Baths
    • 4,599 Home (sqft)
    • 6 Baths
    • 1.77 Lot (ac)
  15. Photo of 729 Main St, Windermere, FL 34786 (MLS # S5116063)
    $2,295,000
    Photo of 729 Main St, Windermere, FL 34786 (MLS # S5116063)
    Photo of 729 Main St, Windermere, FL 34786 (MLS # S5116063)
    729 Main St, Windermere, FL
    729 Main St
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,950 Home (sqft)
    • 4 Baths
    • 16,118 Lot (sqft)
  16. Photo of 6245 Little Lake Sawyer Drive, Windermere, FL 34786 (MLS # O6260736)
    $2,497,000
    Photo of 6245 Little Lake Sawyer Drive, Windermere, FL 34786 (MLS # O6260736)
    Photo of 6245 Little Lake Sawyer Drive, Windermere, FL 34786 (MLS # O6260736)
    6245 Little Lake Sawyer Drive, Windermere, FL
    6245 Little Lake Sawyer Drive
    Windermere, FL
    • 7 Beds
    • 5 Baths
    • 5,300 Home (sqft)
    • 5 Baths
    • 24,394 Lot (sqft)
  17. Photo of 5002 Autumn Ridge Court, Windermere, FL 34786 (MLS # O6256198)
    $1,080,000
    Photo of 5002 Autumn Ridge Court, Windermere, FL 34786 (MLS # O6256198)
    Photo of 5002 Autumn Ridge Court, Windermere, FL 34786 (MLS # O6256198)
    5002 Autumn Ridge Court, Windermere, FL
    5002 Autumn Ridge Court
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,328 Home (sqft)
    • 3 Baths
    • 1.03 Lot (ac)
  18. Photo of 12983 Westside Village Loop, Windermere, FL 34786 (MLS # O6259749)
    $1,098,000
    Photo of 12983 Westside Village Loop, Windermere, FL 34786 (MLS # O6259749)
    Photo of 12983 Westside Village Loop, Windermere, FL 34786 (MLS # O6259749)
    12983 Westside Village Loop, Windermere, FL
    12983 Westside Village Loop
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,064 Home (sqft)
    • 4 Baths
    • 5,663 Lot (sqft)
  19. Photo of 5939 Blakeford Drive, Windermere, FL 34786 (MLS # S5115840)
    $1,650,000
    Photo of 5939 Blakeford Drive, Windermere, FL 34786 (MLS # S5115840)
    Photo of 5939 Blakeford Drive, Windermere, FL 34786 (MLS # S5115840)
    5939 Blakeford Drive, Windermere, FL
    5939 Blakeford Drive
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 3,922 Home (sqft)
    • 5 Baths
    • 16,989 Lot (sqft)
  20. Photo of 7508 Lake Albert Drive, Windermere, FL 34786 (MLS # O6258207)
    $915,000
    Photo of 7508 Lake Albert Drive, Windermere, FL 34786 (MLS # O6258207)
    Photo of 7508 Lake Albert Drive, Windermere, FL 34786 (MLS # O6258207)
    7508 Lake Albert Drive, Windermere, FL
    7508 Lake Albert Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,059 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  21. Photo of 4011 Isabella Circle, Windermere, FL 34786 (MLS # O6257592)
    $2,895,900
    Photo of 4011 Isabella Circle, Windermere, FL 34786 (MLS # O6257592)
    Photo of 4011 Isabella Circle, Windermere, FL 34786 (MLS # O6257592)
    59
     
    4011 Isabella Circle, Windermere, FL
    4011 Isabella Circle
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 5,418 Home (sqft)
    • 7 Baths
    • 26,136 Lot (sqft)
  22. Photo of 2045 Woody Drive, Windermere, FL 34786 (MLS # O6256946)
    $995,000
    Photo of 2045 Woody Drive, Windermere, FL 34786 (MLS # O6256946)
    Photo of 2045 Woody Drive, Windermere, FL 34786 (MLS # O6256946)
    51
     
    2045 Woody Drive, Windermere, FL
    2045 Woody Drive
    Windermere, FL
    • 5 Beds
    • 3 Baths
    • 2,831 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
  23. Photo of 9792 Wild Oak Drive, Windermere, FL 34786 (MLS # O6256640)
    $940,000
    Photo of 9792 Wild Oak Drive, Windermere, FL 34786 (MLS # O6256640)
    Photo of 9792 Wild Oak Drive, Windermere, FL 34786 (MLS # O6256640)
    9792 Wild Oak Drive, Windermere, FL
    9792 Wild Oak Drive
    Windermere, FL
    • 3 Beds
    • 4 Baths
    • 3,102 Home (sqft)
    • 4 Baths
    • 15,682 Lot (sqft)
  24. Photo of 6102 S Hampshire Court, Windermere, FL 34786 (MLS # O6257113)
    $2,775,000
    Photo of 6102 S Hampshire Court, Windermere, FL 34786 (MLS # O6257113)
    Photo of 6102 S Hampshire Court, Windermere, FL 34786 (MLS # O6257113)
    6102 S Hampshire Court, Windermere, FL
    6102 S Hampshire Court
    Windermere, FL
    • 4 Beds
    • 6 Baths
    • 4,968 Home (sqft)
    • 6 Baths
    • 19,167 Lot (sqft)
  25. Photo of 98 E 10th Ave, Windermere, FL 34786 (MLS # S5115380)
    $2,300,000
    Photo of 98 E 10th Ave, Windermere, FL 34786 (MLS # S5115380)
    Photo of 98 E 10th Ave, Windermere, FL 34786 (MLS # S5115380)
    98 E 10th Ave, Windermere, FL
    98 E 10th Ave
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,650 Home (sqft)
    • 4 Baths
    • 12,633 Lot (sqft)
  26. Photo of 1548 Lake Rhea Drive, Windermere, FL 34786 (MLS # O6255319)
    $1,289,000
    Photo of 1548 Lake Rhea Drive, Windermere, FL 34786 (MLS # O6255319)
    Photo of 1548 Lake Rhea Drive, Windermere, FL 34786 (MLS # O6255319)
    1548 Lake Rhea Drive, Windermere, FL
    1548 Lake Rhea Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,413 Home (sqft)
    • 4 Baths
    • 12,197 Lot (sqft)
  27. Photo of 4236 Isabella Circle, Windermere, FL 34786 (MLS # O6255112)
    $3,500,000
    Photo of 4236 Isabella Circle, Windermere, FL 34786 (MLS # O6255112)
    Photo of 4236 Isabella Circle, Windermere, FL 34786 (MLS # O6255112)
    4236 Isabella Circle, Windermere, FL
    4236 Isabella Circle
    Windermere, FL
    • 5 Beds
    • 6 Baths
    • 5,393 Home (sqft)
    • 6 Baths
    • 38,333 Lot (sqft)
  28. Photo of 11401 Camden Park Drive, Windermere, FL 34786 (MLS # O6254809)
    $1,575,000
    Photo of 11401 Camden Park Drive, Windermere, FL 34786 (MLS # O6254809)
    Photo of 11401 Camden Park Drive, Windermere, FL 34786 (MLS # O6254809)
    11401 Camden Park Drive, Windermere, FL
    11401 Camden Park Drive
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 3,480 Home (sqft)
    • 5 Baths
    • 12,633 Lot (sqft)
  29. Photo of 4071 Isabella Circle, Windermere, FL 34786 (MLS # O6245923)
    $3,299,000
    Photo of 4071 Isabella Circle, Windermere, FL 34786 (MLS # O6245923)
    Photo of 4071 Isabella Circle, Windermere, FL 34786 (MLS # O6245923)
    4071 Isabella Circle, Windermere, FL
    4071 Isabella Circle
    Windermere, FL
    • 5 Beds
    • 8 Baths
    • 6,752 Home (sqft)
    • 8 Baths
    • 41,382 Lot (sqft)
  30. Photo of 3428 Chaine Du Lac Boulevard, Windermere, FL 34786 (MLS # O6251205)
    $4,500,000
    Photo of 3428 Chaine Du Lac Boulevard, Windermere, FL 34786 (MLS # O6251205)
    Photo of 3428 Chaine Du Lac Boulevard, Windermere, FL 34786 (MLS # O6251205)
    3428 Chaine Du Lac Boulevard, Windermere, FL
    3428 Chaine Du Lac Boulevard
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 6,196 Home (sqft)
    • 7 Baths
    • 1.09 Lot (ac)
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The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 12/23/24 12:20 AM PST.

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