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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 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 11410 Rapallo Lane, Windermere, FL 34786 (MLS # O6265256)
    $780,000
    Photo of 11410 Rapallo Lane, Windermere, FL 34786 (MLS # O6265256)
    Photo of 11410 Rapallo Lane, Windermere, FL 34786 (MLS # O6265256)
    11410 Rapallo Lane, Windermere, FL
    11410 Rapallo Lane
    Windermere, FL
    • 6 Beds
    • 6 Baths
    • 3,336 Home (sqft)
    • 6 Baths
    • 7,406 Lot (sqft)
  2. Photo of Windermere, FL 34786 (MLS # O6265091)
    $749,000
    Photo of Windermere, FL 34786 (MLS # O6265091)
    Photo of Windermere, FL 34786 (MLS # O6265091)
    MLS # O6265091, Windermere, FL
    MLS # O6265091
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,864 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  3. Photo of 647 Ridgewood Drive, Windermere, FL 34786 (MLS # O6263552)
    $2,349,000
    Photo of 647 Ridgewood Drive, Windermere, FL 34786 (MLS # O6263552)
    Photo of 647 Ridgewood Drive, Windermere, FL 34786 (MLS # O6263552)
    647 Ridgewood Drive, Windermere, FL
    647 Ridgewood Drive
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,681 Home (sqft)
    • 3 Baths
    • 1.43 Lot (ac)
  4. 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)
  5. 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)
  6. 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)
  7. 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)
  8. 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)
  9. Photo of 11313 Via Andiamo, Windermere, FL 34786 (MLS # O6264533)
    $659,000
    Photo of 11313 Via Andiamo, Windermere, FL 34786 (MLS # O6264533)
    Photo of 11313 Via Andiamo, Windermere, FL 34786 (MLS # O6264533)
    11313 Via Andiamo, Windermere, FL
    11313 Via Andiamo
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,727 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  10. Photo of 14268 Crest Palm Avenue, Windermere, FL 34786 (MLS # O6264935)
    $1,185,860
    Photo of 14268 Crest Palm Avenue, Windermere, FL 34786 (MLS # O6264935)
    Photo of 14268 Crest Palm Avenue, Windermere, FL 34786 (MLS # O6264935)
    14268 Crest Palm Avenue, Windermere, FL
    14268 Crest Palm Avenue
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,100 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  11. 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)
  12. 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)
  13. 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)
  14. 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)
  15. Photo of 7282 Backwoods Trail, Windermere, FL 34786 (MLS # O6260409)
    $729,000
    Photo of 7282 Backwoods Trail, Windermere, FL 34786 (MLS # O6260409)
    Photo of 7282 Backwoods Trail, Windermere, FL 34786 (MLS # O6260409)
    7282 Backwoods Trail, Windermere, FL
    7282 Backwoods Trail
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,588 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  16. Photo of 14285 Crest Palm Avenue, Windermere, FL 34786 (MLS # O6264873)
    $1,167,355
    Photo of 14285 Crest Palm Avenue, Windermere, FL 34786 (MLS # O6264873)
    Photo of 14285 Crest Palm Avenue, Windermere, FL 34786 (MLS # O6264873)
    14285 Crest Palm Avenue, Windermere, FL
    14285 Crest Palm Avenue
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,100 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
  17. Photo of 14279 Crest Palm Avenue, Windermere, FL 34786 (MLS # O6264780)
    $1,134,769
    Photo of 14279 Crest Palm Avenue, Windermere, FL 34786 (MLS # O6264780)
    Photo of 14279 Crest Palm Avenue, Windermere, FL 34786 (MLS # O6264780)
    14279 Crest Palm Avenue, Windermere, FL
    14279 Crest Palm Avenue
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,687 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  18. 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)
  19. 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)
  20. 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)
  21. Photo of 6818 Trellis Vine Loop, Windermere, FL 34786 (MLS # S5116794)
    $649,000
    Photo of 6818 Trellis Vine Loop, Windermere, FL 34786 (MLS # S5116794)
    Photo of 6818 Trellis Vine Loop, Windermere, FL 34786 (MLS # S5116794)
    6818 Trellis Vine Loop, Windermere, FL
    6818 Trellis Vine Loop
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,015 Home (sqft)
    • 4 Baths
    • 11,326 Lot (sqft)
  22. 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)
  23. Photo of 12023 Gold Creek Trail, Windermere, FL 34786 (MLS # O6261968)
    $1,500,000
    Photo of 12023 Gold Creek Trail, Windermere, FL 34786 (MLS # O6261968)
    Photo of 12023 Gold Creek Trail, Windermere, FL 34786 (MLS # O6261968)
    12023 Gold Creek Trail, Windermere, FL
    12023 Gold Creek Trail
    Windermere, FL
    • 7 Beds
    • 4 Baths
    • 3,928 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  24. Photo of 5516 Remsen Cay Lane, Windermere, FL 34786 (MLS # O6261911)
    $949,000
    Photo of 5516 Remsen Cay Lane, Windermere, FL 34786 (MLS # O6261911)
    Photo of 5516 Remsen Cay Lane, Windermere, FL 34786 (MLS # O6261911)
    5516 Remsen Cay Lane, Windermere, FL
    5516 Remsen Cay Lane
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,070 Home (sqft)
    • 4 Baths
    • 1.27 Lot (ac)
  25. 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)
  26. 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)
  27. 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)
  28. Photo of 9094 Outlook Rock Trail, Windermere, FL 34786 (MLS # S5116451)
    $688,000
    Photo of 9094 Outlook Rock Trail, Windermere, FL 34786 (MLS # S5116451)
    Photo of 9094 Outlook Rock Trail, Windermere, FL 34786 (MLS # S5116451)
    9094 Outlook Rock Trail, Windermere, FL
    9094 Outlook Rock Trail
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,786 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  29. Photo of 8311 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6260434)
    $649,900
    Photo of 8311 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6260434)
    Photo of 8311 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6260434)
    8311 Lookout Pointe Drive, Windermere, FL
    8311 Lookout Pointe Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,460 Home (sqft)
    • 4 Baths
    • 5,228 Lot (sqft)
  30. 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)
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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 12/22/24 12:20 PM PST.

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