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Real estate in the city of Windermere

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  1. Photo of 11524 Claymont Circle, Windermere, FL 34786 (MLS # O6410754)
    $1,288,999
    Photo of 11524 Claymont Circle, Windermere, FL 34786 (MLS # O6410754)
    Photo of 11524 Claymont Circle, Windermere, FL 34786 (MLS # O6410754)
    11524 Claymont Circle, Windermere, FL
    11524 Claymont Circle
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,358 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
  2. Photo of 9317 Gladys Garden Court, Windermere, FL 34786 (MLS # O6410843)
    $7,999,000
    Photo of 9317 Gladys Garden Court, Windermere, FL 34786 (MLS # O6410843)
    Photo of 9317 Gladys Garden Court, Windermere, FL 34786 (MLS # O6410843)
    3
     
    9317 Gladys Garden Court, Windermere, FL
    9317 Gladys Garden Court
    Windermere, FL
    • 6 Beds
    • 9 Baths
    • 8,038 Home (sqft)
    • 9 Baths
    • 11,326 Lot (sqft)
  3. Photo of 5199 Latrobe Dr, Windermere, FL 34786 (MLS # O6409961)
    $5,300,000
    Photo of 5199 Latrobe Dr, Windermere, FL 34786 (MLS # O6409961)
    Photo of 5199 Latrobe Dr, Windermere, FL 34786 (MLS # O6409961)
    5199 Latrobe Dr, Windermere, FL
    5199 Latrobe Dr
    Windermere, FL
    • 6 Beds
    • 7 Baths
    • 4,665 Home (sqft)
    • 7 Baths
    • 22,652 Lot (sqft)
  4. Photo of 12784 Garridan Avenue, Windermere, FL 34786 (MLS # O6411120)
    $3,100
    Photo of 12784 Garridan Avenue, Windermere, FL 34786 (MLS # O6411120)
    Photo of 12784 Garridan Avenue, Windermere, FL 34786 (MLS # O6411120)
    12784 Garridan Avenue, Windermere, FL
    12784 Garridan Avenue
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 1,970 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  5. Photo of 12623 Park Avenue, Windermere, FL 34786 (MLS # O6410693)
    $3,800,000
    Photo of 12623 Park Avenue, Windermere, FL 34786 (MLS # O6410693)
    Photo of 12623 Park Avenue, Windermere, FL 34786 (MLS # O6410693)
    12623 Park Avenue, Windermere, FL
    12623 Park Avenue
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 7,120 Home (sqft)
    • 7 Baths
    • 1.02 Lot (ac)
  6. Photo of 17514 Black Rail Street, Windermere, FL 34786 (MLS # O6410722)
    $3,995
    Photo of 17514 Black Rail Street, Windermere, FL 34786 (MLS # O6410722)
    Photo of 17514 Black Rail Street, Windermere, FL 34786 (MLS # O6410722)
    17514 Black Rail Street, Windermere, FL
    17514 Black Rail Street
    Windermere, FL
    • 4 Beds
    • 2 Baths
    • 2,373 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  7. Photo of 13730 Calera Alley, Windermere, FL 34786 (MLS # O6410129)
    $465,000
    Photo of 13730 Calera Alley, Windermere, FL 34786 (MLS # O6410129)
    Photo of 13730 Calera Alley, Windermere, FL 34786 (MLS # O6410129)
    13730 Calera Alley, Windermere, FL
    13730 Calera Alley
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,091 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  8. Photo of 1700 Lake Roberts Court, Windermere, FL 34786 (MLS # O6410847)
    $1,450,000
    Photo of 1700 Lake Roberts Court, Windermere, FL 34786 (MLS # O6410847)
    Photo of 1700 Lake Roberts Court, Windermere, FL 34786 (MLS # O6410847)
    1700 Lake Roberts Court, Windermere, FL
    1700 Lake Roberts Court
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,929 Home (sqft)
    • 4 Baths
    • 25,265 Lot (sqft)
  9. Photo of 11538 Delwick Drive, Windermere, FL 34786 (MLS # O6410311)
    $6,150
    Photo of 11538 Delwick Drive, Windermere, FL 34786 (MLS # O6410311)
    Photo of 11538 Delwick Drive, Windermere, FL 34786 (MLS # O6410311)
    11538 Delwick Drive, Windermere, FL
    11538 Delwick Drive
    Windermere, FL
    • 6 Beds
    • 5 Baths
    • 4,028 Home (sqft)
    • 5 Baths
    • 11,762 Lot (sqft)
  10. Photo of 7867 Berkshire Oak Alley, Windermere, FL 34786 (MLS # S5149947)
    $539,000
    Photo of 7867 Berkshire Oak Alley, Windermere, FL 34786 (MLS # S5149947)
    Photo of 7867 Berkshire Oak Alley, Windermere, FL 34786 (MLS # S5149947)
    7867 Berkshire Oak Alley, Windermere, FL
    7867 Berkshire Oak Alley
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,221 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  11. Photo of 2230 Ridgewind Way, Windermere, FL 34786 (MLS # O6410264)
    $1,259,000
    Photo of 2230 Ridgewind Way, Windermere, FL 34786 (MLS # O6410264)
    Photo of 2230 Ridgewind Way, Windermere, FL 34786 (MLS # O6410264)
    39
     
    2230 Ridgewind Way, Windermere, FL
    2230 Ridgewind Way
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,064 Home (sqft)
    • 4 Baths
    • 22,216 Lot (sqft)
  12. Photo of 14252 Confetti Drive, Windermere, FL 34786 (MLS # O6410196)
    $3,099
    Photo of 14252 Confetti Drive, Windermere, FL 34786 (MLS # O6410196)
    Photo of 14252 Confetti Drive, Windermere, FL 34786 (MLS # O6410196)
    14252 Confetti Drive, Windermere, FL
    14252 Confetti Drive
    Windermere, FL
    • 1 Bed
    • 1 Bath
    • 320 Home (sqft)
    • 1 Bath
    • 3,050 Lot (sqft)
  13. Photo of 12702 Salomon Cove Drive, Windermere, FL 34786 (MLS # O6408108)
    $2,600
    Photo of 12702 Salomon Cove Drive, Windermere, FL 34786 (MLS # O6408108)
    Photo of 12702 Salomon Cove Drive, Windermere, FL 34786 (MLS # O6408108)
    12702 Salomon Cove Drive, Windermere, FL
    12702 Salomon Cove Drive
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,670 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  14. Photo of 14442 Desert Haven Street #4305, Windermere, FL 34786 (MLS # O6410152)
    $359,900
    Photo of 14442 Desert Haven Street #4305, Windermere, FL 34786 (MLS # O6410152)
    Photo of 14442 Desert Haven Street #4305, Windermere, FL 34786 (MLS # O6410152)
    14442 Desert Haven Street #4305, Windermere, FL
    14442 Desert Haven Street #4305
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,534 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  15. Photo of 4303 Isabella Circle, Windermere, FL 34786 (MLS # O6409406)
    $2,899,000
    Photo of 4303 Isabella Circle, Windermere, FL 34786 (MLS # O6409406)
    Photo of 4303 Isabella Circle, Windermere, FL 34786 (MLS # O6409406)
    100
     
     
    4303 Isabella Circle, Windermere, FL
    4303 Isabella Circle
    Windermere, FL
    • 7 Beds
    • 6 Baths
    • 5,122 Home (sqft)
    • 6 Baths
    • 27,443 Lot (sqft)
  16. Photo of 811 Main Street, Windermere, FL 34786 (MLS # O6409463)
    $649,999
    Photo of 811 Main Street, Windermere, FL 34786 (MLS # O6409463)
    Photo of 811 Main Street, Windermere, FL 34786 (MLS # O6409463)
    811 Main Street, Windermere, FL
    811 Main Street
    Windermere, FL
    • 2 Beds
    • 2 Baths
    • 1,398 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  17. Photo of 11326 Ledgement Lane, Windermere, FL 34786 (MLS # O6409714)
    $899,999
    Photo of 11326 Ledgement Lane, Windermere, FL 34786 (MLS # O6409714)
    Photo of 11326 Ledgement Lane, Windermere, FL 34786 (MLS # O6409714)
    11326 Ledgement Lane, Windermere, FL
    11326 Ledgement Lane
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,182 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
  18. Photo of 8180 Boat Hook Loop #109, Windermere, FL 34786 (MLS # S5150297)
    $299,500
    Photo of 8180 Boat Hook Loop #109, Windermere, FL 34786 (MLS # S5150297)
    Photo of 8180 Boat Hook Loop #109, Windermere, FL 34786 (MLS # S5150297)
    8180 Boat Hook Loop #109, Windermere, FL
    8180 Boat Hook Loop #109
    Windermere, FL
    • 2 Beds
    • 2 Baths
    • 1,161 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  19. Photo of 9527 Queensbury Court, Windermere, FL 34786 (MLS # O6408997)
    $1,499,900
    Photo of 9527 Queensbury Court, Windermere, FL 34786 (MLS # O6408997)
    Photo of 9527 Queensbury Court, Windermere, FL 34786 (MLS # O6408997)
    9527 Queensbury Court, Windermere, FL
    9527 Queensbury Court
    Windermere, FL
    • 5 Beds
    • 6 Baths
    • 5,378 Home (sqft)
    • 6 Baths
    • 21,345 Lot (sqft)
  20. Photo of 13272 Penshurst Lane, Windermere, FL 34786 (MLS # S5150230)
    $4,000
    Photo of 13272 Penshurst Lane, Windermere, FL 34786 (MLS # S5150230)
    Photo of 13272 Penshurst Lane, Windermere, FL 34786 (MLS # S5150230)
    13272 Penshurst Lane, Windermere, FL
    13272 Penshurst Lane
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,472 Home (sqft)
    • 4 Baths
    • 6,534 Lot (sqft)
  21. Photo of 7652 Ripplepointe Way, Windermere, FL 34786 (MLS # O6409167)
    $2,750
    Photo of 7652 Ripplepointe Way, Windermere, FL 34786 (MLS # O6409167)
    Photo of 7652 Ripplepointe Way, Windermere, FL 34786 (MLS # O6409167)
    7652 Ripplepointe Way, Windermere, FL
    7652 Ripplepointe Way
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,743 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  22. Photo of 14341 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5112469)
    $1,130,643
    Photo of 14341 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5112469)
    Photo of 14341 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5112469)
    1
     
    14341 Crest Palm Avenue, Windermere, FL
    14341 Crest Palm Avenue
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,153 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
  23. Photo of 9109 Legado Drive, Windermere, FL 34786 (MLS # O6408400)
    $2,900
    Photo of 9109 Legado Drive, Windermere, FL 34786 (MLS # O6408400)
    Photo of 9109 Legado Drive, Windermere, FL 34786 (MLS # O6408400)
    9109 Legado Drive, Windermere, FL
    9109 Legado Drive
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,687 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  24. Photo of 9548 Crown Prince Lane, Windermere, FL 34786 (MLS # O6407352)
    $1,450,000
    Photo of 9548 Crown Prince Lane, Windermere, FL 34786 (MLS # O6407352)
    Photo of 9548 Crown Prince Lane, Windermere, FL 34786 (MLS # O6407352)
    9548 Crown Prince Lane, Windermere, FL
    9548 Crown Prince Lane
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,997 Home (sqft)
    • 4 Baths
    • 20,909 Lot (sqft)
  25. Photo of 1661 Roberts Landing Road, Windermere, FL 34786 (MLS # O6407725)
    $549,900
    Photo of 1661 Roberts Landing Road, Windermere, FL 34786 (MLS # O6407725)
    Photo of 1661 Roberts Landing Road, Windermere, FL 34786 (MLS # O6407725)
    1661 Roberts Landing Road, Windermere, FL
    1661 Roberts Landing Road
    Windermere, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 2.62 Lot (ac)
  26. Photo of 8866 Herencia Aly, Windermere, FL 34786 (MLS # O6407518)
    $430,000
    Photo of 8866 Herencia Aly, Windermere, FL 34786 (MLS # O6407518)
    Photo of 8866 Herencia Aly, Windermere, FL 34786 (MLS # O6407518)
    8866 Herencia Aly, Windermere, FL
    8866 Herencia Aly
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,577 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  27. Photo of 8355 Torcello Isle Drive, Windermere, FL 34786 (MLS # O6407061)
    $950,000
    Photo of 8355 Torcello Isle Drive, Windermere, FL 34786 (MLS # O6407061)
    Photo of 8355 Torcello Isle Drive, Windermere, FL 34786 (MLS # O6407061)
    73
     
    8355 Torcello Isle Drive, Windermere, FL
    8355 Torcello Isle Drive
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 4,202 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
  28. Photo of 5603 Marleon Drive, Windermere, FL 34786 (MLS # O6404938)
    $27,000,000
    Photo of 5603 Marleon Drive, Windermere, FL 34786 (MLS # O6404938)
    Photo of 5603 Marleon Drive, Windermere, FL 34786 (MLS # O6404938)
    92
     
    5603 Marleon Drive, Windermere, FL
    5603 Marleon Drive
    Windermere, FL
    • 7 Beds
    • 10 Baths
    • 22,108 Home (sqft)
    • 10 Baths
    • 11.58 Lot (ac)
  29. Photo of 33 Main Street, Windermere, FL 34786 (MLS # O6406887)
    $1,575,000
    Photo of 33 Main Street, Windermere, FL 34786 (MLS # O6406887)
    Photo of 33 Main Street, Windermere, FL 34786 (MLS # O6406887)
    4
     
    33 Main Street, Windermere, FL
    33 Main Street
    Windermere, FL
    • 4 Beds
    • 2 Baths
    • 2,130 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  30. Photo of 6462 Deacon Cir, Windermere, FL 34786 (MLS # O6407107)
    $6,950,000
    Photo of 6462 Deacon Cir, Windermere, FL 34786 (MLS # O6407107)
    Photo of 6462 Deacon Cir, Windermere, FL 34786 (MLS # O6407107)
    6462 Deacon Cir, Windermere, FL
    6462 Deacon Cir
    Windermere, FL
    • 5 Beds
    • 6 Baths
    • 7,178 Home (sqft)
    • 6 Baths
    • 27,879 Lot (sqft)
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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 6/30/26 11:41 PM PDT.

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