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Real estate in the city of Windermere

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  1. Photo of 13833 Bridgewater Crossings Boulevard, Windermere, FL 34786 (MLS # O6333262)
    $3,250
    Photo of 13833 Bridgewater Crossings Boulevard, Windermere, FL 34786 (MLS # O6333262)
    Photo of 13833 Bridgewater Crossings Boulevard, Windermere, FL 34786 (MLS # O6333262)
    13833 Bridgewater Crossings Boulevard, Windermere, FL
    13833 Bridgewater Crossings Boulevard
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,451 Home (sqft)
    • 4 Baths
    • 2,614 Lot (sqft)
  2. Photo of 13333 Gorgona Isle Drive, Windermere, FL 34786 (MLS # O6330691)
    $480,000
    Photo of 13333 Gorgona Isle Drive, Windermere, FL 34786 (MLS # O6330691)
    Photo of 13333 Gorgona Isle Drive, Windermere, FL 34786 (MLS # O6330691)
    13333 Gorgona Isle Drive, Windermere, FL
    13333 Gorgona Isle Drive
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,779 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  3. Photo of 8582 Powder Ridge Trail, Windermere, FL 34786 (MLS # S5132123)
    $695,000
    Photo of 8582 Powder Ridge Trail, Windermere, FL 34786 (MLS # S5132123)
    Photo of 8582 Powder Ridge Trail, Windermere, FL 34786 (MLS # S5132123)
    8582 Powder Ridge Trail, Windermere, FL
    8582 Powder Ridge Trail
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,297 Home (sqft)
    • 4 Baths
    • 3,921 Lot (sqft)
  4. Photo of 8370 Lookout Point Dr., Windermere, FL 34786 (MLS # S5132148)
    $4,950
    Photo of 8370 Lookout Point Dr., Windermere, FL 34786 (MLS # S5132148)
    Photo of 8370 Lookout Point Dr., Windermere, FL 34786 (MLS # S5132148)
    8370 Lookout Point Dr., Windermere, FL
    8370 Lookout Point Dr.
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 3,934 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  5. Photo of 10702 Reams Road, Windermere, FL 34786 (MLS # S5132145)
    $2,900
    Photo of 10702 Reams Road, Windermere, FL 34786 (MLS # S5132145)
    Photo of 10702 Reams Road, Windermere, FL 34786 (MLS # S5132145)
    10702 Reams Road, Windermere, FL
    10702 Reams Road
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,092 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  6. Photo of 9621 Windy Ridge Road, Windermere, FL 34786 (MLS # O6333091)
    $13,985,000
    Photo of 9621 Windy Ridge Road, Windermere, FL 34786 (MLS # O6333091)
    Photo of 9621 Windy Ridge Road, Windermere, FL 34786 (MLS # O6333091)
    9621 Windy Ridge Road, Windermere, FL
    9621 Windy Ridge Road
    Windermere, FL
    • 9 Beds
    • 16 Baths
    • 20,445 Home (sqft)
    • 16 Baths
    • 2.50 Lot (ac)
  7. Photo of 2107 Westover Reserve Boulevard, Windermere, FL 34786 (MLS # O6333377)
    $1,170,000
    Photo of 2107 Westover Reserve Boulevard, Windermere, FL 34786 (MLS # O6333377)
    Photo of 2107 Westover Reserve Boulevard, Windermere, FL 34786 (MLS # O6333377)
    2107 Westover Reserve Boulevard, Windermere, FL
    2107 Westover Reserve Boulevard
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 4,676 Home (sqft)
    • 4 Baths
    • 16,118 Lot (sqft)
  8. Photo of 14377 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5100373)
    $949,990
    Photo of 14377 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5100373)
    Photo of 14377 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5100373)
    2
     
    14377 Crest Palm Avenue, Windermere, FL
    14377 Crest Palm Avenue
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 3,100 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  9. Photo of 14427 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5100372)
    $1,099,990
    Photo of 14427 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5100372)
    Photo of 14427 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5100372)
    14427 Crest Palm Avenue, Windermere, FL
    14427 Crest Palm Avenue
    Windermere, FL
    • 6 Beds
    • 5 Baths
    • 4,443 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  10. Photo of 9701 Lake Isleworth Court, Windermere, FL 34786 (MLS # O6332649)
    $11,500
    Photo of 9701 Lake Isleworth Court, Windermere, FL 34786 (MLS # O6332649)
    Photo of 9701 Lake Isleworth Court, Windermere, FL 34786 (MLS # O6332649)
    31
     
    9701 Lake Isleworth Court, Windermere, FL
    9701 Lake Isleworth Court
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 3,532 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
  11. Photo of 8192 Boat Hook Loop #206, Windermere, FL 34786 (MLS # O6332621)
    $2,350
    Photo of 8192 Boat Hook Loop #206, Windermere, FL 34786 (MLS # O6332621)
    Photo of 8192 Boat Hook Loop #206, Windermere, FL 34786 (MLS # O6332621)
    8192 Boat Hook Loop #206, Windermere, FL
    8192 Boat Hook Loop #206
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,455 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
  12. Photo of 13730 Lensdale Lane, Windermere, FL 34786 (MLS # O6334553)
    $375,000
    Photo of 13730 Lensdale Lane, Windermere, FL 34786 (MLS # O6334553)
    Photo of 13730 Lensdale Lane, Windermere, FL 34786 (MLS # O6334553)
    13730 Lensdale Lane, Windermere, FL
    13730 Lensdale Lane
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 1,640 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  13. Photo of 8180 Boat Hook Loop #108/301, Windermere, FL 34786 (MLS # TB8413408)
    $325,500
    Photo of 8180 Boat Hook Loop #108/301, Windermere, FL 34786 (MLS # TB8413408)
    Photo of 8180 Boat Hook Loop #108/301, Windermere, FL 34786 (MLS # TB8413408)
    8180 Boat Hook Loop #108/301, Windermere, FL
    8180 Boat Hook Loop #108/301
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,442 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  14. Photo of 8349 Vivaro Isle Way, Windermere, FL 34786 (MLS # O6332473)
    $1,220,000
    Photo of 8349 Vivaro Isle Way, Windermere, FL 34786 (MLS # O6332473)
    Photo of 8349 Vivaro Isle Way, Windermere, FL 34786 (MLS # O6332473)
    51
     
    8349 Vivaro Isle Way, Windermere, FL
    8349 Vivaro Isle Way
    Windermere, FL
    • 6 Beds
    • 4 Baths
    • 4,202 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  15. Photo of 8873 Herencia Alley, Windermere, FL 34786 (MLS # O6332434)
    $2,550
    Photo of 8873 Herencia Alley, Windermere, FL 34786 (MLS # O6332434)
    Photo of 8873 Herencia Alley, Windermere, FL 34786 (MLS # O6332434)
    8873 Herencia Alley, Windermere, FL
    8873 Herencia Alley
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,666 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  16. Photo of 4302 Isabella Circle, Windermere, FL 34786 (MLS # O6331872)
    $15,000
    Photo of 4302 Isabella Circle, Windermere, FL 34786 (MLS # O6331872)
    Photo of 4302 Isabella Circle, Windermere, FL 34786 (MLS # O6331872)
    4302 Isabella Circle, Windermere, FL
    4302 Isabella Circle
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 5,104 Home (sqft)
    • 7 Baths
    • 38,333 Lot (sqft)
  17. Photo of 9731 Chestnut Ridge Drive, Windermere, FL 34786 (MLS # O6336655)
    $3,400,000
    Photo of 9731 Chestnut Ridge Drive, Windermere, FL 34786 (MLS # O6336655)
    Photo of 9731 Chestnut Ridge Drive, Windermere, FL 34786 (MLS # O6336655)
    57
     
    9731 Chestnut Ridge Drive, Windermere, FL
    9731 Chestnut Ridge Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 4,877 Home (sqft)
    • 4 Baths
    • 23,523 Lot (sqft)
  18. Photo of 1433 Whitney Isles Drive, Windermere, FL 34786 (MLS # O6331550)
    $819,990
    Photo of 1433 Whitney Isles Drive, Windermere, FL 34786 (MLS # O6331550)
    Photo of 1433 Whitney Isles Drive, Windermere, FL 34786 (MLS # O6331550)
    1433 Whitney Isles Drive, Windermere, FL
    1433 Whitney Isles Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,402 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  19. Photo of 11223 Rapallo Ln, Windermere, FL 34786 (MLS # TB8411833)
    $629,000
    Photo of 11223 Rapallo Ln, Windermere, FL 34786 (MLS # TB8411833)
    Photo of 11223 Rapallo Ln, Windermere, FL 34786 (MLS # TB8411833)
    11223 Rapallo Ln, Windermere, FL
    11223 Rapallo Ln
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,181 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  20. Photo of 6208 Winter Garden Vineland Road, Windermere, FL 34786 (MLS # O6330996)
    $3,900,000
    Photo of 6208 Winter Garden Vineland Road, Windermere, FL 34786 (MLS # O6330996)
    Photo of 6208 Winter Garden Vineland Road, Windermere, FL 34786 (MLS # O6330996)
    6208 Winter Garden Vineland Road, Windermere, FL
    6208 Winter Garden Vineland Road
    Windermere, FL
    • 6 Beds
    • 8 Baths
    • 5,441 Home (sqft)
    • 8 Baths
    • 1.29 Lot (ac)
  21. Photo of 6139 Andreozzi Lane, Windermere, FL 34786 (MLS # O6330995)
    $675,000
    Photo of 6139 Andreozzi Lane, Windermere, FL 34786 (MLS # O6330995)
    Photo of 6139 Andreozzi Lane, Windermere, FL 34786 (MLS # O6330995)
    6139 Andreozzi Lane, Windermere, FL
    6139 Andreozzi Lane
    Windermere, FL
    • 4 Beds
    • 2 Baths
    • 2,555 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  22. Photo of 11880 Water Run Alley, Windermere, FL 34786 (MLS # O6320753)
    $2,600
    Photo of 11880 Water Run Alley, Windermere, FL 34786 (MLS # O6320753)
    Photo of 11880 Water Run Alley, Windermere, FL 34786 (MLS # O6320753)
    11880 Water Run Alley, Windermere, FL
    11880 Water Run Alley
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,569 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  23. Photo of 11073 Bagley Alley, Windermere, FL 34786 (MLS # S5131871)
    $3,200
    Photo of 11073 Bagley Alley, Windermere, FL 34786 (MLS # S5131871)
    Photo of 11073 Bagley Alley, Windermere, FL 34786 (MLS # S5131871)
    11073 Bagley Alley, Windermere, FL
    11073 Bagley Alley
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,204 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  24. Photo of 11021 Hawkshead Court, Windermere, FL 34786 (MLS # O6328889)
    $1,375,000
    Photo of 11021 Hawkshead Court, Windermere, FL 34786 (MLS # O6328889)
    Photo of 11021 Hawkshead Court, Windermere, FL 34786 (MLS # O6328889)
    11021 Hawkshead Court, Windermere, FL
    11021 Hawkshead Court
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,557 Home (sqft)
    • 4 Baths
    • 14,811 Lot (sqft)
  25. Photo of 6315 Clearmeadow Court, Windermere, FL 34786 (MLS # O6330497)
    $678,888
    Photo of 6315 Clearmeadow Court, Windermere, FL 34786 (MLS # O6330497)
    Photo of 6315 Clearmeadow Court, Windermere, FL 34786 (MLS # O6330497)
    6315 Clearmeadow Court, Windermere, FL
    6315 Clearmeadow Court
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 2,077 Home (sqft)
    • 2 Baths
    • 18,296 Lot (sqft)
  26. Photo of 11445 Vicolo Loop, Windermere, FL 34786 (MLS # O6330080)
    $5,300
    Photo of 11445 Vicolo Loop, Windermere, FL 34786 (MLS # O6330080)
    Photo of 11445 Vicolo Loop, Windermere, FL 34786 (MLS # O6330080)
    11445 Vicolo Loop, Windermere, FL
    11445 Vicolo Loop
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,144 Home (sqft)
    • 4 Baths
    • 9,584 Lot (sqft)
  27. Photo of 6266 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6328057)
    $570,000
    Photo of 6266 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6328057)
    Photo of 6266 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6328057)
    6266 Golden Dewdrop Trail, Windermere, FL
    6266 Golden Dewdrop Trail
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,984 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  28. Photo of 7752 Moser Avenue, Windermere, FL 34786 (MLS # O6329985)
    $409,900
    Photo of 7752 Moser Avenue, Windermere, FL 34786 (MLS # O6329985)
    Photo of 7752 Moser Avenue, Windermere, FL 34786 (MLS # O6329985)
    7752 Moser Avenue, Windermere, FL
    7752 Moser Avenue
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,644 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  29. Photo of 12815 Westside Village Loop, Windermere, FL 34786 (MLS # S5131405)
    $688,000
    Photo of 12815 Westside Village Loop, Windermere, FL 34786 (MLS # S5131405)
    Photo of 12815 Westside Village Loop, Windermere, FL 34786 (MLS # S5131405)
    12815 Westside Village Loop, Windermere, FL
    12815 Westside Village Loop
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,463 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  30. Photo of 8259 Maritime Flag Street #4, Windermere, FL 34786 (MLS # O6329585)
    $345,000
    Photo of 8259 Maritime Flag Street #4, Windermere, FL 34786 (MLS # O6329585)
    Photo of 8259 Maritime Flag Street #4, Windermere, FL 34786 (MLS # O6329585)
    8259 Maritime Flag Street #4, Windermere, FL
    8259 Maritime Flag Street #4
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,460 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
Previous Page 3 of 12 Next
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 8/21/25 4:46 PM PDT.

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