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Real estate in the city of Windermere

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  1. 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)
  2. Photo of 12508 Langstaff Drive, Windermere, FL 34786 (MLS # O6326543)
    $2,300
    Photo of 12508 Langstaff Drive, Windermere, FL 34786 (MLS # O6326543)
    Photo of 12508 Langstaff Drive, Windermere, FL 34786 (MLS # O6326543)
    12508 Langstaff Drive, Windermere, FL
    12508 Langstaff Drive
    Windermere, FL
    • 2 Beds
    • 3 Baths
    • 1,380 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  3. Photo of 8937 Matriarca Alley, Windermere, FL 34786 (MLS # O6329541)
    $2,775
    Photo of 8937 Matriarca Alley, Windermere, FL 34786 (MLS # O6329541)
    Photo of 8937 Matriarca Alley, Windermere, FL 34786 (MLS # O6329541)
    8937 Matriarca Alley, Windermere, FL
    8937 Matriarca Alley
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,756 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  4. Photo of 8179 Maritime Flag Street #210, Windermere, FL 34786 (MLS # O6328716)
    $2,300
    Photo of 8179 Maritime Flag Street #210, Windermere, FL 34786 (MLS # O6328716)
    Photo of 8179 Maritime Flag Street #210, Windermere, FL 34786 (MLS # O6328716)
    8179 Maritime Flag Street #210, Windermere, FL
    8179 Maritime Flag Street #210
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,442 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
  5. Photo of 1524 Lake Rhea Drive, Windermere, FL 34786 (MLS # O6329319)
    $1,596,027
    Photo of 1524 Lake Rhea Drive, Windermere, FL 34786 (MLS # O6329319)
    Photo of 1524 Lake Rhea Drive, Windermere, FL 34786 (MLS # O6329319)
    1524 Lake Rhea Drive, Windermere, FL
    1524 Lake Rhea Drive
    Windermere, FL
    • 7 Beds
    • 5 Baths
    • 4,940 Home (sqft)
    • 5 Baths
    • 12,197 Lot (sqft)
  6. Photo of 8855 Herencia Alley, Windermere, FL 34786 (MLS # O6329466)
    $2,600
    Photo of 8855 Herencia Alley, Windermere, FL 34786 (MLS # O6329466)
    Photo of 8855 Herencia Alley, Windermere, FL 34786 (MLS # O6329466)
    8855 Herencia Alley, Windermere, FL
    8855 Herencia Alley
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,556 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  7. Photo of 8277 Maritime Flag Street #205, Windermere, FL 34786 (MLS # O6328453)
    $310,000
    Photo of 8277 Maritime Flag Street #205, Windermere, FL 34786 (MLS # O6328453)
    Photo of 8277 Maritime Flag Street #205, Windermere, FL 34786 (MLS # O6328453)
    8277 Maritime Flag Street #205, Windermere, FL
    8277 Maritime Flag Street #205
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,455 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
  8. Photo of 6679 Duncaster Street, Windermere, FL 34786 (MLS # A4659606)
    $3,000
    Photo of 6679 Duncaster Street, Windermere, FL 34786 (MLS # A4659606)
    Photo of 6679 Duncaster Street, Windermere, FL 34786 (MLS # A4659606)
    6679 Duncaster Street, Windermere, FL
    6679 Duncaster Street
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,926 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  9. Photo of 8399 Bowden Way, Windermere, FL 34786 (MLS # O6329027)
    $6,750
    Photo of 8399 Bowden Way, Windermere, FL 34786 (MLS # O6329027)
    Photo of 8399 Bowden Way, Windermere, FL 34786 (MLS # O6329027)
    8399 Bowden Way, Windermere, FL
    8399 Bowden Way
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,851 Home (sqft)
    • 3 Baths
    • 11,326 Lot (sqft)
  10. Photo of 8620 Wellington Blue Ln, Windermere, FL 34786 (MLS # O6325630)
    $2,800
    Photo of 8620 Wellington Blue Ln, Windermere, FL 34786 (MLS # O6325630)
    Photo of 8620 Wellington Blue Ln, Windermere, FL 34786 (MLS # O6325630)
    22
     
    8620 Wellington Blue Ln, Windermere, FL
    8620 Wellington Blue Ln
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,768 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  11. Photo of 6354 Swanson Street, Windermere, FL 34786 (MLS # O6327412)
    $3,995
    Photo of 6354 Swanson Street, Windermere, FL 34786 (MLS # O6327412)
    Photo of 6354 Swanson Street, Windermere, FL 34786 (MLS # O6327412)
    24
     
    6354 Swanson Street, Windermere, FL
    6354 Swanson Street
    Windermere, FL
    • 4 Beds
    • 2 Baths
    • 2,370 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  12. Photo of 13315 Gorgona Isle Drive, Windermere, FL 34786 (MLS # TB8408122)
    $2,550
    Photo of 13315 Gorgona Isle Drive, Windermere, FL 34786 (MLS # TB8408122)
    Photo of 13315 Gorgona Isle Drive, Windermere, FL 34786 (MLS # TB8408122)
    13315 Gorgona Isle Drive, Windermere, FL
    13315 Gorgona Isle Drive
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,556 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  13. Photo of 8575 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6318359)
    $550,000
    Photo of 8575 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6318359)
    Photo of 8575 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6318359)
    8575 Lookout Pointe Drive, Windermere, FL
    8575 Lookout Pointe Drive
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,154 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  14. Photo of Windermere, FL 34786 (MLS # O6328070)
    $2,950
    Photo of Windermere, FL 34786 (MLS # O6328070)
    Photo of Windermere, FL 34786 (MLS # O6328070)
    MLS # O6328070, Windermere, FL
    MLS # O6328070
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,028 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
  15. Photo of 11520 Via Lucerna Circle, Windermere, FL 34786 (MLS # O6326550)
    $630,000
    Photo of 11520 Via Lucerna Circle, Windermere, FL 34786 (MLS # O6326550)
    Photo of 11520 Via Lucerna Circle, Windermere, FL 34786 (MLS # O6326550)
    11520 Via Lucerna Circle, Windermere, FL
    11520 Via Lucerna Circle
    Windermere, FL
    • 4 Beds
    • 2 Baths
    • 2,505 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  16. Photo of 13254 Penshurst Lane, Windermere, FL 34786 (MLS # O6327286)
    $799,000
    Photo of 13254 Penshurst Lane, Windermere, FL 34786 (MLS # O6327286)
    Photo of 13254 Penshurst Lane, Windermere, FL 34786 (MLS # O6327286)
    13254 Penshurst Lane, Windermere, FL
    13254 Penshurst Lane
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,720 Home (sqft)
    • 4 Baths
    • 6,534 Lot (sqft)
  17. Photo of 1020 Oakdale Street, Windermere, FL 34786 (MLS # O6322270)
    $2,200,000
    Photo of 1020 Oakdale Street, Windermere, FL 34786 (MLS # O6322270)
    Photo of 1020 Oakdale Street, Windermere, FL 34786 (MLS # O6322270)
    1020 Oakdale Street, Windermere, FL
    1020 Oakdale Street
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 3,994 Home (sqft)
    • 5 Baths
    • 12,633 Lot (sqft)
  18. Photo of 11661 Black Rail Street, Windermere, FL 34786 (MLS # O6327776)
    $2,800
    Photo of 11661 Black Rail Street, Windermere, FL 34786 (MLS # O6327776)
    Photo of 11661 Black Rail Street, Windermere, FL 34786 (MLS # O6327776)
    11661 Black Rail Street, Windermere, FL
    11661 Black Rail Street
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,139 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  19. Photo of 14155 Ancilla Boulevard, Windermere, FL 34786 (MLS # O6327707)
    $415,000
    Photo of 14155 Ancilla Boulevard, Windermere, FL 34786 (MLS # O6327707)
    Photo of 14155 Ancilla Boulevard, Windermere, FL 34786 (MLS # O6327707)
    14155 Ancilla Boulevard, Windermere, FL
    14155 Ancilla Boulevard
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,629 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  20. Photo of 10615 Village Lake Road, Windermere, FL 34786 (MLS # O6327030)
    $459,000
    Photo of 10615 Village Lake Road, Windermere, FL 34786 (MLS # O6327030)
    Photo of 10615 Village Lake Road, Windermere, FL 34786 (MLS # O6327030)
    10615 Village Lake Road, Windermere, FL
    10615 Village Lake Road
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 1,834 Home (sqft)
    • 4 Baths
    • 3,050 Lot (sqft)
  21. Photo of 11660 Delwick Drive, Windermere, FL 34786 (MLS # O6327464)
    $895,000
    Photo of 11660 Delwick Drive, Windermere, FL 34786 (MLS # O6327464)
    Photo of 11660 Delwick Drive, Windermere, FL 34786 (MLS # O6327464)
    11660 Delwick Drive, Windermere, FL
    11660 Delwick Drive
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 3,051 Home (sqft)
    • 5 Baths
    • 10,455 Lot (sqft)
  22. Photo of 11096 Ledgement Lane, Windermere, FL 34786 (MLS # O6328218)
    $974,900
    Photo of 11096 Ledgement Lane, Windermere, FL 34786 (MLS # O6328218)
    Photo of 11096 Ledgement Lane, Windermere, FL 34786 (MLS # O6328218)
    11096 Ledgement Lane, Windermere, FL
    11096 Ledgement Lane
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 3,285 Home (sqft)
    • 5 Baths
    • 14,375 Lot (sqft)
  23. Photo of 11637 Brickyard Pond Lane, Windermere, FL 34786 (MLS # O6328177)
    $1,580,000
    Photo of 11637 Brickyard Pond Lane, Windermere, FL 34786 (MLS # O6328177)
    Photo of 11637 Brickyard Pond Lane, Windermere, FL 34786 (MLS # O6328177)
    11637 Brickyard Pond Lane, Windermere, FL
    11637 Brickyard Pond Lane
    Windermere, FL
    • 5 Beds
    • 6 Baths
    • 5,120 Home (sqft)
    • 6 Baths
    • 36,591 Lot (sqft)
  24. Photo of 11585 Claymont Circle, Windermere, FL 34786 (MLS # O6327531)
    $5,000
    Photo of 11585 Claymont Circle, Windermere, FL 34786 (MLS # O6327531)
    Photo of 11585 Claymont Circle, Windermere, FL 34786 (MLS # O6327531)
    11585 Claymont Circle, Windermere, FL
    11585 Claymont Circle
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,384 Home (sqft)
    • 3 Baths
    • 11,326 Lot (sqft)
  25. Photo of 7135 Horizon Circle, Windermere, FL 34786 (MLS # O6327225)
    $1,490,000
    Photo of 7135 Horizon Circle, Windermere, FL 34786 (MLS # O6327225)
    Photo of 7135 Horizon Circle, Windermere, FL 34786 (MLS # O6327225)
    7135 Horizon Circle, Windermere, FL
    7135 Horizon Circle
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,359 Home (sqft)
    • 4 Baths
    • 32,235 Lot (sqft)
  26. Photo of 11209 Macaw Court, Windermere, FL 34786 (MLS # O6326947)
    $2,895,000
    Photo of 11209 Macaw Court, Windermere, FL 34786 (MLS # O6326947)
    Photo of 11209 Macaw Court, Windermere, FL 34786 (MLS # O6326947)
    11209 Macaw Court, Windermere, FL
    11209 Macaw Court
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 6,105 Home (sqft)
    • 7 Baths
    • 17,860 Lot (sqft)
  27. Photo of 11922 Angle Pond Avenue, Windermere, FL 34786 (MLS # O6328443)
    $800,000
    Photo of 11922 Angle Pond Avenue, Windermere, FL 34786 (MLS # O6328443)
    Photo of 11922 Angle Pond Avenue, Windermere, FL 34786 (MLS # O6328443)
    11922 Angle Pond Avenue, Windermere, FL
    11922 Angle Pond Avenue
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,382 Home (sqft)
    • 4 Baths
    • 6,534 Lot (sqft)
  28. Photo of 6947 Cucamelon Court, Windermere, FL 34786 (MLS # O6327502)
    $1,099,000
    Photo of 6947 Cucamelon Court, Windermere, FL 34786 (MLS # O6327502)
    Photo of 6947 Cucamelon Court, Windermere, FL 34786 (MLS # O6327502)
    6947 Cucamelon Court, Windermere, FL
    6947 Cucamelon Court
    Windermere, FL
    • 5 Beds
    • 6 Baths
    • 3,680 Home (sqft)
    • 6 Baths
    • 6,099 Lot (sqft)
  29. Photo of 6926 Cucamelon Court, Windermere, FL 34786 (MLS # O6327172)
    $949,000
    Photo of 6926 Cucamelon Court, Windermere, FL 34786 (MLS # O6327172)
    Photo of 6926 Cucamelon Court, Windermere, FL 34786 (MLS # O6327172)
    6926 Cucamelon Court, Windermere, FL
    6926 Cucamelon Court
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 2,872 Home (sqft)
    • 4 Baths
    • 6,970 Lot (sqft)
  30. Photo of 12023 Gold Creek Trail, Windermere, FL 34786 (MLS # O6327082)
    $1,200,000
    Photo of 12023 Gold Creek Trail, Windermere, FL 34786 (MLS # O6327082)
    Photo of 12023 Gold Creek Trail, Windermere, FL 34786 (MLS # O6327082)
    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)
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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 8/21/25 8:46 PM PDT.

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