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Real estate in the city of Windermere

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  1. Photo of 6558 Helmsley Circle, Windermere, FL 34786 (MLS # S5151342)
    $630,000
    Photo of 6558 Helmsley Circle, Windermere, FL 34786 (MLS # S5151342)
    Photo of 6558 Helmsley Circle, Windermere, FL 34786 (MLS # S5151342)
    6558 Helmsley Circle, Windermere, FL
    6558 Helmsley Circle
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,575 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  2. Photo of 1125 Lascala Drive, Windermere, FL 34786 (MLS # O6409403)
    $3,500
    Photo of 1125 Lascala Drive, Windermere, FL 34786 (MLS # O6409403)
    Photo of 1125 Lascala Drive, Windermere, FL 34786 (MLS # O6409403)
    1125 Lascala Drive, Windermere, FL
    1125 Lascala Drive
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 2,874 Home (sqft)
    • 5 Baths
    • 6,099 Lot (sqft)
  3. Photo of 11544 Willow Gardens Drive, Windermere, FL 34786 (MLS # O6412655)
    $1,000,000
    Photo of 11544 Willow Gardens Drive, Windermere, FL 34786 (MLS # O6412655)
    Photo of 11544 Willow Gardens Drive, Windermere, FL 34786 (MLS # O6412655)
    11544 Willow Gardens Drive, Windermere, FL
    11544 Willow Gardens Drive
    Windermere, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 2.71 Lot (ac)
  4. Photo of 8625 Greenbank Blvd, Windermere, FL 34786 (MLS # O6413262)
    $3,100
    Photo of 8625 Greenbank Blvd, Windermere, FL 34786 (MLS # O6413262)
    Photo of 8625 Greenbank Blvd, Windermere, FL 34786 (MLS # O6413262)
    8625 Greenbank Blvd, Windermere, FL
    8625 Greenbank Blvd
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,190 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  5. Photo of 6288 Blakeford Drive, Windermere, FL 34786 (MLS # S5151608)
    $2,474,000
    Photo of 6288 Blakeford Drive, Windermere, FL 34786 (MLS # S5151608)
    Photo of 6288 Blakeford Drive, Windermere, FL 34786 (MLS # S5151608)
    6288 Blakeford Drive, Windermere, FL
    6288 Blakeford Drive
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 5,366 Home (sqft)
    • 7 Baths
    • 18,296 Lot (sqft)
  6. Photo of 13743 Calera Alley, Windermere, FL 34786 (MLS # O6413535)
    $439,500
    Photo of 13743 Calera Alley, Windermere, FL 34786 (MLS # O6413535)
    Photo of 13743 Calera Alley, Windermere, FL 34786 (MLS # O6413535)
    13743 Calera Alley, Windermere, FL
    13743 Calera Alley
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,997 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  7. Photo of 13324 Longacre Drive, Windermere, FL 34786 (MLS # S5151263)
    $510,000
    Photo of 13324 Longacre Drive, Windermere, FL 34786 (MLS # S5151263)
    Photo of 13324 Longacre Drive, Windermere, FL 34786 (MLS # S5151263)
    13324 Longacre Drive, Windermere, FL
    13324 Longacre Drive
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 2,058 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  8. Photo of 11406 Waterstone Loop Dr, Windermere, FL 34786 (MLS # O6412522)
    $9,500
    Photo of 11406 Waterstone Loop Dr, Windermere, FL 34786 (MLS # O6412522)
    Photo of 11406 Waterstone Loop Dr, Windermere, FL 34786 (MLS # O6412522)
    11406 Waterstone Loop Dr, Windermere, FL
    11406 Waterstone Loop Dr
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 5,205 Home (sqft)
    • 7 Baths
    • 5,003.00 Lot (ac)
  9. Photo of 6601 Duncaster Street, Windermere, FL 34786 (MLS # O6416272)
    $627,900
    Photo of 6601 Duncaster Street, Windermere, FL 34786 (MLS # O6416272)
    Photo of 6601 Duncaster Street, Windermere, FL 34786 (MLS # O6416272)
    6601 Duncaster Street, Windermere, FL
    6601 Duncaster Street
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 3,001 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  10. Photo of 8266 Bryce Canyon Avenue, Windermere, FL 34786 (MLS # O6410344)
    $489,500
    Photo of 8266 Bryce Canyon Avenue, Windermere, FL 34786 (MLS # O6410344)
    Photo of 8266 Bryce Canyon Avenue, Windermere, FL 34786 (MLS # O6410344)
    8266 Bryce Canyon Avenue, Windermere, FL
    8266 Bryce Canyon Avenue
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,825 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  11. Photo of 8821 Danforth Drive, Windermere, FL 34786 (MLS # O6415522)
    $353,500
    Photo of 8821 Danforth Drive, Windermere, FL 34786 (MLS # O6415522)
    Photo of 8821 Danforth Drive, Windermere, FL 34786 (MLS # O6415522)
    8821 Danforth Drive, Windermere, FL
    8821 Danforth Drive
    Windermere, FL
    • 2 Beds
    • 3 Baths
    • 1,480 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  12. Photo of 4071 Isabella Circle, Windermere, FL 34786 (MLS # O6413509)
    $3,290,000
    Photo of 4071 Isabella Circle, Windermere, FL 34786 (MLS # O6413509)
    Photo of 4071 Isabella Circle, Windermere, FL 34786 (MLS # O6413509)
    100
     
     
    4071 Isabella Circle, Windermere, FL
    4071 Isabella Circle
    Windermere, FL
    • 5 Beds
    • 9 Baths
    • 7,058 Home (sqft)
    • 9 Baths
    • 41,382 Lot (sqft)
  13. Photo of 412 Forest Street, Windermere, FL 34786 (MLS # O6414200)
    $840,000
    Photo of 412 Forest Street, Windermere, FL 34786 (MLS # O6414200)
    Photo of 412 Forest Street, Windermere, FL 34786 (MLS # O6414200)
    412 Forest Street, Windermere, FL
    412 Forest Street
    Windermere, FL
    • 5 Beds
    • 3 Baths
    • 2,539 Home (sqft)
    • 3 Baths
    • 18,296 Lot (sqft)
  14. Photo of 2128 Lake Crescent Court, Windermere, FL 34786 (MLS # O6415043)
    $832,000
    Photo of 2128 Lake Crescent Court, Windermere, FL 34786 (MLS # O6415043)
    Photo of 2128 Lake Crescent Court, Windermere, FL 34786 (MLS # O6415043)
    19
     
    2128 Lake Crescent Court, Windermere, FL
    2128 Lake Crescent Court
    Windermere, FL
    • 4 Beds
    • 2 Baths
    • 2,987 Home (sqft)
    • 2 Baths
    • 34,848 Lot (sqft)
  15. Photo of 9656 Weatherstone Court, Windermere, FL 34786 (MLS # O6414766)
    $2,999,990
    Photo of 9656 Weatherstone Court, Windermere, FL 34786 (MLS # O6414766)
    Photo of 9656 Weatherstone Court, Windermere, FL 34786 (MLS # O6414766)
    9656 Weatherstone Court, Windermere, FL
    9656 Weatherstone Court
    Windermere, FL
    • 6 Beds
    • 7 Baths
    • 7,016 Home (sqft)
    • 7 Baths
    • 6.43 Lot (ac)
  16. Photo of 6119 Foxfield Court, Windermere, FL 34786 (MLS # O6414743)
    $8,500
    Photo of 6119 Foxfield Court, Windermere, FL 34786 (MLS # O6414743)
    Photo of 6119 Foxfield Court, Windermere, FL 34786 (MLS # O6414743)
    6119 Foxfield Court, Windermere, FL
    6119 Foxfield Court
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 3,200 Home (sqft)
    • 3 Baths
    • 11,326 Lot (sqft)
  17. Photo of 11768 Hampstead Street, Windermere, FL 34786 (MLS # O6414500)
    $1,318,000
    Photo of 11768 Hampstead Street, Windermere, FL 34786 (MLS # O6414500)
    Photo of 11768 Hampstead Street, Windermere, FL 34786 (MLS # O6414500)
    11768 Hampstead Street, Windermere, FL
    11768 Hampstead Street
    Windermere, FL
    • 6 Beds
    • 4 Baths
    • 3,900 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  18. Photo of 9117 Outlook Rock Trail, Windermere, FL 34786 (MLS # O6413948)
    $1,125,000
    Photo of 9117 Outlook Rock Trail, Windermere, FL 34786 (MLS # O6413948)
    Photo of 9117 Outlook Rock Trail, Windermere, FL 34786 (MLS # O6413948)
    9117 Outlook Rock Trail, Windermere, FL
    9117 Outlook Rock Trail
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 4,936 Home (sqft)
    • 5 Baths
    • 7,841 Lot (sqft)
  19. Photo of 6873 Northwich Drive, Windermere, FL 34786 (MLS # O6414222)
    $3,395
    Photo of 6873 Northwich Drive, Windermere, FL 34786 (MLS # O6414222)
    Photo of 6873 Northwich Drive, Windermere, FL 34786 (MLS # O6414222)
    6873 Northwich Drive, Windermere, FL
    6873 Northwich Drive
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,229 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  20. Photo of 13786 Summer Harbor Court, Windermere, FL 34786 (MLS # O6414239)
    $625,000
    Photo of 13786 Summer Harbor Court, Windermere, FL 34786 (MLS # O6414239)
    Photo of 13786 Summer Harbor Court, Windermere, FL 34786 (MLS # O6414239)
    13786 Summer Harbor Court, Windermere, FL
    13786 Summer Harbor Court
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,236 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  21. Photo of 7242 Londale Boulevard, Windermere, FL 34786 (MLS # O6414025)
    $749,900
    Photo of 7242 Londale Boulevard, Windermere, FL 34786 (MLS # O6414025)
    Photo of 7242 Londale Boulevard, Windermere, FL 34786 (MLS # O6414025)
    7242 Londale Boulevard, Windermere, FL
    7242 Londale Boulevard
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,690 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  22. Photo of 11035 Schooner Way, Windermere, FL 34786 (MLS # O6413965)
    $1,500,000
    Photo of 11035 Schooner Way, Windermere, FL 34786 (MLS # O6413965)
    Photo of 11035 Schooner Way, Windermere, FL 34786 (MLS # O6413965)
    4
     
    11035 Schooner Way, Windermere, FL
    11035 Schooner Way
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 3,517 Home (sqft)
    • 3 Baths
    • 1.05 Lot (ac)
  23. Photo of 8394 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6413196)
    $1,150,000
    Photo of 8394 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6413196)
    Photo of 8394 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6413196)
    8394 Lookout Pointe Drive, Windermere, FL
    8394 Lookout Pointe Drive
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,971 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  24. Photo of 14392 Bridgewater Crossings Boulevard, Windermere, FL 34786 (MLS # O6413077)
    $2,800
    Photo of 14392 Bridgewater Crossings Boulevard, Windermere, FL 34786 (MLS # O6413077)
    Photo of 14392 Bridgewater Crossings Boulevard, Windermere, FL 34786 (MLS # O6413077)
    14392 Bridgewater Crossings Boulevard, Windermere, FL
    14392 Bridgewater Crossings Boulevard
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,642 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  25. Photo of 5073 Latrobe Dr, Windermere, FL 34786 (MLS # O6414325)
    $2,999,000
    Photo of 5073 Latrobe Dr, Windermere, FL 34786 (MLS # O6414325)
    Photo of 5073 Latrobe Dr, Windermere, FL 34786 (MLS # O6414325)
    34
     
    5073 Latrobe Dr, Windermere, FL
    5073 Latrobe Dr
    Windermere, FL
    • 4 Beds
    • 6 Baths
    • 4,706 Home (sqft)
    • 6 Baths
    • 24,830 Lot (sqft)
  26. Photo of Windermere, FL 34786 (MLS # O6413985)
    $2,400
    Photo of Windermere, FL 34786 (MLS # O6413985)
    Photo of Windermere, FL 34786 (MLS # O6413985)
    MLS # O6413985, Windermere, FL
    MLS # O6413985
    Windermere, FL
    • 2 Beds
    • 3 Baths
    • 1,214 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  27. Photo of 728 Forest Street, Windermere, FL 34786 (MLS # O6411906)
    $10,200,000
    Photo of 728 Forest Street, Windermere, FL 34786 (MLS # O6411906)
    Photo of 728 Forest Street, Windermere, FL 34786 (MLS # O6411906)
    728 Forest Street, Windermere, FL
    728 Forest Street
    Windermere, FL
    • 6 Beds
    • 9 Baths
    • 6,457 Home (sqft)
    • 9 Baths
    • 36,155 Lot (sqft)
  28. Photo of 7324 Ella Lane, Windermere, FL 34786 (MLS # O6413621)
    $2,600
    Photo of 7324 Ella Lane, Windermere, FL 34786 (MLS # O6413621)
    Photo of 7324 Ella Lane, Windermere, FL 34786 (MLS # O6413621)
    7324 Ella Lane, Windermere, FL
    7324 Ella Lane
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,748 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  29. Photo of 820 East Boulevard, Windermere, FL 34786 (MLS # O6407655)
    $6,000
    Photo of 820 East Boulevard, Windermere, FL 34786 (MLS # O6407655)
    Photo of 820 East Boulevard, Windermere, FL 34786 (MLS # O6407655)
    820 East Boulevard, Windermere, FL
    820 East Boulevard
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,713 Home (sqft)
    • 2 Baths
    • 20,474 Lot (sqft)
  30. Photo of 11848 Gray Rock Trail, Windermere, FL 34786 (MLS # S5151219)
    $3,800
    Photo of 11848 Gray Rock Trail, Windermere, FL 34786 (MLS # S5151219)
    Photo of 11848 Gray Rock Trail, Windermere, FL 34786 (MLS # S5151219)
    11848 Gray Rock Trail, Windermere, FL
    11848 Gray Rock Trail
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,662 Home (sqft)
    • 4 Baths
    • 6,534 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 6:38 PM PDT.

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