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Real estate in the city of Windermere

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  1. Photo of 13339 Roskin Lane, Windermere, FL 34786 (MLS # S5141148)
    $680,000
    Photo of 13339 Roskin Lane, Windermere, FL 34786 (MLS # S5141148)
    Photo of 13339 Roskin Lane, Windermere, FL 34786 (MLS # S5141148)
    13339 Roskin Lane, Windermere, FL
    13339 Roskin Lane
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,947 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  2. Photo of 6117 Louise Cove Drive, Windermere, FL 34786 (MLS # O6372197)
    $5,250,000
    Photo of 6117 Louise Cove Drive, Windermere, FL 34786 (MLS # O6372197)
    Photo of 6117 Louise Cove Drive, Windermere, FL 34786 (MLS # O6372197)
    6117 Louise Cove Drive, Windermere, FL
    6117 Louise Cove Drive
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 5,752 Home (sqft)
    • 5 Baths
    • 34,413 Lot (sqft)
  3. Photo of 14354 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5106241)
    $1,119,990
    Photo of 14354 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5106241)
    Photo of 14354 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5106241)
    14354 Crest Palm Avenue, Windermere, FL
    14354 Crest Palm Avenue
    Windermere, FL
    • 6 Beds
    • 5 Baths
    • 3,542 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  4. Photo of 2844 Midsummer Drive, Windermere, FL 34786 (MLS # O6371115)
    $7,500
    Photo of 2844 Midsummer Drive, Windermere, FL 34786 (MLS # O6371115)
    Photo of 2844 Midsummer Drive, Windermere, FL 34786 (MLS # O6371115)
    1
     
    2844 Midsummer Drive, Windermere, FL
    2844 Midsummer Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,328 Home (sqft)
    • 4 Baths
    • 2.67 Lot (ac)
  5. Photo of 8225 Bryce Canyon Avenue, Windermere, FL 34786 (MLS # O6371960)
    $560,000
    Photo of 8225 Bryce Canyon Avenue, Windermere, FL 34786 (MLS # O6371960)
    Photo of 8225 Bryce Canyon Avenue, Windermere, FL 34786 (MLS # O6371960)
    8225 Bryce Canyon Avenue, Windermere, FL
    8225 Bryce Canyon Avenue
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 1,840 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  6. Photo of 5050 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6372348)
    $3,390,000
    Photo of 5050 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6372348)
    Photo of 5050 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6372348)
    5050 Isleworth Country Club Drive, Windermere, FL
    5050 Isleworth Country Club Drive
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 3,365 Home (sqft)
    • 5 Baths
    • 22,652 Lot (sqft)
  7. Photo of 7307 Ella Lane, Windermere, FL 34786 (MLS # O6370761)
    $3,800
    Photo of 7307 Ella Lane, Windermere, FL 34786 (MLS # O6370761)
    Photo of 7307 Ella Lane, Windermere, FL 34786 (MLS # O6370761)
    7307 Ella Lane, Windermere, FL
    7307 Ella Lane
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,988 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  8. Photo of 9725 Chestnut Ridge Drive, Windermere, FL 34786 (MLS # O6370294)
    $6,950,000
    Photo of 9725 Chestnut Ridge Drive, Windermere, FL 34786 (MLS # O6370294)
    Photo of 9725 Chestnut Ridge Drive, Windermere, FL 34786 (MLS # O6370294)
    9725 Chestnut Ridge Drive, Windermere, FL
    9725 Chestnut Ridge Drive
    Windermere, FL
    • 7 Beds
    • 7 Baths
    • 8,000 Home (sqft)
    • 7 Baths
    • 24,394 Lot (sqft)
  9. Photo of 13312 Longacre Drive, Windermere, FL 34786 (MLS # S5141031)
    $534,900
    Photo of 13312 Longacre Drive, Windermere, FL 34786 (MLS # S5141031)
    Photo of 13312 Longacre Drive, Windermere, FL 34786 (MLS # S5141031)
    13312 Longacre Drive, Windermere, FL
    13312 Longacre Drive
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 2,058 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  10. Photo of 12418 Park Avenue, Windermere, FL 34786 (MLS # O6370377)
    $4,395,000
    Photo of 12418 Park Avenue, Windermere, FL 34786 (MLS # O6370377)
    Photo of 12418 Park Avenue, Windermere, FL 34786 (MLS # O6370377)
    12418 Park Avenue, Windermere, FL
    12418 Park Avenue
    Windermere, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 43,560 Lot (sqft)
  11. Photo of 1351 Glenwick Drive, Windermere, FL 34786 (MLS # O6369599)
    $4,500
    Photo of 1351 Glenwick Drive, Windermere, FL 34786 (MLS # O6369599)
    Photo of 1351 Glenwick Drive, Windermere, FL 34786 (MLS # O6369599)
    1351 Glenwick Drive, Windermere, FL
    1351 Glenwick Drive
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,300 Home (sqft)
    • 4 Baths
    • 11,762 Lot (sqft)
  12. Photo of 6310 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6368983)
    $490,000
    Photo of 6310 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6368983)
    Photo of 6310 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6368983)
    6310 Golden Dewdrop Trail, Windermere, FL
    6310 Golden Dewdrop Trail
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,977 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  13. Photo of 6343 Merrick Landing Boulevard, Windermere, FL 34786 (MLS # O6368529)
    $325,000
    Photo of 6343 Merrick Landing Boulevard, Windermere, FL 34786 (MLS # O6368529)
    Photo of 6343 Merrick Landing Boulevard, Windermere, FL 34786 (MLS # O6368529)
    6343 Merrick Landing Boulevard, Windermere, FL
    6343 Merrick Landing Boulevard
    Windermere, FL
    • 2 Beds
    • 2 Baths
    • 1,068 Home (sqft)
    • 2 Baths
    • 2,614 Lot (sqft)
  14. Photo of 8601 Via Tavoleria Way, Windermere, FL 34786 (MLS # O6394940)
    $465,000
    Photo of 8601 Via Tavoleria Way, Windermere, FL 34786 (MLS # O6394940)
    Photo of 8601 Via Tavoleria Way, Windermere, FL 34786 (MLS # O6394940)
    8601 Via Tavoleria Way, Windermere, FL
    8601 Via Tavoleria Way
    Windermere, FL
    • 3 Beds
    • 4 Baths
    • 1,936 Home (sqft)
    • 4 Baths
    • 3,485 Lot (sqft)
  15. Photo of 713 Main Street, Windermere, FL 34786 (MLS # O6368185)
    $2,235,000
    Photo of 713 Main Street, Windermere, FL 34786 (MLS # O6368185)
    Photo of 713 Main Street, Windermere, FL 34786 (MLS # O6368185)
    713 Main Street, Windermere, FL
    713 Main Street
    Windermere, FL
    • 6 Beds
    • 6 Baths
    • 5,031 Home (sqft)
    • 6 Baths
    • 16,118 Lot (sqft)
  16. Photo of 11334 Camden Loop Way, Windermere, FL 34786 (MLS # O6367433)
    $1,250,000
    Photo of 11334 Camden Loop Way, Windermere, FL 34786 (MLS # O6367433)
    Photo of 11334 Camden Loop Way, Windermere, FL 34786 (MLS # O6367433)
    11334 Camden Loop Way, Windermere, FL
    11334 Camden Loop Way
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 3,021 Home (sqft)
    • 3 Baths
    • 11,326 Lot (sqft)
  17. Photo of 4226 Downeast Lane, Windermere, FL 34786 (MLS # O6367852)
    $10,500,000
    Photo of 4226 Downeast Lane, Windermere, FL 34786 (MLS # O6367852)
    Photo of 4226 Downeast Lane, Windermere, FL 34786 (MLS # O6367852)
    4226 Downeast Lane, Windermere, FL
    4226 Downeast Lane
    Windermere, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 9.03 Lot (ac)
  18. Photo of 8447 Bowden Way, Windermere, FL 34786 (MLS # O6365817)
    $5,500
    Photo of 8447 Bowden Way, Windermere, FL 34786 (MLS # O6365817)
    Photo of 8447 Bowden Way, Windermere, FL 34786 (MLS # O6365817)
    8447 Bowden Way, Windermere, FL
    8447 Bowden Way
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 2,056 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  19. Photo of 13106 Orange Isle Drive, Windermere, FL 34786 (MLS # O6361057)
    $815,000
    Photo of 13106 Orange Isle Drive, Windermere, FL 34786 (MLS # O6361057)
    Photo of 13106 Orange Isle Drive, Windermere, FL 34786 (MLS # O6361057)
    13106 Orange Isle Drive, Windermere, FL
    13106 Orange Isle Drive
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 3,312 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  20. Photo of 12941 Westside Village Loop, Windermere, FL 34786 (MLS # O6363541)
    $929,900
    Photo of 12941 Westside Village Loop, Windermere, FL 34786 (MLS # O6363541)
    Photo of 12941 Westside Village Loop, Windermere, FL 34786 (MLS # O6363541)
    12941 Westside Village Loop, Windermere, FL
    12941 Westside Village Loop
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,717 Home (sqft)
    • 4 Baths
    • 5,663 Lot (sqft)
  21. Photo of 2125 Kane Park Way, Windermere, FL 34786 (MLS # O6358139)
    $999,998
    Photo of 2125 Kane Park Way, Windermere, FL 34786 (MLS # O6358139)
    Photo of 2125 Kane Park Way, Windermere, FL 34786 (MLS # O6358139)
    2125 Kane Park Way, Windermere, FL
    2125 Kane Park Way
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,743 Home (sqft)
    • 3 Baths
    • 30,928 Lot (sqft)
  22. Photo of 9088 Outlook Rock Trail, Windermere, FL 34786 (MLS # O6365212)
    $3,950
    Photo of 9088 Outlook Rock Trail, Windermere, FL 34786 (MLS # O6365212)
    Photo of 9088 Outlook Rock Trail, Windermere, FL 34786 (MLS # O6365212)
    9088 Outlook Rock Trail, Windermere, FL
    9088 Outlook Rock Trail
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 2,800 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  23. Photo of 3103 Seigneury Drive, Windermere, FL 34786 (MLS # O6364283)
    $2,700,000
    Photo of 3103 Seigneury Drive, Windermere, FL 34786 (MLS # O6364283)
    Photo of 3103 Seigneury Drive, Windermere, FL 34786 (MLS # O6364283)
    3103 Seigneury Drive, Windermere, FL
    3103 Seigneury Drive
    Windermere, FL
    • 8 Beds
    • 6 Baths
    • 5,607 Home (sqft)
    • 6 Baths
    • 1.04 Lot (ac)
  24. Photo of 311 E 8th Avenue, Windermere, FL 34786 (MLS # O6364016)
    $6,000
    Photo of 311 E 8th Avenue, Windermere, FL 34786 (MLS # O6364016)
    Photo of 311 E 8th Avenue, Windermere, FL 34786 (MLS # O6364016)
    311 E 8th Avenue, Windermere, FL
    311 E 8th Avenue
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,805 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  25. Photo of 12333 Via Derna Place, Windermere, FL 34786 (MLS # O6362685)
    $459,000
    Photo of 12333 Via Derna Place, Windermere, FL 34786 (MLS # O6362685)
    Photo of 12333 Via Derna Place, Windermere, FL 34786 (MLS # O6362685)
    12333 Via Derna Place, Windermere, FL
    12333 Via Derna Place
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,919 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  26. Photo of 6130 Grosvenor Shore Drive, Windermere, FL 34786 (MLS # O6361099)
    $3,500,000
    Photo of 6130 Grosvenor Shore Drive, Windermere, FL 34786 (MLS # O6361099)
    Photo of 6130 Grosvenor Shore Drive, Windermere, FL 34786 (MLS # O6361099)
    6130 Grosvenor Shore Drive, Windermere, FL
    6130 Grosvenor Shore Drive
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 4,676 Home (sqft)
    • 5 Baths
    • 23,958 Lot (sqft)
  27. Photo of 8145 Serenity Spring Drive #GE, Windermere, FL 34786 (MLS # O6361898)
    $2,400
    Photo of 8145 Serenity Spring Drive #GE, Windermere, FL 34786 (MLS # O6361898)
    Photo of 8145 Serenity Spring Drive #GE, Windermere, FL 34786 (MLS # O6361898)
    8145 Serenity Spring Drive #GE, Windermere, FL
    8145 Serenity Spring Drive #GE
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,512 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  28. Photo of 5243 W Lake Butler Road, Windermere, FL 34786 (MLS # O6362021)
    $9,999
    Photo of 5243 W Lake Butler Road, Windermere, FL 34786 (MLS # O6362021)
    Photo of 5243 W Lake Butler Road, Windermere, FL 34786 (MLS # O6362021)
    5243 W Lake Butler Road, Windermere, FL
    5243 W Lake Butler Road
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 3,255 Home (sqft)
    • 3 Baths
    • 24,394 Lot (sqft)
  29. Photo of 81 Oakdale Street, Windermere, FL 34786 (MLS # S5138567)
    $2,300,000
    Photo of 81 Oakdale Street, Windermere, FL 34786 (MLS # S5138567)
    Photo of 81 Oakdale Street, Windermere, FL 34786 (MLS # S5138567)
    81 Oakdale Street, Windermere, FL
    81 Oakdale Street
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 4,284 Home (sqft)
    • 5 Baths
    • 18,296 Lot (sqft)
  30. Photo of 6799 Helmsley Circle, Windermere, FL 34786 (MLS # O6361417)
    $670,000
    Photo of 6799 Helmsley Circle, Windermere, FL 34786 (MLS # O6361417)
    Photo of 6799 Helmsley Circle, Windermere, FL 34786 (MLS # O6361417)
    6799 Helmsley Circle, Windermere, FL
    6799 Helmsley Circle
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,615 Home (sqft)
    • 4 Baths
    • 5,663 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 4/8/26 12:00 PM PDT.

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