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Real estate in the city of Windermere

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  1. Photo of 414 E 5th Avenue, Windermere, FL 34786 (MLS # O6387808)
    $1,200,000
    Photo of 414 E 5th Avenue, Windermere, FL 34786 (MLS # O6387808)
    Photo of 414 E 5th Avenue, Windermere, FL 34786 (MLS # O6387808)
    414 E 5th Avenue, Windermere, FL
    414 E 5th Avenue
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 2,521 Home (sqft)
    • 2 Baths
    • 28,750 Lot (sqft)
  2. Photo of 6314 Clearmeadow Court, Windermere, FL 34786 (MLS # O6387216)
    $825,000
    Photo of 6314 Clearmeadow Court, Windermere, FL 34786 (MLS # O6387216)
    Photo of 6314 Clearmeadow Court, Windermere, FL 34786 (MLS # O6387216)
    6314 Clearmeadow Court, Windermere, FL
    6314 Clearmeadow Court
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,581 Home (sqft)
    • 3 Baths
    • 18,296 Lot (sqft)
  3. Photo of 11802 Waterstone Loop Drive, Windermere, FL 34786 (MLS # O6387172)
    $1,395,000
    Photo of 11802 Waterstone Loop Drive, Windermere, FL 34786 (MLS # O6387172)
    Photo of 11802 Waterstone Loop Drive, Windermere, FL 34786 (MLS # O6387172)
    11802 Waterstone Loop Drive, Windermere, FL
    11802 Waterstone Loop Drive
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 3,396 Home (sqft)
    • 5 Baths
    • 12,633 Lot (sqft)
  4. Photo of 12720 Jacob Grace Court, Windermere, FL 34786 (MLS # TB8476930)
    $3,050,000
    Photo of 12720 Jacob Grace Court, Windermere, FL 34786 (MLS # TB8476930)
    Photo of 12720 Jacob Grace Court, Windermere, FL 34786 (MLS # TB8476930)
    12720 Jacob Grace Court, Windermere, FL
    12720 Jacob Grace Court
    Windermere, FL
    • 6 Beds
    • 7 Baths
    • 5,882 Home (sqft)
    • 7 Baths
    • 1.87 Lot (ac)
  5. Photo of 7264 Backwoods Trail, Windermere, FL 34786 (MLS # O6387913)
    $650,000
    Photo of 7264 Backwoods Trail, Windermere, FL 34786 (MLS # O6387913)
    Photo of 7264 Backwoods Trail, Windermere, FL 34786 (MLS # O6387913)
    7264 Backwoods Trail, Windermere, FL
    7264 Backwoods Trail
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,214 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  6. Photo of 8532 Bowden Way, Windermere, FL 34786 (MLS # O6380872)
    $9,800
    Photo of 8532 Bowden Way, Windermere, FL 34786 (MLS # O6380872)
    Photo of 8532 Bowden Way, Windermere, FL 34786 (MLS # O6380872)
    28
     
    8532 Bowden Way, Windermere, FL
    8532 Bowden Way
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,885 Home (sqft)
    • 4 Baths
    • 13,940 Lot (sqft)
  7. Photo of 4029 Isabella Circle, Windermere, FL 34786 (MLS # O6387864)
    $3,499,000
    Photo of 4029 Isabella Circle, Windermere, FL 34786 (MLS # O6387864)
    Photo of 4029 Isabella Circle, Windermere, FL 34786 (MLS # O6387864)
    4029 Isabella Circle, Windermere, FL
    4029 Isabella Circle
    Windermere, FL
    • 6 Beds
    • 8 Baths
    • 7,217 Home (sqft)
    • 8 Baths
    • 37,026 Lot (sqft)
  8. Photo of 1602 Roberts Landing Road, Windermere, FL 34786 (MLS # O6387865)
    $3,000
    Photo of 1602 Roberts Landing Road, Windermere, FL 34786 (MLS # O6387865)
    Photo of 1602 Roberts Landing Road, Windermere, FL 34786 (MLS # O6387865)
    1602 Roberts Landing Road, Windermere, FL
    1602 Roberts Landing Road
    Windermere, FL
    • 4 Beds
    • 2 Baths
    • 2,352 Home (sqft)
    • 2 Baths
    • 1.11 Lot (ac)
  9. Photo of 43 Main Street, Windermere, FL 34786 (MLS # O6387626)
    $3,500,000
    Photo of 43 Main Street, Windermere, FL 34786 (MLS # O6387626)
    Photo of 43 Main Street, Windermere, FL 34786 (MLS # O6387626)
    1
     
    43 Main Street, Windermere, FL
    43 Main Street
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,500 Home (sqft)
    • 4 Baths
    • 16,118 Lot (sqft)
  10. Photo of 12327 Cruxbury Drive, Windermere, FL 34786 (MLS # S5144545)
    $355,000
    Photo of 12327 Cruxbury Drive, Windermere, FL 34786 (MLS # S5144545)
    Photo of 12327 Cruxbury Drive, Windermere, FL 34786 (MLS # S5144545)
    12327 Cruxbury Drive, Windermere, FL
    12327 Cruxbury Drive
    Windermere, FL
    • 2 Beds
    • 3 Baths
    • 1,211 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  11. Photo of 12761 Bideford Avenue, Windermere, FL 34786 (MLS # O6387477)
    $3,500
    Photo of 12761 Bideford Avenue, Windermere, FL 34786 (MLS # O6387477)
    Photo of 12761 Bideford Avenue, Windermere, FL 34786 (MLS # O6387477)
    12761 Bideford Avenue, Windermere, FL
    12761 Bideford Avenue
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 3,011 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  12. Photo of 11 Main Street, Windermere, FL 34786 (MLS # O6387596)
    $6,700,000
    Photo of 11 Main Street, Windermere, FL 34786 (MLS # O6387596)
    Photo of 11 Main Street, Windermere, FL 34786 (MLS # O6387596)
    4
     
    11 Main Street, Windermere, FL
    11 Main Street
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 4,723 Home (sqft)
    • 5 Baths
    • 17,860 Lot (sqft)
  13. Photo of 8226 Serenity Spring Drive #2402, Windermere, FL 34786 (MLS # O6386960)
    $399,900
    Photo of 8226 Serenity Spring Drive #2402, Windermere, FL 34786 (MLS # O6386960)
    Photo of 8226 Serenity Spring Drive #2402, Windermere, FL 34786 (MLS # O6386960)
    8226 Serenity Spring Drive #2402, Windermere, FL
    8226 Serenity Spring Drive #2402
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,028 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
  14. Photo of 9155 Panzani Place, Windermere, FL 34786 (MLS # O6383334)
    $975,000
    Photo of 9155 Panzani Place, Windermere, FL 34786 (MLS # O6383334)
    Photo of 9155 Panzani Place, Windermere, FL 34786 (MLS # O6383334)
    9155 Panzani Place, Windermere, FL
    9155 Panzani Place
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,088 Home (sqft)
    • 4 Baths
    • 12,197 Lot (sqft)
  15. Photo of 11401 Evesham Drive, Windermere, FL 34786 (MLS # O6386678)
    $460,000
    Photo of 11401 Evesham Drive, Windermere, FL 34786 (MLS # O6386678)
    Photo of 11401 Evesham Drive, Windermere, FL 34786 (MLS # O6386678)
    11401 Evesham Drive, Windermere, FL
    11401 Evesham Drive
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,847 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  16. Photo of 6871 Helmsley Circle, Windermere, FL 34786 (MLS # O6387593)
    $554,000
    Photo of 6871 Helmsley Circle, Windermere, FL 34786 (MLS # O6387593)
    Photo of 6871 Helmsley Circle, Windermere, FL 34786 (MLS # O6387593)
    6871 Helmsley Circle, Windermere, FL
    6871 Helmsley Circle
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,772 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  17. Photo of 735 Oakdale Street, Windermere, FL 34786 (MLS # S5144907)
    $975,000
    Photo of 735 Oakdale Street, Windermere, FL 34786 (MLS # S5144907)
    Photo of 735 Oakdale Street, Windermere, FL 34786 (MLS # S5144907)
    735 Oakdale Street, Windermere, FL
    735 Oakdale Street
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,475 Home (sqft)
    • 3 Baths
    • 16,553 Lot (sqft)
  18. Photo of 13118 Sunkiss Loop, Windermere, FL 34786 (MLS # O6385211)
    $588,000
    Photo of 13118 Sunkiss Loop, Windermere, FL 34786 (MLS # O6385211)
    Photo of 13118 Sunkiss Loop, Windermere, FL 34786 (MLS # O6385211)
    13118 Sunkiss Loop, Windermere, FL
    13118 Sunkiss Loop
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,547 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  19. Photo of 7314 Brightland Street, Windermere, FL 34786 (MLS # O6386905)
    $2,450
    Photo of 7314 Brightland Street, Windermere, FL 34786 (MLS # O6386905)
    Photo of 7314 Brightland Street, Windermere, FL 34786 (MLS # O6386905)
    7314 Brightland Street, Windermere, FL
    7314 Brightland Street
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,720 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  20. Photo of 11866 Camden Park Drive, Windermere, FL 34786 (MLS # O6381558)
    $984,900
    Photo of 11866 Camden Park Drive, Windermere, FL 34786 (MLS # O6381558)
    Photo of 11866 Camden Park Drive, Windermere, FL 34786 (MLS # O6381558)
    11866 Camden Park Drive, Windermere, FL
    11866 Camden Park Drive
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,337 Home (sqft)
    • 4 Baths
    • 11,326 Lot (sqft)
  21. Photo of 5468 Tildens Grove Boulevard, Windermere, FL 34786 (MLS # O6386658)
    $9,500
    Photo of 5468 Tildens Grove Boulevard, Windermere, FL 34786 (MLS # O6386658)
    Photo of 5468 Tildens Grove Boulevard, Windermere, FL 34786 (MLS # O6386658)
    5468 Tildens Grove Boulevard, Windermere, FL
    5468 Tildens Grove Boulevard
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 4,091 Home (sqft)
    • 4 Baths
    • 23,087 Lot (sqft)
  22. Photo of 13887 Reams Road, Windermere, FL 34786 (MLS # O6386815)
    $999,999
    Photo of 13887 Reams Road, Windermere, FL 34786 (MLS # O6386815)
    Photo of 13887 Reams Road, Windermere, FL 34786 (MLS # O6386815)
    13887 Reams Road, Windermere, FL
    13887 Reams Road
    Windermere, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 5.05 Lot (ac)
  23. Photo of 8563 Greenbank Boulevard, Windermere, FL 34786 (MLS # O6386388)
    $3,700
    Photo of 8563 Greenbank Boulevard, Windermere, FL 34786 (MLS # O6386388)
    Photo of 8563 Greenbank Boulevard, Windermere, FL 34786 (MLS # O6386388)
    60
     
    8563 Greenbank Boulevard, Windermere, FL
    8563 Greenbank Boulevard
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,666 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
  24. Photo of 14235 Desert Haven Street #3503, Windermere, FL 34786 (MLS # O6386593)
    $2,750
    Photo of 14235 Desert Haven Street #3503, Windermere, FL 34786 (MLS # O6386593)
    Photo of 14235 Desert Haven Street #3503, Windermere, FL 34786 (MLS # O6386593)
    14235 Desert Haven Street #3503, Windermere, FL
    14235 Desert Haven Street #3503
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,028 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
  25. Photo of 721 Magnolia Street, Windermere, FL 34786 (MLS # S5144805)
    $2,250
    Photo of 721 Magnolia Street, Windermere, FL 34786 (MLS # S5144805)
    Photo of 721 Magnolia Street, Windermere, FL 34786 (MLS # S5144805)
    721 Magnolia Street, Windermere, FL
    721 Magnolia Street
    Windermere, FL
    • 2 Beds
    • 1 Bath
    • 891 Home (sqft)
    • 1 Bath
    • 16,553 Lot (sqft)
  26. Photo of 13240 Roskin Lane, Windermere, FL 34786 (MLS # S5144759)
    $739,000
    Photo of 13240 Roskin Lane, Windermere, FL 34786 (MLS # S5144759)
    Photo of 13240 Roskin Lane, Windermere, FL 34786 (MLS # S5144759)
    13240 Roskin Lane, Windermere, FL
    13240 Roskin Lane
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,108 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  27. Photo of 13040 Overstreet Road, Windermere, FL 34786 (MLS # S5144750)
    $2,900
    Photo of 13040 Overstreet Road, Windermere, FL 34786 (MLS # S5144750)
    Photo of 13040 Overstreet Road, Windermere, FL 34786 (MLS # S5144750)
    13040 Overstreet Road, Windermere, FL
    13040 Overstreet Road
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,203 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  28. Photo of 4773 Blue Major Drive, Windermere, FL 34786 (MLS # O6386132)
    $619,900
    Photo of 4773 Blue Major Drive, Windermere, FL 34786 (MLS # O6386132)
    Photo of 4773 Blue Major Drive, Windermere, FL 34786 (MLS # O6386132)
    29
     
    4773 Blue Major Drive, Windermere, FL
    4773 Blue Major Drive
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,620 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  29. Photo of 9548 Crown Prince Lane, Windermere, FL 34786 (MLS # S5144606)
    $1,460,000
    Photo of 9548 Crown Prince Lane, Windermere, FL 34786 (MLS # S5144606)
    Photo of 9548 Crown Prince Lane, Windermere, FL 34786 (MLS # S5144606)
    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)
  30. Photo of 2641 Hempel Avenue, Windermere, FL 34786 (MLS # O6384773)
    $824,900
    Photo of 2641 Hempel Avenue, Windermere, FL 34786 (MLS # O6384773)
    Photo of 2641 Hempel Avenue, Windermere, FL 34786 (MLS # O6384773)
    2641 Hempel Avenue, Windermere, FL
    2641 Hempel Avenue
    Windermere, FL
    • 4 Beds
    • 2 Baths
    • 2,404 Home (sqft)
    • 2 Baths
    • 43,560 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 3/6/26 5:46 AM PST.

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