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Real estate in the city of Windermere

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  1. Photo of 8626 Crescendo Avenue, Windermere, FL 34786 (MLS # O6365595)
    $3,750
    Photo of 8626 Crescendo Avenue, Windermere, FL 34786 (MLS # O6365595)
    Photo of 8626 Crescendo Avenue, Windermere, FL 34786 (MLS # O6365595)
    8626 Crescendo Avenue, Windermere, FL
    8626 Crescendo Avenue
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,399 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  2. Photo of 12941 Westside Village Loop, Windermere, FL 34786 (MLS # O6363541)
    $950,000
    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)
  3. Photo of 13808 Ancilla Boulevard, Windermere, FL 34786 (MLS # S5139822)
    $414,999
    Photo of 13808 Ancilla Boulevard, Windermere, FL 34786 (MLS # S5139822)
    Photo of 13808 Ancilla Boulevard, Windermere, FL 34786 (MLS # S5139822)
    40
     
    13808 Ancilla Boulevard, Windermere, FL
    13808 Ancilla Boulevard
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,461 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  4. Photo of 7167 Beek Street, Windermere, FL 34786 (MLS # O6364480)
    $759,900
    Photo of 7167 Beek Street, Windermere, FL 34786 (MLS # O6364480)
    Photo of 7167 Beek Street, Windermere, FL 34786 (MLS # O6364480)
    69
     
    7167 Beek Street, Windermere, FL
    7167 Beek Street
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,425 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  5. Photo of 7601 Ripplepointe Way, Windermere, FL 34786 (MLS # O6363832)
    $2,700
    Photo of 7601 Ripplepointe Way, Windermere, FL 34786 (MLS # O6363832)
    Photo of 7601 Ripplepointe Way, Windermere, FL 34786 (MLS # O6363832)
    7601 Ripplepointe Way, Windermere, FL
    7601 Ripplepointe Way
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,881 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  6. Photo of 2125 Kane Park Way, Windermere, FL 34786 (MLS # O6358139)
    $1,075,000
    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)
  7. Photo of 13833 Ancilla Boulevard, Windermere, FL 34786 (MLS # O6364332)
    $355,000
    Photo of 13833 Ancilla Boulevard, Windermere, FL 34786 (MLS # O6364332)
    Photo of 13833 Ancilla Boulevard, Windermere, FL 34786 (MLS # O6364332)
    36
     
    13833 Ancilla Boulevard, Windermere, FL
    13833 Ancilla Boulevard
    Windermere, FL
    • 2 Beds
    • 2 Baths
    • 1,155 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  8. Photo of 13638 Ancilla Boulevard, Windermere, FL 34786 (MLS # S5139748)
    $3,750
    Photo of 13638 Ancilla Boulevard, Windermere, FL 34786 (MLS # S5139748)
    Photo of 13638 Ancilla Boulevard, Windermere, FL 34786 (MLS # S5139748)
    13638 Ancilla Boulevard, Windermere, FL
    13638 Ancilla Boulevard
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,770 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  9. Photo of 6222 Lecco Way, Windermere, FL 34786 (MLS # O6354662)
    $1,629,000
    Photo of 6222 Lecco Way, Windermere, FL 34786 (MLS # O6354662)
    Photo of 6222 Lecco Way, Windermere, FL 34786 (MLS # O6354662)
    6222 Lecco Way, Windermere, FL
    6222 Lecco Way
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,967 Home (sqft)
    • 4 Baths
    • 12,633 Lot (sqft)
  10. Photo of 1804 Maple Leaf Drive, Windermere, FL 34786 (MLS # O6364182)
    $1,025,000
    Photo of 1804 Maple Leaf Drive, Windermere, FL 34786 (MLS # O6364182)
    Photo of 1804 Maple Leaf Drive, Windermere, FL 34786 (MLS # O6364182)
    1804 Maple Leaf Drive, Windermere, FL
    1804 Maple Leaf Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,971 Home (sqft)
    • 4 Baths
    • 21,780 Lot (sqft)
  11. Photo of Windermere, FL 34786 (MLS # TB8453727)
    $3,149
    Photo of Windermere, FL 34786 (MLS # TB8453727)
    Photo of Windermere, FL 34786 (MLS # TB8453727)
    MLS # TB8453727, Windermere, FL
    MLS # TB8453727
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,659 Home (sqft)
    • 4 Baths
    • 9,584 Lot (sqft)
  12. Photo of Windermere, FL 34786 (MLS # TB8453714)
    $3,489
    Photo of Windermere, FL 34786 (MLS # TB8453714)
    Photo of Windermere, FL 34786 (MLS # TB8453714)
    MLS # TB8453714, Windermere, FL
    MLS # TB8453714
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,745 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  13. 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)
  14. Photo of 8436 Greenbank Boulevard, Windermere, FL 34786 (MLS # O6364887)
    $2,850
    Photo of 8436 Greenbank Boulevard, Windermere, FL 34786 (MLS # O6364887)
    Photo of 8436 Greenbank Boulevard, Windermere, FL 34786 (MLS # O6364887)
    8436 Greenbank Boulevard, Windermere, FL
    8436 Greenbank Boulevard
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,894 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  15. Photo of 6920 Helmsley Circle, Windermere, FL 34786 (MLS # O6364850)
    $2,900
    Photo of 6920 Helmsley Circle, Windermere, FL 34786 (MLS # O6364850)
    Photo of 6920 Helmsley Circle, Windermere, FL 34786 (MLS # O6364850)
    6920 Helmsley Circle, Windermere, FL
    6920 Helmsley Circle
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 2,156 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  16. Photo of 13927 Bluebird Pond Road, Windermere, FL 34786 (MLS # O6363255)
    $535,000
    Photo of 13927 Bluebird Pond Road, Windermere, FL 34786 (MLS # O6363255)
    Photo of 13927 Bluebird Pond Road, Windermere, FL 34786 (MLS # O6363255)
    13927 Bluebird Pond Road, Windermere, FL
    13927 Bluebird Pond Road
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,345 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  17. Photo of 12661 Calderdale Avenue, Windermere, FL 34786 (MLS # O6364859)
    $495,000
    Photo of 12661 Calderdale Avenue, Windermere, FL 34786 (MLS # O6364859)
    Photo of 12661 Calderdale Avenue, Windermere, FL 34786 (MLS # O6364859)
    12661 Calderdale Avenue, Windermere, FL
    12661 Calderdale Avenue
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,696 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  18. Photo of 12530 Climbing Vine Court, Windermere, FL 34786 (MLS # O6364745)
    $999,000
    Photo of 12530 Climbing Vine Court, Windermere, FL 34786 (MLS # O6364745)
    Photo of 12530 Climbing Vine Court, Windermere, FL 34786 (MLS # O6364745)
    12530 Climbing Vine Court, Windermere, FL
    12530 Climbing Vine Court
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,407 Home (sqft)
    • 4 Baths
    • 14,375 Lot (sqft)
  19. Photo of 5723 Oxford Moor Boulevard, Windermere, FL 34786 (MLS # O6364421)
    $8,500
    Photo of 5723 Oxford Moor Boulevard, Windermere, FL 34786 (MLS # O6364421)
    Photo of 5723 Oxford Moor Boulevard, Windermere, FL 34786 (MLS # O6364421)
    5723 Oxford Moor Boulevard, Windermere, FL
    5723 Oxford Moor Boulevard
    Windermere, FL
    • 4 Beds
    • 6 Baths
    • 4,629 Home (sqft)
    • 6 Baths
    • 26,572 Lot (sqft)
  20. Photo of 12235 Montalcino Circle, Windermere, FL 34786 (MLS # O6365656)
    $1,999,000
    Photo of 12235 Montalcino Circle, Windermere, FL 34786 (MLS # O6365656)
    Photo of 12235 Montalcino Circle, Windermere, FL 34786 (MLS # O6365656)
    12235 Montalcino Circle, Windermere, FL
    12235 Montalcino Circle
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 4,550 Home (sqft)
    • 5 Baths
    • 9,584 Lot (sqft)
  21. Photo of 1626 Whitney Isles Drive, Windermere, FL 34786 (MLS # O6364998)
    $3,400
    Photo of 1626 Whitney Isles Drive, Windermere, FL 34786 (MLS # O6364998)
    Photo of 1626 Whitney Isles Drive, Windermere, FL 34786 (MLS # O6364998)
    1626 Whitney Isles Drive, Windermere, FL
    1626 Whitney Isles Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,645 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  22. 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)
  23. Photo of 311 E 8th Avenue, Windermere, FL 34786 (MLS # O6364016)
    $6,750
    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)
  24. Photo of 7028 Ventnor Drive, Windermere, FL 34786 (MLS # O6363663)
    $520,000
    Photo of 7028 Ventnor Drive, Windermere, FL 34786 (MLS # O6363663)
    Photo of 7028 Ventnor Drive, Windermere, FL 34786 (MLS # O6363663)
    7028 Ventnor Drive, Windermere, FL
    7028 Ventnor Drive
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 1,980 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  25. Photo of 8222 Stone Mason Court, Windermere, FL 34786 (MLS # O6363713)
    $2,895,000
    Photo of 8222 Stone Mason Court, Windermere, FL 34786 (MLS # O6363713)
    Photo of 8222 Stone Mason Court, Windermere, FL 34786 (MLS # O6363713)
    54
     
    8222 Stone Mason Court, Windermere, FL
    8222 Stone Mason Court
    Windermere, FL
    • 6 Beds
    • 7 Baths
    • 6,834 Home (sqft)
    • 7 Baths
    • 18,731 Lot (sqft)
  26. Photo of 11738 Camden Park Drive, Windermere, FL 34786 (MLS # O6363590)
    $1,125,000
    Photo of 11738 Camden Park Drive, Windermere, FL 34786 (MLS # O6363590)
    Photo of 11738 Camden Park Drive, Windermere, FL 34786 (MLS # O6363590)
    11738 Camden Park Drive, Windermere, FL
    11738 Camden Park Drive
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,635 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
  27. Photo of 2046 Westover Reserve Boulevard, Windermere, FL 34786 (MLS # O6364090)
    $999,000
    Photo of 2046 Westover Reserve Boulevard, Windermere, FL 34786 (MLS # O6364090)
    Photo of 2046 Westover Reserve Boulevard, Windermere, FL 34786 (MLS # O6364090)
    2046 Westover Reserve Boulevard, Windermere, FL
    2046 Westover Reserve Boulevard
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,516 Home (sqft)
    • 4 Baths
    • 11,326 Lot (sqft)
  28. Photo of 8746 Crescendo Avenue, Windermere, FL 34786 (MLS # O6363595)
    $5,350
    Photo of 8746 Crescendo Avenue, Windermere, FL 34786 (MLS # O6363595)
    Photo of 8746 Crescendo Avenue, Windermere, FL 34786 (MLS # O6363595)
    8746 Crescendo Avenue, Windermere, FL
    8746 Crescendo Avenue
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,050 Home (sqft)
    • 4 Baths
    • 6,970 Lot (sqft)
  29. Photo of 7625 Sutherton Lane, Windermere, FL 34786 (MLS # O6363486)
    $439,000
    Photo of 7625 Sutherton Lane, Windermere, FL 34786 (MLS # O6363486)
    Photo of 7625 Sutherton Lane, Windermere, FL 34786 (MLS # O6363486)
    33
     
    7625 Sutherton Lane, Windermere, FL
    7625 Sutherton Lane
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,505 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  30. Photo of 101 Lee Street, Windermere, FL 34786 (MLS # O6363362)
    $8,000
    Photo of 101 Lee Street, Windermere, FL 34786 (MLS # O6363362)
    Photo of 101 Lee Street, Windermere, FL 34786 (MLS # O6363362)
    100
     
     
    101 Lee Street, Windermere, FL
    101 Lee Street
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 4,186 Home (sqft)
    • 4 Baths
    • 18,296 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 12/7/25 7:08 AM PST.

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