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Real estate in the city of Windermere

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  1. Photo of 7448 Leighside Drive, Windermere, FL 34786 (MLS # S5137210)
    $2,700
    Photo of 7448 Leighside Drive, Windermere, FL 34786 (MLS # S5137210)
    Photo of 7448 Leighside Drive, Windermere, FL 34786 (MLS # S5137210)
    35
     
    7448 Leighside Drive, Windermere, FL
    7448 Leighside Drive
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,881 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  2. Photo of 13094 Kegan Street, Windermere, FL 34786 (MLS # S5137190)
    $3,100
    Photo of 13094 Kegan Street, Windermere, FL 34786 (MLS # S5137190)
    Photo of 13094 Kegan Street, Windermere, FL 34786 (MLS # S5137190)
    1
     
    13094 Kegan Street, Windermere, FL
    13094 Kegan Street
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,203 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  3. Photo of 5426 Gemgold Court, Windermere, FL 34786 (MLS # O6354639)
    $4,500
    Photo of 5426 Gemgold Court, Windermere, FL 34786 (MLS # O6354639)
    Photo of 5426 Gemgold Court, Windermere, FL 34786 (MLS # O6354639)
    5426 Gemgold Court, Windermere, FL
    5426 Gemgold Court
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,648 Home (sqft)
    • 3 Baths
    • 35,284 Lot (sqft)
  4. Photo of 11450 Arborside Bend Way, Windermere, FL 34786 (MLS # O6354816)
    $765,000
    Photo of 11450 Arborside Bend Way, Windermere, FL 34786 (MLS # O6354816)
    Photo of 11450 Arborside Bend Way, Windermere, FL 34786 (MLS # O6354816)
    11450 Arborside Bend Way, Windermere, FL
    11450 Arborside Bend Way
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,622 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  5. Photo of 8533 Greenbank Boulevard, Windermere, FL 34786 (MLS # O6354672)
    $670,000
    Photo of 8533 Greenbank Boulevard, Windermere, FL 34786 (MLS # O6354672)
    Photo of 8533 Greenbank Boulevard, Windermere, FL 34786 (MLS # O6354672)
    8533 Greenbank Boulevard, Windermere, FL
    8533 Greenbank Boulevard
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,551 Home (sqft)
    • 4 Baths
    • 9,584 Lot (sqft)
  6. Photo of 7654 Fairgrove Avenue, Windermere, FL 34786 (MLS # O6354642)
    $2,700
    Photo of 7654 Fairgrove Avenue, Windermere, FL 34786 (MLS # O6354642)
    Photo of 7654 Fairgrove Avenue, Windermere, FL 34786 (MLS # O6354642)
    7654 Fairgrove Avenue, Windermere, FL
    7654 Fairgrove Avenue
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 1,866 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  7. Photo of 6115 Orta Court, Windermere, FL 34786 (MLS # O6354423)
    $18,500
    Photo of 6115 Orta Court, Windermere, FL 34786 (MLS # O6354423)
    Photo of 6115 Orta Court, Windermere, FL 34786 (MLS # O6354423)
    6115 Orta Court, Windermere, FL
    6115 Orta Court
    Windermere, FL
    • 6 Beds
    • 8 Baths
    • 6,853 Home (sqft)
    • 8 Baths
    • 6.27 Lot (ac)
  8. Photo of 11837 Cave Run Avenue, Windermere, FL 34786 (MLS # O6354247)
    $4,800
    Photo of 11837 Cave Run Avenue, Windermere, FL 34786 (MLS # O6354247)
    Photo of 11837 Cave Run Avenue, Windermere, FL 34786 (MLS # O6354247)
    11837 Cave Run Avenue, Windermere, FL
    11837 Cave Run Avenue
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,407 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  9. Photo of 6846 Helmsley Circle, Windermere, FL 34786 (MLS # O6342692)
    $699,000
    Photo of 6846 Helmsley Circle, Windermere, FL 34786 (MLS # O6342692)
    Photo of 6846 Helmsley Circle, Windermere, FL 34786 (MLS # O6342692)
    6846 Helmsley Circle, Windermere, FL
    6846 Helmsley Circle
    Windermere, FL
    • 5 Beds
    • 3 Baths
    • 2,555 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  10. Photo of 12716 Langstaff Drive, Windermere, FL 34786 (MLS # O6352910)
    $374,900
    Photo of 12716 Langstaff Drive, Windermere, FL 34786 (MLS # O6352910)
    Photo of 12716 Langstaff Drive, Windermere, FL 34786 (MLS # O6352910)
    12716 Langstaff Drive, Windermere, FL
    12716 Langstaff Drive
    Windermere, FL
    • 2 Beds
    • 3 Baths
    • 1,181 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  11. Photo of 1803 Glenbay Court, Windermere, FL 34786 (MLS # O6352338)
    $875,000
    Photo of 1803 Glenbay Court, Windermere, FL 34786 (MLS # O6352338)
    Photo of 1803 Glenbay Court, Windermere, FL 34786 (MLS # O6352338)
    62
     
    1803 Glenbay Court, Windermere, FL
    1803 Glenbay Court
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 3,040 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
  12. Photo of 13225 Charfield Street, Windermere, FL 34786 (MLS # O6354078)
    $4,200
    Photo of 13225 Charfield Street, Windermere, FL 34786 (MLS # O6354078)
    Photo of 13225 Charfield Street, Windermere, FL 34786 (MLS # O6354078)
    13225 Charfield Street, Windermere, FL
    13225 Charfield Street
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,413 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  13. Photo of 8153 Jailene Drive, Windermere, FL 34786 (MLS # O6354298)
    $3,200
    Photo of 8153 Jailene Drive, Windermere, FL 34786 (MLS # O6354298)
    Photo of 8153 Jailene Drive, Windermere, FL 34786 (MLS # O6354298)
    8153 Jailene Drive, Windermere, FL
    8153 Jailene Drive
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,286 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  14. Photo of 1003 Down Reserve Court, Windermere, FL 34786 (MLS # O6353952)
    $5,499,999
    Photo of 1003 Down Reserve Court, Windermere, FL 34786 (MLS # O6353952)
    Photo of 1003 Down Reserve Court, Windermere, FL 34786 (MLS # O6353952)
    72
     
    1003 Down Reserve Court, Windermere, FL
    1003 Down Reserve Court
    Windermere, FL
    • 6 Beds
    • 8 Baths
    • 6,816 Home (sqft)
    • 8 Baths
    • 30,057 Lot (sqft)
  15. Photo of 7711 Fairgrove Avenue, Windermere, FL 34786 (MLS # O6352360)
    $394,900
    Photo of 7711 Fairgrove Avenue, Windermere, FL 34786 (MLS # O6352360)
    Photo of 7711 Fairgrove Avenue, Windermere, FL 34786 (MLS # O6352360)
    7711 Fairgrove Avenue, Windermere, FL
    7711 Fairgrove Avenue
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,680 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  16. Photo of 9106 Panzani Place, Windermere, FL 34786 (MLS # O6353426)
    $950,000
    Photo of 9106 Panzani Place, Windermere, FL 34786 (MLS # O6353426)
    Photo of 9106 Panzani Place, Windermere, FL 34786 (MLS # O6353426)
    9106 Panzani Place, Windermere, FL
    9106 Panzani Place
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,610 Home (sqft)
    • 4 Baths
    • 12,633 Lot (sqft)
  17. Photo of 4012 Isabella Circle, Windermere, FL 34786 (MLS # O6354060)
    $14,800
    Photo of 4012 Isabella Circle, Windermere, FL 34786 (MLS # O6354060)
    Photo of 4012 Isabella Circle, Windermere, FL 34786 (MLS # O6354060)
    4012 Isabella Circle, Windermere, FL
    4012 Isabella Circle
    Windermere, FL
    • 6 Beds
    • 9 Baths
    • 7,337 Home (sqft)
    • 9 Baths
    • 23,523 Lot (sqft)
  18. Photo of 11818 Water Run Alley, Windermere, FL 34786 (MLS # O6353649)
    $428,000
    Photo of 11818 Water Run Alley, Windermere, FL 34786 (MLS # O6353649)
    Photo of 11818 Water Run Alley, Windermere, FL 34786 (MLS # O6353649)
    11818 Water Run Alley, Windermere, FL
    11818 Water Run Alley
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,588 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  19. Photo of 43 Main Street, Windermere, FL 34786 (MLS # O6351531)
    $2,650
    Photo of 43 Main Street, Windermere, FL 34786 (MLS # O6351531)
    Photo of 43 Main Street, Windermere, FL 34786 (MLS # O6351531)
    22
     
    43 Main Street, Windermere, FL
    43 Main Street
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,332 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  20. Photo of 8639 Via Trieste Drive, Windermere, FL 34786 (MLS # TB8436408)
    $1,250
    Photo of 8639 Via Trieste Drive, Windermere, FL 34786 (MLS # TB8436408)
    Photo of 8639 Via Trieste Drive, Windermere, FL 34786 (MLS # TB8436408)
    8639 Via Trieste Drive, Windermere, FL
    8639 Via Trieste Drive
    Windermere, FL
    • 1 Bed
    • 1 Bath
    • 534 Home (sqft)
    • 1 Bath
    • 5,228 Lot (sqft)
  21. Photo of 11636 Water Run Alley, Windermere, FL 34786 (MLS # S5136888)
    $450,000
    Photo of 11636 Water Run Alley, Windermere, FL 34786 (MLS # S5136888)
    Photo of 11636 Water Run Alley, Windermere, FL 34786 (MLS # S5136888)
    11636 Water Run Alley, Windermere, FL
    11636 Water Run Alley
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,584 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  22. Photo of 6352 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6353453)
    $2,950
    Photo of 6352 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6353453)
    Photo of 6352 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6353453)
    6352 Golden Dewdrop Trail, Windermere, FL
    6352 Golden Dewdrop Trail
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,984 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  23. Photo of 1927 Watermere Lane, Windermere, FL 34786 (MLS # O6353108)
    $5,500
    Photo of 1927 Watermere Lane, Windermere, FL 34786 (MLS # O6353108)
    Photo of 1927 Watermere Lane, Windermere, FL 34786 (MLS # O6353108)
    1927 Watermere Lane, Windermere, FL
    1927 Watermere Lane
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,053 Home (sqft)
    • 4 Baths
    • 36,591 Lot (sqft)
  24. Photo of 4301 Down Point Lane, Windermere, FL 34786 (MLS # O6351950)
    $3,350,000
    Photo of 4301 Down Point Lane, Windermere, FL 34786 (MLS # O6351950)
    Photo of 4301 Down Point Lane, Windermere, FL 34786 (MLS # O6351950)
    4301 Down Point Lane, Windermere, FL
    4301 Down Point Lane
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 6,834 Home (sqft)
    • 4 Baths
    • 3.47 Lot (ac)
  25. Photo of 8179 Maritime Flag Street #202/108, Windermere, FL 34786 (MLS # S5136502)
    $350,000
    Photo of 8179 Maritime Flag Street #202/108, Windermere, FL 34786 (MLS # S5136502)
    Photo of 8179 Maritime Flag Street #202/108, Windermere, FL 34786 (MLS # S5136502)
    8179 Maritime Flag Street #202/108, Windermere, FL
    8179 Maritime Flag Street #202/108
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,442 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
  26. Photo of 1238 Lake Whitney Drive, Windermere, FL 34786 (MLS # O6354755)
    $2,400,000
    Photo of 1238 Lake Whitney Drive, Windermere, FL 34786 (MLS # O6354755)
    Photo of 1238 Lake Whitney Drive, Windermere, FL 34786 (MLS # O6354755)
    1238 Lake Whitney Drive, Windermere, FL
    1238 Lake Whitney Drive
    Windermere, FL
    • 4 Beds
    • 6 Baths
    • 5,266 Home (sqft)
    • 6 Baths
    • 22,652 Lot (sqft)
  27. Photo of 7451 Fairgrove Avenue, Windermere, FL 34786 (MLS # O6351291)
    $605,000
    Photo of 7451 Fairgrove Avenue, Windermere, FL 34786 (MLS # O6351291)
    Photo of 7451 Fairgrove Avenue, Windermere, FL 34786 (MLS # O6351291)
    7451 Fairgrove Avenue, Windermere, FL
    7451 Fairgrove Avenue
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 2,092 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  28. Photo of 13131 Penshurst Lane, Windermere, FL 34786 (MLS # O6346220)
    $2,799
    Photo of 13131 Penshurst Lane, Windermere, FL 34786 (MLS # O6346220)
    Photo of 13131 Penshurst Lane, Windermere, FL 34786 (MLS # O6346220)
    13131 Penshurst Lane, Windermere, FL
    13131 Penshurst Lane
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,948 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  29. Photo of 14008 Luminous Lane #802, Windermere, FL 34786 (MLS # O6352495)
    $374,900
    Photo of 14008 Luminous Lane #802, Windermere, FL 34786 (MLS # O6352495)
    Photo of 14008 Luminous Lane #802, Windermere, FL 34786 (MLS # O6352495)
    14008 Luminous Lane #802, Windermere, FL
    14008 Luminous Lane #802
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,974 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
  30. Photo of 11162 Ledgement Lane, Windermere, FL 34786 (MLS # O6346461)
    $1,045,000
    Photo of 11162 Ledgement Lane, Windermere, FL 34786 (MLS # O6346461)
    Photo of 11162 Ledgement Lane, Windermere, FL 34786 (MLS # O6346461)
    11162 Ledgement Lane, Windermere, FL
    11162 Ledgement Lane
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,248 Home (sqft)
    • 4 Baths
    • 14,375 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 10/23/25 8:51 PM PDT.

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