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Real estate in the city of Windermere

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  1. Photo of 2 Chase Road, Windermere, FL 34786 (MLS # O6345181)
    $650,000
    Photo of 2 Chase Road, Windermere, FL 34786 (MLS # O6345181)
    Photo of 2 Chase Road, Windermere, FL 34786 (MLS # O6345181)
    1
     
    2 Chase Road, Windermere, FL
    2 Chase Road
    Windermere, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 19,167 Lot (sqft)
  2. Photo of 12132 Montalcino Circle, Windermere, FL 34786 (MLS # O6319854)
    $4,199,000
    Photo of 12132 Montalcino Circle, Windermere, FL 34786 (MLS # O6319854)
    Photo of 12132 Montalcino Circle, Windermere, FL 34786 (MLS # O6319854)
    12132 Montalcino Circle, Windermere, FL
    12132 Montalcino Circle
    Windermere, FL
    • 6 Beds
    • 7 Baths
    • 5,709 Home (sqft)
    • 7 Baths
    • 36,155 Lot (sqft)
  3. Photo of 299 W 4th Avenue, Windermere, FL 34786 (MLS # O6357207)
    $895,000
    Photo of 299 W 4th Avenue, Windermere, FL 34786 (MLS # O6357207)
    Photo of 299 W 4th Avenue, Windermere, FL 34786 (MLS # O6357207)
    299 W 4th Avenue, Windermere, FL
    299 W 4th Avenue
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,410 Home (sqft)
    • 3 Baths
    • 16,553 Lot (sqft)
  4. Photo of 8180 Boat Hook Loop #304, Windermere, FL 34786 (MLS # O6358068)
    $2,400
    Photo of 8180 Boat Hook Loop #304, Windermere, FL 34786 (MLS # O6358068)
    Photo of 8180 Boat Hook Loop #304, Windermere, FL 34786 (MLS # O6358068)
    8180 Boat Hook Loop #304, Windermere, FL
    8180 Boat Hook Loop #304
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,455 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  5. Photo of 7211 Still Pond Lane, Windermere, FL 34786 (MLS # S5137978)
    $4,490
    Photo of 7211 Still Pond Lane, Windermere, FL 34786 (MLS # S5137978)
    Photo of 7211 Still Pond Lane, Windermere, FL 34786 (MLS # S5137978)
    17
     
    7211 Still Pond Lane, Windermere, FL
    7211 Still Pond Lane
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,091 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  6. Photo of 11819 Vermillion Avenue, Windermere, FL 34786 (MLS # O6358065)
    $2,800
    Photo of 11819 Vermillion Avenue, Windermere, FL 34786 (MLS # O6358065)
    Photo of 11819 Vermillion Avenue, Windermere, FL 34786 (MLS # O6358065)
    11819 Vermillion Avenue, Windermere, FL
    11819 Vermillion Avenue
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,760 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  7. Photo of 13752 Bressler Alley, Windermere, FL 34786 (MLS # O6358878)
    $468,000
    Photo of 13752 Bressler Alley, Windermere, FL 34786 (MLS # O6358878)
    Photo of 13752 Bressler Alley, Windermere, FL 34786 (MLS # O6358878)
    13752 Bressler Alley, Windermere, FL
    13752 Bressler Alley
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,976 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  8. Photo of 11692 Water Run Alley, Windermere, FL 34786 (MLS # O6358611)
    $459,000
    Photo of 11692 Water Run Alley, Windermere, FL 34786 (MLS # O6358611)
    Photo of 11692 Water Run Alley, Windermere, FL 34786 (MLS # O6358611)
    11692 Water Run Alley, Windermere, FL
    11692 Water Run Alley
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,712 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  9. Photo of 11438 Arborside Bend Way, Windermere, FL 34786 (MLS # S5137869)
    $655,000
    Photo of 11438 Arborside Bend Way, Windermere, FL 34786 (MLS # S5137869)
    Photo of 11438 Arborside Bend Way, Windermere, FL 34786 (MLS # S5137869)
    11438 Arborside Bend Way, Windermere, FL
    11438 Arborside Bend Way
    Windermere, FL
    • 4 Beds
    • 2 Baths
    • 2,019 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  10. Photo of 12821 Westside Village Loop, Windermere, FL 34786 (MLS # O6357888)
    $4,150
    Photo of 12821 Westside Village Loop, Windermere, FL 34786 (MLS # O6357888)
    Photo of 12821 Westside Village Loop, Windermere, FL 34786 (MLS # O6357888)
    12821 Westside Village Loop, Windermere, FL
    12821 Westside Village Loop
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,689 Home (sqft)
    • 4 Baths
    • 6,970 Lot (sqft)
  11. Photo of 805 Oakdale Street, Windermere, FL 34786 (MLS # O6357829)
    $2,800
    Photo of 805 Oakdale Street, Windermere, FL 34786 (MLS # O6357829)
    Photo of 805 Oakdale Street, Windermere, FL 34786 (MLS # O6357829)
    805 Oakdale Street, Windermere, FL
    805 Oakdale Street
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,710 Home (sqft)
    • 2 Baths
    • 14,811 Lot (sqft)
  12. Photo of 9733 Carillon Park Drive, Windermere, FL 34786 (MLS # O6355029)
    $5,250,000
    Photo of 9733 Carillon Park Drive, Windermere, FL 34786 (MLS # O6355029)
    Photo of 9733 Carillon Park Drive, Windermere, FL 34786 (MLS # O6355029)
    9733 Carillon Park Drive, Windermere, FL
    9733 Carillon Park Drive
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 7,600 Home (sqft)
    • 7 Baths
    • 37,026 Lot (sqft)
  13. Photo of 6615 Helmsley Circle, Windermere, FL 34786 (MLS # G5104075)
    $833,333
    Photo of 6615 Helmsley Circle, Windermere, FL 34786 (MLS # G5104075)
    Photo of 6615 Helmsley Circle, Windermere, FL 34786 (MLS # G5104075)
    6615 Helmsley Circle, Windermere, FL
    6615 Helmsley Circle
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,390 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  14. Photo of 11342 S Camden Commons Drive, Windermere, FL 34786 (MLS # O6357423)
    $7,500
    Photo of 11342 S Camden Commons Drive, Windermere, FL 34786 (MLS # O6357423)
    Photo of 11342 S Camden Commons Drive, Windermere, FL 34786 (MLS # O6357423)
    11342 S Camden Commons Drive, Windermere, FL
    11342 S Camden Commons Drive
    Windermere, FL
    • 6 Beds
    • 7 Baths
    • 3,625 Home (sqft)
    • 7 Baths
    • 10,890 Lot (sqft)
  15. Photo of 2943 Marquesas Court, Windermere, FL 34786 (MLS # O6357519)
    $4,200
    Photo of 2943 Marquesas Court, Windermere, FL 34786 (MLS # O6357519)
    Photo of 2943 Marquesas Court, Windermere, FL 34786 (MLS # O6357519)
    2943 Marquesas Court, Windermere, FL
    2943 Marquesas Court
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,145 Home (sqft)
    • 3 Baths
    • 43,560 Lot (sqft)
  16. Photo of 14284 Desert Haven Street #806, Windermere, FL 34786 (MLS # O6357673)
    $2,500
    Photo of 14284 Desert Haven Street #806, Windermere, FL 34786 (MLS # O6357673)
    Photo of 14284 Desert Haven Street #806, Windermere, FL 34786 (MLS # O6357673)
    14284 Desert Haven Street #806, Windermere, FL
    14284 Desert Haven Street #806
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,840 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  17. Photo of 2958 Marquesas Court, Windermere, FL 34786 (MLS # O6357302)
    $1,998,000
    Photo of 2958 Marquesas Court, Windermere, FL 34786 (MLS # O6357302)
    Photo of 2958 Marquesas Court, Windermere, FL 34786 (MLS # O6357302)
    2958 Marquesas Court, Windermere, FL
    2958 Marquesas Court
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 4,716 Home (sqft)
    • 5 Baths
    • 1.10 Lot (ac)
  18. Photo of 8265 Maritime Flag Street #101, Windermere, FL 34786 (MLS # O6357575)
    $2,375
    Photo of 8265 Maritime Flag Street #101, Windermere, FL 34786 (MLS # O6357575)
    Photo of 8265 Maritime Flag Street #101, Windermere, FL 34786 (MLS # O6357575)
    8265 Maritime Flag Street #101, Windermere, FL
    8265 Maritime Flag Street #101
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,644 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  19. Photo of 8156 Boat Hook Loop #303, Windermere, FL 34786 (MLS # O6357403)
    $2,095
    Photo of 8156 Boat Hook Loop #303, Windermere, FL 34786 (MLS # O6357403)
    Photo of 8156 Boat Hook Loop #303, Windermere, FL 34786 (MLS # O6357403)
    8156 Boat Hook Loop #303, Windermere, FL
    8156 Boat Hook Loop #303
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,442 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  20. Photo of 6626 Bridgewater Village Road, Windermere, FL 34786 (MLS # O6349184)
    $615,000
    Photo of 6626 Bridgewater Village Road, Windermere, FL 34786 (MLS # O6349184)
    Photo of 6626 Bridgewater Village Road, Windermere, FL 34786 (MLS # O6349184)
    6626 Bridgewater Village Road, Windermere, FL
    6626 Bridgewater Village Road
    Windermere, FL
    • 3 Beds
    • 4 Baths
    • 2,720 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
  21. Photo of 11562 Amidship Lane #208, Windermere, FL 34786 (MLS # O6357378)
    $2,095
    Photo of 11562 Amidship Lane #208, Windermere, FL 34786 (MLS # O6357378)
    Photo of 11562 Amidship Lane #208, Windermere, FL 34786 (MLS # O6357378)
    11562 Amidship Lane #208, Windermere, FL
    11562 Amidship Lane #208
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,442 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  22. Photo of 12609 Salomon Cove Dr, Windermere, FL 34786 (MLS # OM711651)
    $2,650
    Photo of 12609 Salomon Cove Dr, Windermere, FL 34786 (MLS # OM711651)
    Photo of 12609 Salomon Cove Dr, Windermere, FL 34786 (MLS # OM711651)
    12609 Salomon Cove Dr, Windermere, FL
    12609 Salomon Cove Dr
    Windermere, FL
    • 3 Beds
    • 2 Baths
    • 1,992 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  23. Photo of 13892 Summerport Trail Loop, Windermere, FL 34786 (MLS # O6357276)
    $2,795
    Photo of 13892 Summerport Trail Loop, Windermere, FL 34786 (MLS # O6357276)
    Photo of 13892 Summerport Trail Loop, Windermere, FL 34786 (MLS # O6357276)
    13892 Summerport Trail Loop, Windermere, FL
    13892 Summerport Trail Loop
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,024 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  24. Photo of 11446 Jasper Kay Terrace #1009, Windermere, FL 34786 (MLS # O6358901)
    $1,900
    Photo of 11446 Jasper Kay Terrace #1009, Windermere, FL 34786 (MLS # O6358901)
    Photo of 11446 Jasper Kay Terrace #1009, Windermere, FL 34786 (MLS # O6358901)
    10
     
    11446 Jasper Kay Terrace #1009, Windermere, FL
    11446 Jasper Kay Terrace #1009
    Windermere, FL
    • 2 Beds
    • 2 Baths
    • 1,161 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  25. Photo of 6507 Rosella Court, Windermere, FL 34786 (MLS # O6353035)
    $7,750,000
    Photo of 6507 Rosella Court, Windermere, FL 34786 (MLS # O6353035)
    Photo of 6507 Rosella Court, Windermere, FL 34786 (MLS # O6353035)
    6507 Rosella Court, Windermere, FL
    6507 Rosella Court
    Windermere, FL
    • 7 Beds
    • 8 Baths
    • 10,485 Home (sqft)
    • 8 Baths
    • 2.19 Lot (ac)
  26. Photo of 14217 Bridgewater Crossings Boulevard, Windermere, FL 34786 (MLS # O6357143)
    $3,000
    Photo of 14217 Bridgewater Crossings Boulevard, Windermere, FL 34786 (MLS # O6357143)
    Photo of 14217 Bridgewater Crossings Boulevard, Windermere, FL 34786 (MLS # O6357143)
    14217 Bridgewater Crossings Boulevard, Windermere, FL
    14217 Bridgewater Crossings Boulevard
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,419 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  27. Photo of 2509 Ridgewind Way, Windermere, FL 34786 (MLS # O6354737)
    $1,585,000
    Photo of 2509 Ridgewind Way, Windermere, FL 34786 (MLS # O6354737)
    Photo of 2509 Ridgewind Way, Windermere, FL 34786 (MLS # O6354737)
    38
     
    2509 Ridgewind Way, Windermere, FL
    2509 Ridgewind Way
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,844 Home (sqft)
    • 4 Baths
    • 32,670 Lot (sqft)
  28. Photo of 5412 Water Creek Drive, Windermere, FL 34786 (MLS # O6356517)
    $1,999,900
    Photo of 5412 Water Creek Drive, Windermere, FL 34786 (MLS # O6356517)
    Photo of 5412 Water Creek Drive, Windermere, FL 34786 (MLS # O6356517)
    5412 Water Creek Drive, Windermere, FL
    5412 Water Creek Drive
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 4,247 Home (sqft)
    • 5 Baths
    • 1.14 Lot (ac)
  29. Photo of 12136 Canyon Sun Trail, Windermere, FL 34786 (MLS # O6333581)
    $525,000
    Photo of 12136 Canyon Sun Trail, Windermere, FL 34786 (MLS # O6333581)
    Photo of 12136 Canyon Sun Trail, Windermere, FL 34786 (MLS # O6333581)
    12136 Canyon Sun Trail, Windermere, FL
    12136 Canyon Sun Trail
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 2,149 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  30. Photo of 8398 Iron Mountain Trail, Windermere, FL 34786 (MLS # O6356155)
    $2,500
    Photo of 8398 Iron Mountain Trail, Windermere, FL 34786 (MLS # O6356155)
    Photo of 8398 Iron Mountain Trail, Windermere, FL 34786 (MLS # O6356155)
    8398 Iron Mountain Trail, Windermere, FL
    8398 Iron Mountain Trail
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,540 Home (sqft)
    • 3 Baths
    • 2,614 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 11/21/25 3:02 AM PST.

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