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Windermere is located in Orange County, 14 miles southwest of Downtown Orlando. Surrounded by the Butler Chain of Lakes, it provides its residents with beautiful water views and gorgeous landscapes. Use our custom search tool to view all homes for sale above $600k in Windermere. Click here to return to the list of surrounding towns and cities in the Orlando area or here for the list in the Kissimmee area. Have questions? Contact us here or schedule your FREE consultation here.


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  1. Photo of 11954 Provincial Way, Windermere, FL 34786 (MLS # O6214196)
    $2,299,000
    Photo of 11954 Provincial Way, Windermere, FL 34786 (MLS # O6214196)
    Photo of 11954 Provincial Way, Windermere, FL 34786 (MLS # O6214196)
    11954 Provincial Way, Windermere, FL
    11954 Provincial Way
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 4,800 Home (sqft)
    • 5 Baths
    • 18,296 Lot (sqft)
  2. Photo of 2119 Willow Brick Road, Windermere, FL 34786 (MLS # O6214365)
    $925,000
    Photo of 2119 Willow Brick Road, Windermere, FL 34786 (MLS # O6214365)
    Photo of 2119 Willow Brick Road, Windermere, FL 34786 (MLS # O6214365)
    2119 Willow Brick Road, Windermere, FL
    2119 Willow Brick Road
    Windermere, FL
    • 5 Beds
    • 3 Baths
    • 2,728 Home (sqft)
    • 3 Baths
    • 30,928 Lot (sqft)
  3. Photo of 11154 Park Avenue, Windermere, FL 34786 (MLS # O6210864)
    $935,000
    Photo of 11154 Park Avenue, Windermere, FL 34786 (MLS # O6210864)
    Photo of 11154 Park Avenue, Windermere, FL 34786 (MLS # O6210864)
    11154 Park Avenue, Windermere, FL
    11154 Park Avenue
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,355 Home (sqft)
    • 4 Baths
    • 13,940 Lot (sqft)
  4. Photo of 8738 Iron Mountain Trail, Windermere, FL 34786 (MLS # S5106197)
    $899,000
    Photo of 8738 Iron Mountain Trail, Windermere, FL 34786 (MLS # S5106197)
    Photo of 8738 Iron Mountain Trail, Windermere, FL 34786 (MLS # S5106197)
    8738 Iron Mountain Trail, Windermere, FL
    8738 Iron Mountain Trail
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,127 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  5. Photo of 9832 Laurel Valley Drive, Windermere, FL 34786 (MLS # O6211352)
    $11,749,000
    Photo of 9832 Laurel Valley Drive, Windermere, FL 34786 (MLS # O6211352)
    Photo of 9832 Laurel Valley Drive, Windermere, FL 34786 (MLS # O6211352)
    9832 Laurel Valley Drive, Windermere, FL
    9832 Laurel Valley Drive
    Windermere, FL
    • 6 Beds
    • 10 Baths
    • 11,100 Home (sqft)
    • 10 Baths
    • 26,136 Lot (sqft)
  6. Photo of 3036 Seigneury Drive, Windermere, FL 34786 (MLS # O6210683)
    $1,950,000
    Photo of 3036 Seigneury Drive, Windermere, FL 34786 (MLS # O6210683)
    Photo of 3036 Seigneury Drive, Windermere, FL 34786 (MLS # O6210683)
    3036 Seigneury Drive, Windermere, FL
    3036 Seigneury Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 4,287 Home (sqft)
    • 4 Baths
    • 28,750 Lot (sqft)
  7. Photo of 6215 Little Lake Sawyer Drive, Windermere, FL 34786 (MLS # O6210320)
    $1,750,000
    Photo of 6215 Little Lake Sawyer Drive, Windermere, FL 34786 (MLS # O6210320)
    Photo of 6215 Little Lake Sawyer Drive, Windermere, FL 34786 (MLS # O6210320)
    6215 Little Lake Sawyer Drive, Windermere, FL
    6215 Little Lake Sawyer Drive
    Windermere, FL
    • 6 Beds
    • 4 Baths
    • 5,110 Home (sqft)
    • 4 Baths
    • 1.11 Lot (ac)
  8. Photo of 9058 Reflection Pointe Drive, Windermere, FL 34786 (MLS # O6208783)
    $709,990
    Photo of 9058 Reflection Pointe Drive, Windermere, FL 34786 (MLS # O6208783)
    Photo of 9058 Reflection Pointe Drive, Windermere, FL 34786 (MLS # O6208783)
    9058 Reflection Pointe Drive, Windermere, FL
    9058 Reflection Pointe Drive
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 3,651 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  9. Photo of 9502 Hempel Cove Boulevard, Windermere, FL 34786 (MLS # S5105459)
    $1,250,000
    Photo of 9502 Hempel Cove Boulevard, Windermere, FL 34786 (MLS # S5105459)
    Photo of 9502 Hempel Cove Boulevard, Windermere, FL 34786 (MLS # S5105459)
    9502 Hempel Cove Boulevard, Windermere, FL
    9502 Hempel Cove Boulevard
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 4,524 Home (sqft)
    • 5 Baths
    • 1.02 Lot (ac)
  10. Photo of 1126 Kelso Boulevard, Windermere, FL 34786 (MLS # O6205965)
    $1,498,000
    Photo of 1126 Kelso Boulevard, Windermere, FL 34786 (MLS # O6205965)
    Photo of 1126 Kelso Boulevard, Windermere, FL 34786 (MLS # O6205965)
    1126 Kelso Boulevard, Windermere, FL
    1126 Kelso Boulevard
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 3,184 Home (sqft)
    • 3 Baths
    • 43,560 Lot (sqft)
  11. Photo of 1516 Hempel Avenue, Windermere, FL 34786 (MLS # O6206281)
    $4,990,000
    Photo of 1516 Hempel Avenue, Windermere, FL 34786 (MLS # O6206281)
    Photo of 1516 Hempel Avenue, Windermere, FL 34786 (MLS # O6206281)
    1516 Hempel Avenue, Windermere, FL
    1516 Hempel Avenue
    Windermere, FL
    • 6 Beds
    • 8 Baths
    • 7,484 Home (sqft)
    • 8 Baths
    • 21,345 Lot (sqft)
  12. Photo of 4029 Isabella Circle, Windermere, FL 34786 (MLS # O6205739)
    $3,999,000
    Photo of 4029 Isabella Circle, Windermere, FL 34786 (MLS # O6205739)
    Photo of 4029 Isabella Circle, Windermere, FL 34786 (MLS # O6205739)
    4029 Isabella Circle, Windermere, FL
    4029 Isabella Circle
    Windermere, FL
    • 6 Beds
    • 8 Baths
    • 7,217 Home (sqft)
    • 8 Baths
    • 37,026 Lot (sqft)
  13. Photo of 13885 Bluebird Pond Road, Windermere, FL 34786 (MLS # O6203651)
    $629,900
    Photo of 13885 Bluebird Pond Road, Windermere, FL 34786 (MLS # O6203651)
    Photo of 13885 Bluebird Pond Road, Windermere, FL 34786 (MLS # O6203651)
    13885 Bluebird Pond Road, Windermere, FL
    13885 Bluebird Pond Road
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,786 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
  14. Photo of 6845 Valhalla Way, Windermere, FL 34786 (MLS # O6200366)
    $3,575,000
    Photo of 6845 Valhalla Way, Windermere, FL 34786 (MLS # O6200366)
    Photo of 6845 Valhalla Way, Windermere, FL 34786 (MLS # O6200366)
    6845 Valhalla Way, Windermere, FL
    6845 Valhalla Way
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 7,438 Home (sqft)
    • 7 Baths
    • 21,780 Lot (sqft)
  15. Photo of 11618 Vinci Drive, Windermere, FL 34786 (MLS # O6201378)
    $5,500,000
    Photo of 11618 Vinci Drive, Windermere, FL 34786 (MLS # O6201378)
    Photo of 11618 Vinci Drive, Windermere, FL 34786 (MLS # O6201378)
    11618 Vinci Drive, Windermere, FL
    11618 Vinci Drive
    Windermere, FL
    • 5 Beds
    • 7 Baths
    • 5,260 Home (sqft)
    • 7 Baths
    • 1.16 Lot (ac)
  16. Photo of 13161 Lake Butler Boulevard, Windermere, FL 34786 (MLS # T3522412)
    $2,400,000
    Photo of 13161 Lake Butler Boulevard, Windermere, FL 34786 (MLS # T3522412)
    Photo of 13161 Lake Butler Boulevard, Windermere, FL 34786 (MLS # T3522412)
    13161 Lake Butler Boulevard, Windermere, FL
    13161 Lake Butler Boulevard
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 4,500 Home (sqft)
    • 5 Baths
    • 1.76 Lot (ac)
  17. Photo of 11113 Lake Butler Boulevard, Windermere, FL 34786 (MLS # O6195201)
    $2,699,000
    Photo of 11113 Lake Butler Boulevard, Windermere, FL 34786 (MLS # O6195201)
    Photo of 11113 Lake Butler Boulevard, Windermere, FL 34786 (MLS # O6195201)
    11113 Lake Butler Boulevard, Windermere, FL
    11113 Lake Butler Boulevard
    Windermere, FL
    • 5 Beds
    • 6 Baths
    • 4,094 Home (sqft)
    • 6 Baths
    • 17,860 Lot (sqft)
  18. Photo of 9621 Windy Ridge Road, Windermere, FL 34786 (MLS # O6184943)
    $15,950,000
    Photo of 9621 Windy Ridge Road, Windermere, FL 34786 (MLS # O6184943)
    Photo of 9621 Windy Ridge Road, Windermere, FL 34786 (MLS # O6184943)
    9621 Windy Ridge Road, Windermere, FL
    9621 Windy Ridge Road
    Windermere, FL
    • 9 Beds
    • 16 Baths
    • 20,445 Home (sqft)
    • 16 Baths
    • 2.50 Lot (ac)
  19. Photo of 6030 Greatwater Drive, Windermere, FL 34786 (MLS # O6194035)
    $3,250,000
    Photo of 6030 Greatwater Drive, Windermere, FL 34786 (MLS # O6194035)
    Photo of 6030 Greatwater Drive, Windermere, FL 34786 (MLS # O6194035)
    6030 Greatwater Drive, Windermere, FL
    6030 Greatwater Drive
    Windermere, FL
    • 6 Beds
    • 7 Baths
    • 6,490 Home (sqft)
    • 7 Baths
    • 19,167 Lot (sqft)
  20. Photo of 10821 Bayshore Drive, Windermere, FL 34786 (MLS # O6189960)
    $5,495,000
    Photo of 10821 Bayshore Drive, Windermere, FL 34786 (MLS # O6189960)
    Photo of 10821 Bayshore Drive, Windermere, FL 34786 (MLS # O6189960)
    10821 Bayshore Drive, Windermere, FL
    10821 Bayshore Drive
    Windermere, FL
    • 4 Beds
    • 6 Baths
    • 5,275 Home (sqft)
    • 6 Baths
    • 2.80 Lot (ac)
  21. Photo of 6443 Cartmel Lane, Windermere, FL 34786 (MLS # O6179128)
    $1,475,000
    Photo of 6443 Cartmel Lane, Windermere, FL 34786 (MLS # O6179128)
    Photo of 6443 Cartmel Lane, Windermere, FL 34786 (MLS # O6179128)
    6443 Cartmel Lane, Windermere, FL
    6443 Cartmel Lane
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 4,257 Home (sqft)
    • 5 Baths
    • 16,118 Lot (sqft)
  22. Photo of 5507 Worsham Ct, Windermere, FL 34786 (MLS # O6180706)
    $8,200,000
    Photo of 5507 Worsham Ct, Windermere, FL 34786 (MLS # O6180706)
    Photo of 5507 Worsham Ct, Windermere, FL 34786 (MLS # O6180706)
    5507 Worsham Ct, Windermere, FL
    5507 Worsham Ct
    Windermere, FL
    • 5 Beds
    • 11 Baths
    • 10,200 Home (sqft)
    • 11 Baths
    • 42,689 Lot (sqft)
  23. Photo of 11617 Waterstone Loop Drive, Windermere, FL 34786 (MLS # O6177372)
    $3,150,000
    Photo of 11617 Waterstone Loop Drive, Windermere, FL 34786 (MLS # O6177372)
    Photo of 11617 Waterstone Loop Drive, Windermere, FL 34786 (MLS # O6177372)
    11617 Waterstone Loop Drive, Windermere, FL
    11617 Waterstone Loop Drive
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 4,957 Home (sqft)
    • 5 Baths
    • 1.07 Lot (ac)
  24. Photo of 8745 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6177463)
    $990,000
    Photo of 8745 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6177463)
    Photo of 8745 Lookout Pointe Drive, Windermere, FL 34786 (MLS # O6177463)
    8745 Lookout Pointe Drive, Windermere, FL
    8745 Lookout Pointe Drive
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 3,483 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
  25. Photo of 14372 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5078125)
    $1,137,907
    Photo of 14372 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5078125)
    Photo of 14372 Crest Palm Avenue, Windermere, FL 34786 (MLS # G5078125)
    14372 Crest Palm Avenue, Windermere, FL
    14372 Crest Palm Avenue
    Windermere, FL
    • 6 Beds
    • 5 Baths
    • 4,443 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  26. Photo of 6008 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6176228)
    $1,250,000
    Photo of 6008 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6176228)
    Photo of 6008 Golden Dewdrop Trail, Windermere, FL 34786 (MLS # O6176228)
    6008 Golden Dewdrop Trail, Windermere, FL
    6008 Golden Dewdrop Trail
    Windermere, FL
    • 8 Beds
    • 5 Baths
    • 4,751 Home (sqft)
    • 5 Baths
    • 8,712 Lot (sqft)
  27. Photo of 4200 Down Point Lane, Windermere, FL 34786 (MLS # O6176070)
    $12,900,000
    Photo of 4200 Down Point Lane, Windermere, FL 34786 (MLS # O6176070)
    Photo of 4200 Down Point Lane, Windermere, FL 34786 (MLS # O6176070)
    4200 Down Point Lane, Windermere, FL
    4200 Down Point Lane
    Windermere, FL
    • 6 Beds
    • 9 Baths
    • 14,435 Home (sqft)
    • 9 Baths
    • 1.60 Lot (ac)
  28. Photo of 5379 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6172675)
    $2,997,000
    Photo of 5379 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6172675)
    Photo of 5379 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6172675)
    5379 Isleworth Country Club Drive, Windermere, FL
    5379 Isleworth Country Club Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,872 Home (sqft)
    • 4 Baths
    • 24,394 Lot (sqft)
  29. Photo of 5190 Latrobe Drive, Windermere, FL 34786 (MLS # O6172519)
    $5,999,999
    Photo of 5190 Latrobe Drive, Windermere, FL 34786 (MLS # O6172519)
    Photo of 5190 Latrobe Drive, Windermere, FL 34786 (MLS # O6172519)
    5190 Latrobe Drive, Windermere, FL
    5190 Latrobe Drive
    Windermere, FL
    • 5 Beds
    • 8 Baths
    • 7,191 Home (sqft)
    • 8 Baths
    • 31,799 Lot (sqft)
  30. Photo of 9844 Laurel Valley Drive, Windermere, FL 34786 (MLS # O6173216)
    $4,950,000
    Photo of 9844 Laurel Valley Drive, Windermere, FL 34786 (MLS # O6173216)
    Photo of 9844 Laurel Valley Drive, Windermere, FL 34786 (MLS # O6173216)
    9844 Laurel Valley Drive, Windermere, FL
    9844 Laurel Valley Drive
    Windermere, FL
    • 5 Beds
    • 6 Baths
    • 5,613 Home (sqft)
    • 6 Baths
    • 25,701 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 12/23/24 6:20 AM PST.

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