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Winter Garden is located 14 miles west of downtown Orlando in the western part of Orange County. Nestled alongside beautiful Lake Apopka, it is a former citrus town incorporated in 1908 and is home to more than 40,000 residents. Its historic downtown is listed on the National Registry of Historic Places and is a favorite destination for residents due to its shops, restaurants, and award-winning West Orange Trail, part of the 250-mile Coast-to-Coast Connector Trail across Central Florida. Use our custom search tool to view all pool homes for sale above $600k in Winter Garden or click here to return to the list of surrounding towns and cities in the Kissimmee area. Have questions? Contact us here or schedule your FREE consultation here.


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  1. Photo of 5308 Golden Apple Drive, Winter Garden, FL 34787 (MLS # O6259909)
    $769,000
    Photo of 5308 Golden Apple Drive, Winter Garden, FL 34787 (MLS # O6259909)
    Photo of 5308 Golden Apple Drive, Winter Garden, FL 34787 (MLS # O6259909)
    5308 Golden Apple Drive, Winter Garden, FL
    5308 Golden Apple Drive
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,724 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  2. Photo of 7905 Minutemen Loop, Winter Garden, FL 34787 (MLS # O6259380)
    $749,900
    Photo of 7905 Minutemen Loop, Winter Garden, FL 34787 (MLS # O6259380)
    Photo of 7905 Minutemen Loop, Winter Garden, FL 34787 (MLS # O6259380)
    7905 Minutemen Loop, Winter Garden, FL
    7905 Minutemen Loop
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,716 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  3. Photo of 7224 Enchanted Lake Dr, Winter Garden, FL 34787 (MLS # O6258598)
    $1,050,000
    Photo of 7224 Enchanted Lake Dr, Winter Garden, FL 34787 (MLS # O6258598)
    Photo of 7224 Enchanted Lake Dr, Winter Garden, FL 34787 (MLS # O6258598)
    7224 Enchanted Lake Dr, Winter Garden, FL
    7224 Enchanted Lake Dr
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,295 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  4. Photo of 423 N Main St, Winter Garden, FL 34787 (MLS # O6259239)
    $725,000
    Photo of 423 N Main St, Winter Garden, FL 34787 (MLS # O6259239)
    Photo of 423 N Main St, Winter Garden, FL 34787 (MLS # O6259239)
    423 N Main St, Winter Garden, FL
    423 N Main St
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,668 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
  5. Photo of 15614 Espalier Way, Winter Garden, FL 34787 (MLS # O6258701)
    $4,500,000
    Photo of 15614 Espalier Way, Winter Garden, FL 34787 (MLS # O6258701)
    Photo of 15614 Espalier Way, Winter Garden, FL 34787 (MLS # O6258701)
    15614 Espalier Way, Winter Garden, FL
    15614 Espalier Way
    Winter Garden, FL
    • 5 Beds
    • 7 Baths
    • 6,601 Home (sqft)
    • 7 Baths
    • 2.19 Lot (ac)
  6. Photo of 15049 Canopy Cover Dr, Winter Garden, FL 34787 (MLS # S5115673)
    $1,150,000
    Photo of 15049 Canopy Cover Dr, Winter Garden, FL 34787 (MLS # S5115673)
    Photo of 15049 Canopy Cover Dr, Winter Garden, FL 34787 (MLS # S5115673)
    15049 Canopy Cover Dr, Winter Garden, FL
    15049 Canopy Cover Dr
    Winter Garden, FL
    • 2 Beds
    • 3 Baths
    • 2,282 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  7. Photo of 15121 Pigeon Plum Lane, Winter Garden, FL 34787 (MLS # O6257200)
    $605,000
    Photo of 15121 Pigeon Plum Lane, Winter Garden, FL 34787 (MLS # O6257200)
    Photo of 15121 Pigeon Plum Lane, Winter Garden, FL 34787 (MLS # O6257200)
    15121 Pigeon Plum Lane, Winter Garden, FL
    15121 Pigeon Plum Lane
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,004 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  8. Photo of 663 Caterpillar Run, Winter Garden, FL 34787 (MLS # O6257520)
    $875,000
    Photo of 663 Caterpillar Run, Winter Garden, FL 34787 (MLS # O6257520)
    Photo of 663 Caterpillar Run, Winter Garden, FL 34787 (MLS # O6257520)
    663 Caterpillar Run, Winter Garden, FL
    663 Caterpillar Run
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 4,258 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
  9. Photo of 7645 Green Mountain Way, Winter Garden, FL 34787 (MLS # O6257850)
    $2,200,000
    Photo of 7645 Green Mountain Way, Winter Garden, FL 34787 (MLS # O6257850)
    Photo of 7645 Green Mountain Way, Winter Garden, FL 34787 (MLS # O6257850)
    7645 Green Mountain Way, Winter Garden, FL
    7645 Green Mountain Way
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 3,296 Home (sqft)
    • 4 Baths
    • 33,977 Lot (sqft)
  10. Photo of 7573 Green Mountain Way, Winter Garden, FL 34787 (MLS # O6257099)
    $1,850,000
    Photo of 7573 Green Mountain Way, Winter Garden, FL 34787 (MLS # O6257099)
    Photo of 7573 Green Mountain Way, Winter Garden, FL 34787 (MLS # O6257099)
    63
     
    7573 Green Mountain Way, Winter Garden, FL
    7573 Green Mountain Way
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 3,388 Home (sqft)
    • 4 Baths
    • 1.26 Lot (ac)
  11. Photo of 15687 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6257188)
    $2,175,000
    Photo of 15687 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6257188)
    Photo of 15687 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6257188)
    15687 Panther Lake Drive, Winter Garden, FL
    15687 Panther Lake Drive
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 4,276 Home (sqft)
    • 5 Baths
    • 20,909 Lot (sqft)
  12. Photo of 2019 Wintermere Pointe Drive, Winter Garden, FL 34787 (MLS # O6257471)
    $669,000
    Photo of 2019 Wintermere Pointe Drive, Winter Garden, FL 34787 (MLS # O6257471)
    Photo of 2019 Wintermere Pointe Drive, Winter Garden, FL 34787 (MLS # O6257471)
    2019 Wintermere Pointe Drive, Winter Garden, FL
    2019 Wintermere Pointe Drive
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,455 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
  13. Photo of 1849 Burdock Drive, Winter Garden, FL 34787 (MLS # O6255830)
    $625,000
    Photo of 1849 Burdock Drive, Winter Garden, FL 34787 (MLS # O6255830)
    Photo of 1849 Burdock Drive, Winter Garden, FL 34787 (MLS # O6255830)
    1849 Burdock Drive, Winter Garden, FL
    1849 Burdock Drive
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,683 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  14. Photo of 17017 Marsh Road, Winter Garden, FL 34787 (MLS # O6254855)
    $12,000,000
    Photo of 17017 Marsh Road, Winter Garden, FL 34787 (MLS # O6254855)
    Photo of 17017 Marsh Road, Winter Garden, FL 34787 (MLS # O6254855)
    17017 Marsh Road, Winter Garden, FL
    17017 Marsh Road
    Winter Garden, FL
    • 6 Beds
    • 6 Baths
    • 6,977 Home (sqft)
    • 6 Baths
    • 17.88 Lot (ac)
  15. Photo of 13412 Fox Glove Street, Winter Garden, FL 34787 (MLS # G5088860)
    $927,900
    Photo of 13412 Fox Glove Street, Winter Garden, FL 34787 (MLS # G5088860)
    Photo of 13412 Fox Glove Street, Winter Garden, FL 34787 (MLS # G5088860)
    13412 Fox Glove Street, Winter Garden, FL
    13412 Fox Glove Street
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 3,954 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  16. Photo of 15663 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6251528)
    $2,450,000
    Photo of 15663 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6251528)
    Photo of 15663 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6251528)
    15663 Panther Lake Drive, Winter Garden, FL
    15663 Panther Lake Drive
    Winter Garden, FL
    • 5 Beds
    • 6 Baths
    • 4,709 Home (sqft)
    • 6 Baths
    • 1.18 Lot (ac)
  17. Photo of 15217 Farm Stand Court, Winter Garden, FL 34787 (MLS # O6252886)
    $2,469,000
    Photo of 15217 Farm Stand Court, Winter Garden, FL 34787 (MLS # O6252886)
    Photo of 15217 Farm Stand Court, Winter Garden, FL 34787 (MLS # O6252886)
    15217 Farm Stand Court, Winter Garden, FL
    15217 Farm Stand Court
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 4,219 Home (sqft)
    • 5 Baths
    • 13,940 Lot (sqft)
  18. Photo of 16653 Toccoa Row, Winter Garden, FL 34787 (MLS # O6253807)
    $795,000
    Photo of 16653 Toccoa Row, Winter Garden, FL 34787 (MLS # O6253807)
    Photo of 16653 Toccoa Row, Winter Garden, FL 34787 (MLS # O6253807)
    16653 Toccoa Row, Winter Garden, FL
    16653 Toccoa Row
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,806 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
  19. Photo of 557 Lake Cove Pointe Cir, Winter Garden, FL 34787 (MLS # O6252812)
    $1,795,000
    Photo of 557 Lake Cove Pointe Cir, Winter Garden, FL 34787 (MLS # O6252812)
    Photo of 557 Lake Cove Pointe Cir, Winter Garden, FL 34787 (MLS # O6252812)
    73
     
    557 Lake Cove Pointe Cir, Winter Garden, FL
    557 Lake Cove Pointe Cir
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 4,176 Home (sqft)
    • 5 Baths
    • 16,989 Lot (sqft)
  20. Photo of 14616 Avenue Of The Rushes, Winter Garden, FL 34787 (MLS # S5114500)
    $2,300,000
    Photo of 14616 Avenue Of The Rushes, Winter Garden, FL 34787 (MLS # S5114500)
    Photo of 14616 Avenue Of The Rushes, Winter Garden, FL 34787 (MLS # S5114500)
    80
     
    14616 Avenue Of The Rushes, Winter Garden, FL
    14616 Avenue Of The Rushes
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 4,583 Home (sqft)
    • 5 Baths
    • 1.55 Lot (ac)
  21. Photo of 2800 Tropic Court, Winter Garden, FL 34787 (MLS # O6251898)
    $850,000
    Photo of 2800 Tropic Court, Winter Garden, FL 34787 (MLS # O6251898)
    Photo of 2800 Tropic Court, Winter Garden, FL 34787 (MLS # O6251898)
    2800 Tropic Court, Winter Garden, FL
    2800 Tropic Court
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 2,873 Home (sqft)
    • 3 Baths
    • 25,701 Lot (sqft)
  22. Photo of 14969 Winter Stay Drive, Winter Garden, FL 34787 (MLS # O6251569)
    $1,050,000
    Photo of 14969 Winter Stay Drive, Winter Garden, FL 34787 (MLS # O6251569)
    Photo of 14969 Winter Stay Drive, Winter Garden, FL 34787 (MLS # O6251569)
    56
     
    14969 Winter Stay Drive, Winter Garden, FL
    14969 Winter Stay Drive
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 3,443 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  23. Photo of 3220 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6251409)
    $939,000
    Photo of 3220 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6251409)
    Photo of 3220 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6251409)
    3220 Sailing Pier Avenue, Winter Garden, FL
    3220 Sailing Pier Avenue
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,363 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  24. Photo of 15404 Orchard Garden Street, Winter Garden, FL 34787 (MLS # O6251194)
    $747,235
    Photo of 15404 Orchard Garden Street, Winter Garden, FL 34787 (MLS # O6251194)
    Photo of 15404 Orchard Garden Street, Winter Garden, FL 34787 (MLS # O6251194)
    15404 Orchard Garden Street, Winter Garden, FL
    15404 Orchard Garden Street
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,870 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  25. Photo of 9123 Tower Pine Drive, Winter Garden, FL 34787 (MLS # O6250967)
    $1,275,000
    Photo of 9123 Tower Pine Drive, Winter Garden, FL 34787 (MLS # O6250967)
    Photo of 9123 Tower Pine Drive, Winter Garden, FL 34787 (MLS # O6250967)
    17
     
    9123 Tower Pine Drive, Winter Garden, FL
    9123 Tower Pine Drive
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,771 Home (sqft)
    • 4 Baths
    • 5.00 Lot (ac)
  26. Photo of 15543 Pebble Ridge Street, Winter Garden, FL 34787 (MLS # O6250356)
    $749,800
    Photo of 15543 Pebble Ridge Street, Winter Garden, FL 34787 (MLS # O6250356)
    Photo of 15543 Pebble Ridge Street, Winter Garden, FL 34787 (MLS # O6250356)
    15543 Pebble Ridge Street, Winter Garden, FL
    15543 Pebble Ridge Street
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 3,359 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  27. Photo of 16328 Wind View Lane, Winter Garden, FL 34787 (MLS # O6247741)
    $949,900
    Photo of 16328 Wind View Lane, Winter Garden, FL 34787 (MLS # O6247741)
    Photo of 16328 Wind View Lane, Winter Garden, FL 34787 (MLS # O6247741)
    16328 Wind View Lane, Winter Garden, FL
    16328 Wind View Lane
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 3,408 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  28. Photo of 10301 Savannah Ridge Lane, Winter Garden, FL 34787 (MLS # G5087732)
    $3,899,000
    Photo of 10301 Savannah Ridge Lane, Winter Garden, FL 34787 (MLS # G5087732)
    Photo of 10301 Savannah Ridge Lane, Winter Garden, FL 34787 (MLS # G5087732)
    10301 Savannah Ridge Lane, Winter Garden, FL
    10301 Savannah Ridge Lane
    Winter Garden, FL
    • 6 Beds
    • 6 Baths
    • 7,428 Home (sqft)
    • 6 Baths
    • 2.96 Lot (ac)
  29. Photo of 15167 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6245196)
    $1,150,000
    Photo of 15167 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6245196)
    Photo of 15167 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6245196)
    15167 Shonan Gold Drive, Winter Garden, FL
    15167 Shonan Gold Drive
    Winter Garden, FL
    • 6 Beds
    • 4 Baths
    • 3,407 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  30. Photo of 109 W Tilden Street, Winter Garden, FL 34787 (MLS # O6242772)
    $915,000
    Photo of 109 W Tilden Street, Winter Garden, FL 34787 (MLS # O6242772)
    Photo of 109 W Tilden Street, Winter Garden, FL 34787 (MLS # O6242772)
    109 W Tilden Street, Winter Garden, FL
    109 W Tilden Street
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,276 Home (sqft)
    • 3 Baths
    • 10,890 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 11/23/24 12:13 AM PST.

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