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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 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 13786 Werrington Drive, Winter Garden, FL 34787 (MLS # O6227476)
    $699,000
    Photo of 13786 Werrington Drive, Winter Garden, FL 34787 (MLS # O6227476)
    Photo of 13786 Werrington Drive, Winter Garden, FL 34787 (MLS # O6227476)
    13786 Werrington Drive, Winter Garden, FL
    13786 Werrington Drive
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,807 Home (sqft)
    • 4 Baths
    • 3,921 Lot (sqft)
  2. Photo of 9313 Quiet Lane, Winter Garden, FL 34787 (MLS # O6226273)
    $1,150,000
    Photo of 9313 Quiet Lane, Winter Garden, FL 34787 (MLS # O6226273)
    Photo of 9313 Quiet Lane, Winter Garden, FL 34787 (MLS # O6226273)
    9313 Quiet Lane, Winter Garden, FL
    9313 Quiet Lane
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,854 Home (sqft)
    • 3 Baths
    • 5.28 Lot (ac)
  3. Photo of 14572 Black Quill Drive, Winter Garden, FL 34787 (MLS # O6226360)
    $949,900
    Photo of 14572 Black Quill Drive, Winter Garden, FL 34787 (MLS # O6226360)
    Photo of 14572 Black Quill Drive, Winter Garden, FL 34787 (MLS # O6226360)
    14572 Black Quill Drive, Winter Garden, FL
    14572 Black Quill Drive
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 4,384 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  4. Photo of 10139 Austrina Oak Loop, Winter Garden, FL 34787 (MLS # O6221759)
    $1,495,000
    Photo of 10139 Austrina Oak Loop, Winter Garden, FL 34787 (MLS # O6221759)
    Photo of 10139 Austrina Oak Loop, Winter Garden, FL 34787 (MLS # O6221759)
    10139 Austrina Oak Loop, Winter Garden, FL
    10139 Austrina Oak Loop
    Winter Garden, FL
    • 6 Beds
    • 5 Baths
    • 4,493 Home (sqft)
    • 5 Baths
    • 13,504 Lot (sqft)
  5. Photo of 14528 Old Thicket Trace, Winter Garden, FL 34787 (MLS # O6226299)
    $780,000
    Photo of 14528 Old Thicket Trace, Winter Garden, FL 34787 (MLS # O6226299)
    Photo of 14528 Old Thicket Trace, Winter Garden, FL 34787 (MLS # O6226299)
    14528 Old Thicket Trace, Winter Garden, FL
    14528 Old Thicket Trace
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,179 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  6. Photo of 420 Newhearth Circle, Winter Garden, FL 34787 (MLS # O6225972)
    $635,000
    Photo of 420 Newhearth Circle, Winter Garden, FL 34787 (MLS # O6225972)
    Photo of 420 Newhearth Circle, Winter Garden, FL 34787 (MLS # O6225972)
    420 Newhearth Circle, Winter Garden, FL
    420 Newhearth Circle
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,287 Home (sqft)
    • 3 Baths
    • 17,860 Lot (sqft)
  7. Photo of 10207 Atwater Bay Drive, Winter Garden, FL 34787 (MLS # O6224829)
    $1,590,000
    Photo of 10207 Atwater Bay Drive, Winter Garden, FL 34787 (MLS # O6224829)
    Photo of 10207 Atwater Bay Drive, Winter Garden, FL 34787 (MLS # O6224829)
    10207 Atwater Bay Drive, Winter Garden, FL
    10207 Atwater Bay Drive
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 3,354 Home (sqft)
    • 5 Baths
    • 33,977 Lot (sqft)
  8. Photo of 3105 W Orange Country Club Drive, Winter Garden, FL 34787 (MLS # G5084857)
    $1,200,000
    Photo of 3105 W Orange Country Club Drive, Winter Garden, FL 34787 (MLS # G5084857)
    Photo of 3105 W Orange Country Club Drive, Winter Garden, FL 34787 (MLS # G5084857)
    3105 W Orange Country Club Drive, Winter Garden, FL
    3105 W Orange Country Club Drive
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 4,443 Home (sqft)
    • 4 Baths
    • 1.08 Lot (ac)
  9. Photo of 15986 Johns Lake Overlook Drive, Winter Garden, FL 34787 (MLS # T3541777)
    $2,175,000
    Photo of 15986 Johns Lake Overlook Drive, Winter Garden, FL 34787 (MLS # T3541777)
    Photo of 15986 Johns Lake Overlook Drive, Winter Garden, FL 34787 (MLS # T3541777)
    15986 Johns Lake Overlook Drive, Winter Garden, FL
    15986 Johns Lake Overlook Drive
    Winter Garden, FL
    • 5 Beds
    • 6 Baths
    • 4,498 Home (sqft)
    • 6 Baths
    • 23,958 Lot (sqft)
  10. Photo of 3125 Winesap Way, Winter Garden, FL 34787 (MLS # O6224218)
    $642,000
    Photo of 3125 Winesap Way, Winter Garden, FL 34787 (MLS # O6224218)
    Photo of 3125 Winesap Way, Winter Garden, FL 34787 (MLS # O6224218)
    3125 Winesap Way, Winter Garden, FL
    3125 Winesap Way
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,505 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  11. Photo of 967 Prosperity Drive, Winter Garden, FL 34787 (MLS # O6214760)
    $949,000
    Photo of 967 Prosperity Drive, Winter Garden, FL 34787 (MLS # O6214760)
    Photo of 967 Prosperity Drive, Winter Garden, FL 34787 (MLS # O6214760)
    967 Prosperity Drive, Winter Garden, FL
    967 Prosperity Drive
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,585 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  12. Photo of 15144 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6219561)
    $1,999,999
    Photo of 15144 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6219561)
    Photo of 15144 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6219561)
    15144 Shonan Gold Drive, Winter Garden, FL
    15144 Shonan Gold Drive
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 4,056 Home (sqft)
    • 5 Baths
    • 3.59 Lot (ac)
  13. Photo of 515 N Boyd Street, Winter Garden, FL 34787 (MLS # O6222919)
    $1,100,000
    Photo of 515 N Boyd Street, Winter Garden, FL 34787 (MLS # O6222919)
    Photo of 515 N Boyd Street, Winter Garden, FL 34787 (MLS # O6222919)
    40
     
    515 N Boyd Street, Winter Garden, FL
    515 N Boyd Street
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,152 Home (sqft)
    • 4 Baths
    • 16,118 Lot (sqft)
  14. Photo of 15515 Sandfield Loop, Winter Garden, FL 34787 (MLS # O6224372)
    $725,000
    Photo of 15515 Sandfield Loop, Winter Garden, FL 34787 (MLS # O6224372)
    Photo of 15515 Sandfield Loop, Winter Garden, FL 34787 (MLS # O6224372)
    15515 Sandfield Loop, Winter Garden, FL
    15515 Sandfield Loop
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,788 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  15. Photo of 16903 Wingspread Loop, Winter Garden, FL 34787 (MLS # O6220966)
    $926,000
    Photo of 16903 Wingspread Loop, Winter Garden, FL 34787 (MLS # O6220966)
    Photo of 16903 Wingspread Loop, Winter Garden, FL 34787 (MLS # O6220966)
    16903 Wingspread Loop, Winter Garden, FL
    16903 Wingspread Loop
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,688 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  16. Photo of 16235 Misty Hills Avenue, Winter Garden, FL 34787 (MLS # O6217971)
    $985,000
    Photo of 16235 Misty Hills Avenue, Winter Garden, FL 34787 (MLS # O6217971)
    Photo of 16235 Misty Hills Avenue, Winter Garden, FL 34787 (MLS # O6217971)
    50
     
    16235 Misty Hills Avenue, Winter Garden, FL
    16235 Misty Hills Avenue
    Winter Garden, FL
    • 6 Beds
    • 5 Baths
    • 4,630 Home (sqft)
    • 5 Baths
    • 7,406 Lot (sqft)
  17. Photo of 17117 Heartwood Loop, Winter Garden, FL 34787 (MLS # O6226613)
    $1,450,000
    Photo of 17117 Heartwood Loop, Winter Garden, FL 34787 (MLS # O6226613)
    Photo of 17117 Heartwood Loop, Winter Garden, FL 34787 (MLS # O6226613)
    53
     
    17117 Heartwood Loop, Winter Garden, FL
    17117 Heartwood Loop
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,265 Home (sqft)
    • 4 Baths
    • 5.31 Lot (ac)
  18. Photo of 15593 Murcott Blossom Boulevard, Winter Garden, FL 34787 (MLS # O6220648)
    $669,000
    Photo of 15593 Murcott Blossom Boulevard, Winter Garden, FL 34787 (MLS # O6220648)
    Photo of 15593 Murcott Blossom Boulevard, Winter Garden, FL 34787 (MLS # O6220648)
    15593 Murcott Blossom Boulevard, Winter Garden, FL
    15593 Murcott Blossom Boulevard
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 2,951 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  19. Photo of 15168 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6220422)
    $2,450,000
    Photo of 15168 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6220422)
    Photo of 15168 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6220422)
    15168 Shonan Gold Drive, Winter Garden, FL
    15168 Shonan Gold Drive
    Winter Garden, FL
    • 5 Beds
    • 6 Baths
    • 5,030 Home (sqft)
    • 6 Baths
    • 42,254 Lot (sqft)
  20. Photo of 1121 Hawkslade Court, Winter Garden, FL 34787 (MLS # O6219558)
    $614,000
    Photo of 1121 Hawkslade Court, Winter Garden, FL 34787 (MLS # O6219558)
    Photo of 1121 Hawkslade Court, Winter Garden, FL 34787 (MLS # O6219558)
    1121 Hawkslade Court, Winter Garden, FL
    1121 Hawkslade Court
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,889 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  21. Photo of 1134 Harbor Hill Street, Winter Garden, FL 34787 (MLS # O6217343)
    $630,900
    Photo of 1134 Harbor Hill Street, Winter Garden, FL 34787 (MLS # O6217343)
    Photo of 1134 Harbor Hill Street, Winter Garden, FL 34787 (MLS # O6217343)
    1134 Harbor Hill Street, Winter Garden, FL
    1134 Harbor Hill Street
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,754 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  22. Photo of 8943 Lakeshore Pointe Drive, Winter Garden, FL 34787 (MLS # OM681024)
    $639,900
    Photo of 8943 Lakeshore Pointe Drive, Winter Garden, FL 34787 (MLS # OM681024)
    Photo of 8943 Lakeshore Pointe Drive, Winter Garden, FL 34787 (MLS # OM681024)
    8943 Lakeshore Pointe Drive, Winter Garden, FL
    8943 Lakeshore Pointe Drive
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,052 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  23. Photo of 16057 Hickory Marsh Lane, Winter Garden, FL 34787 (MLS # O6226374)
    $875,000
    Photo of 16057 Hickory Marsh Lane, Winter Garden, FL 34787 (MLS # O6226374)
    Photo of 16057 Hickory Marsh Lane, Winter Garden, FL 34787 (MLS # O6226374)
    16057 Hickory Marsh Lane, Winter Garden, FL
    16057 Hickory Marsh Lane
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,535 Home (sqft)
    • 4 Baths
    • 11,762 Lot (sqft)
  24. Photo of 15474 Camp Dubois Crescent, Winter Garden, FL 34787 (MLS # O6215809)
    $765,000
    Photo of 15474 Camp Dubois Crescent, Winter Garden, FL 34787 (MLS # O6215809)
    Photo of 15474 Camp Dubois Crescent, Winter Garden, FL 34787 (MLS # O6215809)
    15474 Camp Dubois Crescent, Winter Garden, FL
    15474 Camp Dubois Crescent
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 3,727 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  25. Photo of 7597 Purple Finch Street, Winter Garden, FL 34787 (MLS # O6212729)
    $850,000
    Photo of 7597 Purple Finch Street, Winter Garden, FL 34787 (MLS # O6212729)
    Photo of 7597 Purple Finch Street, Winter Garden, FL 34787 (MLS # O6212729)
    7597 Purple Finch Street, Winter Garden, FL
    7597 Purple Finch Street
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 3,244 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  26. Photo of 1641 Cranleigh Drive, Winter Garden, FL 34787 (MLS # O6214792)
    $670,000
    Photo of 1641 Cranleigh Drive, Winter Garden, FL 34787 (MLS # O6214792)
    Photo of 1641 Cranleigh Drive, Winter Garden, FL 34787 (MLS # O6214792)
    1641 Cranleigh Drive, Winter Garden, FL
    1641 Cranleigh Drive
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,510 Home (sqft)
    • 3 Baths
    • 15,246 Lot (sqft)
  27. Photo of 12736 Lavender Bloom Alley #170, Winter Garden, FL 34787 (MLS # O6214551)
    $637,830
    Photo of 12736 Lavender Bloom Alley #170, Winter Garden, FL 34787 (MLS # O6214551)
    Photo of 12736 Lavender Bloom Alley #170, Winter Garden, FL 34787 (MLS # O6214551)
    12736 Lavender Bloom Alley #170, Winter Garden, FL
    12736 Lavender Bloom Alley #170
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,200 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  28. Photo of 17404 Lake Star Road, Winter Garden, FL 34787 (MLS # O6192659)
    $698,900
    Photo of 17404 Lake Star Road, Winter Garden, FL 34787 (MLS # O6192659)
    Photo of 17404 Lake Star Road, Winter Garden, FL 34787 (MLS # O6192659)
    17404 Lake Star Road, Winter Garden, FL
    17404 Lake Star Road
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,122 Home (sqft)
    • 3 Baths
    • 11,326 Lot (sqft)
  29. Photo of 1073 Vinsetta Circle, Winter Garden, FL 34787 (MLS # P4930706)
    $815,000
    Photo of 1073 Vinsetta Circle, Winter Garden, FL 34787 (MLS # P4930706)
    Photo of 1073 Vinsetta Circle, Winter Garden, FL 34787 (MLS # P4930706)
    1073 Vinsetta Circle, Winter Garden, FL
    1073 Vinsetta Circle
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 3,568 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  30. Photo of 3186 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6210649)
    $747,000
    Photo of 3186 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6210649)
    Photo of 3186 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6210649)
    22
     
    3186 Sailing Pier Avenue, Winter Garden, FL
    3186 Sailing Pier Avenue
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,336 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
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