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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 between $400k - $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 13115 Fox Glove Street, Winter Garden, FL 34787 (MLS # O6237862)
    $549,900
    Photo of 13115 Fox Glove Street, Winter Garden, FL 34787 (MLS # O6237862)
    Photo of 13115 Fox Glove Street, Winter Garden, FL 34787 (MLS # O6237862)
    13115 Fox Glove Street, Winter Garden, FL
    13115 Fox Glove Street
    Winter Garden, FL
    • 4 Beds
    • 2 Baths
    • 2,122 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  2. Photo of 15605 Orange Harvest Loop, Winter Garden, FL 34787 (MLS # O6238051)
    $435,000
    Photo of 15605 Orange Harvest Loop, Winter Garden, FL 34787 (MLS # O6238051)
    Photo of 15605 Orange Harvest Loop, Winter Garden, FL 34787 (MLS # O6238051)
    15605 Orange Harvest Loop, Winter Garden, FL
    15605 Orange Harvest Loop
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,708 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  3. Photo of 17682 Northlake Grove Drive, Winter Garden, FL 34787 (MLS # O6237536)
    $530,000
    Photo of 17682 Northlake Grove Drive, Winter Garden, FL 34787 (MLS # O6237536)
    Photo of 17682 Northlake Grove Drive, Winter Garden, FL 34787 (MLS # O6237536)
    17682 Northlake Grove Drive, Winter Garden, FL
    17682 Northlake Grove Drive
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,906 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  4. Photo of 6644 Pasturelands Place, Winter Garden, FL 34787 (MLS # O6236819)
    $475,000
    Photo of 6644 Pasturelands Place, Winter Garden, FL 34787 (MLS # O6236819)
    Photo of 6644 Pasturelands Place, Winter Garden, FL 34787 (MLS # O6236819)
    23
     
    6644 Pasturelands Place, Winter Garden, FL
    6644 Pasturelands Place
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,328 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  5. Photo of 434 Millwood Place, Winter Garden, FL 34787 (MLS # O6235644)
    $510,000
    Photo of 434 Millwood Place, Winter Garden, FL 34787 (MLS # O6235644)
    Photo of 434 Millwood Place, Winter Garden, FL 34787 (MLS # O6235644)
    434 Millwood Place, Winter Garden, FL
    434 Millwood Place
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,696 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  6. Photo of 14501 Grove Resort Avenue #1634, Winter Garden, FL 34787 (MLS # S5110956)
    $420,000
    Photo of 14501 Grove Resort Avenue #1634, Winter Garden, FL 34787 (MLS # S5110956)
    Photo of 14501 Grove Resort Avenue #1634, Winter Garden, FL 34787 (MLS # S5110956)
    14501 Grove Resort Avenue #1634, Winter Garden, FL
    14501 Grove Resort Avenue #1634
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  7. Photo of 16019 Pebble Bluff Loop, Winter Garden, FL 34787 (MLS # O6234558)
    $484,190
    Photo of 16019 Pebble Bluff Loop, Winter Garden, FL 34787 (MLS # O6234558)
    Photo of 16019 Pebble Bluff Loop, Winter Garden, FL 34787 (MLS # O6234558)
    16019 Pebble Bluff Loop, Winter Garden, FL
    16019 Pebble Bluff Loop
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,685 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  8. Photo of 15060 Stuttgart Alley, Winter Garden, FL 34787 (MLS # O6234599)
    $520,000
    Photo of 15060 Stuttgart Alley, Winter Garden, FL 34787 (MLS # O6234599)
    Photo of 15060 Stuttgart Alley, Winter Garden, FL 34787 (MLS # O6234599)
    15060 Stuttgart Alley, Winter Garden, FL
    15060 Stuttgart Alley
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 1,696 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  9. Photo of 16033 Mangrove Road, Winter Garden, FL 34787 (MLS # O6229623)
    $520,000
    Photo of 16033 Mangrove Road, Winter Garden, FL 34787 (MLS # O6229623)
    Photo of 16033 Mangrove Road, Winter Garden, FL 34787 (MLS # O6229623)
    16033 Mangrove Road, Winter Garden, FL
    16033 Mangrove Road
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,029 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  10. Photo of 17030 Clear Mind Alley, Winter Garden, FL 34787 (MLS # G5085933)
    $560,206
    Photo of 17030 Clear Mind Alley, Winter Garden, FL 34787 (MLS # G5085933)
    Photo of 17030 Clear Mind Alley, Winter Garden, FL 34787 (MLS # G5085933)
    17030 Clear Mind Alley, Winter Garden, FL
    17030 Clear Mind Alley
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,083 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  11. Photo of 17018 Clear Mind Alley, Winter Garden, FL 34787 (MLS # G5085931)
    $535,719
    Photo of 17018 Clear Mind Alley, Winter Garden, FL 34787 (MLS # G5085931)
    Photo of 17018 Clear Mind Alley, Winter Garden, FL 34787 (MLS # G5085931)
    17018 Clear Mind Alley, Winter Garden, FL
    17018 Clear Mind Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,836 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  12. Photo of 747 Bending Oak Trail, Winter Garden, FL 34787 (MLS # O6232887)
    $464,900
    Photo of 747 Bending Oak Trail, Winter Garden, FL 34787 (MLS # O6232887)
    Photo of 747 Bending Oak Trail, Winter Garden, FL 34787 (MLS # O6232887)
    747 Bending Oak Trail, Winter Garden, FL
    747 Bending Oak Trail
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,269 Home (sqft)
    • 4 Baths
    • 4,356 Lot (sqft)
  13. Photo of 687 E Plant Street, Winter Garden, FL 34787 (MLS # O6231047)
    $489,000
    Photo of 687 E Plant Street, Winter Garden, FL 34787 (MLS # O6231047)
    Photo of 687 E Plant Street, Winter Garden, FL 34787 (MLS # O6231047)
    687 E Plant Street, Winter Garden, FL
    687 E Plant Street
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,688 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  14. Photo of 344 E Maple Street, Winter Garden, FL 34787 (MLS # O6233175)
    $439,990
    Photo of 344 E Maple Street, Winter Garden, FL 34787 (MLS # O6233175)
    Photo of 344 E Maple Street, Winter Garden, FL 34787 (MLS # O6233175)
    344 E Maple Street, Winter Garden, FL
    344 E Maple Street
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,678 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  15. Photo of 11054 Hanlon Terrace Alley, Winter Garden, FL 34787 (MLS # S5110234)
    $468,000
    Photo of 11054 Hanlon Terrace Alley, Winter Garden, FL 34787 (MLS # S5110234)
    Photo of 11054 Hanlon Terrace Alley, Winter Garden, FL 34787 (MLS # S5110234)
    11054 Hanlon Terrace Alley, Winter Garden, FL
    11054 Hanlon Terrace Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,732 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  16. Photo of 14501 Grove Resort Avenue #3724, Winter Garden, FL 34787 (MLS # O6223534)
    $450,000
    Photo of 14501 Grove Resort Avenue #3724, Winter Garden, FL 34787 (MLS # O6223534)
    Photo of 14501 Grove Resort Avenue #3724, Winter Garden, FL 34787 (MLS # O6223534)
    14501 Grove Resort Avenue #3724, Winter Garden, FL
    14501 Grove Resort Avenue #3724
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,375 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  17. Photo of 1140 Harbor Hill Street, Winter Garden, FL 34787 (MLS # O6234324)
    $475,000
    Photo of 1140 Harbor Hill Street, Winter Garden, FL 34787 (MLS # O6234324)
    Photo of 1140 Harbor Hill Street, Winter Garden, FL 34787 (MLS # O6234324)
    1140 Harbor Hill Street, Winter Garden, FL
    1140 Harbor Hill Street
    Winter Garden, FL
    • 4 Beds
    • 2 Baths
    • 2,180 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  18. Photo of 12737 Brodlove Lane, Winter Garden, FL 34787 (MLS # O6230935)
    $538,800
    Photo of 12737 Brodlove Lane, Winter Garden, FL 34787 (MLS # O6230935)
    Photo of 12737 Brodlove Lane, Winter Garden, FL 34787 (MLS # O6230935)
    12737 Brodlove Lane, Winter Garden, FL
    12737 Brodlove Lane
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,346 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  19. Photo of 13037 Tollcross Way, Winter Garden, FL 34787 (MLS # O6230198)
    $569,000
    Photo of 13037 Tollcross Way, Winter Garden, FL 34787 (MLS # O6230198)
    Photo of 13037 Tollcross Way, Winter Garden, FL 34787 (MLS # O6230198)
    13037 Tollcross Way, Winter Garden, FL
    13037 Tollcross Way
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,160 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  20. Photo of 14075 Lochend Way, Winter Garden, FL 34787 (MLS # O6229481)
    $517,000
    Photo of 14075 Lochend Way, Winter Garden, FL 34787 (MLS # O6229481)
    Photo of 14075 Lochend Way, Winter Garden, FL 34787 (MLS # O6229481)
    14075 Lochend Way, Winter Garden, FL
    14075 Lochend Way
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,094 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  21. Photo of 444 Lake Amberleigh Drive, Winter Garden, FL 34787 (MLS # O6228138)
    $489,900
    Photo of 444 Lake Amberleigh Drive, Winter Garden, FL 34787 (MLS # O6228138)
    Photo of 444 Lake Amberleigh Drive, Winter Garden, FL 34787 (MLS # O6228138)
    444 Lake Amberleigh Drive, Winter Garden, FL
    444 Lake Amberleigh Drive
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 2,183 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  22. Photo of 4969 Coral Bean Alley, Winter Garden, FL 34787 (MLS # O6229135)
    $538,000
    Photo of 4969 Coral Bean Alley, Winter Garden, FL 34787 (MLS # O6229135)
    Photo of 4969 Coral Bean Alley, Winter Garden, FL 34787 (MLS # O6229135)
    4969 Coral Bean Alley, Winter Garden, FL
    4969 Coral Bean Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,678 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  23. Photo of 16944 Arrowhead Boulevard, Winter Garden, FL 34787 (MLS # O6229034)
    $520,000
    Photo of 16944 Arrowhead Boulevard, Winter Garden, FL 34787 (MLS # O6229034)
    Photo of 16944 Arrowhead Boulevard, Winter Garden, FL 34787 (MLS # O6229034)
    16944 Arrowhead Boulevard, Winter Garden, FL
    16944 Arrowhead Boulevard
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,008 Home (sqft)
    • 2 Baths
    • 1.23 Lot (ac)
  24. Photo of 15162 Book Club Road, Winter Garden, FL 34787 (MLS # G5085300)
    $565,000
    Photo of 15162 Book Club Road, Winter Garden, FL 34787 (MLS # G5085300)
    Photo of 15162 Book Club Road, Winter Garden, FL 34787 (MLS # G5085300)
    15162 Book Club Road, Winter Garden, FL
    15162 Book Club Road
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 2,089 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  25. Photo of 15424 Enchanted Melody Way, Winter Garden, FL 34787 (MLS # S5109394)
    $512,500
    Photo of 15424 Enchanted Melody Way, Winter Garden, FL 34787 (MLS # S5109394)
    Photo of 15424 Enchanted Melody Way, Winter Garden, FL 34787 (MLS # S5109394)
    15424 Enchanted Melody Way, Winter Garden, FL
    15424 Enchanted Melody Way
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,536 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  26. Photo of 13460 Princess Street, Winter Garden, FL 34787 (MLS # O6227746)
    $478,000
    Photo of 13460 Princess Street, Winter Garden, FL 34787 (MLS # O6227746)
    Photo of 13460 Princess Street, Winter Garden, FL 34787 (MLS # O6227746)
    13460 Princess Street, Winter Garden, FL
    13460 Princess Street
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,579 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  27. Photo of 9987 Tawny Meadow Alley, Winter Garden, FL 34787 (MLS # O6228065)
    $529,000
    Photo of 9987 Tawny Meadow Alley, Winter Garden, FL 34787 (MLS # O6228065)
    Photo of 9987 Tawny Meadow Alley, Winter Garden, FL 34787 (MLS # O6228065)
    9987 Tawny Meadow Alley, Winter Garden, FL
    9987 Tawny Meadow Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,204 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  28. Photo of 5551 New Independence Parkway, Winter Garden, FL 34787 (MLS # O6227265)
    $473,000
    Photo of 5551 New Independence Parkway, Winter Garden, FL 34787 (MLS # O6227265)
    Photo of 5551 New Independence Parkway, Winter Garden, FL 34787 (MLS # O6227265)
    5551 New Independence Parkway, Winter Garden, FL
    5551 New Independence Parkway
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,644 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  29. Photo of 708 Parkmont Place, Winter Garden, FL 34787 (MLS # O6225758)
    $549,000
    Photo of 708 Parkmont Place, Winter Garden, FL 34787 (MLS # O6225758)
    Photo of 708 Parkmont Place, Winter Garden, FL 34787 (MLS # O6225758)
    708 Parkmont Place, Winter Garden, FL
    708 Parkmont Place
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,043 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  30. Photo of 11090 Silver Surfer Alley, Winter Garden, FL 34787 (MLS # O6224222)
    $529,000
    Photo of 11090 Silver Surfer Alley, Winter Garden, FL 34787 (MLS # O6224222)
    Photo of 11090 Silver Surfer Alley, Winter Garden, FL 34787 (MLS # O6224222)
    11090 Silver Surfer Alley, Winter Garden, FL
    11090 Silver Surfer Alley
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,042 Home (sqft)
    • 3 Baths
    • 3,921 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 11/24/24 6:13 AM PST.

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