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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 11972 Bracco Street, Winter Garden, FL 34787 (MLS # O6243475)
    $542,855
    Photo of 11972 Bracco Street, Winter Garden, FL 34787 (MLS # O6243475)
    Photo of 11972 Bracco Street, Winter Garden, FL 34787 (MLS # O6243475)
    11972 Bracco Street, Winter Garden, FL
    11972 Bracco Street
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,788 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  2. Photo of 11984 Bracco Street, Winter Garden, FL 34787 (MLS # O6243483)
    $566,450
    Photo of 11984 Bracco Street, Winter Garden, FL 34787 (MLS # O6243483)
    Photo of 11984 Bracco Street, Winter Garden, FL 34787 (MLS # O6243483)
    11984 Bracco Street, Winter Garden, FL
    11984 Bracco Street
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,985 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  3. Photo of 14501 Grove Resort Avenue #2704, Winter Garden, FL 34787 (MLS # O6246079)
    $400,000
    Photo of 14501 Grove Resort Avenue #2704, Winter Garden, FL 34787 (MLS # O6246079)
    Photo of 14501 Grove Resort Avenue #2704, Winter Garden, FL 34787 (MLS # O6246079)
    14501 Grove Resort Avenue #2704, Winter Garden, FL
    14501 Grove Resort Avenue #2704
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,375 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  4. Photo of 1563 Loch Avich Road, Winter Garden, FL 34787 (MLS # O6245402)
    $460,000
    Photo of 1563 Loch Avich Road, Winter Garden, FL 34787 (MLS # O6245402)
    Photo of 1563 Loch Avich Road, Winter Garden, FL 34787 (MLS # O6245402)
    15
     
    1563 Loch Avich Road, Winter Garden, FL
    1563 Loch Avich Road
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,541 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  5. Photo of 3178 Winesap Way, Winter Garden, FL 34787 (MLS # O6245083)
    $590,000
    Photo of 3178 Winesap Way, Winter Garden, FL 34787 (MLS # O6245083)
    Photo of 3178 Winesap Way, Winter Garden, FL 34787 (MLS # O6245083)
    38
     
    3178 Winesap Way, Winter Garden, FL
    3178 Winesap Way
    Winter Garden, FL
    • 4 Beds
    • 2 Baths
    • 2,115 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  6. Photo of 15459 Honeybell Drive, Winter Garden, FL 34787 (MLS # O6244145)
    $435,000
    Photo of 15459 Honeybell Drive, Winter Garden, FL 34787 (MLS # O6244145)
    Photo of 15459 Honeybell Drive, Winter Garden, FL 34787 (MLS # O6244145)
    15459 Honeybell Drive, Winter Garden, FL
    15459 Honeybell Drive
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,645 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  7. Photo of 15859 Tollington Alley, Winter Garden, FL 34787 (MLS # O6244118)
    $479,990
    Photo of 15859 Tollington Alley, Winter Garden, FL 34787 (MLS # O6244118)
    Photo of 15859 Tollington Alley, Winter Garden, FL 34787 (MLS # O6244118)
    15859 Tollington Alley, Winter Garden, FL
    15859 Tollington Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,835 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  8. Photo of 15871 Tollington Alley, Winter Garden, FL 34787 (MLS # O6244092)
    $449,990
    Photo of 15871 Tollington Alley, Winter Garden, FL 34787 (MLS # O6244092)
    Photo of 15871 Tollington Alley, Winter Garden, FL 34787 (MLS # O6244092)
    15871 Tollington Alley, Winter Garden, FL
    15871 Tollington Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,693 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  9. Photo of 10277 Austrina Oak Loop, Winter Garden, FL 34787 (MLS # O6242393)
    $499,200
    Photo of 10277 Austrina Oak Loop, Winter Garden, FL 34787 (MLS # O6242393)
    Photo of 10277 Austrina Oak Loop, Winter Garden, FL 34787 (MLS # O6242393)
    10277 Austrina Oak Loop, Winter Garden, FL
    10277 Austrina Oak Loop
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,082 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  10. Photo of 2432 Balforn Tower Way, Winter Garden, FL 34787 (MLS # O6243968)
    $539,990
    Photo of 2432 Balforn Tower Way, Winter Garden, FL 34787 (MLS # O6243968)
    Photo of 2432 Balforn Tower Way, Winter Garden, FL 34787 (MLS # O6243968)
    2432 Balforn Tower Way, Winter Garden, FL
    2432 Balforn Tower Way
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 2,172 Home (sqft)
    • 4 Baths
    • 5,663 Lot (sqft)
  11. Photo of 2261 Romanum Drive, Winter Garden, FL 34787 (MLS # O6243734)
    $585,000
    Photo of 2261 Romanum Drive, Winter Garden, FL 34787 (MLS # O6243734)
    Photo of 2261 Romanum Drive, Winter Garden, FL 34787 (MLS # O6243734)
    29
     
    2261 Romanum Drive, Winter Garden, FL
    2261 Romanum Drive
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,410 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  12. Photo of 7290 Duxbury Lane, Winter Garden, FL 34787 (MLS # O6243042)
    $429,100
    Photo of 7290 Duxbury Lane, Winter Garden, FL 34787 (MLS # O6243042)
    Photo of 7290 Duxbury Lane, Winter Garden, FL 34787 (MLS # O6243042)
    7290 Duxbury Lane, Winter Garden, FL
    7290 Duxbury Lane
    Winter Garden, FL
    • 2 Beds
    • 3 Baths
    • 1,800 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  13. Photo of 10241 Love Story Street, Winter Garden, FL 34787 (MLS # O6242871)
    $589,000
    Photo of 10241 Love Story Street, Winter Garden, FL 34787 (MLS # O6242871)
    Photo of 10241 Love Story Street, Winter Garden, FL 34787 (MLS # O6242871)
    10241 Love Story Street, Winter Garden, FL
    10241 Love Story Street
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,502 Home (sqft)
    • 4 Baths
    • 4,356 Lot (sqft)
  14. Photo of 724 Grisham St, Winter Garden, FL 34787 (MLS # O6242709)
    $450,000
    Photo of 724 Grisham St, Winter Garden, FL 34787 (MLS # O6242709)
    Photo of 724 Grisham St, Winter Garden, FL 34787 (MLS # O6242709)
    724 Grisham St, Winter Garden, FL
    724 Grisham St
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,345 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  15. Photo of 16938 Hamlin Oasis Loop, Winter Garden, FL 34787 (MLS # G5086573)
    $549,896
    Photo of 16938 Hamlin Oasis Loop, Winter Garden, FL 34787 (MLS # G5086573)
    Photo of 16938 Hamlin Oasis Loop, Winter Garden, FL 34787 (MLS # G5086573)
    16938 Hamlin Oasis Loop, Winter Garden, FL
    16938 Hamlin Oasis Loop
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,083 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  16. Photo of 5649 New Independence Parkway, Winter Garden, FL 34787 (MLS # O6241653)
    $429,900
    Photo of 5649 New Independence Parkway, Winter Garden, FL 34787 (MLS # O6241653)
    Photo of 5649 New Independence Parkway, Winter Garden, FL 34787 (MLS # O6241653)
    32
     
    5649 New Independence Parkway, Winter Garden, FL
    5649 New Independence Parkway
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,131 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  17. Photo of 200 Meljane Drive, Winter Garden, FL 34787 (MLS # O6241546)
    $450,000
    Photo of 200 Meljane Drive, Winter Garden, FL 34787 (MLS # O6241546)
    Photo of 200 Meljane Drive, Winter Garden, FL 34787 (MLS # O6241546)
    200 Meljane Drive, Winter Garden, FL
    200 Meljane Drive
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,385 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
  18. Photo of 15131 Grove Lake Drive, Winter Garden, FL 34787 (MLS # O6240770)
    $534,630
    Photo of 15131 Grove Lake Drive, Winter Garden, FL 34787 (MLS # O6240770)
    Photo of 15131 Grove Lake Drive, Winter Garden, FL 34787 (MLS # O6240770)
    17
     
    15131 Grove Lake Drive, Winter Garden, FL
    15131 Grove Lake Drive
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,846 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  19. Photo of 1053 Priory Circle, Winter Garden, FL 34787 (MLS # R4908318)
    $435,000
    Photo of 1053 Priory Circle, Winter Garden, FL 34787 (MLS # R4908318)
    Photo of 1053 Priory Circle, Winter Garden, FL 34787 (MLS # R4908318)
    1053 Priory Circle, Winter Garden, FL
    1053 Priory Circle
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,638 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  20. Photo of 14401 Black Lake Preserve Street, Winter Garden, FL 34787 (MLS # O6241051)
    $594,000
    Photo of 14401 Black Lake Preserve Street, Winter Garden, FL 34787 (MLS # O6241051)
    Photo of 14401 Black Lake Preserve Street, Winter Garden, FL 34787 (MLS # O6241051)
    14401 Black Lake Preserve Street, Winter Garden, FL
    14401 Black Lake Preserve Street
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 2,511 Home (sqft)
    • 3 Baths
    • 9,584 Lot (sqft)
  21. Photo of 9467 Cinzel Alley, Winter Garden, FL 34787 (MLS # O6239940)
    $469,900
    Photo of 9467 Cinzel Alley, Winter Garden, FL 34787 (MLS # O6239940)
    Photo of 9467 Cinzel Alley, Winter Garden, FL 34787 (MLS # O6239940)
    9467 Cinzel Alley, Winter Garden, FL
    9467 Cinzel Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,814 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  22. Photo of 9267 Gran Teatro Drive, Winter Garden, FL 34787 (MLS # O6240736)
    $489,990
    Photo of 9267 Gran Teatro Drive, Winter Garden, FL 34787 (MLS # O6240736)
    Photo of 9267 Gran Teatro Drive, Winter Garden, FL 34787 (MLS # O6240736)
    9267 Gran Teatro Drive, Winter Garden, FL
    9267 Gran Teatro Drive
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,835 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  23. Photo of 9279 Gran Teatro Drive, Winter Garden, FL 34787 (MLS # O6240755)
    $474,990
    Photo of 9279 Gran Teatro Drive, Winter Garden, FL 34787 (MLS # O6240755)
    Photo of 9279 Gran Teatro Drive, Winter Garden, FL 34787 (MLS # O6240755)
    9279 Gran Teatro Drive, Winter Garden, FL
    9279 Gran Teatro Drive
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,693 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  24. Photo of 17036 Clear Mind Alley, Winter Garden, FL 34787 (MLS # G5086910)
    $553,356
    Photo of 17036 Clear Mind Alley, Winter Garden, FL 34787 (MLS # G5086910)
    Photo of 17036 Clear Mind Alley, Winter Garden, FL 34787 (MLS # G5086910)
    17036 Clear Mind Alley, Winter Garden, FL
    17036 Clear Mind Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,836 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  25. Photo of 13109 Calming Breeze Way, Winter Garden, FL 34787 (MLS # G5086909)
    $571,182
    Photo of 13109 Calming Breeze Way, Winter Garden, FL 34787 (MLS # G5086909)
    Photo of 13109 Calming Breeze Way, Winter Garden, FL 34787 (MLS # G5086909)
    13109 Calming Breeze Way, Winter Garden, FL
    13109 Calming Breeze Way
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,083 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  26. Photo of 821 E Story Road, Winter Garden, FL 34787 (MLS # O6239753)
    $415,800
    Photo of 821 E Story Road, Winter Garden, FL 34787 (MLS # O6239753)
    Photo of 821 E Story Road, Winter Garden, FL 34787 (MLS # O6239753)
    821 E Story Road, Winter Garden, FL
    821 E Story Road
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,346 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  27. Photo of 5827 Cypress Hill Road, Winter Garden, FL 34787 (MLS # S5112284)
    $409,000
    Photo of 5827 Cypress Hill Road, Winter Garden, FL 34787 (MLS # S5112284)
    Photo of 5827 Cypress Hill Road, Winter Garden, FL 34787 (MLS # S5112284)
    5827 Cypress Hill Road, Winter Garden, FL
    5827 Cypress Hill Road
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,716 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  28. Photo of 14029 Title Way, Winter Garden, FL 34787 (MLS # S5111877)
    $465,000
    Photo of 14029 Title Way, Winter Garden, FL 34787 (MLS # S5111877)
    Photo of 14029 Title Way, Winter Garden, FL 34787 (MLS # S5111877)
    14029 Title Way, Winter Garden, FL
    14029 Title Way
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,636 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  29. Photo of 15104 Windflower Alley, Winter Garden, FL 34787 (MLS # O6239135)
    $424,990
    Photo of 15104 Windflower Alley, Winter Garden, FL 34787 (MLS # O6239135)
    Photo of 15104 Windflower Alley, Winter Garden, FL 34787 (MLS # O6239135)
    15104 Windflower Alley, Winter Garden, FL
    15104 Windflower Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,536 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  30. Photo of 15119 Kirsty Alley, Winter Garden, FL 34787 (MLS # O6237106)
    $589,000
    Photo of 15119 Kirsty Alley, Winter Garden, FL 34787 (MLS # O6237106)
    Photo of 15119 Kirsty Alley, Winter Garden, FL 34787 (MLS # O6237106)
    15119 Kirsty Alley, Winter Garden, FL
    15119 Kirsty Alley
    Winter Garden, FL
    • 3 Beds
    • 4 Baths
    • 2,133 Home (sqft)
    • 4 Baths
    • 4,356 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 4:13 AM PST.

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