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Winter Park is home to a plethora of world-class museums, high-end boutiques, some of the area's finest restaurants, and is centrally located being only minutes from downtown Orlando. Use our custom search tool to view all homes for sale between $400k - $600k in Winter Park or click here to return to the list of surrounding towns and cities in the Orlando area. Have questions? Contact us here or schedule your FREE consultation here.


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  1. Photo of 1926 Natalen Road, Winter Park, FL 32792 (MLS # O6245119)
    $520,000
    Photo of 1926 Natalen Road, Winter Park, FL 32792 (MLS # O6245119)
    Photo of 1926 Natalen Road, Winter Park, FL 32792 (MLS # O6245119)
    1926 Natalen Road, Winter Park, FL
    1926 Natalen Road
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,369 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  2. Photo of 4013 Quenita Drive, Winter Park, FL 32792 (MLS # O6243744)
    $535,000
    Photo of 4013 Quenita Drive, Winter Park, FL 32792 (MLS # O6243744)
    Photo of 4013 Quenita Drive, Winter Park, FL 32792 (MLS # O6243744)
    4013 Quenita Drive, Winter Park, FL
    4013 Quenita Drive
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,327 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  3. Photo of 2252 Shadowland Loop, Winter Park, FL 32792 (MLS # O6243641)
    $445,000
    Photo of 2252 Shadowland Loop, Winter Park, FL 32792 (MLS # O6243641)
    Photo of 2252 Shadowland Loop, Winter Park, FL 32792 (MLS # O6243641)
    2252 Shadowland Loop, Winter Park, FL
    2252 Shadowland Loop
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,755 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  4. Photo of 1008 Dupont Avenue, Winter Park, FL 32789 (MLS # O6241497)
    $499,000
    Photo of 1008 Dupont Avenue, Winter Park, FL 32789 (MLS # O6241497)
    Photo of 1008 Dupont Avenue, Winter Park, FL 32789 (MLS # O6241497)
    1008 Dupont Avenue, Winter Park, FL
    1008 Dupont Avenue
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 1,970 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  5. Photo of 5210 Poinsetta Avenue, Winter Park, FL 32792 (MLS # O6240219)
    $429,999
    Photo of 5210 Poinsetta Avenue, Winter Park, FL 32792 (MLS # O6240219)
    Photo of 5210 Poinsetta Avenue, Winter Park, FL 32792 (MLS # O6240219)
    5210 Poinsetta Avenue, Winter Park, FL
    5210 Poinsetta Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,476 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  6. Photo of 3455 Athena Drive, Winter Park, FL 32792 (MLS # O6240165)
    $465,500
    Photo of 3455 Athena Drive, Winter Park, FL 32792 (MLS # O6240165)
    Photo of 3455 Athena Drive, Winter Park, FL 32792 (MLS # O6240165)
    3455 Athena Drive, Winter Park, FL
    3455 Athena Drive
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 2,161 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  7. Photo of 1663 Meadowgold Court, Winter Park, FL 32792 (MLS # O6236929)
    $469,900
    Photo of 1663 Meadowgold Court, Winter Park, FL 32792 (MLS # O6236929)
    Photo of 1663 Meadowgold Court, Winter Park, FL 32792 (MLS # O6236929)
    34
     
    1663 Meadowgold Court, Winter Park, FL
    1663 Meadowgold Court
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 1,851 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  8. Photo of 5329 Poinsetta Avenue, Winter Park, FL 32792 (MLS # S5109828)
    $425,000
    Photo of 5329 Poinsetta Avenue, Winter Park, FL 32792 (MLS # S5109828)
    Photo of 5329 Poinsetta Avenue, Winter Park, FL 32792 (MLS # S5109828)
    5329 Poinsetta Avenue, Winter Park, FL
    5329 Poinsetta Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,287 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  9. Photo of 2189 Sussex Road, Winter Park, FL 32792 (MLS # T3546898)
    $439,000
    Photo of 2189 Sussex Road, Winter Park, FL 32792 (MLS # T3546898)
    Photo of 2189 Sussex Road, Winter Park, FL 32792 (MLS # T3546898)
    2189 Sussex Road, Winter Park, FL
    2189 Sussex Road
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,776 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  10. Photo of 1842 Puritan Avenue, Winter Park, FL 32792 (MLS # S5108745)
    $419,000
    Photo of 1842 Puritan Avenue, Winter Park, FL 32792 (MLS # S5108745)
    Photo of 1842 Puritan Avenue, Winter Park, FL 32792 (MLS # S5108745)
    1842 Puritan Avenue, Winter Park, FL
    1842 Puritan Avenue
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,836 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  11. Photo of 2144 Ridge Drive, Winter Park, FL 32792 (MLS # O6214075)
    $429,000
    Photo of 2144 Ridge Drive, Winter Park, FL 32792 (MLS # O6214075)
    Photo of 2144 Ridge Drive, Winter Park, FL 32792 (MLS # O6214075)
    2144 Ridge Drive, Winter Park, FL
    2144 Ridge Drive
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 3,020 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  12. Photo of 1955 Dundee Drive, Winter Park, FL 32792 (MLS # O6214438)
    $549,000
    Photo of 1955 Dundee Drive, Winter Park, FL 32792 (MLS # O6214438)
    Photo of 1955 Dundee Drive, Winter Park, FL 32792 (MLS # O6214438)
    1955 Dundee Drive, Winter Park, FL
    1955 Dundee Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,144 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  13. Photo of 1216 Park Green Place, Winter Park, FL 32789 (MLS # NS1081669)
    $529,900
    Photo of 1216 Park Green Place, Winter Park, FL 32789 (MLS # NS1081669)
    Photo of 1216 Park Green Place, Winter Park, FL 32789 (MLS # NS1081669)
    1216 Park Green Place, Winter Park, FL
    1216 Park Green Place
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,020 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  14. Photo of 7320 Fieldcrest Avenue, Winter Park, FL 32792 (MLS # O6200506)
    $488,000
    Photo of 7320 Fieldcrest Avenue, Winter Park, FL 32792 (MLS # O6200506)
    Photo of 7320 Fieldcrest Avenue, Winter Park, FL 32792 (MLS # O6200506)
    7320 Fieldcrest Avenue, Winter Park, FL
    7320 Fieldcrest Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,919 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  15. Photo of 7543 Dockside Street, Winter Park, FL 32792 (MLS # S5103770)
    $427,900
    Photo of 7543 Dockside Street, Winter Park, FL 32792 (MLS # S5103770)
    Photo of 7543 Dockside Street, Winter Park, FL 32792 (MLS # S5103770)
    7543 Dockside Street, Winter Park, FL
    7543 Dockside Street
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,434 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  16. Photo of 4041 Yacht Court, Winter Park, FL 32792 (MLS # O6194323)
    $549,000
    Photo of 4041 Yacht Court, Winter Park, FL 32792 (MLS # O6194323)
    Photo of 4041 Yacht Court, Winter Park, FL 32792 (MLS # O6194323)
    4041 Yacht Court, Winter Park, FL
    4041 Yacht Court
    Winter Park, FL
    • 5 Beds
    • 3 Baths
    • 2,153 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
  17. Photo of 2313 Loch Lomond Drive, Winter Park, FL 32792 (MLS # O6182627)
    $539,000
    Photo of 2313 Loch Lomond Drive, Winter Park, FL 32792 (MLS # O6182627)
    Photo of 2313 Loch Lomond Drive, Winter Park, FL 32792 (MLS # O6182627)
    2313 Loch Lomond Drive, Winter Park, FL
    2313 Loch Lomond Drive
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 1,570 Home (sqft)
    • 1 Bath
    • 16,553 Lot (sqft)
  18. Photo of 2627 Ambergate Road, Winter Park, FL 32792 (MLS # O6093816)
    $550,000
    Photo of 2627 Ambergate Road, Winter Park, FL 32792 (MLS # O6093816)
    Photo of 2627 Ambergate Road, Winter Park, FL 32792 (MLS # O6093816)
    2627 Ambergate Road, Winter Park, FL
    2627 Ambergate Road
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 1,805 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
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