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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 2774 Bright Bird Lane, Winter Park, FL 32792 (MLS # O6266098)
    $580,000
    Photo of 2774 Bright Bird Lane, Winter Park, FL 32792 (MLS # O6266098)
    Photo of 2774 Bright Bird Lane, Winter Park, FL 32792 (MLS # O6266098)
    2774 Bright Bird Lane, Winter Park, FL
    2774 Bright Bird Lane
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,907 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  2. Photo of 2112 Staunton Avenue, Winter Park, FL 32789 (MLS # O6265145)
    $449,000
    Photo of 2112 Staunton Avenue, Winter Park, FL 32789 (MLS # O6265145)
    Photo of 2112 Staunton Avenue, Winter Park, FL 32789 (MLS # O6265145)
    2112 Staunton Avenue, Winter Park, FL
    2112 Staunton Avenue
    Winter Park, FL
    • 3 Beds
    • 1 Bath
    • 1,438 Home (sqft)
    • 1 Bath
    • 9,584 Lot (sqft)
  3. Photo of 1550 Indiana Avenue, Winter Park, FL 32789 (MLS # O6264959)
    $459,990
    Photo of 1550 Indiana Avenue, Winter Park, FL 32789 (MLS # O6264959)
    Photo of 1550 Indiana Avenue, Winter Park, FL 32789 (MLS # O6264959)
    1550 Indiana Avenue, Winter Park, FL
    1550 Indiana Avenue
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,032 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  4. Photo of 1608 Bomi Circle, Winter Park, FL 32792 (MLS # O6265870)
    $525,000
    Photo of 1608 Bomi Circle, Winter Park, FL 32792 (MLS # O6265870)
    Photo of 1608 Bomi Circle, Winter Park, FL 32792 (MLS # O6265870)
    1608 Bomi Circle, Winter Park, FL
    1608 Bomi Circle
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,807 Home (sqft)
    • 2 Baths
    • 19,602 Lot (sqft)
  5. Photo of 3324 Alena Court, Winter Park, FL 32792 (MLS # O6263431)
    $435,000
    Photo of 3324 Alena Court, Winter Park, FL 32792 (MLS # O6263431)
    Photo of 3324 Alena Court, Winter Park, FL 32792 (MLS # O6263431)
    3324 Alena Court, Winter Park, FL
    3324 Alena Court
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,873 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  6. Photo of 1005 Carvell Drive, Winter Park, FL 32792 (MLS # O6263657)
    $469,995
    Photo of 1005 Carvell Drive, Winter Park, FL 32792 (MLS # O6263657)
    Photo of 1005 Carvell Drive, Winter Park, FL 32792 (MLS # O6263657)
    1005 Carvell Drive, Winter Park, FL
    1005 Carvell Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,932 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  7. Photo of 3425 Balsam Drive, Winter Park, FL 32792 (MLS # G5090195)
    $459,900
    Photo of 3425 Balsam Drive, Winter Park, FL 32792 (MLS # G5090195)
    Photo of 3425 Balsam Drive, Winter Park, FL 32792 (MLS # G5090195)
    3425 Balsam Drive, Winter Park, FL
    3425 Balsam Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,516 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  8. Photo of 2158 Sussex Road, Winter Park, FL 32792 (MLS # O6262737)
    $465,000
    Photo of 2158 Sussex Road, Winter Park, FL 32792 (MLS # O6262737)
    Photo of 2158 Sussex Road, Winter Park, FL 32792 (MLS # O6262737)
    2158 Sussex Road, Winter Park, FL
    2158 Sussex Road
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,669 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  9. Photo of 4026 Tenita Drive, Winter Park, FL 32792 (MLS # O6262359)
    $555,000
    Photo of 4026 Tenita Drive, Winter Park, FL 32792 (MLS # O6262359)
    Photo of 4026 Tenita Drive, Winter Park, FL 32792 (MLS # O6262359)
    4026 Tenita Drive, Winter Park, FL
    4026 Tenita Drive
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 2,122 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  10. Photo of 3607 Datura Court, Winter Park, FL 32792 (MLS # O6259616)
    $409,900
    Photo of 3607 Datura Court, Winter Park, FL 32792 (MLS # O6259616)
    Photo of 3607 Datura Court, Winter Park, FL 32792 (MLS # O6259616)
    3607 Datura Court, Winter Park, FL
    3607 Datura Court
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,380 Home (sqft)
    • 2 Baths
    • 12,633 Lot (sqft)
  11. Photo of 1566 Lawndale Circle, Winter Park, FL 32792 (MLS # G5089688)
    $465,000
    Photo of 1566 Lawndale Circle, Winter Park, FL 32792 (MLS # G5089688)
    Photo of 1566 Lawndale Circle, Winter Park, FL 32792 (MLS # G5089688)
    1566 Lawndale Circle, Winter Park, FL
    1566 Lawndale Circle
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,592 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  12. Photo of 1621 Puritan Avenue, Winter Park, FL 32792 (MLS # O6260883)
    $499,000
    Photo of 1621 Puritan Avenue, Winter Park, FL 32792 (MLS # O6260883)
    Photo of 1621 Puritan Avenue, Winter Park, FL 32792 (MLS # O6260883)
    34
     
    1621 Puritan Avenue, Winter Park, FL
    1621 Puritan Avenue
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,765 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  13. Photo of 690 Osceola Avenue #405, Winter Park, FL 32789 (MLS # A4629027)
    $525,000
    Photo of 690 Osceola Avenue #405, Winter Park, FL 32789 (MLS # A4629027)
    Photo of 690 Osceola Avenue #405, Winter Park, FL 32789 (MLS # A4629027)
    690 Osceola Avenue #405, Winter Park, FL
    690 Osceola Avenue #405
    Winter Park, FL
    • 1 Bed
    • 2 Baths
    • 850 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  14. Photo of 3304 Ellwood Court, Winter Park, FL 32792 (MLS # O6257150)
    $475,000
    Photo of 3304 Ellwood Court, Winter Park, FL 32792 (MLS # O6257150)
    Photo of 3304 Ellwood Court, Winter Park, FL 32792 (MLS # O6257150)
    3304 Ellwood Court, Winter Park, FL
    3304 Ellwood Court
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,629 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  15. Photo of 3076 Crane Strand Drive, Winter Park, FL 32792 (MLS # O6259399)
    $440,000
    Photo of 3076 Crane Strand Drive, Winter Park, FL 32792 (MLS # O6259399)
    Photo of 3076 Crane Strand Drive, Winter Park, FL 32792 (MLS # O6259399)
    3076 Crane Strand Drive, Winter Park, FL
    3076 Crane Strand Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,200 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  16. Photo of 690 Osceola Avenue #610, Winter Park, FL 32789 (MLS # O6257677)
    $499,000
    Photo of 690 Osceola Avenue #610, Winter Park, FL 32789 (MLS # O6257677)
    Photo of 690 Osceola Avenue #610, Winter Park, FL 32789 (MLS # O6257677)
    690 Osceola Avenue #610, Winter Park, FL
    690 Osceola Avenue #610
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,328 Home (sqft)
    • 2 Baths
    • 1.56 Lot (ac)
  17. Photo of 2341 Devon Court, Winter Park, FL 32789 (MLS # O6257142)
    $499,000
    Photo of 2341 Devon Court, Winter Park, FL 32789 (MLS # O6257142)
    Photo of 2341 Devon Court, Winter Park, FL 32789 (MLS # O6257142)
    2341 Devon Court, Winter Park, FL
    2341 Devon Court
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,773 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
  18. Photo of 3092 Nicholson Drive, Winter Park, FL 32792 (MLS # O6255970)
    $429,900
    Photo of 3092 Nicholson Drive, Winter Park, FL 32792 (MLS # O6255970)
    Photo of 3092 Nicholson Drive, Winter Park, FL 32792 (MLS # O6255970)
    3092 Nicholson Drive, Winter Park, FL
    3092 Nicholson Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,738 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  19. Photo of 1712 Bomi Circle, Winter Park, FL 32792 (MLS # O6256132)
    $569,000
    Photo of 1712 Bomi Circle, Winter Park, FL 32792 (MLS # O6256132)
    Photo of 1712 Bomi Circle, Winter Park, FL 32792 (MLS # O6256132)
    1712 Bomi Circle, Winter Park, FL
    1712 Bomi Circle
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 2,012 Home (sqft)
    • 2 Baths
    • 20,909 Lot (sqft)
  20. Photo of 627 Carvell Drive, Winter Park, FL 32792 (MLS # O6255765)
    $448,800
    Photo of 627 Carvell Drive, Winter Park, FL 32792 (MLS # O6255765)
    Photo of 627 Carvell Drive, Winter Park, FL 32792 (MLS # O6255765)
    627 Carvell Drive, Winter Park, FL
    627 Carvell Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,346 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  21. Photo of 512 Byron Road, Winter Park, FL 32792 (MLS # O6255318)
    $436,000
    Photo of 512 Byron Road, Winter Park, FL 32792 (MLS # O6255318)
    Photo of 512 Byron Road, Winter Park, FL 32792 (MLS # O6255318)
    512 Byron Road, Winter Park, FL
    512 Byron Road
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,353 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  22. Photo of 1820 Blaine Terrace, Winter Park, FL 32792 (MLS # O6254945)
    $439,000
    Photo of 1820 Blaine Terrace, Winter Park, FL 32792 (MLS # O6254945)
    Photo of 1820 Blaine Terrace, Winter Park, FL 32792 (MLS # O6254945)
    1820 Blaine Terrace, Winter Park, FL
    1820 Blaine Terrace
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,725 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  23. Photo of 5240 N Lake Burkett Lane, Winter Park, FL 32792 (MLS # O6254524)
    $535,000
    Photo of 5240 N Lake Burkett Lane, Winter Park, FL 32792 (MLS # O6254524)
    Photo of 5240 N Lake Burkett Lane, Winter Park, FL 32792 (MLS # O6254524)
    5240 N Lake Burkett Lane, Winter Park, FL
    5240 N Lake Burkett Lane
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,290 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  24. Photo of 2865 Clever Lane, Winter Park, FL 32792 (MLS # O6252450)
    $454,990
    Photo of 2865 Clever Lane, Winter Park, FL 32792 (MLS # O6252450)
    Photo of 2865 Clever Lane, Winter Park, FL 32792 (MLS # O6252450)
    2865 Clever Lane, Winter Park, FL
    2865 Clever Lane
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,907 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  25. Photo of 2891 Naples Drive, Winter Park, FL 32789 (MLS # O6250674)
    $537,000
    Photo of 2891 Naples Drive, Winter Park, FL 32789 (MLS # O6250674)
    Photo of 2891 Naples Drive, Winter Park, FL 32789 (MLS # O6250674)
    2891 Naples Drive, Winter Park, FL
    2891 Naples Drive
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,899 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  26. Photo of 1455 Broad Wing Lane, Winter Park, FL 32792 (MLS # O6251457)
    $479,900
    Photo of 1455 Broad Wing Lane, Winter Park, FL 32792 (MLS # O6251457)
    Photo of 1455 Broad Wing Lane, Winter Park, FL 32792 (MLS # O6251457)
    1455 Broad Wing Lane, Winter Park, FL
    1455 Broad Wing Lane
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,755 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  27. Photo of 2821 Chantilly Avenue, Winter Park, FL 32789 (MLS # O6249965)
    $539,000
    Photo of 2821 Chantilly Avenue, Winter Park, FL 32789 (MLS # O6249965)
    Photo of 2821 Chantilly Avenue, Winter Park, FL 32789 (MLS # O6249965)
    2821 Chantilly Avenue, Winter Park, FL
    2821 Chantilly Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,440 Home (sqft)
    • 2 Baths
    • 32,670 Lot (sqft)
  28. Photo of 213 E Canton Avenue #213, Winter Park, FL 32789 (MLS # O6248526)
    $559,000
    Photo of 213 E Canton Avenue #213, Winter Park, FL 32789 (MLS # O6248526)
    Photo of 213 E Canton Avenue #213, Winter Park, FL 32789 (MLS # O6248526)
    213 E Canton Avenue #213, Winter Park, FL
    213 E Canton Avenue #213
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,040 Home (sqft)
    • 2 Baths
    • 1.09 Lot (ac)
  29. Photo of 920 Gloriosa Avenue, Winter Park, FL 32789 (MLS # G5088048)
    $435,000
    Photo of 920 Gloriosa Avenue, Winter Park, FL 32789 (MLS # G5088048)
    Photo of 920 Gloriosa Avenue, Winter Park, FL 32789 (MLS # G5088048)
    920 Gloriosa Avenue, Winter Park, FL
    920 Gloriosa Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,540 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  30. Photo of 2140 Ridge Drive, Winter Park, FL 32792 (MLS # O6244737)
    $410,000
    Photo of 2140 Ridge Drive, Winter Park, FL 32792 (MLS # O6244737)
    Photo of 2140 Ridge Drive, Winter Park, FL 32792 (MLS # O6244737)
    2140 Ridge Drive, Winter Park, FL
    2140 Ridge Drive
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,554 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
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