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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 1424 Cavendish Road, Winter Park, FL 32789 (MLS # O6272801)
    $589,000
    Photo of 1424 Cavendish Road, Winter Park, FL 32789 (MLS # O6272801)
    Photo of 1424 Cavendish Road, Winter Park, FL 32789 (MLS # O6272801)
    1424 Cavendish Road, Winter Park, FL
    1424 Cavendish Road
    Winter Park, FL
    • 2 Beds
    • 1 Bath
    • 1,132 Home (sqft)
    • 1 Bath
    • 7,406 Lot (sqft)
  2. Photo of 2111 Staunton Avenue, Winter Park, FL 32789 (MLS # O6274702)
    $431,000
    Photo of 2111 Staunton Avenue, Winter Park, FL 32789 (MLS # O6274702)
    Photo of 2111 Staunton Avenue, Winter Park, FL 32789 (MLS # O6274702)
    2111 Staunton Avenue, Winter Park, FL
    2111 Staunton Avenue
    Winter Park, FL
    • 3 Beds
    • 1 Bath
    • 1,292 Home (sqft)
    • 1 Bath
    • 8,712 Lot (sqft)
  3. Photo of 2719 Bright Bird Lane, Winter Park, FL 32792 (MLS # O6274269)
    $479,900
    Photo of 2719 Bright Bird Lane, Winter Park, FL 32792 (MLS # O6274269)
    Photo of 2719 Bright Bird Lane, Winter Park, FL 32792 (MLS # O6274269)
    2719 Bright Bird Lane, Winter Park, FL
    2719 Bright Bird Lane
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,907 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  4. Photo of 1025 Early Avenue, Winter Park, FL 32789 (MLS # O6273679)
    $420,000
    Photo of 1025 Early Avenue, Winter Park, FL 32789 (MLS # O6273679)
    Photo of 1025 Early Avenue, Winter Park, FL 32789 (MLS # O6273679)
    1025 Early Avenue, Winter Park, FL
    1025 Early Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,333 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  5. Photo of 1496 Broad Wing Lane, Winter Park, FL 32792 (MLS # O6273365)
    $440,000
    Photo of 1496 Broad Wing Lane, Winter Park, FL 32792 (MLS # O6273365)
    Photo of 1496 Broad Wing Lane, Winter Park, FL 32792 (MLS # O6273365)
    1496 Broad Wing Lane, Winter Park, FL
    1496 Broad Wing Lane
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,755 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  6. Photo of 2855 Cady Way, Winter Park, FL 32792 (MLS # O6272945)
    $589,000
    Photo of 2855 Cady Way, Winter Park, FL 32792 (MLS # O6272945)
    Photo of 2855 Cady Way, Winter Park, FL 32792 (MLS # O6272945)
    2855 Cady Way, Winter Park, FL
    2855 Cady Way
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,736 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  7. Photo of 5405 Justine Way, Winter Park, FL 32792 (MLS # O6273248)
    $439,900
    Photo of 5405 Justine Way, Winter Park, FL 32792 (MLS # O6273248)
    Photo of 5405 Justine Way, Winter Park, FL 32792 (MLS # O6273248)
    5405 Justine Way, Winter Park, FL
    5405 Justine Way
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,247 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  8. Photo of 5102 Lake Howell Road, Winter Park, FL 32792 (MLS # O6272918)
    $400,000
    Photo of 5102 Lake Howell Road, Winter Park, FL 32792 (MLS # O6272918)
    Photo of 5102 Lake Howell Road, Winter Park, FL 32792 (MLS # O6272918)
    5102 Lake Howell Road, Winter Park, FL
    5102 Lake Howell Road
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,452 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  9. Photo of 2809 Bower Road, Winter Park, FL 32792 (MLS # R4908735)
    $599,000
    Photo of 2809 Bower Road, Winter Park, FL 32792 (MLS # R4908735)
    Photo of 2809 Bower Road, Winter Park, FL 32792 (MLS # R4908735)
    2809 Bower Road, Winter Park, FL
    2809 Bower Road
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,488 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  10. Photo of 1904 Houndslake Drive, Winter Park, FL 32792 (MLS # O6272912)
    $499,900
    Photo of 1904 Houndslake Drive, Winter Park, FL 32792 (MLS # O6272912)
    Photo of 1904 Houndslake Drive, Winter Park, FL 32792 (MLS # O6272912)
    1904 Houndslake Drive, Winter Park, FL
    1904 Houndslake Drive
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,840 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  11. Photo of 3084 Heartleaf Place, Winter Park, FL 32792 (MLS # NS1083572)
    $559,900
    Photo of 3084 Heartleaf Place, Winter Park, FL 32792 (MLS # NS1083572)
    Photo of 3084 Heartleaf Place, Winter Park, FL 32792 (MLS # NS1083572)
    3084 Heartleaf Place, Winter Park, FL
    3084 Heartleaf Place
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 2,439 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  12. Photo of 525 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6271152)
    $549,000
    Photo of 525 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6271152)
    Photo of 525 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6271152)
    27
     
    525 S Lakemont Avenue, Winter Park, FL
    525 S Lakemont Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,520 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  13. Photo of 2229 Shadowland Loop, Winter Park, FL 32792 (MLS # O6271629)
    $474,900
    Photo of 2229 Shadowland Loop, Winter Park, FL 32792 (MLS # O6271629)
    Photo of 2229 Shadowland Loop, Winter Park, FL 32792 (MLS # O6271629)
    2229 Shadowland Loop, Winter Park, FL
    2229 Shadowland Loop
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,964 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  14. Photo of 1710 Aster Drive, Winter Park, FL 32792 (MLS # O6272155)
    $504,900
    Photo of 1710 Aster Drive, Winter Park, FL 32792 (MLS # O6272155)
    Photo of 1710 Aster Drive, Winter Park, FL 32792 (MLS # O6272155)
    1710 Aster Drive, Winter Park, FL
    1710 Aster Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,664 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  15. Photo of 1061 Lundy Court, Winter Park, FL 32792 (MLS # O6267820)
    $480,000
    Photo of 1061 Lundy Court, Winter Park, FL 32792 (MLS # O6267820)
    Photo of 1061 Lundy Court, Winter Park, FL 32792 (MLS # O6267820)
    1061 Lundy Court, Winter Park, FL
    1061 Lundy Court
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,346 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  16. Photo of 1354 Tierra Circle, Winter Park, FL 32792 (MLS # O6271121)
    $485,000
    Photo of 1354 Tierra Circle, Winter Park, FL 32792 (MLS # O6271121)
    Photo of 1354 Tierra Circle, Winter Park, FL 32792 (MLS # O6271121)
    1354 Tierra Circle, Winter Park, FL
    1354 Tierra Circle
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,827 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  17. Photo of 1116 Fairway Drive, Winter Park, FL 32792 (MLS # O6265989)
    $599,900
    Photo of 1116 Fairway Drive, Winter Park, FL 32792 (MLS # O6265989)
    Photo of 1116 Fairway Drive, Winter Park, FL 32792 (MLS # O6265989)
    1116 Fairway Drive, Winter Park, FL
    1116 Fairway Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,738 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  18. Photo of 2073 Shadyhill Terrace, Winter Park, FL 32792 (MLS # O6270271)
    $525,000
    Photo of 2073 Shadyhill Terrace, Winter Park, FL 32792 (MLS # O6270271)
    Photo of 2073 Shadyhill Terrace, Winter Park, FL 32792 (MLS # O6270271)
    2073 Shadyhill Terrace, Winter Park, FL
    2073 Shadyhill Terrace
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,647 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  19. Photo of 2909 Clever Lane, Winter Park, FL 32792 (MLS # O6269922)
    $485,000
    Photo of 2909 Clever Lane, Winter Park, FL 32792 (MLS # O6269922)
    Photo of 2909 Clever Lane, Winter Park, FL 32792 (MLS # O6269922)
    2909 Clever Lane, Winter Park, FL
    2909 Clever Lane
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,907 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  20. Photo of 513 Cornwall Road, Winter Park, FL 32792 (MLS # O6259041)
    $600,000
    Photo of 513 Cornwall Road, Winter Park, FL 32792 (MLS # O6259041)
    Photo of 513 Cornwall Road, Winter Park, FL 32792 (MLS # O6259041)
    513 Cornwall Road, Winter Park, FL
    513 Cornwall Road
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,735 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  21. Photo of 5400 Ferrol Drive, Winter Park, FL 32792 (MLS # O6268855)
    $529,900
    Photo of 5400 Ferrol Drive, Winter Park, FL 32792 (MLS # O6268855)
    Photo of 5400 Ferrol Drive, Winter Park, FL 32792 (MLS # O6268855)
    5400 Ferrol Drive, Winter Park, FL
    5400 Ferrol Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,713 Home (sqft)
    • 2 Baths
    • 14,375 Lot (sqft)
  22. Photo of 5144 Orange Avenue, Winter Park, FL 32792 (MLS # O6268961)
    $415,000
    Photo of 5144 Orange Avenue, Winter Park, FL 32792 (MLS # O6268961)
    Photo of 5144 Orange Avenue, Winter Park, FL 32792 (MLS # O6268961)
    28
     
    5144 Orange Avenue, Winter Park, FL
    5144 Orange Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,274 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  23. Photo of 1860 Gladiolas Drive, Winter Park, FL 32792 (MLS # O6268293)
    $465,000
    Photo of 1860 Gladiolas Drive, Winter Park, FL 32792 (MLS # O6268293)
    Photo of 1860 Gladiolas Drive, Winter Park, FL 32792 (MLS # O6268293)
    1860 Gladiolas Drive, Winter Park, FL
    1860 Gladiolas Drive
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,653 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  24. Photo of 1422 Tierra Circle, Winter Park, FL 32792 (MLS # O6267207)
    $535,000
    Photo of 1422 Tierra Circle, Winter Park, FL 32792 (MLS # O6267207)
    Photo of 1422 Tierra Circle, Winter Park, FL 32792 (MLS # O6267207)
    1422 Tierra Circle, Winter Park, FL
    1422 Tierra Circle
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,827 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  25. Photo of 1397 Hyde Park Drive, Winter Park, FL 32792 (MLS # O6257679)
    $425,000
    Photo of 1397 Hyde Park Drive, Winter Park, FL 32792 (MLS # O6257679)
    Photo of 1397 Hyde Park Drive, Winter Park, FL 32792 (MLS # O6257679)
    1397 Hyde Park Drive, Winter Park, FL
    1397 Hyde Park Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,518 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  26. Photo of 2827 Euston Road, Winter Park, FL 32789 (MLS # O6261905)
    $420,000
    Photo of 2827 Euston Road, Winter Park, FL 32789 (MLS # O6261905)
    Photo of 2827 Euston Road, Winter Park, FL 32789 (MLS # O6261905)
    2827 Euston Road, Winter Park, FL
    2827 Euston Road
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,568 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  27. Photo of 2309 Dunbury Court, Winter Park, FL 32792 (MLS # O6267071)
    $466,000
    Photo of 2309 Dunbury Court, Winter Park, FL 32792 (MLS # O6267071)
    Photo of 2309 Dunbury Court, Winter Park, FL 32792 (MLS # O6267071)
    2309 Dunbury Court, Winter Park, FL
    2309 Dunbury Court
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 2,470 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  28. Photo of 215 E Canton Avenue #215, Winter Park, FL 32789 (MLS # O6263364)
    $499,000
    Photo of 215 E Canton Avenue #215, Winter Park, FL 32789 (MLS # O6263364)
    Photo of 215 E Canton Avenue #215, Winter Park, FL 32789 (MLS # O6263364)
    215 E Canton Avenue #215, Winter Park, FL
    215 E Canton Avenue #215
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,057 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  29. 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)
  30. 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)
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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 1/27/25 6:30 PM PST.

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