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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 pool 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 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)
  2. 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)
  3. 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)
  4. 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)
  5. 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)
  6. 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)
  7. 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)
  8. 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)
  9. 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)
  10. 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)
  11. 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)
  12. 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)
  13. 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)
  14. 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)
  15. 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)
  16. 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)
  17. 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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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 12/22/24 2:33 PM PST.

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