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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 1248 Park Green Place, Winter Park, FL 32789 (MLS # S5115699)
    $473,700
    Photo of 1248 Park Green Place, Winter Park, FL 32789 (MLS # S5115699)
    Photo of 1248 Park Green Place, Winter Park, FL 32789 (MLS # S5115699)
    1248 Park Green Place, Winter Park, FL
    1248 Park Green Place
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,820 Home (sqft)
    • 2 Baths
    • 2,614 Lot (sqft)
  2. Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    $400,000
    Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    1757 Chilean Lane, Winter Park, FL
    1757 Chilean Lane
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,413 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  3. Photo of 1712 Bomi Circle, Winter Park, FL 32792 (MLS # O6256132)
    $598,000
    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)
  4. Photo of 1402 Bessmor Road, Winter Park, FL 32789 (MLS # O6254390)
    $469,900
    Photo of 1402 Bessmor Road, Winter Park, FL 32789 (MLS # O6254390)
    Photo of 1402 Bessmor Road, Winter Park, FL 32789 (MLS # O6254390)
    1402 Bessmor Road, Winter Park, FL
    1402 Bessmor Road
    Winter Park, FL
    • 4 Beds
    • 1 Bath
    • 1,100 Home (sqft)
    • 1 Bath
    • 6,970 Lot (sqft)
  5. Photo of 721 Roughbeard Road, Winter Park, FL 32792 (MLS # O6250720)
    $559,000
    Photo of 721 Roughbeard Road, Winter Park, FL 32792 (MLS # O6250720)
    Photo of 721 Roughbeard Road, Winter Park, FL 32792 (MLS # O6250720)
    721 Roughbeard Road, Winter Park, FL
    721 Roughbeard Road
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,964 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  6. Photo of 213 E Canton Avenue #213, Winter Park, FL 32789 (MLS # O6248526)
    $579,000
    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)
  7. Photo of 5231 Ardmore Drive, Winter Park, FL 32792 (MLS # O6246287)
    $425,000
    Photo of 5231 Ardmore Drive, Winter Park, FL 32792 (MLS # O6246287)
    Photo of 5231 Ardmore Drive, Winter Park, FL 32792 (MLS # O6246287)
    5231 Ardmore Drive, Winter Park, FL
    5231 Ardmore Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,645 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  8. Photo of 1710 Aster Drive, Winter Park, FL 32792 (MLS # O6246271)
    $504,900
    Photo of 1710 Aster Drive, Winter Park, FL 32792 (MLS # O6246271)
    Photo of 1710 Aster Drive, Winter Park, FL 32792 (MLS # O6246271)
    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)
  9. Photo of 4444 Steed Terrace, Winter Park, FL 32792 (MLS # S5113221)
    $470,000
    Photo of 4444 Steed Terrace, Winter Park, FL 32792 (MLS # S5113221)
    Photo of 4444 Steed Terrace, Winter Park, FL 32792 (MLS # S5113221)
    4444 Steed Terrace, Winter Park, FL
    4444 Steed Terrace
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,928 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
  10. Photo of 1926 Natalen Road, Winter Park, FL 32792 (MLS # O6245119)
    $595,000
    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)
    $468,900
    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 2877 Euston Road, Winter Park, FL 32789 (MLS # T3552787)
    $500,000
    Photo of 2877 Euston Road, Winter Park, FL 32789 (MLS # T3552787)
    Photo of 2877 Euston Road, Winter Park, FL 32789 (MLS # T3552787)
    2877 Euston Road, Winter Park, FL
    2877 Euston Road
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,692 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  14. 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)
  15. Photo of 2144 Ridge Drive, Winter Park, FL 32792 (MLS # O6214075)
    $450,000
    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)
  16. 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)
  17. 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)
  18. Photo of 1976 Shadyhill Terrace, Winter Park, FL 32792 (MLS # O6156969)
    $535,000
    Photo of 1976 Shadyhill Terrace, Winter Park, FL 32792 (MLS # O6156969)
    Photo of 1976 Shadyhill Terrace, Winter Park, FL 32792 (MLS # O6156969)
    1976 Shadyhill Terrace, Winter Park, FL
    1976 Shadyhill Terrace
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,300 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  19. Photo of 2627 Ambergate Road, Winter Park, FL 32792 (MLS # O6093816)
    $560,000
    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 11/21/24 4:12 AM PST.

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