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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 above $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 344 Starling Road, Winter Park, FL 32789 (MLS # O6259309)
    $649,000
    Photo of 344 Starling Road, Winter Park, FL 32789 (MLS # O6259309)
    Photo of 344 Starling Road, Winter Park, FL 32789 (MLS # O6259309)
    344 Starling Road, Winter Park, FL
    344 Starling Road
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,345 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  2. Photo of 800 Greens Avenue, Winter Park, FL 32789 (MLS # O6257931)
    $745,000
    Photo of 800 Greens Avenue, Winter Park, FL 32789 (MLS # O6257931)
    Photo of 800 Greens Avenue, Winter Park, FL 32789 (MLS # O6257931)
    39
     
    800 Greens Avenue, Winter Park, FL
    800 Greens Avenue
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,218 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
  3. Photo of 1885 Temple Drive, Winter Park, FL 32789 (MLS # O6258468)
    $1,200,000
    Photo of 1885 Temple Drive, Winter Park, FL 32789 (MLS # O6258468)
    Photo of 1885 Temple Drive, Winter Park, FL 32789 (MLS # O6258468)
    1885 Temple Drive, Winter Park, FL
    1885 Temple Drive
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,691 Home (sqft)
    • 4 Baths
    • 10,455 Lot (sqft)
  4. Photo of 660 Osceola Avenue #104, Winter Park, FL 32789 (MLS # O6257901)
    $2,395,000
    Photo of 660 Osceola Avenue #104, Winter Park, FL 32789 (MLS # O6257901)
    Photo of 660 Osceola Avenue #104, Winter Park, FL 32789 (MLS # O6257901)
    660 Osceola Avenue #104, Winter Park, FL
    660 Osceola Avenue #104
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,632 Home (sqft)
    • 3 Baths
    • 1.55 Lot (ac)
  5. Photo of 7440 Aloma Ave, Winter Park, FL 32792 (MLS # O6258176)
    $1,299,000
    Photo of 7440 Aloma Ave, Winter Park, FL 32792 (MLS # O6258176)
    Photo of 7440 Aloma Ave, Winter Park, FL 32792 (MLS # O6258176)
    7440 Aloma Ave, Winter Park, FL
    7440 Aloma Ave
    Winter Park, FL
    • 5 Beds
    • 5 Baths
    • 4,435 Home (sqft)
    • 5 Baths
    • 9,148 Lot (sqft)
  6. Photo of 1781 Goodrich Avenue, Winter Park, FL 32789 (MLS # O6257832)
    $1,950,000
    Photo of 1781 Goodrich Avenue, Winter Park, FL 32789 (MLS # O6257832)
    Photo of 1781 Goodrich Avenue, Winter Park, FL 32789 (MLS # O6257832)
    1781 Goodrich Avenue, Winter Park, FL
    1781 Goodrich Avenue
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,701 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  7. Photo of 1341 College Point, Winter Park, FL 32789 (MLS # O6257650)
    $4,250,000
    Photo of 1341 College Point, Winter Park, FL 32789 (MLS # O6257650)
    Photo of 1341 College Point, Winter Park, FL 32789 (MLS # O6257650)
    1341 College Point, Winter Park, FL
    1341 College Point
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 4,279 Home (sqft)
    • 4 Baths
    • 16,989 Lot (sqft)
  8. Photo of 1429 Chapman Circle, Winter Park, FL 32789 (MLS # O6257912)
    $1,699,000
    Photo of 1429 Chapman Circle, Winter Park, FL 32789 (MLS # O6257912)
    Photo of 1429 Chapman Circle, Winter Park, FL 32789 (MLS # O6257912)
    1429 Chapman Circle, Winter Park, FL
    1429 Chapman Circle
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,116 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  9. Photo of 1620 Oneco Avenue, Winter Park, FL 32789 (MLS # O6257787)
    $2,800,000
    Photo of 1620 Oneco Avenue, Winter Park, FL 32789 (MLS # O6257787)
    Photo of 1620 Oneco Avenue, Winter Park, FL 32789 (MLS # O6257787)
    50
     
    1620 Oneco Avenue, Winter Park, FL
    1620 Oneco Avenue
    Winter Park, FL
    • 5 Beds
    • 5 Baths
    • 3,911 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  10. Photo of 326 S Ranger Boulevard, Winter Park, FL 32792 (MLS # OM688636)
    $649,900
    Photo of 326 S Ranger Boulevard, Winter Park, FL 32792 (MLS # OM688636)
    Photo of 326 S Ranger Boulevard, Winter Park, FL 32792 (MLS # OM688636)
    326 S Ranger Boulevard, Winter Park, FL
    326 S Ranger Boulevard
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 2,086 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  11. Photo of 1316 Fountain Hills Court, Winter Park, FL 32792 (MLS # O6257903)
    $835,000
    Photo of 1316 Fountain Hills Court, Winter Park, FL 32792 (MLS # O6257903)
    Photo of 1316 Fountain Hills Court, Winter Park, FL 32792 (MLS # O6257903)
    1316 Fountain Hills Court, Winter Park, FL
    1316 Fountain Hills Court
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,823 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  12. Photo of 2550 Venetian Way, Winter Park, FL 32789 (MLS # O6258445)
    $3,299,000
    Photo of 2550 Venetian Way, Winter Park, FL 32789 (MLS # O6258445)
    Photo of 2550 Venetian Way, Winter Park, FL 32789 (MLS # O6258445)
    2550 Venetian Way, Winter Park, FL
    2550 Venetian Way
    Winter Park, FL
    • 4 Beds
    • 6 Baths
    • 4,875 Home (sqft)
    • 6 Baths
    • 11,762 Lot (sqft)
  13. Photo of 432 W Swoope Avenue, Winter Park, FL 32789 (MLS # O6257130)
    $725,000
    Photo of 432 W Swoope Avenue, Winter Park, FL 32789 (MLS # O6257130)
    Photo of 432 W Swoope Avenue, Winter Park, FL 32789 (MLS # O6257130)
    432 W Swoope Avenue, Winter Park, FL
    432 W Swoope Avenue
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,317 Home (sqft)
    • 4 Baths
    • 872 Lot (sqft)
  14. Photo of 101 S New York Ave #302, Winter Park, FL 32789 (MLS # O6256094)
    $1,695,000
    Photo of 101 S New York Ave #302, Winter Park, FL 32789 (MLS # O6256094)
    Photo of 101 S New York Ave #302, Winter Park, FL 32789 (MLS # O6256094)
    101 S New York Ave #302, Winter Park, FL
    101 S New York Ave #302
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 3,174 Home (sqft)
    • 4 Baths
    • 20,038 Lot (sqft)
  15. Photo of 1751 Glencoe Road, Winter Park, FL 32789 (MLS # O6255877)
    $4,100,000
    Photo of 1751 Glencoe Road, Winter Park, FL 32789 (MLS # O6255877)
    Photo of 1751 Glencoe Road, Winter Park, FL 32789 (MLS # O6255877)
    1751 Glencoe Road, Winter Park, FL
    1751 Glencoe Road
    Winter Park, FL
    • 5 Beds
    • 6 Baths
    • 4,520 Home (sqft)
    • 6 Baths
    • 13,068 Lot (sqft)
  16. Photo of 2518 Sweetwater Trail, Winter Park, FL 32789 (MLS # O6255305)
    $654,900
    Photo of 2518 Sweetwater Trail, Winter Park, FL 32789 (MLS # O6255305)
    Photo of 2518 Sweetwater Trail, Winter Park, FL 32789 (MLS # O6255305)
    41
     
    2518 Sweetwater Trail, Winter Park, FL
    2518 Sweetwater Trail
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 2,205 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  17. Photo of 640 Worthington Drive, Winter Park, FL 32789 (MLS # O6255730)
    $980,000
    Photo of 640 Worthington Drive, Winter Park, FL 32789 (MLS # O6255730)
    Photo of 640 Worthington Drive, Winter Park, FL 32789 (MLS # O6255730)
    640 Worthington Drive, Winter Park, FL
    640 Worthington Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 2,012 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  18. Photo of 1010 N Pennsylvania Avenue, Winter Park, FL 32789 (MLS # O6254839)
    $2,800,000
    Photo of 1010 N Pennsylvania Avenue, Winter Park, FL 32789 (MLS # O6254839)
    Photo of 1010 N Pennsylvania Avenue, Winter Park, FL 32789 (MLS # O6254839)
    1010 N Pennsylvania Avenue, Winter Park, FL
    1010 N Pennsylvania Avenue
    Winter Park, FL
    • 4 Beds
    • 5 Baths
    • 4,074 Home (sqft)
    • 5 Baths
    • 9,584 Lot (sqft)
  19. Photo of 1795 Walker Avenue, Winter Park, FL 32789 (MLS # O6254742)
    $969,000
    Photo of 1795 Walker Avenue, Winter Park, FL 32789 (MLS # O6254742)
    Photo of 1795 Walker Avenue, Winter Park, FL 32789 (MLS # O6254742)
    37
     
    1795 Walker Avenue, Winter Park, FL
    1795 Walker Avenue
    Winter Park, FL
    • 5 Beds
    • 3 Baths
    • 1,813 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  20. Photo of 1716 Palmer Avenue, Winter Park, FL 32789 (MLS # TB8316437)
    $1,729,000
    Photo of 1716 Palmer Avenue, Winter Park, FL 32789 (MLS # TB8316437)
    Photo of 1716 Palmer Avenue, Winter Park, FL 32789 (MLS # TB8316437)
    1716 Palmer Avenue, Winter Park, FL
    1716 Palmer Avenue
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 3,270 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  21. Photo of 1570 Grove Terrace, Winter Park, FL 32789 (MLS # O6253722)
    $750,000
    Photo of 1570 Grove Terrace, Winter Park, FL 32789 (MLS # O6253722)
    Photo of 1570 Grove Terrace, Winter Park, FL 32789 (MLS # O6253722)
    1570 Grove Terrace, Winter Park, FL
    1570 Grove Terrace
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,663 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  22. Photo of 1804 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248830)
    $719,900
    Photo of 1804 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248830)
    Photo of 1804 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248830)
    1804 Mondrian Circle, Winter Park, FL
    1804 Mondrian Circle
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 2,016 Home (sqft)
    • 4 Baths
    • 1,743 Lot (sqft)
  23. Photo of 870 Carver Street, Winter Park, FL 32789 (MLS # O6250529)
    $995,000
    Photo of 870 Carver Street, Winter Park, FL 32789 (MLS # O6250529)
    Photo of 870 Carver Street, Winter Park, FL 32789 (MLS # O6250529)
    870 Carver Street, Winter Park, FL
    870 Carver Street
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 1,844 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  24. Photo of 1900 W Fawsett Road, Winter Park, FL 32789 (MLS # O6251960)
    $3,575,000
    Photo of 1900 W Fawsett Road, Winter Park, FL 32789 (MLS # O6251960)
    Photo of 1900 W Fawsett Road, Winter Park, FL 32789 (MLS # O6251960)
    1900 W Fawsett Road, Winter Park, FL
    1900 W Fawsett Road
    Winter Park, FL
    • 4 Beds
    • 5 Baths
    • 4,600 Home (sqft)
    • 5 Baths
    • 1.10 Lot (ac)
  25. Photo of 1681 Blue Ridge Road, Winter Park, FL 32789 (MLS # O6251187)
    $1,395,000
    Photo of 1681 Blue Ridge Road, Winter Park, FL 32789 (MLS # O6251187)
    Photo of 1681 Blue Ridge Road, Winter Park, FL 32789 (MLS # O6251187)
    1681 Blue Ridge Road, Winter Park, FL
    1681 Blue Ridge Road
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,762 Home (sqft)
    • 4 Baths
    • 13,504 Lot (sqft)
  26. Photo of 8077 Pleasant Pine Circle, Winter Park, FL 32792 (MLS # O6252394)
    $699,900
    Photo of 8077 Pleasant Pine Circle, Winter Park, FL 32792 (MLS # O6252394)
    Photo of 8077 Pleasant Pine Circle, Winter Park, FL 32792 (MLS # O6252394)
    8077 Pleasant Pine Circle, Winter Park, FL
    8077 Pleasant Pine Circle
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,215 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  27. Photo of 2418 Euston Road, Winter Park, FL 32789 (MLS # O6250903)
    $795,000
    Photo of 2418 Euston Road, Winter Park, FL 32789 (MLS # O6250903)
    Photo of 2418 Euston Road, Winter Park, FL 32789 (MLS # O6250903)
    2418 Euston Road, Winter Park, FL
    2418 Euston Road
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,228 Home (sqft)
    • 3 Baths
    • 11,762 Lot (sqft)
  28. Photo of 2128 Sycamore Drive, Winter Park, FL 32789 (MLS # L4948316)
    $890,000
    Photo of 2128 Sycamore Drive, Winter Park, FL 32789 (MLS # L4948316)
    Photo of 2128 Sycamore Drive, Winter Park, FL 32789 (MLS # L4948316)
    2128 Sycamore Drive, Winter Park, FL
    2128 Sycamore Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,760 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  29. Photo of 1571 Oneco Avenue, Winter Park, FL 32789 (MLS # O6250954)
    $1,190,000
    Photo of 1571 Oneco Avenue, Winter Park, FL 32789 (MLS # O6250954)
    Photo of 1571 Oneco Avenue, Winter Park, FL 32789 (MLS # O6250954)
    1571 Oneco Avenue, Winter Park, FL
    1571 Oneco Avenue
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,510 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  30. Photo of 632 Country Club Drive, Winter Park, FL 32789 (MLS # O6250417)
    $1,450,000
    Photo of 632 Country Club Drive, Winter Park, FL 32789 (MLS # O6250417)
    Photo of 632 Country Club Drive, Winter Park, FL 32789 (MLS # O6250417)
    632 Country Club Drive, Winter Park, FL
    632 Country Club Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 2,342 Home (sqft)
    • 2 Baths
    • 22,652 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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