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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 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)
  2. 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)
  3. 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)
  4. 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)
  5. 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)
  6. Photo of 648 Callahan Street, Winter Park, FL 32789 (MLS # O6250649)
    $899,000
    Photo of 648 Callahan Street, Winter Park, FL 32789 (MLS # O6250649)
    Photo of 648 Callahan Street, Winter Park, FL 32789 (MLS # O6250649)
    648 Callahan Street, Winter Park, FL
    648 Callahan Street
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,898 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  7. Photo of 2228 Azalea Place, Winter Park, FL 32789 (MLS # O6250411)
    $5,400,000
    Photo of 2228 Azalea Place, Winter Park, FL 32789 (MLS # O6250411)
    Photo of 2228 Azalea Place, Winter Park, FL 32789 (MLS # O6250411)
    2228 Azalea Place, Winter Park, FL
    2228 Azalea Place
    Winter Park, FL
    • 5 Beds
    • 6 Baths
    • 5,072 Home (sqft)
    • 6 Baths
    • 14,375 Lot (sqft)
  8. Photo of 2522 Lafayette Avenue, Winter Park, FL 32789 (MLS # O6250342)
    $2,399,000
    Photo of 2522 Lafayette Avenue, Winter Park, FL 32789 (MLS # O6250342)
    Photo of 2522 Lafayette Avenue, Winter Park, FL 32789 (MLS # O6250342)
    2522 Lafayette Avenue, Winter Park, FL
    2522 Lafayette Avenue
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,399 Home (sqft)
    • 4 Baths
    • 10,455 Lot (sqft)
  9. Photo of 3136 Heartleaf Place, Winter Park, FL 32792 (MLS # O6253346)
    $749,999
    Photo of 3136 Heartleaf Place, Winter Park, FL 32792 (MLS # O6253346)
    Photo of 3136 Heartleaf Place, Winter Park, FL 32792 (MLS # O6253346)
    3136 Heartleaf Place, Winter Park, FL
    3136 Heartleaf Place
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,717 Home (sqft)
    • 4 Baths
    • 10,455 Lot (sqft)
  10. Photo of 678 Depugh Street, Winter Park, FL 32789 (MLS # O6247628)
    $700,000
    Photo of 678 Depugh Street, Winter Park, FL 32789 (MLS # O6247628)
    Photo of 678 Depugh Street, Winter Park, FL 32789 (MLS # O6247628)
    678 Depugh Street, Winter Park, FL
    678 Depugh Street
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 1,940 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  11. Photo of 3906 Cool Water Court, Winter Park, FL 32792 (MLS # O6249859)
    $695,000
    Photo of 3906 Cool Water Court, Winter Park, FL 32792 (MLS # O6249859)
    Photo of 3906 Cool Water Court, Winter Park, FL 32792 (MLS # O6249859)
    3906 Cool Water Court, Winter Park, FL
    3906 Cool Water Court
    Winter Park, FL
    • 5 Beds
    • 4 Baths
    • 2,990 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  12. Photo of 2040 Venetian Way, Winter Park, FL 32789 (MLS # O6249727)
    $9,995,000
    Photo of 2040 Venetian Way, Winter Park, FL 32789 (MLS # O6249727)
    Photo of 2040 Venetian Way, Winter Park, FL 32789 (MLS # O6249727)
    2040 Venetian Way, Winter Park, FL
    2040 Venetian Way
    Winter Park, FL
    • 6 Beds
    • 8 Baths
    • 8,082 Home (sqft)
    • 8 Baths
    • 1.84 Lot (ac)
  13. Photo of 100 S Virginia Avenue #201, Winter Park, FL 32789 (MLS # O6249016)
    $1,175,000
    Photo of 100 S Virginia Avenue #201, Winter Park, FL 32789 (MLS # O6249016)
    Photo of 100 S Virginia Avenue #201, Winter Park, FL 32789 (MLS # O6249016)
    49
     
    100 S Virginia Avenue #201, Winter Park, FL
    100 S Virginia Avenue #201
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,756 Home (sqft)
    • 3 Baths
    • 21,780 Lot (sqft)
  14. Photo of 1818 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248828)
    $825,000
    Photo of 1818 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248828)
    Photo of 1818 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248828)
    1818 Mondrian Circle, Winter Park, FL
    1818 Mondrian Circle
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 2,265 Home (sqft)
    • 4 Baths
    • 1,743 Lot (sqft)
  15. Photo of 1391 Richmond Road, Winter Park, FL 32789 (MLS # O6246352)
    $3,892,000
    Photo of 1391 Richmond Road, Winter Park, FL 32789 (MLS # O6246352)
    Photo of 1391 Richmond Road, Winter Park, FL 32789 (MLS # O6246352)
    1391 Richmond Road, Winter Park, FL
    1391 Richmond Road
    Winter Park, FL
    • 4 Beds
    • 6 Baths
    • 4,635 Home (sqft)
    • 6 Baths
    • 19,602 Lot (sqft)
  16. Photo of 210 Chelton Circle, Winter Park, FL 32789 (MLS # O6239351)
    $5,695,000
    Photo of 210 Chelton Circle, Winter Park, FL 32789 (MLS # O6239351)
    Photo of 210 Chelton Circle, Winter Park, FL 32789 (MLS # O6239351)
    210 Chelton Circle, Winter Park, FL
    210 Chelton Circle
    Winter Park, FL
    • 5 Beds
    • 6 Baths
    • 5,264 Home (sqft)
    • 6 Baths
    • 18,296 Lot (sqft)
  17. Photo of 1981 Japonica Road, Winter Park, FL 32792 (MLS # O6246791)
    $624,900
    Photo of 1981 Japonica Road, Winter Park, FL 32792 (MLS # O6246791)
    Photo of 1981 Japonica Road, Winter Park, FL 32792 (MLS # O6246791)
    1981 Japonica Road, Winter Park, FL
    1981 Japonica Road
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,040 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  18. Photo of 1001 Tuscany Place, Winter Park, FL 32789 (MLS # O6245474)
    $1,168,000
    Photo of 1001 Tuscany Place, Winter Park, FL 32789 (MLS # O6245474)
    Photo of 1001 Tuscany Place, Winter Park, FL 32789 (MLS # O6245474)
    1001 Tuscany Place, Winter Park, FL
    1001 Tuscany Place
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 2,458 Home (sqft)
    • 2 Baths
    • 16,989 Lot (sqft)
  19. Photo of 140 E Morse Boulevard #J, Winter Park, FL 32789 (MLS # O6245393)
    $2,890,000
    Photo of 140 E Morse Boulevard #J, Winter Park, FL 32789 (MLS # O6245393)
    Photo of 140 E Morse Boulevard #J, Winter Park, FL 32789 (MLS # O6245393)
    140 E Morse Boulevard #J, Winter Park, FL
    140 E Morse Boulevard #J
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,143 Home (sqft)
    • 3 Baths
    • 13,940 Lot (sqft)
  20. Photo of 1312 Golfside Drive, Winter Park, FL 32792 (MLS # O6244963)
    $799,000
    Photo of 1312 Golfside Drive, Winter Park, FL 32792 (MLS # O6244963)
    Photo of 1312 Golfside Drive, Winter Park, FL 32792 (MLS # O6244963)
    1312 Golfside Drive, Winter Park, FL
    1312 Golfside Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,867 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  21. Photo of 1830 Pineview Circle, Winter Park, FL 32792 (MLS # O6236875)
    $1,499,000
    Photo of 1830 Pineview Circle, Winter Park, FL 32792 (MLS # O6236875)
    Photo of 1830 Pineview Circle, Winter Park, FL 32792 (MLS # O6236875)
    1830 Pineview Circle, Winter Park, FL
    1830 Pineview Circle
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,843 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  22. Photo of 1371 Lyndale Boulevard, Winter Park, FL 32789 (MLS # O6245047)
    $1,495,000
    Photo of 1371 Lyndale Boulevard, Winter Park, FL 32789 (MLS # O6245047)
    Photo of 1371 Lyndale Boulevard, Winter Park, FL 32789 (MLS # O6245047)
    1371 Lyndale Boulevard, Winter Park, FL
    1371 Lyndale Boulevard
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,739 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  23. Photo of 104 S Interlachen Avenue #215D, Winter Park, FL 32789 (MLS # O6243220)
    $615,000
    Photo of 104 S Interlachen Avenue #215D, Winter Park, FL 32789 (MLS # O6243220)
    Photo of 104 S Interlachen Avenue #215D, Winter Park, FL 32789 (MLS # O6243220)
    104 S Interlachen Avenue #215D, Winter Park, FL
    104 S Interlachen Avenue #215D
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,267 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  24. Photo of 417 Gilbert Road, Winter Park, FL 32792 (MLS # O6242880)
    $675,000
    Photo of 417 Gilbert Road, Winter Park, FL 32792 (MLS # O6242880)
    Photo of 417 Gilbert Road, Winter Park, FL 32792 (MLS # O6242880)
    417 Gilbert Road, Winter Park, FL
    417 Gilbert Road
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,231 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  25. Photo of 1458 Aloma Avenue, Winter Park, FL 32789 (MLS # O6242682)
    $1,500,000
    Photo of 1458 Aloma Avenue, Winter Park, FL 32789 (MLS # O6242682)
    Photo of 1458 Aloma Avenue, Winter Park, FL 32789 (MLS # O6242682)
    1458 Aloma Avenue, Winter Park, FL
    1458 Aloma Avenue
    Winter Park, FL
    • 5 Beds
    • 4 Baths
    • 3,446 Home (sqft)
    • 4 Baths
    • 28,314 Lot (sqft)
  26. Photo of 1917 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6238835)
    $909,000
    Photo of 1917 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6238835)
    Photo of 1917 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6238835)
    1917 S Lakemont Avenue, Winter Park, FL
    1917 S Lakemont Avenue
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 2,051 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  27. Photo of 2201 Kindel Avenue, Winter Park, FL 32789 (MLS # O6242752)
    $824,999
    Photo of 2201 Kindel Avenue, Winter Park, FL 32789 (MLS # O6242752)
    Photo of 2201 Kindel Avenue, Winter Park, FL 32789 (MLS # O6242752)
    42
     
    2201 Kindel Avenue, Winter Park, FL
    2201 Kindel Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,407 Home (sqft)
    • 2 Baths
    • 1.41 Lot (ac)
  28. Photo of 654 W Morse Boulevard, Winter Park, FL 32789 (MLS # O6240628)
    $6,975,000
    Photo of 654 W Morse Boulevard, Winter Park, FL 32789 (MLS # O6240628)
    Photo of 654 W Morse Boulevard, Winter Park, FL 32789 (MLS # O6240628)
    654 W Morse Boulevard, Winter Park, FL
    654 W Morse Boulevard
    Winter Park, FL
    • 5 Beds
    • 8 Baths
    • 8,752 Home (sqft)
    • 8 Baths
    • 7,841 Lot (sqft)
  29. Photo of 2139 Blossom Lane, Winter Park, FL 32789 (MLS # O6241493)
    $1,990,000
    Photo of 2139 Blossom Lane, Winter Park, FL 32789 (MLS # O6241493)
    Photo of 2139 Blossom Lane, Winter Park, FL 32789 (MLS # O6241493)
    2139 Blossom Lane, Winter Park, FL
    2139 Blossom Lane
    Winter Park, FL
    • 5 Beds
    • 4 Baths
    • 3,174 Home (sqft)
    • 4 Baths
    • 20,038 Lot (sqft)
  30. Photo of 1417.5 Miller Avenue, Winter Park, FL 32789 (MLS # O6240812)
    $995,000
    Photo of 1417.5 Miller Avenue, Winter Park, FL 32789 (MLS # O6240812)
    Photo of 1417.5 Miller Avenue, Winter Park, FL 32789 (MLS # O6240812)
    1417.5 Miller Avenue, Winter Park, FL
    1417.5 Miller Avenue
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,002 Home (sqft)
    • 3 Baths
    • 4,792 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 11/22/24 10:13 PM PST.

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