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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 1417 Miller Avenue, Winter Park, FL 32789 (MLS # O6240798)
    $995,000
    Photo of 1417 Miller Avenue, Winter Park, FL 32789 (MLS # O6240798)
    Photo of 1417 Miller Avenue, Winter Park, FL 32789 (MLS # O6240798)
    1417 Miller Avenue, Winter Park, FL
    1417 Miller Avenue
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,002 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  2. Photo of 2350 Sherbrooke Road, Winter Park, FL 32792 (MLS # O6241415)
    $774,990
    Photo of 2350 Sherbrooke Road, Winter Park, FL 32792 (MLS # O6241415)
    Photo of 2350 Sherbrooke Road, Winter Park, FL 32792 (MLS # O6241415)
    2350 Sherbrooke Road, Winter Park, FL
    2350 Sherbrooke Road
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,200 Home (sqft)
    • 3 Baths
    • 11,762 Lot (sqft)
  3. Photo of 2015 Summerfield Road, Winter Park, FL 32792 (MLS # O6240903)
    $1,500,000
    Photo of 2015 Summerfield Road, Winter Park, FL 32792 (MLS # O6240903)
    Photo of 2015 Summerfield Road, Winter Park, FL 32792 (MLS # O6240903)
    2015 Summerfield Road, Winter Park, FL
    2015 Summerfield Road
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,958 Home (sqft)
    • 4 Baths
    • 10,890 Lot (sqft)
  4. Photo of 439 N Capen Avenue, Winter Park, FL 32789 (MLS # O6238453)
    $899,900
    Photo of 439 N Capen Avenue, Winter Park, FL 32789 (MLS # O6238453)
    Photo of 439 N Capen Avenue, Winter Park, FL 32789 (MLS # O6238453)
    439 N Capen Avenue, Winter Park, FL
    439 N Capen Avenue
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,861 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  5. Photo of 2235 Coldstream Drive, Winter Park, FL 32792 (MLS # O6240342)
    $750,000
    Photo of 2235 Coldstream Drive, Winter Park, FL 32792 (MLS # O6240342)
    Photo of 2235 Coldstream Drive, Winter Park, FL 32792 (MLS # O6240342)
    2235 Coldstream Drive, Winter Park, FL
    2235 Coldstream Drive
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,347 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  6. Photo of 1919 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6238841)
    $949,000
    Photo of 1919 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6238841)
    Photo of 1919 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6238841)
    1919 S Lakemont Avenue, Winter Park, FL
    1919 S Lakemont Avenue
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 2,085 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  7. Photo of 607 Dunblane Drive, Winter Park, FL 32792 (MLS # O6239168)
    $815,000
    Photo of 607 Dunblane Drive, Winter Park, FL 32792 (MLS # O6239168)
    Photo of 607 Dunblane Drive, Winter Park, FL 32792 (MLS # O6239168)
    607 Dunblane Drive, Winter Park, FL
    607 Dunblane Drive
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,046 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  8. Photo of 345 Sylvan Boulevard, Winter Park, FL 32789 (MLS # O6239390)
    $1,075,000
    Photo of 345 Sylvan Boulevard, Winter Park, FL 32789 (MLS # O6239390)
    Photo of 345 Sylvan Boulevard, Winter Park, FL 32789 (MLS # O6239390)
    345 Sylvan Boulevard, Winter Park, FL
    345 Sylvan Boulevard
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,011 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  9. Photo of 1915 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6226388)
    $879,000
    Photo of 1915 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6226388)
    Photo of 1915 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6226388)
    1915 S Lakemont Avenue, Winter Park, FL
    1915 S Lakemont Avenue
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 2,104 Home (sqft)
    • 4 Baths
    • 2,178 Lot (sqft)
  10. Photo of 840 W. Comstock Ave, Winter Park, FL 32789 (MLS # O6238899)
    $1,500,000
    Photo of 840 W. Comstock Ave, Winter Park, FL 32789 (MLS # O6238899)
    Photo of 840 W. Comstock Ave, Winter Park, FL 32789 (MLS # O6238899)
    840 W. Comstock Ave, Winter Park, FL
    840 W. Comstock Ave
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,350 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  11. Photo of 311 E Morse Boulevard #6-18, Winter Park, FL 32789 (MLS # O6237750)
    $1,199,000
    Photo of 311 E Morse Boulevard #6-18, Winter Park, FL 32789 (MLS # O6237750)
    Photo of 311 E Morse Boulevard #6-18, Winter Park, FL 32789 (MLS # O6237750)
    311 E Morse Boulevard #6-18, Winter Park, FL
    311 E Morse Boulevard #6-18
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 2,096 Home (sqft)
    • 2 Baths
    • 2.77 Lot (ac)
  12. Photo of 1451 Lyndale Boulevard, Winter Park, FL 32789 (MLS # O6237975)
    $1,999,993
    Photo of 1451 Lyndale Boulevard, Winter Park, FL 32789 (MLS # O6237975)
    Photo of 1451 Lyndale Boulevard, Winter Park, FL 32789 (MLS # O6237975)
    1451 Lyndale Boulevard, Winter Park, FL
    1451 Lyndale Boulevard
    Winter Park, FL
    • 6 Beds
    • 4 Baths
    • 3,853 Home (sqft)
    • 4 Baths
    • 15,246 Lot (sqft)
  13. Photo of 850 Georgia Avenue, Winter Park, FL 32789 (MLS # O6236795)
    $3,950,000
    Photo of 850 Georgia Avenue, Winter Park, FL 32789 (MLS # O6236795)
    Photo of 850 Georgia Avenue, Winter Park, FL 32789 (MLS # O6236795)
    850 Georgia Avenue, Winter Park, FL
    850 Georgia Avenue
    Winter Park, FL
    • 3 Beds
    • 6 Baths
    • 4,627 Home (sqft)
    • 6 Baths
    • 27,008 Lot (sqft)
  14. Photo of 1848 Mizell Avenue, Winter Park, FL 32789 (MLS # O6236639)
    $649,000
    Photo of 1848 Mizell Avenue, Winter Park, FL 32789 (MLS # O6236639)
    Photo of 1848 Mizell Avenue, Winter Park, FL 32789 (MLS # O6236639)
    1848 Mizell Avenue, Winter Park, FL
    1848 Mizell Avenue
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,162 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  15. Photo of 274 N Ranger Boulevard, Winter Park, FL 32792 (MLS # O6222908)
    $630,000
    Photo of 274 N Ranger Boulevard, Winter Park, FL 32792 (MLS # O6222908)
    Photo of 274 N Ranger Boulevard, Winter Park, FL 32792 (MLS # O6222908)
    274 N Ranger Boulevard, Winter Park, FL
    274 N Ranger Boulevard
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,420 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
  16. Photo of 1730 Winchester Drive, Winter Park, FL 32789 (MLS # O6235073)
    $3,295,000
    Photo of 1730 Winchester Drive, Winter Park, FL 32789 (MLS # O6235073)
    Photo of 1730 Winchester Drive, Winter Park, FL 32789 (MLS # O6235073)
    1730 Winchester Drive, Winter Park, FL
    1730 Winchester Drive
    Winter Park, FL
    • 5 Beds
    • 6 Baths
    • 4,080 Home (sqft)
    • 6 Baths
    • 12,197 Lot (sqft)
  17. Photo of 660 Arjay Way, Winter Park, FL 32789 (MLS # O6237059)
    $1,650,000
    Photo of 660 Arjay Way, Winter Park, FL 32789 (MLS # O6237059)
    Photo of 660 Arjay Way, Winter Park, FL 32789 (MLS # O6237059)
    660 Arjay Way, Winter Park, FL
    660 Arjay Way
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,237 Home (sqft)
    • 4 Baths
    • 11,326 Lot (sqft)
  18. Photo of 1764 Elizabeths Walk, Winter Park, FL 32789 (MLS # O6234031)
    $1,950,000
    Photo of 1764 Elizabeths Walk, Winter Park, FL 32789 (MLS # O6234031)
    Photo of 1764 Elizabeths Walk, Winter Park, FL 32789 (MLS # O6234031)
    1764 Elizabeths Walk, Winter Park, FL
    1764 Elizabeths Walk
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,989 Home (sqft)
    • 4 Baths
    • 10,890 Lot (sqft)
  19. Photo of 2260 Hawick Lane, Winter Park, FL 32792 (MLS # O6232951)
    $1,050,000
    Photo of 2260 Hawick Lane, Winter Park, FL 32792 (MLS # O6232951)
    Photo of 2260 Hawick Lane, Winter Park, FL 32792 (MLS # O6232951)
    2260 Hawick Lane, Winter Park, FL
    2260 Hawick Lane
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,374 Home (sqft)
    • 2 Baths
    • 19,602 Lot (sqft)
  20. Photo of 2632 Mandan Trl, Winter Park, FL 32789 (MLS # O6232937)
    $799,500
    Photo of 2632 Mandan Trl, Winter Park, FL 32789 (MLS # O6232937)
    Photo of 2632 Mandan Trl, Winter Park, FL 32789 (MLS # O6232937)
    2632 Mandan Trl, Winter Park, FL
    2632 Mandan Trl
    Winter Park, FL
    • 5 Beds
    • 3 Baths
    • 2,441 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  21. Photo of 1806 Mondrian Circle, Winter Park, FL 32789 (MLS # O6232883)
    $725,000
    Photo of 1806 Mondrian Circle, Winter Park, FL 32789 (MLS # O6232883)
    Photo of 1806 Mondrian Circle, Winter Park, FL 32789 (MLS # O6232883)
    1806 Mondrian Circle, Winter Park, FL
    1806 Mondrian Circle
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 2,016 Home (sqft)
    • 4 Baths
    • 1,743 Lot (sqft)
  22. Photo of 279 Rippling Lane, Winter Park, FL 32789 (MLS # O6230955)
    $1,795,000
    Photo of 279 Rippling Lane, Winter Park, FL 32789 (MLS # O6230955)
    Photo of 279 Rippling Lane, Winter Park, FL 32789 (MLS # O6230955)
    279 Rippling Lane, Winter Park, FL
    279 Rippling Lane
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 3,472 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
  23. Photo of 731 Midget Drive, Winter Park, FL 32789 (MLS # O6232383)
    $850,000
    Photo of 731 Midget Drive, Winter Park, FL 32789 (MLS # O6232383)
    Photo of 731 Midget Drive, Winter Park, FL 32789 (MLS # O6232383)
    731 Midget Drive, Winter Park, FL
    731 Midget Drive
    Winter Park, FL
    • 2 Beds
    • 1 Bath
    • 960 Home (sqft)
    • 1 Bath
    • 8,277 Lot (sqft)
  24. Photo of 1238 Formosa Avenue, Winter Park, FL 32789 (MLS # O6227285)
    $630,000
    Photo of 1238 Formosa Avenue, Winter Park, FL 32789 (MLS # O6227285)
    Photo of 1238 Formosa Avenue, Winter Park, FL 32789 (MLS # O6227285)
    1238 Formosa Avenue, Winter Park, FL
    1238 Formosa Avenue
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 1,893 Home (sqft)
    • 4 Baths
    • 2,178 Lot (sqft)
  25. Photo of 625 N Interlachen Avenue #A, Winter Park, FL 32789 (MLS # O6222843)
    $1,185,000
    Photo of 625 N Interlachen Avenue #A, Winter Park, FL 32789 (MLS # O6222843)
    Photo of 625 N Interlachen Avenue #A, Winter Park, FL 32789 (MLS # O6222843)
    625 N Interlachen Avenue #A, Winter Park, FL
    625 N Interlachen Avenue #A
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,718 Home (sqft)
    • 2 Baths
    • 23,523 Lot (sqft)
  26. Photo of 1840 Biscayne Drive, Winter Park, FL 32789 (MLS # O6226190)
    $1,189,000
    Photo of 1840 Biscayne Drive, Winter Park, FL 32789 (MLS # O6226190)
    Photo of 1840 Biscayne Drive, Winter Park, FL 32789 (MLS # O6226190)
    1840 Biscayne Drive, Winter Park, FL
    1840 Biscayne Drive
    Winter Park, FL
    • 5 Beds
    • 3 Baths
    • 2,641 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  27. Photo of 1650 Lakehurst Avenue, Winter Park, FL 32789 (MLS # O6225250)
    $1,695,000
    Photo of 1650 Lakehurst Avenue, Winter Park, FL 32789 (MLS # O6225250)
    Photo of 1650 Lakehurst Avenue, Winter Park, FL 32789 (MLS # O6225250)
    1650 Lakehurst Avenue, Winter Park, FL
    1650 Lakehurst Avenue
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,777 Home (sqft)
    • 4 Baths
    • 16,553 Lot (sqft)
  28. Photo of 363 N Phelps Avenue, Winter Park, FL 32789 (MLS # O6223564)
    $1,130,000
    Photo of 363 N Phelps Avenue, Winter Park, FL 32789 (MLS # O6223564)
    Photo of 363 N Phelps Avenue, Winter Park, FL 32789 (MLS # O6223564)
    363 N Phelps Avenue, Winter Park, FL
    363 N Phelps Avenue
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,871 Home (sqft)
    • 3 Baths
    • 16,553 Lot (sqft)
  29. Photo of 3031 Northwood Boulevard, Winter Park, FL 32789 (MLS # O6223922)
    $1,599,995
    Photo of 3031 Northwood Boulevard, Winter Park, FL 32789 (MLS # O6223922)
    Photo of 3031 Northwood Boulevard, Winter Park, FL 32789 (MLS # O6223922)
    3031 Northwood Boulevard, Winter Park, FL
    3031 Northwood Boulevard
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,978 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  30. Photo of 335 W Welbourne Avenue #103, Winter Park, FL 32789 (MLS # V4937374)
    $1,348,900
    Photo of 335 W Welbourne Avenue #103, Winter Park, FL 32789 (MLS # V4937374)
    Photo of 335 W Welbourne Avenue #103, Winter Park, FL 32789 (MLS # V4937374)
    335 W Welbourne Avenue #103, Winter Park, FL
    335 W Welbourne Avenue #103
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,734 Home (sqft)
    • 3 Baths
    • 0 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 11/23/24 2:13 AM PST.

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