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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 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 1400 Place Picardy, Winter Park, FL 32789 (MLS # O6265769)
    $2,995,000
    Photo of 1400 Place Picardy, Winter Park, FL 32789 (MLS # O6265769)
    Photo of 1400 Place Picardy, Winter Park, FL 32789 (MLS # O6265769)
    1400 Place Picardy, Winter Park, FL
    1400 Place Picardy
    Winter Park, FL
    • 5 Beds
    • 6 Baths
    • 4,411 Home (sqft)
    • 6 Baths
    • 14,375 Lot (sqft)
  2. Photo of 1417 Miller Avenue, Winter Park, FL 32789 (MLS # O6271186)
    $1,599,900
    Photo of 1417 Miller Avenue, Winter Park, FL 32789 (MLS # O6271186)
    Photo of 1417 Miller Avenue, Winter Park, FL 32789 (MLS # O6271186)
    1417 Miller Avenue, Winter Park, FL
    1417 Miller Avenue
    Winter Park, FL
    • 5 Beds
    • 4 Baths
    • 3,312 Home (sqft)
    • 4 Baths
    • 9,584 Lot (sqft)
  3. Photo of 350 Carolina Avenue #301, Winter Park, FL 32789 (MLS # O6273285)
    $725,000
    Photo of 350 Carolina Avenue #301, Winter Park, FL 32789 (MLS # O6273285)
    Photo of 350 Carolina Avenue #301, Winter Park, FL 32789 (MLS # O6273285)
    350 Carolina Avenue #301, Winter Park, FL
    350 Carolina Avenue #301
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,544 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
  4. Photo of 2100 Suffield Drive, Winter Park, FL 32792 (MLS # O6271064)
    $649,000
    Photo of 2100 Suffield Drive, Winter Park, FL 32792 (MLS # O6271064)
    Photo of 2100 Suffield Drive, Winter Park, FL 32792 (MLS # O6271064)
    2100 Suffield Drive, Winter Park, FL
    2100 Suffield Drive
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,807 Home (sqft)
    • 3 Baths
    • 18,296 Lot (sqft)
  5. Photo of 702 Via Bella, Winter Park, FL 32789 (MLS # O6273466)
    $4,500,000
    Photo of 702 Via Bella, Winter Park, FL 32789 (MLS # O6273466)
    Photo of 702 Via Bella, Winter Park, FL 32789 (MLS # O6273466)
    702 Via Bella, Winter Park, FL
    702 Via Bella
    Winter Park, FL
    • 5 Beds
    • 6 Baths
    • 3,720 Home (sqft)
    • 6 Baths
    • 10,019 Lot (sqft)
  6. Photo of 744 London Road, Winter Park, FL 32792 (MLS # O6269464)
    $849,000
    Photo of 744 London Road, Winter Park, FL 32792 (MLS # O6269464)
    Photo of 744 London Road, Winter Park, FL 32792 (MLS # O6269464)
    744 London Road, Winter Park, FL
    744 London Road
    Winter Park, FL
    • 5 Beds
    • 3 Baths
    • 2,804 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  7. Photo of 1120 Preserve Point Drive, Winter Park, FL 32789 (MLS # O6269585)
    $11,900,000
    Photo of 1120 Preserve Point Drive, Winter Park, FL 32789 (MLS # O6269585)
    Photo of 1120 Preserve Point Drive, Winter Park, FL 32789 (MLS # O6269585)
    1120 Preserve Point Drive, Winter Park, FL
    1120 Preserve Point Drive
    Winter Park, FL
    • 7 Beds
    • 11 Baths
    • 11,255 Home (sqft)
    • 11 Baths
    • 1.63 Lot (ac)
  8. Photo of 541 Virginia Drive, Winter Park, FL 32789 (MLS # O6268853)
    $6,250,000
    Photo of 541 Virginia Drive, Winter Park, FL 32789 (MLS # O6268853)
    Photo of 541 Virginia Drive, Winter Park, FL 32789 (MLS # O6268853)
    541 Virginia Drive, Winter Park, FL
    541 Virginia Drive
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 4,725 Home (sqft)
    • 4 Baths
    • 22,216 Lot (sqft)
  9. Photo of 1860 Linden Road, Winter Park, FL 32792 (MLS # O6267381)
    $699,495
    Photo of 1860 Linden Road, Winter Park, FL 32792 (MLS # O6267381)
    Photo of 1860 Linden Road, Winter Park, FL 32792 (MLS # O6267381)
    1860 Linden Road, Winter Park, FL
    1860 Linden Road
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,820 Home (sqft)
    • 2 Baths
    • 19,167 Lot (sqft)
  10. Photo of 1032 Early Avenue, Winter Park, FL 32789 (MLS # NS1083137)
    $2,300,000
    Photo of 1032 Early Avenue, Winter Park, FL 32789 (MLS # NS1083137)
    Photo of 1032 Early Avenue, Winter Park, FL 32789 (MLS # NS1083137)
    1032 Early Avenue, Winter Park, FL
    1032 Early Avenue
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,894 Home (sqft)
    • 3 Baths
    • 5.15 Lot (ac)
  11. Photo of 1970 Laurel Road, Winter Park, FL 32789 (MLS # O6265919)
    $1,999,999
    Photo of 1970 Laurel Road, Winter Park, FL 32789 (MLS # O6265919)
    Photo of 1970 Laurel Road, Winter Park, FL 32789 (MLS # O6265919)
    1970 Laurel Road, Winter Park, FL
    1970 Laurel Road
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,440 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  12. Photo of 2161 Sharon Road, Winter Park, FL 32789 (MLS # O6263091)
    $4,985,000
    Photo of 2161 Sharon Road, Winter Park, FL 32789 (MLS # O6263091)
    Photo of 2161 Sharon Road, Winter Park, FL 32789 (MLS # O6263091)
    90
     
    2161 Sharon Road, Winter Park, FL
    2161 Sharon Road
    Winter Park, FL
    • 5 Beds
    • 7 Baths
    • 6,338 Home (sqft)
    • 7 Baths
    • 25,265 Lot (sqft)
  13. Photo of 708 Balmoral Road, Winter Park, FL 32789 (MLS # O6262593)
    $1,150,000
    Photo of 708 Balmoral Road, Winter Park, FL 32789 (MLS # O6262593)
    Photo of 708 Balmoral Road, Winter Park, FL 32789 (MLS # O6262593)
    708 Balmoral Road, Winter Park, FL
    708 Balmoral Road
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,786 Home (sqft)
    • 3 Baths
    • 15,246 Lot (sqft)
  14. Photo of 2661 Via Tuscany, Winter Park, FL 32789 (MLS # O6260493)
    $10,999,999
    Photo of 2661 Via Tuscany, Winter Park, FL 32789 (MLS # O6260493)
    Photo of 2661 Via Tuscany, Winter Park, FL 32789 (MLS # O6260493)
    2661 Via Tuscany, Winter Park, FL
    2661 Via Tuscany
    Winter Park, FL
    • 4 Beds
    • 5 Baths
    • 4,564 Home (sqft)
    • 5 Baths
    • 15,682 Lot (sqft)
  15. 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)
  16. Photo of 1781 Goodrich Avenue, Winter Park, FL 32789 (MLS # O6257832)
    $1,800,000
    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)
  17. 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)
  18. 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)
  19. Photo of 2518 Sweetwater Trail, Winter Park, FL 32789 (MLS # O6255305)
    $639,900
    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)
  20. Photo of 1010 N Pennsylvania Avenue, Winter Park, FL 32789 (MLS # O6254839)
    $2,650,000
    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)
  21. 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)
  22. 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)
  23. 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)
  24. Photo of 3136 Heartleaf Place, Winter Park, FL 32792 (MLS # O6253346)
    $730,000
    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)
  25. 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)
  26. 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)
  27. Photo of 840 W Comstock Avenue, Winter Park, FL 32789 (MLS # O6238899)
    $1,470,000
    Photo of 840 W Comstock Avenue, Winter Park, FL 32789 (MLS # O6238899)
    Photo of 840 W Comstock Avenue, Winter Park, FL 32789 (MLS # O6238899)
    840 W Comstock Avenue, Winter Park, FL
    840 W Comstock Avenue
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,350 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  28. 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)
  29. Photo of 274 N Ranger Boulevard, Winter Park, FL 32792 (MLS # O6222908)
    $615,000
    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)
  30. 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)
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