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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 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)
  2. Photo of 585 Via Lugano, Winter Park, FL 32789 (MLS # O6265815)
    $2,999,999
    Photo of 585 Via Lugano, Winter Park, FL 32789 (MLS # O6265815)
    Photo of 585 Via Lugano, Winter Park, FL 32789 (MLS # O6265815)
    585 Via Lugano, Winter Park, FL
    585 Via Lugano
    Winter Park, FL
    • 5 Beds
    • 4 Baths
    • 4,390 Home (sqft)
    • 4 Baths
    • 27,443 Lot (sqft)
  3. 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)
  4. 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)
  5. Photo of 26 Stymie Place, Winter Park, FL 32789 (MLS # O6262839)
    $1,379,900
    Photo of 26 Stymie Place, Winter Park, FL 32789 (MLS # O6262839)
    Photo of 26 Stymie Place, Winter Park, FL 32789 (MLS # O6262839)
    26 Stymie Place, Winter Park, FL
    26 Stymie Place
    Winter Park, FL
    • 4 Beds
    • 5 Baths
    • 3,252 Home (sqft)
    • 5 Baths
    • 7,406 Lot (sqft)
  6. Photo of 350 Carolina Avenue #304, Winter Park, FL 32789 (MLS # O6260045)
    $675,000
    Photo of 350 Carolina Avenue #304, Winter Park, FL 32789 (MLS # O6260045)
    Photo of 350 Carolina Avenue #304, Winter Park, FL 32789 (MLS # O6260045)
    27
     
    350 Carolina Avenue #304, Winter Park, FL
    350 Carolina Avenue #304
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,523 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  7. Photo of 1333 Orchid Avenue, Winter Park, FL 32789 (MLS # O6259878)
    $675,000
    Photo of 1333 Orchid Avenue, Winter Park, FL 32789 (MLS # O6259878)
    Photo of 1333 Orchid Avenue, Winter Park, FL 32789 (MLS # O6259878)
    1333 Orchid Avenue, Winter Park, FL
    1333 Orchid Avenue
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 1,631 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  8. Photo of 1885 Temple Drive, Winter Park, FL 32789 (MLS # O6258468)
    $1,190,000
    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)
  9. 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)
  10. 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)
  11. Photo of 1341 College Point, Winter Park, FL 32789 (MLS # O6257650)
    $4,100,000
    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)
  12. 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)
  13. 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)
  14. 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)
  15. 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)
  16. 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)
  17. 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)
  18. 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)
  19. 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)
  20. 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)
  21. 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)
  22. 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)
  23. 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)
  24. 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)
  25. Photo of 274 N Ranger Boulevard, Winter Park, FL 32792 (MLS # O6222908)
    $627,000
    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)
  26. 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)
  27. 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)
  28. 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
    • 4 Beds
    • 3 Baths
    • 2,441 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  29. Photo of 1618 Holts Grove Circle, Winter Park, FL 32789 (MLS # O6220012)
    $3,225,000
    Photo of 1618 Holts Grove Circle, Winter Park, FL 32789 (MLS # O6220012)
    Photo of 1618 Holts Grove Circle, Winter Park, FL 32789 (MLS # O6220012)
    1618 Holts Grove Circle, Winter Park, FL
    1618 Holts Grove Circle
    Winter Park, FL
    • 5 Beds
    • 8 Baths
    • 4,807 Home (sqft)
    • 8 Baths
    • 15,246 Lot (sqft)
  30. Photo of 2234 Via Luna, Winter Park, FL 32789 (MLS # O6217019)
    $2,190,000
    Photo of 2234 Via Luna, Winter Park, FL 32789 (MLS # O6217019)
    Photo of 2234 Via Luna, Winter Park, FL 32789 (MLS # O6217019)
    2234 Via Luna, Winter Park, FL
    2234 Via Luna
    Winter Park, FL
    • 6 Beds
    • 4 Baths
    • 3,554 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
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