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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 under $400k 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.


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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 667 Montego Bay Court #S, Winter Park, FL 32792 (MLS # O6257948)
    $235,000
    Photo of 667 Montego Bay Court #S, Winter Park, FL 32792 (MLS # O6257948)
    Photo of 667 Montego Bay Court #S, Winter Park, FL 32792 (MLS # O6257948)
    21
     
    667 Montego Bay Court #S, Winter Park, FL
    667 Montego Bay Court #S
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,120 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  3. Photo of 3390 Cedar Spring Place #163, Winter Park, FL 32792 (MLS # O6257246)
    $225,000
    Photo of 3390 Cedar Spring Place #163, Winter Park, FL 32792 (MLS # O6257246)
    Photo of 3390 Cedar Spring Place #163, Winter Park, FL 32792 (MLS # O6257246)
    3390 Cedar Spring Place #163, Winter Park, FL
    3390 Cedar Spring Place #163
    Winter Park, FL
    • 2 Beds
    • 3 Baths
    • 1,031 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  4. 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)
  5. Photo of 173 Scottsdale Square #173, Winter Park, FL 32792 (MLS # S5115907)
    $125,000
    Photo of 173 Scottsdale Square #173, Winter Park, FL 32792 (MLS # S5115907)
    Photo of 173 Scottsdale Square #173, Winter Park, FL 32792 (MLS # S5115907)
    173 Scottsdale Square #173, Winter Park, FL
    173 Scottsdale Square #173
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 785 Home (sqft)
    • 1 Bath
    • 8,712 Lot (sqft)
  6. 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)
  7. Photo of 1000 S Semoran Boulevard #606, Winter Park, FL 32792 (MLS # O6258290)
    $214,900
    Photo of 1000 S Semoran Boulevard #606, Winter Park, FL 32792 (MLS # O6258290)
    Photo of 1000 S Semoran Boulevard #606, Winter Park, FL 32792 (MLS # O6258290)
    1000 S Semoran Boulevard #606, Winter Park, FL
    1000 S Semoran Boulevard #606
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,049 Home (sqft)
    • 2 Baths
    • 6.04 Lot (ac)
  8. 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)
  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 690 Osceola Avenue #610, Winter Park, FL 32789 (MLS # O6257677)
    $499,000
    Photo of 690 Osceola Avenue #610, Winter Park, FL 32789 (MLS # O6257677)
    Photo of 690 Osceola Avenue #610, Winter Park, FL 32789 (MLS # O6257677)
    690 Osceola Avenue #610, Winter Park, FL
    690 Osceola Avenue #610
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,328 Home (sqft)
    • 2 Baths
    • 1.56 Lot (ac)
  11. 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)
  12. 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)
  13. Photo of 924 Beard Avenue, Winter Park, FL 32789 (MLS # O6257350)
    $399,900
    Photo of 924 Beard Avenue, Winter Park, FL 32789 (MLS # O6257350)
    Photo of 924 Beard Avenue, Winter Park, FL 32789 (MLS # O6257350)
    924 Beard Avenue, Winter Park, FL
    924 Beard Avenue
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,518 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  14. 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)
  15. Photo of 4786 Tangerine Avenue #4786, Winter Park, FL 32792 (MLS # O6257765)
    $249,900
    Photo of 4786 Tangerine Avenue #4786, Winter Park, FL 32792 (MLS # O6257765)
    Photo of 4786 Tangerine Avenue #4786, Winter Park, FL 32792 (MLS # O6257765)
    4786 Tangerine Avenue #4786, Winter Park, FL
    4786 Tangerine Avenue #4786
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,281 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
  16. 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)
  17. 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)
  18. 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)
  19. 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)
  20. Photo of 1248 Park Green Place, Winter Park, FL 32789 (MLS # S5115699)
    $473,700
    Photo of 1248 Park Green Place, Winter Park, FL 32789 (MLS # S5115699)
    Photo of 1248 Park Green Place, Winter Park, FL 32789 (MLS # S5115699)
    1248 Park Green Place, Winter Park, FL
    1248 Park Green Place
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,820 Home (sqft)
    • 2 Baths
    • 2,614 Lot (sqft)
  21. Photo of 851 Miles Avenue #15, Winter Park, FL 32789 (MLS # O6257241)
    $245,000
    Photo of 851 Miles Avenue #15, Winter Park, FL 32789 (MLS # O6257241)
    Photo of 851 Miles Avenue #15, Winter Park, FL 32789 (MLS # O6257241)
    851 Miles Avenue #15, Winter Park, FL
    851 Miles Avenue #15
    Winter Park, FL
    • 2 Beds
    • 1 Bath
    • 808 Home (sqft)
    • 1 Bath
    • 1.05 Lot (ac)
  22. 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)
  23. Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    $400,000
    Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    1757 Chilean Lane, Winter Park, FL
    1757 Chilean Lane
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,413 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  24. Photo of 3651 N Goldenrod Road #208E, Winter Park, FL 32792 (MLS # O6256664)
    $195,000
    Photo of 3651 N Goldenrod Road #208E, Winter Park, FL 32792 (MLS # O6256664)
    Photo of 3651 N Goldenrod Road #208E, Winter Park, FL 32792 (MLS # O6256664)
    3651 N Goldenrod Road #208E, Winter Park, FL
    3651 N Goldenrod Road #208E
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 840 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  25. Photo of 2341 Devon Court, Winter Park, FL 32789 (MLS # O6257142)
    $499,000
    Photo of 2341 Devon Court, Winter Park, FL 32789 (MLS # O6257142)
    Photo of 2341 Devon Court, Winter Park, FL 32789 (MLS # O6257142)
    2341 Devon Court, Winter Park, FL
    2341 Devon Court
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,773 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
  26. Photo of 3053 George Mason Avenue #8, Winter Park, FL 32792 (MLS # O6256375)
    $164,900
    Photo of 3053 George Mason Avenue #8, Winter Park, FL 32792 (MLS # O6256375)
    Photo of 3053 George Mason Avenue #8, Winter Park, FL 32792 (MLS # O6256375)
    21
     
    3053 George Mason Avenue #8, Winter Park, FL
    3053 George Mason Avenue #8
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,030 Home (sqft)
    • 2 Baths
    • 10.07 Lot (ac)
  27. Photo of 2494 Timberline Drive #2494, Winter Park, FL 32792 (MLS # O6251296)
    $250,000
    Photo of 2494 Timberline Drive #2494, Winter Park, FL 32792 (MLS # O6251296)
    Photo of 2494 Timberline Drive #2494, Winter Park, FL 32792 (MLS # O6251296)
    2494 Timberline Drive #2494, Winter Park, FL
    2494 Timberline Drive #2494
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,316 Home (sqft)
    • 2 Baths
    • 2,614 Lot (sqft)
  28. Photo of 3092 Nicholson Drive, Winter Park, FL 32792 (MLS # O6255970)
    $439,000
    Photo of 3092 Nicholson Drive, Winter Park, FL 32792 (MLS # O6255970)
    Photo of 3092 Nicholson Drive, Winter Park, FL 32792 (MLS # O6255970)
    3092 Nicholson Drive, Winter Park, FL
    3092 Nicholson Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,738 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  29. Photo of 535 N Interlachen Avenue #304, Winter Park, FL 32789 (MLS # O6256275)
    $395,000
    Photo of 535 N Interlachen Avenue #304, Winter Park, FL 32789 (MLS # O6256275)
    Photo of 535 N Interlachen Avenue #304, Winter Park, FL 32789 (MLS # O6256275)
    19
     
    535 N Interlachen Avenue #304, Winter Park, FL
    535 N Interlachen Avenue #304
    Winter Park, FL
    • 1 Bed
    • 2 Baths
    • 726 Home (sqft)
    • 2 Baths
    • 26,572 Lot (sqft)
  30. Photo of 1712 Bomi Circle, Winter Park, FL 32792 (MLS # O6256132)
    $598,000
    Photo of 1712 Bomi Circle, Winter Park, FL 32792 (MLS # O6256132)
    Photo of 1712 Bomi Circle, Winter Park, FL 32792 (MLS # O6256132)
    1712 Bomi Circle, Winter Park, FL
    1712 Bomi Circle
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 2,012 Home (sqft)
    • 2 Baths
    • 20,909 Lot (sqft)
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