fbpx

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.


Hide Map
  • List View
  • Grid View
Sorted by
1 - 30 of 301 | Previous Page 1 of 11 Next
  1. Photo of 1211 Via Estrella, Winter Park, FL 32789 (MLS # O6259686)
    $2,800,000
    Photo of 1211 Via Estrella, Winter Park, FL 32789 (MLS # O6259686)
    Photo of 1211 Via Estrella, Winter Park, FL 32789 (MLS # O6259686)
    1211 Via Estrella, Winter Park, FL
    1211 Via Estrella
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,653 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  2. 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)
  3. Photo of 1323 Merrydale Way, Winter Park, FL 32792 (MLS # O6258940)
    $449,000
    Photo of 1323 Merrydale Way, Winter Park, FL 32792 (MLS # O6258940)
    Photo of 1323 Merrydale Way, Winter Park, FL 32792 (MLS # O6258940)
    1323 Merrydale Way, Winter Park, FL
    1323 Merrydale Way
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,964 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  4. Photo of 1000 S Semoran Boulevard #815, Winter Park, FL 32792 (MLS # O6259572)
    $200,000
    Photo of 1000 S Semoran Boulevard #815, Winter Park, FL 32792 (MLS # O6259572)
    Photo of 1000 S Semoran Boulevard #815, Winter Park, FL 32792 (MLS # O6259572)
    1000 S Semoran Boulevard #815, Winter Park, FL
    1000 S Semoran Boulevard #815
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,003 Home (sqft)
    • 2 Baths
    • 6.04 Lot (ac)
  5. Photo of 3304 Ellwood Court, Winter Park, FL 32792 (MLS # O6257150)
    $475,000
    Photo of 3304 Ellwood Court, Winter Park, FL 32792 (MLS # O6257150)
    Photo of 3304 Ellwood Court, Winter Park, FL 32792 (MLS # O6257150)
    3304 Ellwood Court, Winter Park, FL
    3304 Ellwood Court
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,629 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  6. Photo of Winter Park, FL 32789 (MLS # O6259545)
    $769,900
    Photo of Winter Park, FL 32789 (MLS # O6259545)
    Photo of Winter Park, FL 32789 (MLS # O6259545)
    MLS # O6259545, Winter Park, FL
    MLS # O6259545
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 2,139 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  7. Photo of 3076 Crane Strand Drive, Winter Park, FL 32792 (MLS # O6259399)
    $440,000
    Photo of 3076 Crane Strand Drive, Winter Park, FL 32792 (MLS # O6259399)
    Photo of 3076 Crane Strand Drive, Winter Park, FL 32792 (MLS # O6259399)
    3076 Crane Strand Drive, Winter Park, FL
    3076 Crane Strand Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,200 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  8. Photo of 777 Halifax Avenue, Winter Park, FL 32792 (MLS # O6258805)
    $1,450,000
    Photo of 777 Halifax Avenue, Winter Park, FL 32792 (MLS # O6258805)
    Photo of 777 Halifax Avenue, Winter Park, FL 32792 (MLS # O6258805)
    777 Halifax Avenue, Winter Park, FL
    777 Halifax Avenue
    Winter Park, FL
    • 5 Beds
    • 5 Baths
    • 3,161 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  9. Photo of 311 Sandlewood Trail #4, Winter Park, FL 32789 (MLS # O6259730)
    $170,000
    Photo of 311 Sandlewood Trail #4, Winter Park, FL 32789 (MLS # O6259730)
    Photo of 311 Sandlewood Trail #4, Winter Park, FL 32789 (MLS # O6259730)
    311 Sandlewood Trail #4, Winter Park, FL
    311 Sandlewood Trail #4
    Winter Park, FL
    • 2 Beds
    • 3 Baths
    • 980 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
  10. 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)
  11. 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)
  12. 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)
  13. 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)
  14. Photo of 2703 Summerfield Road, Winter Park, FL 32792 (MLS # O6258737)
    $725,000
    Photo of 2703 Summerfield Road, Winter Park, FL 32792 (MLS # O6258737)
    Photo of 2703 Summerfield Road, Winter Park, FL 32792 (MLS # O6258737)
    2703 Summerfield Road, Winter Park, FL
    2703 Summerfield Road
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,746 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  15. 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)
  16. 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)
  17. 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)
  18. 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)
  19. 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)
  20. 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)
  21. 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)
  22. 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)
  23. 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)
  24. 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)
  25. 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)
  26. 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)
  27. 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)
  28. 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)
  29. 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)
  30. 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)
Previous Page 1 of 11 Next
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 4:13 AM PST.

This IDX is (c) Diverse Solutions 2024. Privacy | Terms & Conditions