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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 1804 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248830)
    $719,900
    Photo of 1804 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248830)
    Photo of 1804 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248830)
    1804 Mondrian Circle, Winter Park, FL
    1804 Mondrian Circle
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 2,016 Home (sqft)
    • 4 Baths
    • 1,743 Lot (sqft)
  2. Photo of 700 Melrose Avenue #E-24, Winter Park, FL 32789 (MLS # O6253203)
    $199,900
    Photo of 700 Melrose Avenue #E-24, Winter Park, FL 32789 (MLS # O6253203)
    Photo of 700 Melrose Avenue #E-24, Winter Park, FL 32789 (MLS # O6253203)
    700 Melrose Avenue #E-24, Winter Park, FL
    700 Melrose Avenue #E-24
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 787 Home (sqft)
    • 1 Bath
    • 5,663 Lot (sqft)
  3. Photo of 992 Carnation Drive, Winter Park, FL 32792 (MLS # O6254779)
    $365,000
    Photo of 992 Carnation Drive, Winter Park, FL 32792 (MLS # O6254779)
    Photo of 992 Carnation Drive, Winter Park, FL 32792 (MLS # O6254779)
    992 Carnation Drive, Winter Park, FL
    992 Carnation Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,000 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  4. Photo of 2865 Clever Lane, Winter Park, FL 32792 (MLS # O6252450)
    $454,990
    Photo of 2865 Clever Lane, Winter Park, FL 32792 (MLS # O6252450)
    Photo of 2865 Clever Lane, Winter Park, FL 32792 (MLS # O6252450)
    2865 Clever Lane, Winter Park, FL
    2865 Clever Lane
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,907 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  5. Photo of 870 Carver Street, Winter Park, FL 32789 (MLS # O6250529)
    $995,000
    Photo of 870 Carver Street, Winter Park, FL 32789 (MLS # O6250529)
    Photo of 870 Carver Street, Winter Park, FL 32789 (MLS # O6250529)
    870 Carver Street, Winter Park, FL
    870 Carver Street
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 1,844 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  6. Photo of 1900 W Fawsett Road, Winter Park, FL 32789 (MLS # O6251960)
    $3,575,000
    Photo of 1900 W Fawsett Road, Winter Park, FL 32789 (MLS # O6251960)
    Photo of 1900 W Fawsett Road, Winter Park, FL 32789 (MLS # O6251960)
    1900 W Fawsett Road, Winter Park, FL
    1900 W Fawsett Road
    Winter Park, FL
    • 4 Beds
    • 5 Baths
    • 4,600 Home (sqft)
    • 5 Baths
    • 1.10 Lot (ac)
  7. Photo of 1681 Blue Ridge Road, Winter Park, FL 32789 (MLS # O6251187)
    $1,395,000
    Photo of 1681 Blue Ridge Road, Winter Park, FL 32789 (MLS # O6251187)
    Photo of 1681 Blue Ridge Road, Winter Park, FL 32789 (MLS # O6251187)
    1681 Blue Ridge Road, Winter Park, FL
    1681 Blue Ridge Road
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,762 Home (sqft)
    • 4 Baths
    • 13,504 Lot (sqft)
  8. Photo of 1041 Aragon Avenue, Winter Park, FL 32789 (MLS # TB8314450)
    $499,000
    Photo of 1041 Aragon Avenue, Winter Park, FL 32789 (MLS # TB8314450)
    Photo of 1041 Aragon Avenue, Winter Park, FL 32789 (MLS # TB8314450)
    1041 Aragon Avenue, Winter Park, FL
    1041 Aragon Avenue
    Winter Park, FL
    • 2 Beds
    • 3 Baths
    • 1,660 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  9. Photo of 8077 Pleasant Pine Circle, Winter Park, FL 32792 (MLS # O6252394)
    $699,900
    Photo of 8077 Pleasant Pine Circle, Winter Park, FL 32792 (MLS # O6252394)
    Photo of 8077 Pleasant Pine Circle, Winter Park, FL 32792 (MLS # O6252394)
    8077 Pleasant Pine Circle, Winter Park, FL
    8077 Pleasant Pine Circle
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,215 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  10. Photo of 3483 Seagrape Drive, Winter Park, FL 32792 (MLS # O6249574)
    $405,900
    Photo of 3483 Seagrape Drive, Winter Park, FL 32792 (MLS # O6249574)
    Photo of 3483 Seagrape Drive, Winter Park, FL 32792 (MLS # O6249574)
    3483 Seagrape Drive, Winter Park, FL
    3483 Seagrape Drive
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,235 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  11. Photo of 2891 Naples Drive, Winter Park, FL 32789 (MLS # O6250674)
    $557,000
    Photo of 2891 Naples Drive, Winter Park, FL 32789 (MLS # O6250674)
    Photo of 2891 Naples Drive, Winter Park, FL 32789 (MLS # O6250674)
    2891 Naples Drive, Winter Park, FL
    2891 Naples Drive
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,899 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  12. Photo of 1455 Broad Wing Lane, Winter Park, FL 32792 (MLS # O6251457)
    $487,500
    Photo of 1455 Broad Wing Lane, Winter Park, FL 32792 (MLS # O6251457)
    Photo of 1455 Broad Wing Lane, Winter Park, FL 32792 (MLS # O6251457)
    1455 Broad Wing Lane, Winter Park, FL
    1455 Broad Wing Lane
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,755 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  13. Photo of 3045 Aaron Burr Avenue #10, Winter Park, FL 32792 (MLS # S5114398)
    $139,000
    Photo of 3045 Aaron Burr Avenue #10, Winter Park, FL 32792 (MLS # S5114398)
    Photo of 3045 Aaron Burr Avenue #10, Winter Park, FL 32792 (MLS # S5114398)
    3045 Aaron Burr Avenue #10, Winter Park, FL
    3045 Aaron Burr Avenue #10
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 803 Home (sqft)
    • 1 Bath
    • 10.07 Lot (ac)
  14. Photo of 250 Lewfield Circle, Winter Park, FL 32792 (MLS # O6251967)
    $200,000
    Photo of 250 Lewfield Circle, Winter Park, FL 32792 (MLS # O6251967)
    Photo of 250 Lewfield Circle, Winter Park, FL 32792 (MLS # O6251967)
    250 Lewfield Circle, Winter Park, FL
    250 Lewfield Circle
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 927 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  15. Photo of 2418 Euston Road, Winter Park, FL 32789 (MLS # O6250903)
    $795,000
    Photo of 2418 Euston Road, Winter Park, FL 32789 (MLS # O6250903)
    Photo of 2418 Euston Road, Winter Park, FL 32789 (MLS # O6250903)
    2418 Euston Road, Winter Park, FL
    2418 Euston Road
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,228 Home (sqft)
    • 3 Baths
    • 11,762 Lot (sqft)
  16. Photo of 721 Roughbeard Road, Winter Park, FL 32792 (MLS # O6250720)
    $559,000
    Photo of 721 Roughbeard Road, Winter Park, FL 32792 (MLS # O6250720)
    Photo of 721 Roughbeard Road, Winter Park, FL 32792 (MLS # O6250720)
    721 Roughbeard Road, Winter Park, FL
    721 Roughbeard Road
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,964 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  17. Photo of 2128 Sycamore Drive, Winter Park, FL 32789 (MLS # L4948316)
    $890,000
    Photo of 2128 Sycamore Drive, Winter Park, FL 32789 (MLS # L4948316)
    Photo of 2128 Sycamore Drive, Winter Park, FL 32789 (MLS # L4948316)
    2128 Sycamore Drive, Winter Park, FL
    2128 Sycamore Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,760 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  18. Photo of 151 North Orlando Ave #142, Winter Park, FL 32789 (MLS # O6250765)
    $199,000
    Photo of 151 North Orlando Ave #142, Winter Park, FL 32789 (MLS # O6250765)
    Photo of 151 North Orlando Ave #142, Winter Park, FL 32789 (MLS # O6250765)
    151 North Orlando Ave #142, Winter Park, FL
    151 North Orlando Ave #142
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 582 Home (sqft)
    • 1 Bath
    • 8,712 Lot (sqft)
  19. Photo of 3651 N Goldenrod Road E #102, Winter Park, FL 32792 (MLS # W7869224)
    $199,999
    Photo of 3651 N Goldenrod Road E #102, Winter Park, FL 32792 (MLS # W7869224)
    Photo of 3651 N Goldenrod Road E #102, Winter Park, FL 32792 (MLS # W7869224)
    3651 N Goldenrod Road E #102, Winter Park, FL
    3651 N Goldenrod Road E #102
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 840 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  20. Photo of 1571 Oneco Avenue, Winter Park, FL 32789 (MLS # O6250954)
    $1,190,000
    Photo of 1571 Oneco Avenue, Winter Park, FL 32789 (MLS # O6250954)
    Photo of 1571 Oneco Avenue, Winter Park, FL 32789 (MLS # O6250954)
    1571 Oneco Avenue, Winter Park, FL
    1571 Oneco Avenue
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,510 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  21. Photo of 740 #3 Killarney Bay Ct, Winter Park, FL 32789 (MLS # O6249823)
    $384,400
    Photo of 740 #3 Killarney Bay Ct, Winter Park, FL 32789 (MLS # O6249823)
    Photo of 740 #3 Killarney Bay Ct, Winter Park, FL 32789 (MLS # O6249823)
    740 #3 Killarney Bay Ct, Winter Park, FL
    740 #3 Killarney Bay Ct
    Winter Park, FL
    • 2 Beds
    • 3 Baths
    • 1,536 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  22. 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)
  23. Photo of 2821 Chantilly Avenue, Winter Park, FL 32789 (MLS # O6249965)
    $539,000
    Photo of 2821 Chantilly Avenue, Winter Park, FL 32789 (MLS # O6249965)
    Photo of 2821 Chantilly Avenue, Winter Park, FL 32789 (MLS # O6249965)
    2821 Chantilly Avenue, Winter Park, FL
    2821 Chantilly Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,440 Home (sqft)
    • 2 Baths
    • 32,670 Lot (sqft)
  24. Photo of 648 Callahan Street, Winter Park, FL 32789 (MLS # O6250649)
    $899,000
    Photo of 648 Callahan Street, Winter Park, FL 32789 (MLS # O6250649)
    Photo of 648 Callahan Street, Winter Park, FL 32789 (MLS # O6250649)
    648 Callahan Street, Winter Park, FL
    648 Callahan Street
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,898 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  25. Photo of 2522 Tahoe Circle, Winter Park, FL 32792 (MLS # O6252111)
    $298,000
    Photo of 2522 Tahoe Circle, Winter Park, FL 32792 (MLS # O6252111)
    Photo of 2522 Tahoe Circle, Winter Park, FL 32792 (MLS # O6252111)
    2522 Tahoe Circle, Winter Park, FL
    2522 Tahoe Circle
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,698 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  26. Photo of 1375 Merrydale Way, Winter Park, FL 32792 (MLS # O6250396)
    $469,900
    Photo of 1375 Merrydale Way, Winter Park, FL 32792 (MLS # O6250396)
    Photo of 1375 Merrydale Way, Winter Park, FL 32792 (MLS # O6250396)
    1375 Merrydale Way, Winter Park, FL
    1375 Merrydale Way
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,756 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  27. 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)
  28. Photo of 7476 Swallow Run #34, Winter Park, FL 32792 (MLS # S5114106)
    $245,000
    Photo of 7476 Swallow Run #34, Winter Park, FL 32792 (MLS # S5114106)
    Photo of 7476 Swallow Run #34, Winter Park, FL 32792 (MLS # S5114106)
    7476 Swallow Run #34, Winter Park, FL
    7476 Swallow Run #34
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,365 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  29. Photo of 5080 Seminole Avenue, Winter Park, FL 32792 (MLS # O6249839)
    $345,000
    Photo of 5080 Seminole Avenue, Winter Park, FL 32792 (MLS # O6249839)
    Photo of 5080 Seminole Avenue, Winter Park, FL 32792 (MLS # O6249839)
    5080 Seminole Avenue, Winter Park, FL
    5080 Seminole Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,078 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  30. 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)
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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 4:13 AM PST.

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