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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 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)
  2. Photo of 678 Depugh Street, Winter Park, FL 32789 (MLS # O6247628)
    $700,000
    Photo of 678 Depugh Street, Winter Park, FL 32789 (MLS # O6247628)
    Photo of 678 Depugh Street, Winter Park, FL 32789 (MLS # O6247628)
    678 Depugh Street, Winter Park, FL
    678 Depugh Street
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 1,940 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  3. Photo of 5418 S Bracken Court, Winter Park, FL 32792 (MLS # O6251052)
    $399,900
    Photo of 5418 S Bracken Court, Winter Park, FL 32792 (MLS # O6251052)
    Photo of 5418 S Bracken Court, Winter Park, FL 32792 (MLS # O6251052)
    30
     
    5418 S Bracken Court, Winter Park, FL
    5418 S Bracken Court
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,301 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  4. Photo of 3906 Cool Water Court, Winter Park, FL 32792 (MLS # O6249859)
    $695,000
    Photo of 3906 Cool Water Court, Winter Park, FL 32792 (MLS # O6249859)
    Photo of 3906 Cool Water Court, Winter Park, FL 32792 (MLS # O6249859)
    3906 Cool Water Court, Winter Park, FL
    3906 Cool Water Court
    Winter Park, FL
    • 5 Beds
    • 4 Baths
    • 2,990 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  5. Photo of 2040 Venetian Way, Winter Park, FL 32789 (MLS # O6249727)
    $9,995,000
    Photo of 2040 Venetian Way, Winter Park, FL 32789 (MLS # O6249727)
    Photo of 2040 Venetian Way, Winter Park, FL 32789 (MLS # O6249727)
    2040 Venetian Way, Winter Park, FL
    2040 Venetian Way
    Winter Park, FL
    • 6 Beds
    • 8 Baths
    • 8,082 Home (sqft)
    • 8 Baths
    • 1.84 Lot (ac)
  6. Photo of 210 Scottsdale Square #210, Winter Park, FL 32792 (MLS # O6249283)
    $149,900
    Photo of 210 Scottsdale Square #210, Winter Park, FL 32792 (MLS # O6249283)
    Photo of 210 Scottsdale Square #210, Winter Park, FL 32792 (MLS # O6249283)
    210 Scottsdale Square #210, Winter Park, FL
    210 Scottsdale Square #210
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,085 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  7. Photo of 2309 Sun Valley Circle, Winter Park, FL 32792 (MLS # O6247851)
    $260,000
    Photo of 2309 Sun Valley Circle, Winter Park, FL 32792 (MLS # O6247851)
    Photo of 2309 Sun Valley Circle, Winter Park, FL 32792 (MLS # O6247851)
    21
     
    2309 Sun Valley Circle, Winter Park, FL
    2309 Sun Valley Circle
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,612 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  8. Photo of 100 S Virginia Avenue #201, Winter Park, FL 32789 (MLS # O6249016)
    $1,175,000
    Photo of 100 S Virginia Avenue #201, Winter Park, FL 32789 (MLS # O6249016)
    Photo of 100 S Virginia Avenue #201, Winter Park, FL 32789 (MLS # O6249016)
    49
     
    100 S Virginia Avenue #201, Winter Park, FL
    100 S Virginia Avenue #201
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,756 Home (sqft)
    • 3 Baths
    • 21,780 Lot (sqft)
  9. Photo of 1818 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248828)
    $825,000
    Photo of 1818 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248828)
    Photo of 1818 Mondrian Circle, Winter Park, FL 32789 (MLS # O6248828)
    1818 Mondrian Circle, Winter Park, FL
    1818 Mondrian Circle
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 2,265 Home (sqft)
    • 4 Baths
    • 1,743 Lot (sqft)
  10. Photo of 3047 George Mason Avenue #9, Winter Park, FL 32792 (MLS # V4938408)
    $135,000
    Photo of 3047 George Mason Avenue #9, Winter Park, FL 32792 (MLS # V4938408)
    Photo of 3047 George Mason Avenue #9, Winter Park, FL 32792 (MLS # V4938408)
    3047 George Mason Avenue #9, Winter Park, FL
    3047 George Mason Avenue #9
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 664 Home (sqft)
    • 1 Bath
    • 10.07 Lot (ac)
  11. Photo of 764 Baffie Avenue, Winter Park, FL 32789 (MLS # O6251973)
    $364,000
    Photo of 764 Baffie Avenue, Winter Park, FL 32789 (MLS # O6251973)
    Photo of 764 Baffie Avenue, Winter Park, FL 32789 (MLS # O6251973)
    764 Baffie Avenue, Winter Park, FL
    764 Baffie Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,080 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  12. Photo of 213 E Canton Avenue #213, Winter Park, FL 32789 (MLS # O6248526)
    $579,000
    Photo of 213 E Canton Avenue #213, Winter Park, FL 32789 (MLS # O6248526)
    Photo of 213 E Canton Avenue #213, Winter Park, FL 32789 (MLS # O6248526)
    213 E Canton Avenue #213, Winter Park, FL
    213 E Canton Avenue #213
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,040 Home (sqft)
    • 2 Baths
    • 1.09 Lot (ac)
  13. Photo of 200 Saint Andrews Boulevard #1402, Winter Park, FL 32792 (MLS # O6248464)
    $260,000
    Photo of 200 Saint Andrews Boulevard #1402, Winter Park, FL 32792 (MLS # O6248464)
    Photo of 200 Saint Andrews Boulevard #1402, Winter Park, FL 32792 (MLS # O6248464)
    200 Saint Andrews Boulevard #1402, Winter Park, FL
    200 Saint Andrews Boulevard #1402
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,165 Home (sqft)
    • 2 Baths
    • 19.03 Lot (ac)
  14. Photo of 1409 Hyde Park Drive, Winter Park, FL 32792 (MLS # O6247920)
    $477,000
    Photo of 1409 Hyde Park Drive, Winter Park, FL 32792 (MLS # O6247920)
    Photo of 1409 Hyde Park Drive, Winter Park, FL 32792 (MLS # O6247920)
    1409 Hyde Park Drive, Winter Park, FL
    1409 Hyde Park Drive
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,018 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  15. Photo of 200 Saint Andrews Boulevard #3102, Winter Park, FL 32792 (MLS # O6248343)
    $215,000
    Photo of 200 Saint Andrews Boulevard #3102, Winter Park, FL 32792 (MLS # O6248343)
    Photo of 200 Saint Andrews Boulevard #3102, Winter Park, FL 32792 (MLS # O6248343)
    200 Saint Andrews Boulevard #3102, Winter Park, FL
    200 Saint Andrews Boulevard #3102
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,219 Home (sqft)
    • 2 Baths
    • 19.03 Lot (ac)
  16. Photo of 1401 Devon Road, Winter Park, FL 32789 (MLS # O6248164)
    $475,000
    Photo of 1401 Devon Road, Winter Park, FL 32789 (MLS # O6248164)
    Photo of 1401 Devon Road, Winter Park, FL 32789 (MLS # O6248164)
    1401 Devon Road, Winter Park, FL
    1401 Devon Road
    Winter Park, FL
    • 2 Beds
    • 1 Bath
    • 1,012 Home (sqft)
    • 1 Bath
    • 6,970 Lot (sqft)
  17. Photo of 1391 Richmond Road, Winter Park, FL 32789 (MLS # O6246352)
    $3,892,000
    Photo of 1391 Richmond Road, Winter Park, FL 32789 (MLS # O6246352)
    Photo of 1391 Richmond Road, Winter Park, FL 32789 (MLS # O6246352)
    1391 Richmond Road, Winter Park, FL
    1391 Richmond Road
    Winter Park, FL
    • 4 Beds
    • 6 Baths
    • 4,635 Home (sqft)
    • 6 Baths
    • 19,602 Lot (sqft)
  18. Photo of 5231 Ardmore Drive, Winter Park, FL 32792 (MLS # O6246287)
    $425,000
    Photo of 5231 Ardmore Drive, Winter Park, FL 32792 (MLS # O6246287)
    Photo of 5231 Ardmore Drive, Winter Park, FL 32792 (MLS # O6246287)
    5231 Ardmore Drive, Winter Park, FL
    5231 Ardmore Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,645 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  19. Photo of 920 Gloriosa Avenue, Winter Park, FL 32789 (MLS # G5088048)
    $435,000
    Photo of 920 Gloriosa Avenue, Winter Park, FL 32789 (MLS # G5088048)
    Photo of 920 Gloriosa Avenue, Winter Park, FL 32789 (MLS # G5088048)
    920 Gloriosa Avenue, Winter Park, FL
    920 Gloriosa Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,540 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  20. Photo of 1102 Azalea Lane, Winter Park, FL 32789 (MLS # O6247132)
    $499,000
    Photo of 1102 Azalea Lane, Winter Park, FL 32789 (MLS # O6247132)
    Photo of 1102 Azalea Lane, Winter Park, FL 32789 (MLS # O6247132)
    1102 Azalea Lane, Winter Park, FL
    1102 Azalea Lane
    Winter Park, FL
    • 2 Beds
    • 3 Baths
    • 1,530 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  21. Photo of 169 Lewfield Circle #169, Winter Park, FL 32792 (MLS # S5113564)
    $167,000
    Photo of 169 Lewfield Circle #169, Winter Park, FL 32792 (MLS # S5113564)
    Photo of 169 Lewfield Circle #169, Winter Park, FL 32792 (MLS # S5113564)
    169 Lewfield Circle #169, Winter Park, FL
    169 Lewfield Circle #169
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 678 Home (sqft)
    • 1 Bath
    • 872 Lot (sqft)
  22. Photo of 1250 S Denning Drive #205, Winter Park, FL 32789 (MLS # O6246194)
    $250,000
    Photo of 1250 S Denning Drive #205, Winter Park, FL 32789 (MLS # O6246194)
    Photo of 1250 S Denning Drive #205, Winter Park, FL 32789 (MLS # O6246194)
    1250 S Denning Drive #205, Winter Park, FL
    1250 S Denning Drive #205
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 908 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  23. 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)
  24. Photo of 1880 Viburnum Lane, Winter Park, FL 32792 (MLS # O6245383)
    $360,000
    Photo of 1880 Viburnum Lane, Winter Park, FL 32792 (MLS # O6245383)
    Photo of 1880 Viburnum Lane, Winter Park, FL 32792 (MLS # O6245383)
    1880 Viburnum Lane, Winter Park, FL
    1880 Viburnum Lane
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,152 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  25. Photo of 3651 N Goldenrod Road #204, Winter Park, FL 32792 (MLS # O6247155)
    $209,000
    Photo of 3651 N Goldenrod Road #204, Winter Park, FL 32792 (MLS # O6247155)
    Photo of 3651 N Goldenrod Road #204, Winter Park, FL 32792 (MLS # O6247155)
    3651 N Goldenrod Road #204, Winter Park, FL
    3651 N Goldenrod Road #204
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 840 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  26. Photo of 2140 Ridge Drive, Winter Park, FL 32792 (MLS # O6244737)
    $410,000
    Photo of 2140 Ridge Drive, Winter Park, FL 32792 (MLS # O6244737)
    Photo of 2140 Ridge Drive, Winter Park, FL 32792 (MLS # O6244737)
    2140 Ridge Drive, Winter Park, FL
    2140 Ridge Drive
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,554 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  27. Photo of 1981 Japonica Road, Winter Park, FL 32792 (MLS # O6246791)
    $624,900
    Photo of 1981 Japonica Road, Winter Park, FL 32792 (MLS # O6246791)
    Photo of 1981 Japonica Road, Winter Park, FL 32792 (MLS # O6246791)
    1981 Japonica Road, Winter Park, FL
    1981 Japonica Road
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,040 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  28. Photo of 1710 Aster Drive, Winter Park, FL 32792 (MLS # O6246271)
    $504,900
    Photo of 1710 Aster Drive, Winter Park, FL 32792 (MLS # O6246271)
    Photo of 1710 Aster Drive, Winter Park, FL 32792 (MLS # O6246271)
    1710 Aster Drive, Winter Park, FL
    1710 Aster Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,664 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  29. Photo of 1510 Winter Green Boulevard, Winter Park, FL 32792 (MLS # O6247202)
    $311,000
    Photo of 1510 Winter Green Boulevard, Winter Park, FL 32792 (MLS # O6247202)
    Photo of 1510 Winter Green Boulevard, Winter Park, FL 32792 (MLS # O6247202)
    1510 Winter Green Boulevard, Winter Park, FL
    1510 Winter Green Boulevard
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,652 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  30. Photo of 1001 Tuscany Place, Winter Park, FL 32789 (MLS # O6245474)
    $1,168,000
    Photo of 1001 Tuscany Place, Winter Park, FL 32789 (MLS # O6245474)
    Photo of 1001 Tuscany Place, Winter Park, FL 32789 (MLS # O6245474)
    1001 Tuscany Place, Winter Park, FL
    1001 Tuscany Place
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 2,458 Home (sqft)
    • 2 Baths
    • 16,989 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 6:13 AM PST.

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