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Winter Springs is located in Seminole County, offering its residents a sparse suburban feel. From arts festivals to movie nights, the long list of community events organized by Winter Springs is just one reason why many residents reside in this city. Use our custom search tool to view all homes for sale under $400k in Winter Springs 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 639 Marni Drive, Winter Springs, FL 32708 (MLS # O6260846)
    $389,900
    Photo of 639 Marni Drive, Winter Springs, FL 32708 (MLS # O6260846)
    Photo of 639 Marni Drive, Winter Springs, FL 32708 (MLS # O6260846)
    639 Marni Drive, Winter Springs, FL
    639 Marni Drive
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,408 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  2. Photo of 4522 Brook Hollow Circle, Winter Springs, FL 32708 (MLS # O6257707)
    $280,000
    Photo of 4522 Brook Hollow Circle, Winter Springs, FL 32708 (MLS # O6257707)
    Photo of 4522 Brook Hollow Circle, Winter Springs, FL 32708 (MLS # O6257707)
    4522 Brook Hollow Circle, Winter Springs, FL
    4522 Brook Hollow Circle
    Winter Springs, FL
    • 2 Beds
    • 2 Baths
    • 1,108 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  3. Photo of 3932 White Birch Run, Winter Springs, FL 32708 (MLS # O6259829)
    $375,000
    Photo of 3932 White Birch Run, Winter Springs, FL 32708 (MLS # O6259829)
    Photo of 3932 White Birch Run, Winter Springs, FL 32708 (MLS # O6259829)
    3932 White Birch Run, Winter Springs, FL
    3932 White Birch Run
    Winter Springs, FL
    • 4 Beds
    • 3 Baths
    • 1,960 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  4. Photo of 469 Cruz Bay Circle, Winter Springs, FL 32708 (MLS # O6257489)
    $399,500
    Photo of 469 Cruz Bay Circle, Winter Springs, FL 32708 (MLS # O6257489)
    Photo of 469 Cruz Bay Circle, Winter Springs, FL 32708 (MLS # O6257489)
    469 Cruz Bay Circle, Winter Springs, FL
    469 Cruz Bay Circle
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,914 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  5. Photo of 411 Sheoah Boulevard #37, Winter Springs, FL 32708 (MLS # S5116031)
    $210,000
    Photo of 411 Sheoah Boulevard #37, Winter Springs, FL 32708 (MLS # S5116031)
    Photo of 411 Sheoah Boulevard #37, Winter Springs, FL 32708 (MLS # S5116031)
    411 Sheoah Boulevard #37, Winter Springs, FL
    411 Sheoah Boulevard #37
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,400 Home (sqft)
    • 3 Baths
    • 436 Lot (sqft)
  6. Photo of 207 Bennett Street, Winter Springs, FL 32708 (MLS # O6258438)
    $345,000
    Photo of 207 Bennett Street, Winter Springs, FL 32708 (MLS # O6258438)
    Photo of 207 Bennett Street, Winter Springs, FL 32708 (MLS # O6258438)
    207 Bennett Street, Winter Springs, FL
    207 Bennett Street
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,120 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  7. Photo of 1501 Fox Glen Drive, Winter Springs, FL 32708 (MLS # O6256955)
    $399,900
    Photo of 1501 Fox Glen Drive, Winter Springs, FL 32708 (MLS # O6256955)
    Photo of 1501 Fox Glen Drive, Winter Springs, FL 32708 (MLS # O6256955)
    1501 Fox Glen Drive, Winter Springs, FL
    1501 Fox Glen Drive
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,476 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  8. Photo of 450 Tradition Lane, Winter Springs, FL 32708 (MLS # V4939293)
    $355,000
    Photo of 450 Tradition Lane, Winter Springs, FL 32708 (MLS # V4939293)
    Photo of 450 Tradition Lane, Winter Springs, FL 32708 (MLS # V4939293)
    450 Tradition Lane, Winter Springs, FL
    450 Tradition Lane
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,468 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  9. Photo of 707 Sunbury Drive, Winter Springs, FL 32708 (MLS # O6257994)
    $360,000
    Photo of 707 Sunbury Drive, Winter Springs, FL 32708 (MLS # O6257994)
    Photo of 707 Sunbury Drive, Winter Springs, FL 32708 (MLS # O6257994)
    707 Sunbury Drive, Winter Springs, FL
    707 Sunbury Drive
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,328 Home (sqft)
    • 2 Baths
    • 14,811 Lot (sqft)
  10. Photo of 608 Alton Road, Winter Springs, FL 32708 (MLS # O6256065)
    $400,000
    Photo of 608 Alton Road, Winter Springs, FL 32708 (MLS # O6256065)
    Photo of 608 Alton Road, Winter Springs, FL 32708 (MLS # O6256065)
    608 Alton Road, Winter Springs, FL
    608 Alton Road
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,304 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  11. Photo of 426 Horizon Drive, Winter Springs, FL 32708 (MLS # O6256123)
    $299,900
    Photo of 426 Horizon Drive, Winter Springs, FL 32708 (MLS # O6256123)
    Photo of 426 Horizon Drive, Winter Springs, FL 32708 (MLS # O6256123)
    426 Horizon Drive, Winter Springs, FL
    426 Horizon Drive
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,069 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  12. Photo of 240 Moree Loop #2, Winter Springs, FL 32708 (MLS # O6255555)
    $215,000
    Photo of 240 Moree Loop #2, Winter Springs, FL 32708 (MLS # O6255555)
    Photo of 240 Moree Loop #2, Winter Springs, FL 32708 (MLS # O6255555)
    240 Moree Loop #2, Winter Springs, FL
    240 Moree Loop #2
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,187 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  13. Photo of 4249 E Weeping Willow Circle, Winter Springs, FL 32708 (MLS # O6252806)
    $314,900
    Photo of 4249 E Weeping Willow Circle, Winter Springs, FL 32708 (MLS # O6252806)
    Photo of 4249 E Weeping Willow Circle, Winter Springs, FL 32708 (MLS # O6252806)
    4249 E Weeping Willow Circle, Winter Springs, FL
    4249 E Weeping Willow Circle
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,348 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  14. Photo of 504 San Gabriel Court, Winter Springs, FL 32708 (MLS # G5088562)
    $295,000
    Photo of 504 San Gabriel Court, Winter Springs, FL 32708 (MLS # G5088562)
    Photo of 504 San Gabriel Court, Winter Springs, FL 32708 (MLS # G5088562)
    504 San Gabriel Court, Winter Springs, FL
    504 San Gabriel Court
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,105 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  15. Photo of 535 Crimson Lane, Winter Springs, FL 32708 (MLS # O6251030)
    $400,000
    Photo of 535 Crimson Lane, Winter Springs, FL 32708 (MLS # O6251030)
    Photo of 535 Crimson Lane, Winter Springs, FL 32708 (MLS # O6251030)
    535 Crimson Lane, Winter Springs, FL
    535 Crimson Lane
    Winter Springs, FL
    • 3 Beds
    • 4 Baths
    • 1,872 Home (sqft)
    • 4 Baths
    • 1,743 Lot (sqft)
  16. Photo of 50 Sheoah Boulevard #34, Winter Springs, FL 32708 (MLS # O6250683)
    $164,000
    Photo of 50 Sheoah Boulevard #34, Winter Springs, FL 32708 (MLS # O6250683)
    Photo of 50 Sheoah Boulevard #34, Winter Springs, FL 32708 (MLS # O6250683)
    50 Sheoah Boulevard #34, Winter Springs, FL
    50 Sheoah Boulevard #34
    Winter Springs, FL
    • 2 Beds
    • 2 Baths
    • 972 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  17. Photo of 429 Sheoah Boulevard #2, Winter Springs, FL 32708 (MLS # O6254313)
    $224,500
    Photo of 429 Sheoah Boulevard #2, Winter Springs, FL 32708 (MLS # O6254313)
    Photo of 429 Sheoah Boulevard #2, Winter Springs, FL 32708 (MLS # O6254313)
    429 Sheoah Boulevard #2, Winter Springs, FL
    429 Sheoah Boulevard #2
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,187 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  18. Photo of 1349 Mill Stream Lane, Winter Springs, FL 32708 (MLS # O6249447)
    $385,000
    Photo of 1349 Mill Stream Lane, Winter Springs, FL 32708 (MLS # O6249447)
    Photo of 1349 Mill Stream Lane, Winter Springs, FL 32708 (MLS # O6249447)
    1349 Mill Stream Lane, Winter Springs, FL
    1349 Mill Stream Lane
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,435 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
  19. Photo of 411 Boxwood Circle, Winter Springs, FL 32708 (MLS # O6247758)
    $355,900
    Photo of 411 Boxwood Circle, Winter Springs, FL 32708 (MLS # O6247758)
    Photo of 411 Boxwood Circle, Winter Springs, FL 32708 (MLS # O6247758)
    411 Boxwood Circle, Winter Springs, FL
    411 Boxwood Circle
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,280 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  20. Photo of 279 Mcleods Way, Winter Springs, FL 32708 (MLS # O6246448)
    $379,900
    Photo of 279 Mcleods Way, Winter Springs, FL 32708 (MLS # O6246448)
    Photo of 279 Mcleods Way, Winter Springs, FL 32708 (MLS # O6246448)
    279 Mcleods Way, Winter Springs, FL
    279 Mcleods Way
    Winter Springs, FL
    • 4 Beds
    • 4 Baths
    • 1,732 Home (sqft)
    • 4 Baths
    • 872 Lot (sqft)
  21. Photo of 576 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6245444)
    $280,000
    Photo of 576 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6245444)
    Photo of 576 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6245444)
    576 Shadow Glenn Place, Winter Springs, FL
    576 Shadow Glenn Place
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,343 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  22. Photo of 736 Summerland Drive, Winter Springs, FL 32708 (MLS # S5112990)
    $259,900
    Photo of 736 Summerland Drive, Winter Springs, FL 32708 (MLS # S5112990)
    Photo of 736 Summerland Drive, Winter Springs, FL 32708 (MLS # S5112990)
    736 Summerland Drive, Winter Springs, FL
    736 Summerland Drive
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,298 Home (sqft)
    • 2 Baths
    • 2,178 Lot (sqft)
  23. Photo of 600 Northern Way #806, Winter Springs, FL 32708 (MLS # O6243168)
    $305,000
    Photo of 600 Northern Way #806, Winter Springs, FL 32708 (MLS # O6243168)
    Photo of 600 Northern Way #806, Winter Springs, FL 32708 (MLS # O6243168)
    600 Northern Way #806, Winter Springs, FL
    600 Northern Way #806
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,447 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  24. Photo of 409 Horizon Drive, Winter Springs, FL 32708 (MLS # O6238660)
    $285,000
    Photo of 409 Horizon Drive, Winter Springs, FL 32708 (MLS # O6238660)
    Photo of 409 Horizon Drive, Winter Springs, FL 32708 (MLS # O6238660)
    24
     
    409 Horizon Drive, Winter Springs, FL
    409 Horizon Drive
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,069 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  25. Photo of 452 Harbor Winds Court, Winter Springs, FL 32708 (MLS # O6243166)
    $389,000
    Photo of 452 Harbor Winds Court, Winter Springs, FL 32708 (MLS # O6243166)
    Photo of 452 Harbor Winds Court, Winter Springs, FL 32708 (MLS # O6243166)
    452 Harbor Winds Court, Winter Springs, FL
    452 Harbor Winds Court
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,914 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  26. Photo of 30 S Devon Avenue, Winter Springs, FL 32708 (MLS # O6242346)
    $259,000
    Photo of 30 S Devon Avenue, Winter Springs, FL 32708 (MLS # O6242346)
    Photo of 30 S Devon Avenue, Winter Springs, FL 32708 (MLS # O6242346)
    30 S Devon Avenue, Winter Springs, FL
    30 S Devon Avenue
    Winter Springs, FL
    • 3 Beds
    • 1 Bath
    • 1,272 Home (sqft)
    • 1 Bath
    • 7,841 Lot (sqft)
  27. Photo of 31 S Edgemon Avenue, Winter Springs, FL 32708 (MLS # O6241179)
    $386,000
    Photo of 31 S Edgemon Avenue, Winter Springs, FL 32708 (MLS # O6241179)
    Photo of 31 S Edgemon Avenue, Winter Springs, FL 32708 (MLS # O6241179)
    31 S Edgemon Avenue, Winter Springs, FL
    31 S Edgemon Avenue
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,270 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  28. Photo of 201 N Cortez Avenue, Winter Springs, FL 32708 (MLS # TB8300710)
    $345,999
    Photo of 201 N Cortez Avenue, Winter Springs, FL 32708 (MLS # TB8300710)
    Photo of 201 N Cortez Avenue, Winter Springs, FL 32708 (MLS # TB8300710)
    201 N Cortez Avenue, Winter Springs, FL
    201 N Cortez Avenue
    Winter Springs, FL
    • 4 Beds
    • 2 Baths
    • 1,730 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  29. Photo of 548 Pinebranch Circle, Winter Springs, FL 32708 (MLS # O6239820)
    $332,500
    Photo of 548 Pinebranch Circle, Winter Springs, FL 32708 (MLS # O6239820)
    Photo of 548 Pinebranch Circle, Winter Springs, FL 32708 (MLS # O6239820)
    548 Pinebranch Circle, Winter Springs, FL
    548 Pinebranch Circle
    Winter Springs, FL
    • 2 Beds
    • 3 Baths
    • 1,516 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
  30. Photo of 1395 San Luis Court, Winter Springs, FL 32708 (MLS # O6240914)
    $362,900
    Photo of 1395 San Luis Court, Winter Springs, FL 32708 (MLS # O6240914)
    Photo of 1395 San Luis Court, Winter Springs, FL 32708 (MLS # O6240914)
    1395 San Luis Court, Winter Springs, FL
    1395 San Luis Court
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,293 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
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