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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 505 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6265467)
    $275,000
    Photo of 505 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6265467)
    Photo of 505 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6265467)
    505 Shadow Glenn Place, Winter Springs, FL
    505 Shadow Glenn Place
    Winter Springs, FL
    • 2 Beds
    • 2 Baths
    • 1,359 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  2. Photo of 611 Huntly Lane, Winter Springs, FL 32708 (MLS # O6266148)
    $325,000
    Photo of 611 Huntly Lane, Winter Springs, FL 32708 (MLS # O6266148)
    Photo of 611 Huntly Lane, Winter Springs, FL 32708 (MLS # O6266148)
    611 Huntly Lane, Winter Springs, FL
    611 Huntly Lane
    Winter Springs, FL
    • 4 Beds
    • 2 Baths
    • 1,778 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  3. Photo of 10 Moree Loop #13, Winter Springs, FL 32708 (MLS # O6265827)
    $180,000
    Photo of 10 Moree Loop #13, Winter Springs, FL 32708 (MLS # O6265827)
    Photo of 10 Moree Loop #13, Winter Springs, FL 32708 (MLS # O6265827)
    10 Moree Loop #13, Winter Springs, FL
    10 Moree Loop #13
    Winter Springs, FL
    • 2 Beds
    • 2 Baths
    • 1,080 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  4. Photo of 565 Green Spring Circle, Winter Springs, FL 32708 (MLS # O6263345)
    $269,900
    Photo of 565 Green Spring Circle, Winter Springs, FL 32708 (MLS # O6263345)
    Photo of 565 Green Spring Circle, Winter Springs, FL 32708 (MLS # O6263345)
    565 Green Spring Circle, Winter Springs, FL
    565 Green Spring Circle
    Winter Springs, FL
    • 2 Beds
    • 2 Baths
    • 1,363 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  5. Photo of 314 Macgregor Road, Winter Springs, FL 32708 (MLS # O6265396)
    $375,000
    Photo of 314 Macgregor Road, Winter Springs, FL 32708 (MLS # O6265396)
    Photo of 314 Macgregor Road, Winter Springs, FL 32708 (MLS # O6265396)
    314 Macgregor Road, Winter Springs, FL
    314 Macgregor Road
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,617 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  6. Photo of 229 Sherry Avenue, Winter Springs, FL 32708 (MLS # O6264350)
    $310,000
    Photo of 229 Sherry Avenue, Winter Springs, FL 32708 (MLS # O6264350)
    Photo of 229 Sherry Avenue, Winter Springs, FL 32708 (MLS # O6264350)
    229 Sherry Avenue, Winter Springs, FL
    229 Sherry Avenue
    Winter Springs, FL
    • 3 Beds
    • 1 Bath
    • 1,104 Home (sqft)
    • 1 Bath
    • 6,099 Lot (sqft)
  7. Photo of 423 Sheoah Boulevard #19, Winter Springs, FL 32708 (MLS # O6263961)
    $205,000
    Photo of 423 Sheoah Boulevard #19, Winter Springs, FL 32708 (MLS # O6263961)
    Photo of 423 Sheoah Boulevard #19, Winter Springs, FL 32708 (MLS # O6263961)
    423 Sheoah Boulevard #19, Winter Springs, FL
    423 Sheoah Boulevard #19
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,187 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  8. Photo of 1021 Nancy Circle, Winter Springs, FL 32708 (MLS # O6262723)
    $399,000
    Photo of 1021 Nancy Circle, Winter Springs, FL 32708 (MLS # O6262723)
    Photo of 1021 Nancy Circle, Winter Springs, FL 32708 (MLS # O6262723)
    1021 Nancy Circle, Winter Springs, FL
    1021 Nancy Circle
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 2,282 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  9. Photo of 600 Northern Way #307, Winter Springs, FL 32708 (MLS # O6263215)
    $280,000
    Photo of 600 Northern Way #307, Winter Springs, FL 32708 (MLS # O6263215)
    Photo of 600 Northern Way #307, Winter Springs, FL 32708 (MLS # O6263215)
    600 Northern Way #307, Winter Springs, FL
    600 Northern Way #307
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,425 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  10. Photo of 530 Harbor Winds Court, Winter Springs, FL 32708 (MLS # O6261038)
    $329,900
    Photo of 530 Harbor Winds Court, Winter Springs, FL 32708 (MLS # O6261038)
    Photo of 530 Harbor Winds Court, Winter Springs, FL 32708 (MLS # O6261038)
    530 Harbor Winds Court, Winter Springs, FL
    530 Harbor Winds Court
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,386 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  11. 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)
  12. 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)
  13. Photo of 3932 White Birch Run, Winter Springs, FL 32708 (MLS # O6259829)
    $369,900
    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)
  14. 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)
  15. Photo of 411 Sheoah Boulevard #37, Winter Springs, FL 32708 (MLS # S5116031)
    $199,999
    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)
  16. 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)
  17. 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)
  18. 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)
  19. 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)
  20. 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)
  21. Photo of 4249 E Weeping Willow Circle, Winter Springs, FL 32708 (MLS # O6252806)
    $309,900
    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)
  22. 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)
  23. 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)
  24. Photo of 50 Sheoah Boulevard #34, Winter Springs, FL 32708 (MLS # O6250683)
    $160,000
    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)
  25. Photo of 429 Sheoah Boulevard #2, Winter Springs, FL 32708 (MLS # O6254313)
    $199,500
    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)
  26. 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)
  27. Photo of 411 Boxwood Circle, Winter Springs, FL 32708 (MLS # O6247758)
    $345,900
    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)
  28. Photo of 576 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6245444)
    $265,000
    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)
  29. 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)
  30. 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)
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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 12/22/24 12:20 PM PST.

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