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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 570 Pinebranch Circle, Winter Springs, FL 32708 (MLS # O6235503)
    $350,000
    Photo of 570 Pinebranch Circle, Winter Springs, FL 32708 (MLS # O6235503)
    Photo of 570 Pinebranch Circle, Winter Springs, FL 32708 (MLS # O6235503)
    570 Pinebranch Circle, Winter Springs, FL
    570 Pinebranch Circle
    Winter Springs, FL
    • 2 Beds
    • 3 Baths
    • 1,466 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
  2. Photo of 40 Sheoah Boulevard #28, Winter Springs, FL 32708 (MLS # O6237638)
    $204,999
    Photo of 40 Sheoah Boulevard #28, Winter Springs, FL 32708 (MLS # O6237638)
    Photo of 40 Sheoah Boulevard #28, Winter Springs, FL 32708 (MLS # O6237638)
    40 Sheoah Boulevard #28, Winter Springs, FL
    40 Sheoah Boulevard #28
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,187 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  3. Photo of 766 Blades Court, Winter Springs, FL 32708 (MLS # O6234229)
    $340,000
    Photo of 766 Blades Court, Winter Springs, FL 32708 (MLS # O6234229)
    Photo of 766 Blades Court, Winter Springs, FL 32708 (MLS # O6234229)
    766 Blades Court, Winter Springs, FL
    766 Blades Court
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,450 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  4. Photo of 614 Pinebranch Circle, Winter Springs, FL 32708 (MLS # O6234072)
    $340,000
    Photo of 614 Pinebranch Circle, Winter Springs, FL 32708 (MLS # O6234072)
    Photo of 614 Pinebranch Circle, Winter Springs, FL 32708 (MLS # O6234072)
    614 Pinebranch Circle, Winter Springs, FL
    614 Pinebranch Circle
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,564 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
  5. Photo of 4447 Brook Hollow Circle, Winter Springs, FL 32708 (MLS # O6233197)
    $300,000
    Photo of 4447 Brook Hollow Circle, Winter Springs, FL 32708 (MLS # O6233197)
    Photo of 4447 Brook Hollow Circle, Winter Springs, FL 32708 (MLS # O6233197)
    4447 Brook Hollow Circle, Winter Springs, FL
    4447 Brook Hollow Circle
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,349 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  6. Photo of 701 Castlewood Drive, Winter Springs, FL 32708 (MLS # O6230143)
    $325,000
    Photo of 701 Castlewood Drive, Winter Springs, FL 32708 (MLS # O6230143)
    Photo of 701 Castlewood Drive, Winter Springs, FL 32708 (MLS # O6230143)
    701 Castlewood Drive, Winter Springs, FL
    701 Castlewood Drive
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,470 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  7. Photo of 384 Innisbrook Lane, Winter Springs, FL 32708 (MLS # O6231156)
    $389,900
    Photo of 384 Innisbrook Lane, Winter Springs, FL 32708 (MLS # O6231156)
    Photo of 384 Innisbrook Lane, Winter Springs, FL 32708 (MLS # O6231156)
    384 Innisbrook Lane, Winter Springs, FL
    384 Innisbrook Lane
    Winter Springs, FL
    • 3 Beds
    • 4 Baths
    • 1,844 Home (sqft)
    • 4 Baths
    • 1,307 Lot (sqft)
  8. Photo of 600 Northern Way #609, Winter Springs, FL 32708 (MLS # O6225775)
    $315,000
    Photo of 600 Northern Way #609, Winter Springs, FL 32708 (MLS # O6225775)
    Photo of 600 Northern Way #609, Winter Springs, FL 32708 (MLS # O6225775)
    600 Northern Way #609, Winter Springs, FL
    600 Northern Way #609
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,447 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  9. Photo of 174 Constitution Way, Winter Springs, FL 32708 (MLS # O6228427)
    $290,000
    Photo of 174 Constitution Way, Winter Springs, FL 32708 (MLS # O6228427)
    Photo of 174 Constitution Way, Winter Springs, FL 32708 (MLS # O6228427)
    174 Constitution Way, Winter Springs, FL
    174 Constitution Way
    Winter Springs, FL
    • 2 Beds
    • 3 Baths
    • 1,275 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  10. Photo of 502 Osprey Lane, Winter Springs, FL 32708 (MLS # NS1082255)
    $394,500
    Photo of 502 Osprey Lane, Winter Springs, FL 32708 (MLS # NS1082255)
    Photo of 502 Osprey Lane, Winter Springs, FL 32708 (MLS # NS1082255)
    502 Osprey Lane, Winter Springs, FL
    502 Osprey Lane
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,708 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  11. Photo of 1493 Casa Park Circle, Winter Springs, FL 32708 (MLS # O6226187)
    $256,000
    Photo of 1493 Casa Park Circle, Winter Springs, FL 32708 (MLS # O6226187)
    Photo of 1493 Casa Park Circle, Winter Springs, FL 32708 (MLS # O6226187)
    1493 Casa Park Circle, Winter Springs, FL
    1493 Casa Park Circle
    Winter Springs, FL
    • 2 Beds
    • 3 Baths
    • 1,156 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  12. Photo of 721 Sailfish Road, Winter Springs, FL 32708 (MLS # O6220995)
    $399,900
    Photo of 721 Sailfish Road, Winter Springs, FL 32708 (MLS # O6220995)
    Photo of 721 Sailfish Road, Winter Springs, FL 32708 (MLS # O6220995)
    721 Sailfish Road, Winter Springs, FL
    721 Sailfish Road
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,378 Home (sqft)
    • 2 Baths
    • 15,682 Lot (sqft)
  13. Photo of 425 Sheoah Boulevard #29, Winter Springs, FL 32708 (MLS # O6220560)
    $244,000
    Photo of 425 Sheoah Boulevard #29, Winter Springs, FL 32708 (MLS # O6220560)
    Photo of 425 Sheoah Boulevard #29, Winter Springs, FL 32708 (MLS # O6220560)
    425 Sheoah Boulevard #29, Winter Springs, FL
    425 Sheoah Boulevard #29
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,400 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
  14. Photo of 10 Moree Loop #1, Winter Springs, FL 32708 (MLS # O6217924)
    $210,000
    Photo of 10 Moree Loop #1, Winter Springs, FL 32708 (MLS # O6217924)
    Photo of 10 Moree Loop #1, Winter Springs, FL 32708 (MLS # O6217924)
    10 Moree Loop #1, Winter Springs, FL
    10 Moree Loop #1
    Winter Springs, FL
    • 2 Beds
    • 2 Baths
    • 1,080 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  15. Photo of 302 Bridie Court, Winter Springs, FL 32708 (MLS # A4614285)
    $339,000
    Photo of 302 Bridie Court, Winter Springs, FL 32708 (MLS # A4614285)
    Photo of 302 Bridie Court, Winter Springs, FL 32708 (MLS # A4614285)
    302 Bridie Court, Winter Springs, FL
    302 Bridie Court
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,401 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  16. Photo of 401 Boxwood Circle, Winter Springs, FL 32708 (MLS # O6214780)
    $359,999
    Photo of 401 Boxwood Circle, Winter Springs, FL 32708 (MLS # O6214780)
    Photo of 401 Boxwood Circle, Winter Springs, FL 32708 (MLS # O6214780)
    401 Boxwood Circle, Winter Springs, FL
    401 Boxwood Circle
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,280 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  17. Photo of 371 Innisbrook Lane, Winter Springs, FL 32708 (MLS # O6215575)
    $398,000
    Photo of 371 Innisbrook Lane, Winter Springs, FL 32708 (MLS # O6215575)
    Photo of 371 Innisbrook Lane, Winter Springs, FL 32708 (MLS # O6215575)
    371 Innisbrook Lane, Winter Springs, FL
    371 Innisbrook Lane
    Winter Springs, FL
    • 3 Beds
    • 4 Baths
    • 1,854 Home (sqft)
    • 4 Baths
    • 1,307 Lot (sqft)
  18. Photo of 336 San Miguel Street, Winter Springs, FL 32708 (MLS # O6209961)
    $209,989
    Photo of 336 San Miguel Street, Winter Springs, FL 32708 (MLS # O6209961)
    Photo of 336 San Miguel Street, Winter Springs, FL 32708 (MLS # O6209961)
    336 San Miguel Street, Winter Springs, FL
    336 San Miguel Street
    Winter Springs, FL
    • 2 Beds
    • 1 Bath
    • 735 Home (sqft)
    • 1 Bath
    • 1,743 Lot (sqft)
  19. Photo of 600 Northern Way #502, Winter Springs, FL 32708 (MLS # O6211463)
    $299,000
    Photo of 600 Northern Way #502, Winter Springs, FL 32708 (MLS # O6211463)
    Photo of 600 Northern Way #502, Winter Springs, FL 32708 (MLS # O6211463)
    600 Northern Way #502, Winter Springs, FL
    600 Northern Way #502
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,425 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  20. Photo of 101 Albert Street, Winter Springs, FL 32708 (MLS # S5106161)
    $329,900
    Photo of 101 Albert Street, Winter Springs, FL 32708 (MLS # S5106161)
    Photo of 101 Albert Street, Winter Springs, FL 32708 (MLS # S5106161)
    101 Albert Street, Winter Springs, FL
    101 Albert Street
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,166 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  21. Photo of 548 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6211360)
    $269,000
    Photo of 548 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6211360)
    Photo of 548 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6211360)
    548 Shadow Glenn Place, Winter Springs, FL
    548 Shadow Glenn Place
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,344 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  22. Photo of 537 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6203460)
    $307,700
    Photo of 537 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6203460)
    Photo of 537 Shadow Glenn Place, Winter Springs, FL 32708 (MLS # O6203460)
    537 Shadow Glenn Place, Winter Springs, FL
    537 Shadow Glenn Place
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,359 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  23. Photo of 487 Harbor Winds Court, Winter Springs, FL 32708 (MLS # O6202229)
    $343,000
    Photo of 487 Harbor Winds Court, Winter Springs, FL 32708 (MLS # O6202229)
    Photo of 487 Harbor Winds Court, Winter Springs, FL 32708 (MLS # O6202229)
    487 Harbor Winds Court, Winter Springs, FL
    487 Harbor Winds Court
    Winter Springs, FL
    • 3 Beds
    • 3 Baths
    • 1,914 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  24. Photo of 751 Summerland Drive, Winter Springs, FL 32708 (MLS # O6195234)
    $368,499
    Photo of 751 Summerland Drive, Winter Springs, FL 32708 (MLS # O6195234)
    Photo of 751 Summerland Drive, Winter Springs, FL 32708 (MLS # O6195234)
    751 Summerland Drive, Winter Springs, FL
    751 Summerland Drive
    Winter Springs, FL
    • 4 Beds
    • 2 Baths
    • 1,561 Home (sqft)
    • 2 Baths
    • 2,614 Lot (sqft)
  25. Photo of 600 Northern Way #108, Winter Springs, FL 32708 (MLS # S5087821)
    $299,000
    Photo of 600 Northern Way #108, Winter Springs, FL 32708 (MLS # S5087821)
    Photo of 600 Northern Way #108, Winter Springs, FL 32708 (MLS # S5087821)
    600 Northern Way #108, Winter Springs, FL
    600 Northern Way #108
    Winter Springs, FL
    • 3 Beds
    • 2 Baths
    • 1,425 Home (sqft)
    • 2 Baths
    • 1,307 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 12/3/24 8:15 AM PST.

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