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Winter Haven is located in Central Florida and known for its canal-linked Chain of Lakes. Several lakes have waterside parks and eateries, as well as boat ramps and water-sports rentals. On Lake Eloise, Legoland Florida Resort includes Cypress Gardens, a 1930s botanical garden, and Lego-brick attractions, rides and a water park. West of the city, Circle B Bar Reserve has forest trails and alligator-inhabited wetlands. Use our custom search tool to view all homes for sale under $400k in Winter Haven or click here to return to the list of surrounding towns and cities in the Kissimmee area. Have questions? Contact us here or schedule your FREE consultation here.


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  1. Photo of 263 Sunfish Drive, Winter Haven, FL 33881 (MLS # O6251860)
    $307,000
    Photo of 263 Sunfish Drive, Winter Haven, FL 33881 (MLS # O6251860)
    Photo of 263 Sunfish Drive, Winter Haven, FL 33881 (MLS # O6251860)
    263 Sunfish Drive, Winter Haven, FL
    263 Sunfish Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,696 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  2. Photo of 5732 Lakeside Landings Boulevard, Winter Haven, FL 33881 (MLS # P4932474)
    $280,000
    Photo of 5732 Lakeside Landings Boulevard, Winter Haven, FL 33881 (MLS # P4932474)
    Photo of 5732 Lakeside Landings Boulevard, Winter Haven, FL 33881 (MLS # P4932474)
    5732 Lakeside Landings Boulevard, Winter Haven, FL
    5732 Lakeside Landings Boulevard
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,748 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  3. Photo of 3126 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4948365)
    $341,595
    Photo of 3126 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4948365)
    Photo of 3126 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4948365)
    3126 Laurel Oak Lane, Winter Haven, FL
    3126 Laurel Oak Lane
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,005 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  4. Photo of 164 Emanuelle Drive, Winter Haven, FL 33884 (MLS # S5114299)
    $359,990
    Photo of 164 Emanuelle Drive, Winter Haven, FL 33884 (MLS # S5114299)
    Photo of 164 Emanuelle Drive, Winter Haven, FL 33884 (MLS # S5114299)
    164 Emanuelle Drive, Winter Haven, FL
    164 Emanuelle Drive
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,616 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  5. Photo of 4601 Reynosa Drive SW, Winter Haven, FL 33880 (MLS # L4948260)
    $395,000
    Photo of 4601 Reynosa Drive SW, Winter Haven, FL 33880 (MLS # L4948260)
    Photo of 4601 Reynosa Drive SW, Winter Haven, FL 33880 (MLS # L4948260)
    4601 Reynosa Drive SW, Winter Haven, FL
    4601 Reynosa Drive SW
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,304 Home (sqft)
    • 3 Baths
    • 17,424 Lot (sqft)
  6. Photo of 129 Alachua Drive, Winter Haven, FL 33884 (MLS # O6250425)
    $269,000
    Photo of 129 Alachua Drive, Winter Haven, FL 33884 (MLS # O6250425)
    Photo of 129 Alachua Drive, Winter Haven, FL 33884 (MLS # O6250425)
    14
     
    129 Alachua Drive, Winter Haven, FL
    129 Alachua Drive
    Winter Haven, FL
    • 5 Beds
    • 2 Baths
    • 1,750 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  7. Photo of 1568 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6251034)
    $309,490
    Photo of 1568 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6251034)
    Photo of 1568 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6251034)
    1568 Hummingbird Road, Winter Haven, FL
    1568 Hummingbird Road
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,720 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  8. Photo of 1576 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6251013)
    $309,990
    Photo of 1576 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6251013)
    Photo of 1576 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6251013)
    1576 Hummingbird Road, Winter Haven, FL
    1576 Hummingbird Road
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,720 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  9. Photo of 1584 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6250942)
    $340,990
    Photo of 1584 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6250942)
    Photo of 1584 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6250942)
    1584 Hummingbird Road, Winter Haven, FL
    1584 Hummingbird Road
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,720 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  10. Photo of 1572 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6250924)
    $349,990
    Photo of 1572 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6250924)
    Photo of 1572 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6250924)
    1572 Hummingbird Road, Winter Haven, FL
    1572 Hummingbird Road
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,308 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  11. Photo of 200 El Camino Drive #110, Winter Haven, FL 33884 (MLS # P4932390)
    $125,000
    Photo of 200 El Camino Drive #110, Winter Haven, FL 33884 (MLS # P4932390)
    Photo of 200 El Camino Drive #110, Winter Haven, FL 33884 (MLS # P4932390)
    200 El Camino Drive #110, Winter Haven, FL
    200 El Camino Drive #110
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,378 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  12. Photo of 1942 Quail Fields Circle, Winter Haven, FL 33884 (MLS # W7869203)
    $342,945
    Photo of 1942 Quail Fields Circle, Winter Haven, FL 33884 (MLS # W7869203)
    Photo of 1942 Quail Fields Circle, Winter Haven, FL 33884 (MLS # W7869203)
    1942 Quail Fields Circle, Winter Haven, FL
    1942 Quail Fields Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,815 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  13. Photo of 1946 Quail Fields Circle, Winter Haven, FL 33884 (MLS # W7869202)
    $359,750
    Photo of 1946 Quail Fields Circle, Winter Haven, FL 33884 (MLS # W7869202)
    Photo of 1946 Quail Fields Circle, Winter Haven, FL 33884 (MLS # W7869202)
    1946 Quail Fields Circle, Winter Haven, FL
    1946 Quail Fields Circle
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,021 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  14. Photo of 1650 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8312643)
    $299,499
    Photo of 1650 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8312643)
    Photo of 1650 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8312643)
    1650 Teagan Lane, Winter Haven, FL
    1650 Teagan Lane
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,936 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  15. Photo of 337 Kayden Cove, Winter Haven, FL 33884 (MLS # TB8312639)
    $302,749
    Photo of 337 Kayden Cove, Winter Haven, FL 33884 (MLS # TB8312639)
    Photo of 337 Kayden Cove, Winter Haven, FL 33884 (MLS # TB8312639)
    337 Kayden Cove, Winter Haven, FL
    337 Kayden Cove
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,879 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  16. Photo of 1744 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8312638)
    $290,795
    Photo of 1744 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8312638)
    Photo of 1744 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8312638)
    1744 Teagan Lane, Winter Haven, FL
    1744 Teagan Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,444 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  17. Photo of 1012 Medinah Drive, Winter Haven, FL 33884 (MLS # P4932452)
    $229,750
    Photo of 1012 Medinah Drive, Winter Haven, FL 33884 (MLS # P4932452)
    Photo of 1012 Medinah Drive, Winter Haven, FL 33884 (MLS # P4932452)
    1012 Medinah Drive, Winter Haven, FL
    1012 Medinah Drive
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,139 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  18. Photo of 535 Reflections Boulevard, Winter Haven, FL 33884 (MLS # P4932440)
    $329,900
    Photo of 535 Reflections Boulevard, Winter Haven, FL 33884 (MLS # P4932440)
    Photo of 535 Reflections Boulevard, Winter Haven, FL 33884 (MLS # P4932440)
    535 Reflections Boulevard, Winter Haven, FL
    535 Reflections Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,005 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  19. Photo of 2610 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250516)
    $329,990
    Photo of 2610 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250516)
    Photo of 2610 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250516)
    2610 Sage Valley Way, Winter Haven, FL
    2610 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,828 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  20. Photo of 2606 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250512)
    $359,990
    Photo of 2606 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250512)
    Photo of 2606 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250512)
    2606 Sage Valley Way, Winter Haven, FL
    2606 Sage Valley Way
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,077 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  21. Photo of 2534 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250509)
    $359,990
    Photo of 2534 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250509)
    Photo of 2534 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250509)
    2534 Sage Valley Way, Winter Haven, FL
    2534 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,828 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  22. Photo of 2538 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250504)
    $358,990
    Photo of 2538 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250504)
    Photo of 2538 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250504)
    2538 Sage Valley Way, Winter Haven, FL
    2538 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,828 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  23. Photo of 451 Sunfish Drive, Winter Haven, FL 33881 (MLS # L4948270)
    $320,000
    Photo of 451 Sunfish Drive, Winter Haven, FL 33881 (MLS # L4948270)
    Photo of 451 Sunfish Drive, Winter Haven, FL 33881 (MLS # L4948270)
    451 Sunfish Drive, Winter Haven, FL
    451 Sunfish Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,696 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  24. Photo of 215 Kingshill Court SE, Winter Haven, FL 33884 (MLS # O6248342)
    $275,000
    Photo of 215 Kingshill Court SE, Winter Haven, FL 33884 (MLS # O6248342)
    Photo of 215 Kingshill Court SE, Winter Haven, FL 33884 (MLS # O6248342)
    215 Kingshill Court SE, Winter Haven, FL
    215 Kingshill Court SE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,437 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  25. Photo of 948 Summer Glen Drive, Winter Haven, FL 33880 (MLS # O6250256)
    $319,000
    Photo of 948 Summer Glen Drive, Winter Haven, FL 33880 (MLS # O6250256)
    Photo of 948 Summer Glen Drive, Winter Haven, FL 33880 (MLS # O6250256)
    948 Summer Glen Drive, Winter Haven, FL
    948 Summer Glen Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,690 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  26. Photo of 2622 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250201)
    $354,900
    Photo of 2622 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250201)
    Photo of 2622 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250201)
    2622 Sage Valley Way, Winter Haven, FL
    2622 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,828 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  27. Photo of 2634 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250151)
    $349,990
    Photo of 2634 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250151)
    Photo of 2634 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250151)
    2634 Sage Valley Way, Winter Haven, FL
    2634 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,828 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  28. Photo of 2638 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250143)
    $344,990
    Photo of 2638 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250143)
    Photo of 2638 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250143)
    2638 Sage Valley Way, Winter Haven, FL
    2638 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,828 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  29. Photo of 3820 Traditions Boulevard N, Winter Haven, FL 33884 (MLS # P4932395)
    $399,000
    Photo of 3820 Traditions Boulevard N, Winter Haven, FL 33884 (MLS # P4932395)
    Photo of 3820 Traditions Boulevard N, Winter Haven, FL 33884 (MLS # P4932395)
    3820 Traditions Boulevard N, Winter Haven, FL
    3820 Traditions Boulevard N
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,400 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  30. Photo of 1668 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6250077)
    $377,990
    Photo of 1668 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6250077)
    Photo of 1668 Hummingbird Road, Winter Haven, FL 33884 (MLS # O6250077)
    1668 Hummingbird Road, Winter Haven, FL
    1668 Hummingbird Road
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,308 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
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