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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 135 Majestic Gardens Court, Winter Haven, FL 33880 (MLS # T3548327)
    $305,000
    Photo of 135 Majestic Gardens Court, Winter Haven, FL 33880 (MLS # T3548327)
    Photo of 135 Majestic Gardens Court, Winter Haven, FL 33880 (MLS # T3548327)
    135 Majestic Gardens Court, Winter Haven, FL
    135 Majestic Gardens Court
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,721 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  2. Photo of 3023 Caneel Street, Winter Haven, FL 33884 (MLS # O6231728)
    $234,994
    Photo of 3023 Caneel Street, Winter Haven, FL 33884 (MLS # O6231728)
    Photo of 3023 Caneel Street, Winter Haven, FL 33884 (MLS # O6231728)
    3023 Caneel Street, Winter Haven, FL
    3023 Caneel Street
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,385 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
  3. Photo of 1515 Kenwood Avenue SW, Winter Haven, FL 33880 (MLS # O6231745)
    $265,000
    Photo of 1515 Kenwood Avenue SW, Winter Haven, FL 33880 (MLS # O6231745)
    Photo of 1515 Kenwood Avenue SW, Winter Haven, FL 33880 (MLS # O6231745)
    1515 Kenwood Avenue SW, Winter Haven, FL
    1515 Kenwood Avenue SW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,484 Home (sqft)
    • 2 Baths
    • 30,928 Lot (sqft)
  4. Photo of 821 Orchid Springs Drive #821, Winter Haven, FL 33884 (MLS # P4931617)
    $129,900
    Photo of 821 Orchid Springs Drive #821, Winter Haven, FL 33884 (MLS # P4931617)
    Photo of 821 Orchid Springs Drive #821, Winter Haven, FL 33884 (MLS # P4931617)
    821 Orchid Springs Drive #821, Winter Haven, FL
    821 Orchid Springs Drive #821
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 851 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  5. Photo of 1013 Sawgrass Drive, Winter Haven, FL 33884 (MLS # P4931483)
    $339,900
    Photo of 1013 Sawgrass Drive, Winter Haven, FL 33884 (MLS # P4931483)
    Photo of 1013 Sawgrass Drive, Winter Haven, FL 33884 (MLS # P4931483)
    1013 Sawgrass Drive, Winter Haven, FL
    1013 Sawgrass Drive
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,824 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  6. Photo of 2 Casarena Court, Winter Haven, FL 33881 (MLS # L4946621)
    $364,500
    Photo of 2 Casarena Court, Winter Haven, FL 33881 (MLS # L4946621)
    Photo of 2 Casarena Court, Winter Haven, FL 33881 (MLS # L4946621)
    2 Casarena Court, Winter Haven, FL
    2 Casarena Court
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,377 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  7. Photo of 1024 31st St NW, Winter Haven, FL 33881 (MLS # S5110238)
    $285,900
    Photo of 1024 31st St NW, Winter Haven, FL 33881 (MLS # S5110238)
    Photo of 1024 31st St NW, Winter Haven, FL 33881 (MLS # S5110238)
    1024 31st St NW, Winter Haven, FL
    1024 31st St NW
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,628 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  8. Photo of 511 Avenue G NW, Winter Haven, FL 33881 (MLS # K4902598)
    $277,900
    Photo of 511 Avenue G NW, Winter Haven, FL 33881 (MLS # K4902598)
    Photo of 511 Avenue G NW, Winter Haven, FL 33881 (MLS # K4902598)
    20
     
    511 Avenue G NW, Winter Haven, FL
    511 Avenue G NW
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,444 Home (sqft)
    • 1 Bath
    • 7,406 Lot (sqft)
  9. Photo of 101 Aviation Drive, Winter Haven, FL 33881 (MLS # U8253147)
    $175,900
    Photo of 101 Aviation Drive, Winter Haven, FL 33881 (MLS # U8253147)
    Photo of 101 Aviation Drive, Winter Haven, FL 33881 (MLS # U8253147)
    11
     
    101 Aviation Drive, Winter Haven, FL
    101 Aviation Drive
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,457 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  10. Photo of 601 Turnberry Court, Winter Haven, FL 33884 (MLS # P4931596)
    $349,900
    Photo of 601 Turnberry Court, Winter Haven, FL 33884 (MLS # P4931596)
    Photo of 601 Turnberry Court, Winter Haven, FL 33884 (MLS # P4931596)
    601 Turnberry Court, Winter Haven, FL
    601 Turnberry Court
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,137 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  11. Photo of 15 Tera Lane, Winter Haven, FL 33880 (MLS # P4931588)
    $395,000
    Photo of 15 Tera Lane, Winter Haven, FL 33880 (MLS # P4931588)
    Photo of 15 Tera Lane, Winter Haven, FL 33880 (MLS # P4931588)
    15 Tera Lane, Winter Haven, FL
    15 Tera Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,864 Home (sqft)
    • 2 Baths
    • 21,780 Lot (sqft)
  12. Photo of 4850 St James Court, Winter Haven, FL 33881 (MLS # P4931386)
    $292,000
    Photo of 4850 St James Court, Winter Haven, FL 33881 (MLS # P4931386)
    Photo of 4850 St James Court, Winter Haven, FL 33881 (MLS # P4931386)
    4850 St James Court, Winter Haven, FL
    4850 St James Court
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,675 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  13. Photo of 2179 Castle Point, Winter Haven, FL 33880 (MLS # P4931577)
    $199,900
    Photo of 2179 Castle Point, Winter Haven, FL 33880 (MLS # P4931577)
    Photo of 2179 Castle Point, Winter Haven, FL 33880 (MLS # P4931577)
    2179 Castle Point, Winter Haven, FL
    2179 Castle Point
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,128 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  14. Photo of 4092 Carteret Drive, Winter Haven, FL 33884 (MLS # P4931570)
    $357,500
    Photo of 4092 Carteret Drive, Winter Haven, FL 33884 (MLS # P4931570)
    Photo of 4092 Carteret Drive, Winter Haven, FL 33884 (MLS # P4931570)
    4092 Carteret Drive, Winter Haven, FL
    4092 Carteret Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,928 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  15. Photo of 2505 Salzburg Loop, Winter Haven, FL 33884 (MLS # P4931555)
    $349,900
    Photo of 2505 Salzburg Loop, Winter Haven, FL 33884 (MLS # P4931555)
    Photo of 2505 Salzburg Loop, Winter Haven, FL 33884 (MLS # P4931555)
    2505 Salzburg Loop, Winter Haven, FL
    2505 Salzburg Loop
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 2,062 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  16. Photo of 5756 Lakeside Landings Boulevard, Winter Haven, FL 33881 (MLS # L4946754)
    $299,999
    Photo of 5756 Lakeside Landings Boulevard, Winter Haven, FL 33881 (MLS # L4946754)
    Photo of 5756 Lakeside Landings Boulevard, Winter Haven, FL 33881 (MLS # L4946754)
    5756 Lakeside Landings Boulevard, Winter Haven, FL
    5756 Lakeside Landings Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,600 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  17. Photo of 1457 Lucerne Loop Road NE, Winter Haven, FL 33881 (MLS # T3546757)
    $285,000
    Photo of 1457 Lucerne Loop Road NE, Winter Haven, FL 33881 (MLS # T3546757)
    Photo of 1457 Lucerne Loop Road NE, Winter Haven, FL 33881 (MLS # T3546757)
    1457 Lucerne Loop Road NE, Winter Haven, FL
    1457 Lucerne Loop Road NE
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,599 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  18. Photo of 160 Osprey Heights Drive, Winter Haven, FL 33880 (MLS # U8252876)
    $305,000
    Photo of 160 Osprey Heights Drive, Winter Haven, FL 33880 (MLS # U8252876)
    Photo of 160 Osprey Heights Drive, Winter Haven, FL 33880 (MLS # U8252876)
    160 Osprey Heights Drive, Winter Haven, FL
    160 Osprey Heights Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,709 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  19. Photo of 3214 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4946724)
    $339,900
    Photo of 3214 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4946724)
    Photo of 3214 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4946724)
    3214 Laurel Oak Lane, Winter Haven, FL
    3214 Laurel Oak Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,744 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  20. Photo of 873 Cambridge Drive, Winter Haven, FL 33881 (MLS # S5109517)
    $280,000
    Photo of 873 Cambridge Drive, Winter Haven, FL 33881 (MLS # S5109517)
    Photo of 873 Cambridge Drive, Winter Haven, FL 33881 (MLS # S5109517)
    46
     
    873 Cambridge Drive, Winter Haven, FL
    873 Cambridge Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,405 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  21. Photo of 706 Canberra Road, Winter Haven, FL 33884 (MLS # P4931554)
    $364,900
    Photo of 706 Canberra Road, Winter Haven, FL 33884 (MLS # P4931554)
    Photo of 706 Canberra Road, Winter Haven, FL 33884 (MLS # P4931554)
    706 Canberra Road, Winter Haven, FL
    706 Canberra Road
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,114 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  22. Photo of 3173 Whispering Trails Avenue, Winter Haven, FL 33884 (MLS # P4931488)
    $289,900
    Photo of 3173 Whispering Trails Avenue, Winter Haven, FL 33884 (MLS # P4931488)
    Photo of 3173 Whispering Trails Avenue, Winter Haven, FL 33884 (MLS # P4931488)
    3173 Whispering Trails Avenue, Winter Haven, FL
    3173 Whispering Trails Avenue
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,508 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  23. Photo of 2181 Knights Road, Winter Haven, FL 33880 (MLS # T3546652)
    $189,000
    Photo of 2181 Knights Road, Winter Haven, FL 33880 (MLS # T3546652)
    Photo of 2181 Knights Road, Winter Haven, FL 33880 (MLS # T3546652)
    2181 Knights Road, Winter Haven, FL
    2181 Knights Road
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,252 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  24. Photo of 1423 Grand Cayman Circle, Winter Haven, FL 33884 (MLS # T3544655)
    $299,900
    Photo of 1423 Grand Cayman Circle, Winter Haven, FL 33884 (MLS # T3544655)
    Photo of 1423 Grand Cayman Circle, Winter Haven, FL 33884 (MLS # T3544655)
    1423 Grand Cayman Circle, Winter Haven, FL
    1423 Grand Cayman Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,588 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  25. Photo of 607 Heather Glen Loop, Winter Haven, FL 33884 (MLS # P4931502)
    $299,000
    Photo of 607 Heather Glen Loop, Winter Haven, FL 33884 (MLS # P4931502)
    Photo of 607 Heather Glen Loop, Winter Haven, FL 33884 (MLS # P4931502)
    607 Heather Glen Loop, Winter Haven, FL
    607 Heather Glen Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,210 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  26. Photo of 524 Haines Trail, Winter Haven, FL 33881 (MLS # L4946622)
    $370,000
    Photo of 524 Haines Trail, Winter Haven, FL 33881 (MLS # L4946622)
    Photo of 524 Haines Trail, Winter Haven, FL 33881 (MLS # L4946622)
    524 Haines Trail, Winter Haven, FL
    524 Haines Trail
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,980 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  27. Photo of 141 Andreas Street, Winter Haven, FL 33881 (MLS # S5109821)
    $358,000
    Photo of 141 Andreas Street, Winter Haven, FL 33881 (MLS # S5109821)
    Photo of 141 Andreas Street, Winter Haven, FL 33881 (MLS # S5109821)
    141 Andreas Street, Winter Haven, FL
    141 Andreas Street
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,364 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  28. Photo of 2470 Salzburg Loop, Winter Haven, FL 33884 (MLS # O6229536)
    $300,000
    Photo of 2470 Salzburg Loop, Winter Haven, FL 33884 (MLS # O6229536)
    Photo of 2470 Salzburg Loop, Winter Haven, FL 33884 (MLS # O6229536)
    2470 Salzburg Loop, Winter Haven, FL
    2470 Salzburg Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,935 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
  29. Photo of 7906 Waterview Way #7906, Winter Haven, FL 33884 (MLS # P4931489)
    $206,400
    Photo of 7906 Waterview Way #7906, Winter Haven, FL 33884 (MLS # P4931489)
    Photo of 7906 Waterview Way #7906, Winter Haven, FL 33884 (MLS # P4931489)
    7906 Waterview Way #7906, Winter Haven, FL
    7906 Waterview Way #7906
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 930 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  30. Photo of 1712 Lime Drive, Winter Haven, FL 33881 (MLS # O6227523)
    $365,000
    Photo of 1712 Lime Drive, Winter Haven, FL 33881 (MLS # O6227523)
    Photo of 1712 Lime Drive, Winter Haven, FL 33881 (MLS # O6227523)
    1712 Lime Drive, Winter Haven, FL
    1712 Lime Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,218 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
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