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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 2642 Rutledge Court, Winter Haven, FL 33884 (MLS # S5117461)
    $220,000
    Photo of 2642 Rutledge Court, Winter Haven, FL 33884 (MLS # S5117461)
    Photo of 2642 Rutledge Court, Winter Haven, FL 33884 (MLS # S5117461)
    2642 Rutledge Court, Winter Haven, FL
    2642 Rutledge Court
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,419 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
  2. Photo of 1548 Hummingbird Road, Winter Haven, FL 33884 (MLS # TB8332206)
    $367,990
    Photo of 1548 Hummingbird Road, Winter Haven, FL 33884 (MLS # TB8332206)
    Photo of 1548 Hummingbird Road, Winter Haven, FL 33884 (MLS # TB8332206)
    1548 Hummingbird Road, Winter Haven, FL
    1548 Hummingbird Road
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,423 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  3. Photo of 1552 Hummingbird Road, Winter Haven, FL 33884 (MLS # TB8332203)
    $332,490
    Photo of 1552 Hummingbird Road, Winter Haven, FL 33884 (MLS # TB8332203)
    Photo of 1552 Hummingbird Road, Winter Haven, FL 33884 (MLS # TB8332203)
    1552 Hummingbird Road, Winter Haven, FL
    1552 Hummingbird Road
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,792 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  4. Photo of 1060 29th Street NW, Winter Haven, FL 33881 (MLS # L4949508)
    $194,500
    Photo of 1060 29th Street NW, Winter Haven, FL 33881 (MLS # L4949508)
    Photo of 1060 29th Street NW, Winter Haven, FL 33881 (MLS # L4949508)
    1060 29th Street NW, Winter Haven, FL
    1060 29th Street NW
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 854 Home (sqft)
    • 1 Bath
    • 8,712 Lot (sqft)
  5. Photo of 2880 Attwater Loop, Winter Haven, FL 33884 (MLS # O6265653)
    $240,000
    Photo of 2880 Attwater Loop, Winter Haven, FL 33884 (MLS # O6265653)
    Photo of 2880 Attwater Loop, Winter Haven, FL 33884 (MLS # O6265653)
    2880 Attwater Loop, Winter Haven, FL
    2880 Attwater Loop
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,400 Home (sqft)
    • 2 Baths
    • 2,614 Lot (sqft)
  6. Photo of 1065 8th Street, Winter Haven, FL 33881 (MLS # P4933113)
    $269,000
    Photo of 1065 8th Street, Winter Haven, FL 33881 (MLS # P4933113)
    Photo of 1065 8th Street, Winter Haven, FL 33881 (MLS # P4933113)
    1065 8th Street, Winter Haven, FL
    1065 8th Street
    Winter Haven, FL
    • 2 Beds
    • 3 Baths
    • 1,836 Home (sqft)
    • 3 Baths
    • 16,989 Lot (sqft)
  7. Photo of 2231 Author Hills Street, Winter Haven, FL 33884 (MLS # O6265529)
    $384,000
    Photo of 2231 Author Hills Street, Winter Haven, FL 33884 (MLS # O6265529)
    Photo of 2231 Author Hills Street, Winter Haven, FL 33884 (MLS # O6265529)
    2231 Author Hills Street, Winter Haven, FL
    2231 Author Hills Street
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,616 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  8. Photo of 1700 6th Street NW #A37, Winter Haven, FL 33881 (MLS # L4949510)
    $108,500
    Photo of 1700 6th Street NW #A37, Winter Haven, FL 33881 (MLS # L4949510)
    Photo of 1700 6th Street NW #A37, Winter Haven, FL 33881 (MLS # L4949510)
    27
     
    1700 6th Street NW #A37, Winter Haven, FL
    1700 6th Street NW #A37
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 840 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  9. Photo of 3226 Oak Tree Lane, Winter Haven, FL 33884 (MLS # L4949446)
    $349,000
    Photo of 3226 Oak Tree Lane, Winter Haven, FL 33884 (MLS # L4949446)
    Photo of 3226 Oak Tree Lane, Winter Haven, FL 33884 (MLS # L4949446)
    3226 Oak Tree Lane, Winter Haven, FL
    3226 Oak Tree Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,086 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  10. Photo of 4060 Lake Marianna Drive, Winter Haven, FL 33881 (MLS # G5090456)
    $390,000
    Photo of 4060 Lake Marianna Drive, Winter Haven, FL 33881 (MLS # G5090456)
    Photo of 4060 Lake Marianna Drive, Winter Haven, FL 33881 (MLS # G5090456)
    4060 Lake Marianna Drive, Winter Haven, FL
    4060 Lake Marianna Drive
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,346 Home (sqft)
    • 3 Baths
    • 16,553 Lot (sqft)
  11. Photo of 3171 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4949478)
    $345,065
    Photo of 3171 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4949478)
    Photo of 3171 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4949478)
    3171 Laurel Oak Lane, Winter Haven, FL
    3171 Laurel Oak Lane
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,029 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  12. Photo of 811 Turner Lane, Winter Haven, FL 33881 (MLS # O6265644)
    $350,000
    Photo of 811 Turner Lane, Winter Haven, FL 33881 (MLS # O6265644)
    Photo of 811 Turner Lane, Winter Haven, FL 33881 (MLS # O6265644)
    811 Turner Lane, Winter Haven, FL
    811 Turner Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,672 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  13. Photo of 839 Sun Burst Road, Winter Haven, FL 33880 (MLS # O6265439)
    $385,000
    Photo of 839 Sun Burst Road, Winter Haven, FL 33880 (MLS # O6265439)
    Photo of 839 Sun Burst Road, Winter Haven, FL 33880 (MLS # O6265439)
    839 Sun Burst Road, Winter Haven, FL
    839 Sun Burst Road
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,616 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  14. Photo of 218 College Grove Circle NE, Winter Haven, FL 33881 (MLS # P4933081)
    $399,500
    Photo of 218 College Grove Circle NE, Winter Haven, FL 33881 (MLS # P4933081)
    Photo of 218 College Grove Circle NE, Winter Haven, FL 33881 (MLS # P4933081)
    218 College Grove Circle NE, Winter Haven, FL
    218 College Grove Circle NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,109 Home (sqft)
    • 2 Baths
    • 12,633 Lot (sqft)
  15. Photo of 409 Greenfield Rd, Winter Haven, FL 33884 (MLS # TB8330828)
    $275,000
    Photo of 409 Greenfield Rd, Winter Haven, FL 33884 (MLS # TB8330828)
    Photo of 409 Greenfield Rd, Winter Haven, FL 33884 (MLS # TB8330828)
    409 Greenfield Rd, Winter Haven, FL
    409 Greenfield Rd
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,048 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  16. Photo of 1988 13th Street NW, Winter Haven, FL 33881 (MLS # P4933079)
    $249,000
    Photo of 1988 13th Street NW, Winter Haven, FL 33881 (MLS # P4933079)
    Photo of 1988 13th Street NW, Winter Haven, FL 33881 (MLS # P4933079)
    1988 13th Street NW, Winter Haven, FL
    1988 13th Street NW
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,255 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  17. Photo of 802 Magnolia Place, Winter Haven, FL 33884 (MLS # P4933085)
    $259,000
    Photo of 802 Magnolia Place, Winter Haven, FL 33884 (MLS # P4933085)
    Photo of 802 Magnolia Place, Winter Haven, FL 33884 (MLS # P4933085)
    802 Magnolia Place, Winter Haven, FL
    802 Magnolia Place
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,012 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  18. Photo of 3931 Avenue R NW, Winter Haven, FL 33881 (MLS # O6264881)
    $214,900
    Photo of 3931 Avenue R NW, Winter Haven, FL 33881 (MLS # O6264881)
    Photo of 3931 Avenue R NW, Winter Haven, FL 33881 (MLS # O6264881)
    3931 Avenue R NW, Winter Haven, FL
    3931 Avenue R NW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,180 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  19. Photo of 128 Stevenson Road, Winter Haven, FL 33884 (MLS # P4933080)
    $240,000
    Photo of 128 Stevenson Road, Winter Haven, FL 33884 (MLS # P4933080)
    Photo of 128 Stevenson Road, Winter Haven, FL 33884 (MLS # P4933080)
    128 Stevenson Road, Winter Haven, FL
    128 Stevenson Road
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,360 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  20. Photo of 2304 Avenue C SW, Winter Haven, FL 33880 (MLS # P4933082)
    $264,995
    Photo of 2304 Avenue C SW, Winter Haven, FL 33880 (MLS # P4933082)
    Photo of 2304 Avenue C SW, Winter Haven, FL 33880 (MLS # P4933082)
    21
     
    2304 Avenue C SW, Winter Haven, FL
    2304 Avenue C SW
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,105 Home (sqft)
    • 2 Baths
    • 15,682 Lot (sqft)
  21. Photo of 841 4th Street, Winter Haven, FL 33881 (MLS # P4933007)
    $214,900
    Photo of 841 4th Street, Winter Haven, FL 33881 (MLS # P4933007)
    Photo of 841 4th Street, Winter Haven, FL 33881 (MLS # P4933007)
    841 4th Street, Winter Haven, FL
    841 4th Street
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 912 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  22. Photo of 305 Laurel Cove Way #305, Winter Haven, FL 33884 (MLS # O6264505)
    $239,000
    Photo of 305 Laurel Cove Way #305, Winter Haven, FL 33884 (MLS # O6264505)
    Photo of 305 Laurel Cove Way #305, Winter Haven, FL 33884 (MLS # O6264505)
    305 Laurel Cove Way #305, Winter Haven, FL
    305 Laurel Cove Way #305
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,096 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  23. Photo of 16 Kendra Court #16, Winter Haven, FL 33880 (MLS # P4933074)
    $150,000
    Photo of 16 Kendra Court #16, Winter Haven, FL 33880 (MLS # P4933074)
    Photo of 16 Kendra Court #16, Winter Haven, FL 33880 (MLS # P4933074)
    16 Kendra Court #16, Winter Haven, FL
    16 Kendra Court #16
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 936 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  24. Photo of 3401 Avenue V NW, Winter Haven, FL 33881 (MLS # A4632371)
    $234,000
    Photo of 3401 Avenue V NW, Winter Haven, FL 33881 (MLS # A4632371)
    Photo of 3401 Avenue V NW, Winter Haven, FL 33881 (MLS # A4632371)
    3401 Avenue V NW, Winter Haven, FL
    3401 Avenue V NW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,300 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  25. Photo of 128 Hawthorne Rd, Winter Haven, FL 33884 (MLS # P4933065)
    $254,900
    Photo of 128 Hawthorne Rd, Winter Haven, FL 33884 (MLS # P4933065)
    Photo of 128 Hawthorne Rd, Winter Haven, FL 33884 (MLS # P4933065)
    50
     
    128 Hawthorne Rd, Winter Haven, FL
    128 Hawthorne Rd
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,352 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  26. Photo of 2418 34th Street NW, Winter Haven, FL 33881 (MLS # O6264592)
    $224,900
    Photo of 2418 34th Street NW, Winter Haven, FL 33881 (MLS # O6264592)
    Photo of 2418 34th Street NW, Winter Haven, FL 33881 (MLS # O6264592)
    2418 34th Street NW, Winter Haven, FL
    2418 34th Street NW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,196 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  27. Photo of 603 Sweet Bay Circle #603, Winter Haven, FL 33884 (MLS # P4933059)
    $210,000
    Photo of 603 Sweet Bay Circle #603, Winter Haven, FL 33884 (MLS # P4933059)
    Photo of 603 Sweet Bay Circle #603, Winter Haven, FL 33884 (MLS # P4933059)
    603 Sweet Bay Circle #603, Winter Haven, FL
    603 Sweet Bay Circle #603
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,090 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  28. Photo of 2521 Avenue A SW, Winter Haven, FL 33880 (MLS # O6264647)
    $319,900
    Photo of 2521 Avenue A SW, Winter Haven, FL 33880 (MLS # O6264647)
    Photo of 2521 Avenue A SW, Winter Haven, FL 33880 (MLS # O6264647)
    2521 Avenue A SW, Winter Haven, FL
    2521 Avenue A SW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,075 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  29. Photo of 666 Avenue B SW, Winter Haven, FL 33880 (MLS # S5116949)
    $359,900
    Photo of 666 Avenue B SW, Winter Haven, FL 33880 (MLS # S5116949)
    Photo of 666 Avenue B SW, Winter Haven, FL 33880 (MLS # S5116949)
    666 Avenue B SW, Winter Haven, FL
    666 Avenue B SW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,088 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  30. Photo of 3825 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6261751)
    $319,090
    Photo of 3825 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6261751)
    Photo of 3825 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6261751)
    3825 Giorgio Drive, Winter Haven, FL
    3825 Giorgio Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,840 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
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