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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 1704 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8307192)
    $360,060
    Photo of 1704 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8307192)
    Photo of 1704 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8307192)
    1704 Teagan Lane, Winter Haven, FL
    1704 Teagan Lane
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,109 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  2. Photo of 1878 Avenue Q SW #1878, Winter Haven, FL 33880 (MLS # P4932200)
    $129,900
    Photo of 1878 Avenue Q SW #1878, Winter Haven, FL 33880 (MLS # P4932200)
    Photo of 1878 Avenue Q SW #1878, Winter Haven, FL 33880 (MLS # P4932200)
    1878 Avenue Q SW #1878, Winter Haven, FL
    1878 Avenue Q SW #1878
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 960 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  3. Photo of 3540 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # P4932131)
    $388,000
    Photo of 3540 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # P4932131)
    Photo of 3540 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # P4932131)
    3540 Julius Estates Boulevard, Winter Haven, FL
    3540 Julius Estates Boulevard
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 3,023 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  4. Photo of 503 Holt Circle, Winter Haven, FL 33880 (MLS # S5112982)
    $279,900
    Photo of 503 Holt Circle, Winter Haven, FL 33880 (MLS # S5112982)
    Photo of 503 Holt Circle, Winter Haven, FL 33880 (MLS # S5112982)
    503 Holt Circle, Winter Haven, FL
    503 Holt Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,305 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  5. Photo of 724 Avenue R NE, Winter Haven, FL 33881 (MLS # P4932149)
    $281,500
    Photo of 724 Avenue R NE, Winter Haven, FL 33881 (MLS # P4932149)
    Photo of 724 Avenue R NE, Winter Haven, FL 33881 (MLS # P4932149)
    724 Avenue R NE, Winter Haven, FL
    724 Avenue R NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,332 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  6. Photo of 145 Lameraux Road, Winter Haven, FL 33884 (MLS # O6244255)
    $355,000
    Photo of 145 Lameraux Road, Winter Haven, FL 33884 (MLS # O6244255)
    Photo of 145 Lameraux Road, Winter Haven, FL 33884 (MLS # O6244255)
    145 Lameraux Road, Winter Haven, FL
    145 Lameraux Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,873 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  7. Photo of 1700 6th Street NW #C1, Winter Haven, FL 33881 (MLS # P4932041)
    $123,000
    Photo of 1700 6th Street NW #C1, Winter Haven, FL 33881 (MLS # P4932041)
    Photo of 1700 6th Street NW #C1, Winter Haven, FL 33881 (MLS # P4932041)
    1700 6th Street NW #C1, Winter Haven, FL
    1700 6th Street NW #C1
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 840 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  8. Photo of 2049 San Marcos Drive SE #127, Winter Haven, FL 33880 (MLS # P4932103)
    $185,000
    Photo of 2049 San Marcos Drive SE #127, Winter Haven, FL 33880 (MLS # P4932103)
    Photo of 2049 San Marcos Drive SE #127, Winter Haven, FL 33880 (MLS # P4932103)
    2049 San Marcos Drive SE #127, Winter Haven, FL
    2049 San Marcos Drive SE #127
    Winter Haven, FL
    • 1 Bed
    • 1 Bath
    • 666 Home (sqft)
    • 1 Bath
    • 436 Lot (sqft)
  9. Photo of 83 Tyler Road, Winter Haven, FL 33884 (MLS # TB8306765)
    $375,000
    Photo of 83 Tyler Road, Winter Haven, FL 33884 (MLS # TB8306765)
    Photo of 83 Tyler Road, Winter Haven, FL 33884 (MLS # TB8306765)
    83 Tyler Road, Winter Haven, FL
    83 Tyler Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,563 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  10. Photo of 6030 Forest Ridge Lane, Winter Haven, FL 33881 (MLS # P4932142)
    $324,900
    Photo of 6030 Forest Ridge Lane, Winter Haven, FL 33881 (MLS # P4932142)
    Photo of 6030 Forest Ridge Lane, Winter Haven, FL 33881 (MLS # P4932142)
    6030 Forest Ridge Lane, Winter Haven, FL
    6030 Forest Ridge Lane
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,526 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  11. Photo of 4728 Magnolia Preserve Avenue, Winter Haven, FL 33880 (MLS # TB8306472)
    $299,900
    Photo of 4728 Magnolia Preserve Avenue, Winter Haven, FL 33880 (MLS # TB8306472)
    Photo of 4728 Magnolia Preserve Avenue, Winter Haven, FL 33880 (MLS # TB8306472)
    32
     
    4728 Magnolia Preserve Avenue, Winter Haven, FL
    4728 Magnolia Preserve Avenue
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,711 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  12. Photo of 385 Corso Loop, Winter Haven, FL 33884 (MLS # L4947711)
    $270,000
    Photo of 385 Corso Loop, Winter Haven, FL 33884 (MLS # L4947711)
    Photo of 385 Corso Loop, Winter Haven, FL 33884 (MLS # L4947711)
    385 Corso Loop, Winter Haven, FL
    385 Corso Loop
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,485 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  13. Photo of 1872 Carnostie Road, Winter Haven, FL 33884 (MLS # S5112759)
    $310,000
    Photo of 1872 Carnostie Road, Winter Haven, FL 33884 (MLS # S5112759)
    Photo of 1872 Carnostie Road, Winter Haven, FL 33884 (MLS # S5112759)
    1872 Carnostie Road, Winter Haven, FL
    1872 Carnostie Road
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,746 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  14. Photo of 345 Banyan Drive, Winter Haven, FL 33884 (MLS # P4931939)
    $295,000
    Photo of 345 Banyan Drive, Winter Haven, FL 33884 (MLS # P4931939)
    Photo of 345 Banyan Drive, Winter Haven, FL 33884 (MLS # P4931939)
    345 Banyan Drive, Winter Haven, FL
    345 Banyan Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,814 Home (sqft)
    • 2 Baths
    • 18,296 Lot (sqft)
  15. Photo of 871 Reflections Loop E, Winter Haven, FL 33884 (MLS # O6241708)
    $290,000
    Photo of 871 Reflections Loop E, Winter Haven, FL 33884 (MLS # O6241708)
    Photo of 871 Reflections Loop E, Winter Haven, FL 33884 (MLS # O6241708)
    871 Reflections Loop E, Winter Haven, FL
    871 Reflections Loop E
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,264 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  16. Photo of 5388 Hogan Lane, Winter Haven, FL 33884 (MLS # P4932110)
    $349,900
    Photo of 5388 Hogan Lane, Winter Haven, FL 33884 (MLS # P4932110)
    Photo of 5388 Hogan Lane, Winter Haven, FL 33884 (MLS # P4932110)
    5388 Hogan Lane, Winter Haven, FL
    5388 Hogan Lane
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,614 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  17. Photo of 105 24th Street SW, Winter Haven, FL 33880 (MLS # TB8306201)
    $285,000
    Photo of 105 24th Street SW, Winter Haven, FL 33880 (MLS # TB8306201)
    Photo of 105 24th Street SW, Winter Haven, FL 33880 (MLS # TB8306201)
    105 24th Street SW, Winter Haven, FL
    105 24th Street SW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,681 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  18. Photo of 829 Howard Terrace NW, Winter Haven, FL 33881 (MLS # S5112740)
    $367,500
    Photo of 829 Howard Terrace NW, Winter Haven, FL 33881 (MLS # S5112740)
    Photo of 829 Howard Terrace NW, Winter Haven, FL 33881 (MLS # S5112740)
    829 Howard Terrace NW, Winter Haven, FL
    829 Howard Terrace NW
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,336 Home (sqft)
    • 3 Baths
    • 20,909 Lot (sqft)
  19. Photo of 1109 Brenton Manor Drive, Winter Haven, FL 33881 (MLS # L4947760)
    $339,900
    Photo of 1109 Brenton Manor Drive, Winter Haven, FL 33881 (MLS # L4947760)
    Photo of 1109 Brenton Manor Drive, Winter Haven, FL 33881 (MLS # L4947760)
    1109 Brenton Manor Drive, Winter Haven, FL
    1109 Brenton Manor Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,976 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  20. Photo of 1397 Axel Circle, Winter Haven, FL 33880 (MLS # O6243543)
    $359,000
    Photo of 1397 Axel Circle, Winter Haven, FL 33880 (MLS # O6243543)
    Photo of 1397 Axel Circle, Winter Haven, FL 33880 (MLS # O6243543)
    1397 Axel Circle, Winter Haven, FL
    1397 Axel Circle
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,842 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  21. Photo of 3334 Avenue J NW, Winter Haven, FL 33881 (MLS # O6243276)
    $255,000
    Photo of 3334 Avenue J NW, Winter Haven, FL 33881 (MLS # O6243276)
    Photo of 3334 Avenue J NW, Winter Haven, FL 33881 (MLS # O6243276)
    3334 Avenue J NW, Winter Haven, FL
    3334 Avenue J NW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,473 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  22. Photo of 142 Avenue F SW, Winter Haven, FL 33880 (MLS # O6242965)
    $210,000
    Photo of 142 Avenue F SW, Winter Haven, FL 33880 (MLS # O6242965)
    Photo of 142 Avenue F SW, Winter Haven, FL 33880 (MLS # O6242965)
    31
     
    142 Avenue F SW, Winter Haven, FL
    142 Avenue F SW
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 1,114 Home (sqft)
    • 1 Bath
    • 6,534 Lot (sqft)
  23. Photo of 4949 Jackson Street, Winter Haven, FL 33884 (MLS # O6242941)
    $357,900
    Photo of 4949 Jackson Street, Winter Haven, FL 33884 (MLS # O6242941)
    Photo of 4949 Jackson Street, Winter Haven, FL 33884 (MLS # O6242941)
    4949 Jackson Street, Winter Haven, FL
    4949 Jackson Street
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,284 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  24. Photo of 4093 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6242854)
    $337,490
    Photo of 4093 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6242854)
    Photo of 4093 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6242854)
    4093 Giorgio Drive, Winter Haven, FL
    4093 Giorgio Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,672 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  25. Photo of 4097 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6242846)
    $351,490
    Photo of 4097 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6242846)
    Photo of 4097 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6242846)
    4097 Giorgio Drive, Winter Haven, FL
    4097 Giorgio Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,828 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  26. Photo of 4101 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6242842)
    $344,490
    Photo of 4101 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6242842)
    Photo of 4101 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6242842)
    4101 Giorgio Drive, Winter Haven, FL
    4101 Giorgio Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,828 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  27. Photo of 333 Lake Howard Drive NW #111C, Winter Haven, FL 33880 (MLS # O6241265)
    $140,000
    Photo of 333 Lake Howard Drive NW #111C, Winter Haven, FL 33880 (MLS # O6241265)
    Photo of 333 Lake Howard Drive NW #111C, Winter Haven, FL 33880 (MLS # O6241265)
    333 Lake Howard Drive NW #111C, Winter Haven, FL
    333 Lake Howard Drive NW #111C
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,030 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  28. Photo of 1042 Brimstone Circle, Winter Haven, FL 33884 (MLS # TB8305175)
    $389,995
    Photo of 1042 Brimstone Circle, Winter Haven, FL 33884 (MLS # TB8305175)
    Photo of 1042 Brimstone Circle, Winter Haven, FL 33884 (MLS # TB8305175)
    1042 Brimstone Circle, Winter Haven, FL
    1042 Brimstone Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,810 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  29. Photo of 2068 Marigold Alley, Winter Haven, FL 33884 (MLS # TB8305160)
    $370,995
    Photo of 2068 Marigold Alley, Winter Haven, FL 33884 (MLS # TB8305160)
    Photo of 2068 Marigold Alley, Winter Haven, FL 33884 (MLS # TB8305160)
    2068 Marigold Alley, Winter Haven, FL
    2068 Marigold Alley
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,423 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  30. Photo of 2060 Marigold Alley, Winter Haven, FL 33884 (MLS # TB8305155)
    $350,995
    Photo of 2060 Marigold Alley, Winter Haven, FL 33884 (MLS # TB8305155)
    Photo of 2060 Marigold Alley, Winter Haven, FL 33884 (MLS # TB8305155)
    2060 Marigold Alley, Winter Haven, FL
    2060 Marigold Alley
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,240 Home (sqft)
    • 3 Baths
    • 5,663 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 11/23/24 12:13 AM PST.

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