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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 4104 Martindale Loop, Winter Haven, FL 33884 (MLS # P4932036)
    $341,900
    Photo of 4104 Martindale Loop, Winter Haven, FL 33884 (MLS # P4932036)
    Photo of 4104 Martindale Loop, Winter Haven, FL 33884 (MLS # P4932036)
    4104 Martindale Loop, Winter Haven, FL
    4104 Martindale Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,862 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  2. Photo of 2410 Brassie Court, Winter Haven, FL 33884 (MLS # O6244666)
    $285,000
    Photo of 2410 Brassie Court, Winter Haven, FL 33884 (MLS # O6244666)
    Photo of 2410 Brassie Court, Winter Haven, FL 33884 (MLS # O6244666)
    2410 Brassie Court, Winter Haven, FL
    2410 Brassie Court
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,464 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  3. Photo of 140 Longfellow Road, Winter Haven, FL 33884 (MLS # O6242790)
    $241,000
    Photo of 140 Longfellow Road, Winter Haven, FL 33884 (MLS # O6242790)
    Photo of 140 Longfellow Road, Winter Haven, FL 33884 (MLS # O6242790)
    140 Longfellow Road, Winter Haven, FL
    140 Longfellow Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,328 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  4. Photo of 2004 Garden Lake Drive #2004, Winter Haven, FL 33884 (MLS # P4931974)
    $174,900
    Photo of 2004 Garden Lake Drive #2004, Winter Haven, FL 33884 (MLS # P4931974)
    Photo of 2004 Garden Lake Drive #2004, Winter Haven, FL 33884 (MLS # P4931974)
    13
     
    2004 Garden Lake Drive #2004, Winter Haven, FL
    2004 Garden Lake Drive #2004
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,103 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  5. Photo of 1103 30th Street NW, Winter Haven, FL 33881 (MLS # O6242500)
    $289,995
    Photo of 1103 30th Street NW, Winter Haven, FL 33881 (MLS # O6242500)
    Photo of 1103 30th Street NW, Winter Haven, FL 33881 (MLS # O6242500)
    1103 30th Street NW, Winter Haven, FL
    1103 30th Street NW
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,167 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  6. Photo of 3769 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6241018)
    $317,305
    Photo of 3769 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6241018)
    Photo of 3769 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6241018)
    3769 Giorgio Drive, Winter Haven, FL
    3769 Giorgio Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,988 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  7. Photo of 121 Coleman Road, Winter Haven, FL 33880 (MLS # L4947719)
    $279,000
    Photo of 121 Coleman Road, Winter Haven, FL 33880 (MLS # L4947719)
    Photo of 121 Coleman Road, Winter Haven, FL 33880 (MLS # L4947719)
    32
     
    121 Coleman Road, Winter Haven, FL
    121 Coleman Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,602 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  8. Photo of 4852 Magnolia Preserve Drive, Winter Haven, FL 33880 (MLS # O6228253)
    $326,999
    Photo of 4852 Magnolia Preserve Drive, Winter Haven, FL 33880 (MLS # O6228253)
    Photo of 4852 Magnolia Preserve Drive, Winter Haven, FL 33880 (MLS # O6228253)
    4852 Magnolia Preserve Drive, Winter Haven, FL
    4852 Magnolia Preserve Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,726 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  9. Photo of 118 5th Jpv Street, Winter Haven, FL 33880 (MLS # TB8304063)
    $239,900
    Photo of 118 5th Jpv Street, Winter Haven, FL 33880 (MLS # TB8304063)
    Photo of 118 5th Jpv Street, Winter Haven, FL 33880 (MLS # TB8304063)
    118 5th Jpv Street, Winter Haven, FL
    118 5th Jpv Street
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,080 Home (sqft)
    • 1 Bath
    • 10,019 Lot (sqft)
  10. Photo of 1560 Leamington Ln, Winter Haven, FL 33884 (MLS # P4932032)
    $360,366
    Photo of 1560 Leamington Ln, Winter Haven, FL 33884 (MLS # P4932032)
    Photo of 1560 Leamington Ln, Winter Haven, FL 33884 (MLS # P4932032)
    1560 Leamington Ln, Winter Haven, FL
    1560 Leamington Ln
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,200 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  11. Photo of Winter Haven, FL 33884 (MLS # P4932030)
    $357,366
    Photo of Winter Haven, FL 33884 (MLS # P4932030)
    Photo of Winter Haven, FL 33884 (MLS # P4932030)
    MLS # P4932030, Winter Haven, FL
    MLS # P4932030
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,200 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  12. Photo of Winter Haven, FL 33884 (MLS # P4932029)
    $321,660
    Photo of Winter Haven, FL 33884 (MLS # P4932029)
    Photo of Winter Haven, FL 33884 (MLS # P4932029)
    MLS # P4932029, Winter Haven, FL
    MLS # P4932029
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,820 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  13. Photo of 333 Lake Howard Drive NW #103A, Winter Haven, FL 33880 (MLS # TB8303272)
    $129,000
    Photo of 333 Lake Howard Drive NW #103A, Winter Haven, FL 33880 (MLS # TB8303272)
    Photo of 333 Lake Howard Drive NW #103A, Winter Haven, FL 33880 (MLS # TB8303272)
    333 Lake Howard Drive NW #103A, Winter Haven, FL
    333 Lake Howard Drive NW #103A
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,030 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  14. Photo of 1480 Leamington Ln, Winter Haven, FL 33884 (MLS # P4932028)
    $350,529
    Photo of 1480 Leamington Ln, Winter Haven, FL 33884 (MLS # P4932028)
    Photo of 1480 Leamington Ln, Winter Haven, FL 33884 (MLS # P4932028)
    1480 Leamington Ln, Winter Haven, FL
    1480 Leamington Ln
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,202 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  15. Photo of 640 Jaxson Boulevard, Winter Haven, FL 33880 (MLS # O6247163)
    $340,000
    Photo of 640 Jaxson Boulevard, Winter Haven, FL 33880 (MLS # O6247163)
    Photo of 640 Jaxson Boulevard, Winter Haven, FL 33880 (MLS # O6247163)
    640 Jaxson Boulevard, Winter Haven, FL
    640 Jaxson Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,816 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  16. Photo of 283 Lake Lucerne Way, Winter Haven, FL 33881 (MLS # P4932022)
    $349,990
    Photo of 283 Lake Lucerne Way, Winter Haven, FL 33881 (MLS # P4932022)
    Photo of 283 Lake Lucerne Way, Winter Haven, FL 33881 (MLS # P4932022)
    283 Lake Lucerne Way, Winter Haven, FL
    283 Lake Lucerne Way
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,944 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  17. Photo of Winter Haven, FL 33881 (MLS # S5112472)
    $305,000
    Photo of Winter Haven, FL 33881 (MLS # S5112472)
    Photo of Winter Haven, FL 33881 (MLS # S5112472)
    MLS # S5112472, Winter Haven, FL
    MLS # S5112472
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,690 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  18. Photo of 50 Winter Ridge Road #50, Winter Haven, FL 33881 (MLS # O6241509)
    $165,000
    Photo of 50 Winter Ridge Road #50, Winter Haven, FL 33881 (MLS # O6241509)
    Photo of 50 Winter Ridge Road #50, Winter Haven, FL 33881 (MLS # O6241509)
    17
     
    50 Winter Ridge Road #50, Winter Haven, FL
    50 Winter Ridge Road #50
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,073 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  19. Photo of 2331 Salzburg Loop, Winter Haven, FL 33884 (MLS # O6241501)
    $284,900
    Photo of 2331 Salzburg Loop, Winter Haven, FL 33884 (MLS # O6241501)
    Photo of 2331 Salzburg Loop, Winter Haven, FL 33884 (MLS # O6241501)
    2331 Salzburg Loop, Winter Haven, FL
    2331 Salzburg Loop
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,838 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  20. Photo of 6612 Winterset Gardens Rd, Winter Haven, FL 33884 (MLS # P4932012)
    $374,900
    Photo of 6612 Winterset Gardens Rd, Winter Haven, FL 33884 (MLS # P4932012)
    Photo of 6612 Winterset Gardens Rd, Winter Haven, FL 33884 (MLS # P4932012)
    6612 Winterset Gardens Rd, Winter Haven, FL
    6612 Winterset Gardens Rd
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,930 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  21. Photo of 1008 Spirit Lake Road, Winter Haven, FL 33880 (MLS # O6241428)
    $283,800
    Photo of 1008 Spirit Lake Road, Winter Haven, FL 33880 (MLS # O6241428)
    Photo of 1008 Spirit Lake Road, Winter Haven, FL 33880 (MLS # O6241428)
    1008 Spirit Lake Road, Winter Haven, FL
    1008 Spirit Lake Road
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,410 Home (sqft)
    • 2 Baths
    • 24,830 Lot (sqft)
  22. Photo of 64 Coleman Road, Winter Haven, FL 33880 (MLS # S5112127)
    $239,000
    Photo of 64 Coleman Road, Winter Haven, FL 33880 (MLS # S5112127)
    Photo of 64 Coleman Road, Winter Haven, FL 33880 (MLS # S5112127)
    64 Coleman Road, Winter Haven, FL
    64 Coleman Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,074 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  23. Photo of 1717 31st St NW, Winter Haven, FL 33881 (MLS # S5112078)
    $240,000
    Photo of 1717 31st St NW, Winter Haven, FL 33881 (MLS # S5112078)
    Photo of 1717 31st St NW, Winter Haven, FL 33881 (MLS # S5112078)
    21
     
    1717 31st St NW, Winter Haven, FL
    1717 31st St NW
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,504 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  24. Photo of 1413 Wallace Manor Pass, Winter Haven, FL 33880 (MLS # L4947599)
    $298,000
    Photo of 1413 Wallace Manor Pass, Winter Haven, FL 33880 (MLS # L4947599)
    Photo of 1413 Wallace Manor Pass, Winter Haven, FL 33880 (MLS # L4947599)
    1413 Wallace Manor Pass, Winter Haven, FL
    1413 Wallace Manor Pass
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,842 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  25. Photo of 1476 Leamington Ln, Winter Haven, FL 33884 (MLS # P4931995)
    $363,967
    Photo of 1476 Leamington Ln, Winter Haven, FL 33884 (MLS # P4931995)
    Photo of 1476 Leamington Ln, Winter Haven, FL 33884 (MLS # P4931995)
    1476 Leamington Ln, Winter Haven, FL
    1476 Leamington Ln
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,405 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  26. Photo of 71 Sunset View Drive, Winter Haven, FL 33884 (MLS # P4931991)
    $379,000
    Photo of 71 Sunset View Drive, Winter Haven, FL 33884 (MLS # P4931991)
    Photo of 71 Sunset View Drive, Winter Haven, FL 33884 (MLS # P4931991)
    71 Sunset View Drive, Winter Haven, FL
    71 Sunset View Drive
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,673 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  27. Photo of 3711 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # S5112162)
    $342,000
    Photo of 3711 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # S5112162)
    Photo of 3711 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # S5112162)
    25
     
    3711 Julius Estates Boulevard, Winter Haven, FL
    3711 Julius Estates Boulevard
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,842 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  28. Photo of 2222 12th Street NW, Winter Haven, FL 33881 (MLS # S5112141)
    $388,000
    Photo of 2222 12th Street NW, Winter Haven, FL 33881 (MLS # S5112141)
    Photo of 2222 12th Street NW, Winter Haven, FL 33881 (MLS # S5112141)
    2222 12th Street NW, Winter Haven, FL
    2222 12th Street NW
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 792 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  29. Photo of 129 Florida Drive, Winter Haven, FL 33881 (MLS # TB8311372)
    $199,900
    Photo of 129 Florida Drive, Winter Haven, FL 33881 (MLS # TB8311372)
    Photo of 129 Florida Drive, Winter Haven, FL 33881 (MLS # TB8311372)
    30
     
    129 Florida Drive, Winter Haven, FL
    129 Florida Drive
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,088 Home (sqft)
    • 1 Bath
    • 7,406 Lot (sqft)
  30. Photo of 515 Avenue F SE, Winter Haven, FL 33880 (MLS # P4931976)
    $225,000
    Photo of 515 Avenue F SE, Winter Haven, FL 33880 (MLS # P4931976)
    Photo of 515 Avenue F SE, Winter Haven, FL 33880 (MLS # P4931976)
    515 Avenue F SE, Winter Haven, FL
    515 Avenue F SE
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,696 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
Previous Page 11 of 17 Next
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 2:13 AM PST.

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