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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 113 5th Eloise Street, Winter Haven, FL 33880 (MLS # P4931752)
    $220,000
    Photo of 113 5th Eloise Street, Winter Haven, FL 33880 (MLS # P4931752)
    Photo of 113 5th Eloise Street, Winter Haven, FL 33880 (MLS # P4931752)
    113 5th Eloise Street, Winter Haven, FL
    113 5th Eloise Street
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 660 Home (sqft)
    • 1 Bath
    • 6,099 Lot (sqft)
  2. Photo of 5716 Lakeside Landings Boulevard, Winter Haven, FL 33881 (MLS # O6235730)
    $299,000
    Photo of 5716 Lakeside Landings Boulevard, Winter Haven, FL 33881 (MLS # O6235730)
    Photo of 5716 Lakeside Landings Boulevard, Winter Haven, FL 33881 (MLS # O6235730)
    5716 Lakeside Landings Boulevard, Winter Haven, FL
    5716 Lakeside Landings Boulevard
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,748 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  3. Photo of 3303 Fox Ridge Drive, Winter Haven, FL 33884 (MLS # O6233613)
    $299,900
    Photo of 3303 Fox Ridge Drive, Winter Haven, FL 33884 (MLS # O6233613)
    Photo of 3303 Fox Ridge Drive, Winter Haven, FL 33884 (MLS # O6233613)
    3303 Fox Ridge Drive, Winter Haven, FL
    3303 Fox Ridge Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,168 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  4. Photo of 393 Kayden Cove, Winter Haven, FL 33884 (MLS # T3550971)
    $350,310
    Photo of 393 Kayden Cove, Winter Haven, FL 33884 (MLS # T3550971)
    Photo of 393 Kayden Cove, Winter Haven, FL 33884 (MLS # T3550971)
    393 Kayden Cove, Winter Haven, FL
    393 Kayden Cove
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,109 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  5. Photo of 3555 Harbor Circle NW, Winter Haven, FL 33881 (MLS # P4931713)
    $279,900
    Photo of 3555 Harbor Circle NW, Winter Haven, FL 33881 (MLS # P4931713)
    Photo of 3555 Harbor Circle NW, Winter Haven, FL 33881 (MLS # P4931713)
    3555 Harbor Circle NW, Winter Haven, FL
    3555 Harbor Circle NW
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,358 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
  6. Photo of 5069 Brenton Manor Avenue, Winter Haven, FL 33881 (MLS # L4946979)
    $299,000
    Photo of 5069 Brenton Manor Avenue, Winter Haven, FL 33881 (MLS # L4946979)
    Photo of 5069 Brenton Manor Avenue, Winter Haven, FL 33881 (MLS # L4946979)
    5069 Brenton Manor Avenue, Winter Haven, FL
    5069 Brenton Manor Avenue
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,895 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  7. Photo of 543 Squires Grove Drive, Winter Haven, FL 33880 (MLS # P4931744)
    $305,000
    Photo of 543 Squires Grove Drive, Winter Haven, FL 33880 (MLS # P4931744)
    Photo of 543 Squires Grove Drive, Winter Haven, FL 33880 (MLS # P4931744)
    543 Squires Grove Drive, Winter Haven, FL
    543 Squires Grove Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,526 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  8. Photo of 140 Solis Drive, Winter Haven, FL 33880 (MLS # L4946522)
    $330,000
    Photo of 140 Solis Drive, Winter Haven, FL 33880 (MLS # L4946522)
    Photo of 140 Solis Drive, Winter Haven, FL 33880 (MLS # L4946522)
    140 Solis Drive, Winter Haven, FL
    140 Solis Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,814 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  9. Photo of 1521 Oakview Circle SE, Winter Haven, FL 33880 (MLS # P4931725)
    $227,000
    Photo of 1521 Oakview Circle SE, Winter Haven, FL 33880 (MLS # P4931725)
    Photo of 1521 Oakview Circle SE, Winter Haven, FL 33880 (MLS # P4931725)
    1521 Oakview Circle SE, Winter Haven, FL
    1521 Oakview Circle SE
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,186 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  10. Photo of 180 Inman Boulevard, Winter Haven, FL 33881 (MLS # L4947004)
    $359,900
    Photo of 180 Inman Boulevard, Winter Haven, FL 33881 (MLS # L4947004)
    Photo of 180 Inman Boulevard, Winter Haven, FL 33881 (MLS # L4947004)
    180 Inman Boulevard, Winter Haven, FL
    180 Inman Boulevard
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,853 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  11. Photo of 1333 Lucerne Loop Road NE, Winter Haven, FL 33881 (MLS # T3546919)
    $294,000
    Photo of 1333 Lucerne Loop Road NE, Winter Haven, FL 33881 (MLS # T3546919)
    Photo of 1333 Lucerne Loop Road NE, Winter Haven, FL 33881 (MLS # T3546919)
    1333 Lucerne Loop Road NE, Winter Haven, FL
    1333 Lucerne Loop Road NE
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,746 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  12. Photo of 1646 Seth Drive, Winter Haven, FL 33880 (MLS # T3551848)
    $366,000
    Photo of 1646 Seth Drive, Winter Haven, FL 33880 (MLS # T3551848)
    Photo of 1646 Seth Drive, Winter Haven, FL 33880 (MLS # T3551848)
    40
     
    1646 Seth Drive, Winter Haven, FL
    1646 Seth Drive
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,523 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  13. Photo of 6023 Country Walk Lane, Winter Haven, FL 33880 (MLS # T3551358)
    $380,000
    Photo of 6023 Country Walk Lane, Winter Haven, FL 33880 (MLS # T3551358)
    Photo of 6023 Country Walk Lane, Winter Haven, FL 33880 (MLS # T3551358)
    6023 Country Walk Lane, Winter Haven, FL
    6023 Country Walk Lane
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,643 Home (sqft)
    • 2 Baths
    • 14,811 Lot (sqft)
  14. Photo of 1502 NE Buckeye Road NE #2, Winter Haven, FL 33881 (MLS # A4620747)
    $209,900
    Photo of 1502 NE Buckeye Road NE #2, Winter Haven, FL 33881 (MLS # A4620747)
    Photo of 1502 NE Buckeye Road NE #2, Winter Haven, FL 33881 (MLS # A4620747)
    1502 NE Buckeye Road NE #2, Winter Haven, FL
    1502 NE Buckeye Road NE #2
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,004 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  15. Photo of 481 Kensington View Drive, Winter Haven, FL 33880 (MLS # P4931709)
    $319,900
    Photo of 481 Kensington View Drive, Winter Haven, FL 33880 (MLS # P4931709)
    Photo of 481 Kensington View Drive, Winter Haven, FL 33880 (MLS # P4931709)
    481 Kensington View Drive, Winter Haven, FL
    481 Kensington View Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,746 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  16. Photo of 1025 W W Lake Hamilton Drive, Winter Haven, FL 33881 (MLS # S5110693)
    $379,900
    Photo of 1025 W W Lake Hamilton Drive, Winter Haven, FL 33881 (MLS # S5110693)
    Photo of 1025 W W Lake Hamilton Drive, Winter Haven, FL 33881 (MLS # S5110693)
    1025 W W Lake Hamilton Drive, Winter Haven, FL
    1025 W W Lake Hamilton Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,785 Home (sqft)
    • 2 Baths
    • 23,958 Lot (sqft)
  17. Photo of 4146 Bedford Ave, Winter Haven, FL 33884 (MLS # P4931674)
    $298,900
    Photo of 4146 Bedford Ave, Winter Haven, FL 33884 (MLS # P4931674)
    Photo of 4146 Bedford Ave, Winter Haven, FL 33884 (MLS # P4931674)
    4146 Bedford Ave, Winter Haven, FL
    4146 Bedford Ave
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,819 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  18. Photo of 1502 NE Buckeye Road NE #3, Winter Haven, FL 33881 (MLS # A4620534)
    $169,900
    Photo of 1502 NE Buckeye Road NE #3, Winter Haven, FL 33881 (MLS # A4620534)
    Photo of 1502 NE Buckeye Road NE #3, Winter Haven, FL 33881 (MLS # A4620534)
    1502 NE Buckeye Road NE #3, Winter Haven, FL
    1502 NE Buckeye Road NE #3
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,257 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
  19. Photo of 118 Orange Avenue, Winter Haven, FL 33880 (MLS # T3545063)
    $225,000
    Photo of 118 Orange Avenue, Winter Haven, FL 33880 (MLS # T3545063)
    Photo of 118 Orange Avenue, Winter Haven, FL 33880 (MLS # T3545063)
    118 Orange Avenue, Winter Haven, FL
    118 Orange Avenue
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,210 Home (sqft)
    • 1 Bath
    • 8,277 Lot (sqft)
  20. Photo of 820 Avenue Z NW, Winter Haven, FL 33881 (MLS # P4931677)
    $318,000
    Photo of 820 Avenue Z NW, Winter Haven, FL 33881 (MLS # P4931677)
    Photo of 820 Avenue Z NW, Winter Haven, FL 33881 (MLS # P4931677)
    820 Avenue Z NW, Winter Haven, FL
    820 Avenue Z NW
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,082 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
  21. Photo of 2214 Avenue F NW, Winter Haven, FL 33880 (MLS # S5110533)
    $210,000
    Photo of 2214 Avenue F NW, Winter Haven, FL 33880 (MLS # S5110533)
    Photo of 2214 Avenue F NW, Winter Haven, FL 33880 (MLS # S5110533)
    2214 Avenue F NW, Winter Haven, FL
    2214 Avenue F NW
    Winter Haven, FL
    • 4 Beds
    • 1 Bath
    • 702 Home (sqft)
    • 1 Bath
    • 6,534 Lot (sqft)
  22. Photo of 1022 30th Street NW, Winter Haven, FL 33881 (MLS # S5110295)
    $250,000
    Photo of 1022 30th Street NW, Winter Haven, FL 33881 (MLS # S5110295)
    Photo of 1022 30th Street NW, Winter Haven, FL 33881 (MLS # S5110295)
    1022 30th Street NW, Winter Haven, FL
    1022 30th Street NW
    Winter Haven, FL
    • 4 Beds
    • 1 Bath
    • 1,129 Home (sqft)
    • 1 Bath
    • 9,148 Lot (sqft)
  23. Photo of 547 Highfin Drive, Winter Haven, FL 33881 (MLS # S5110172)
    $350,000
    Photo of 547 Highfin Drive, Winter Haven, FL 33881 (MLS # S5110172)
    Photo of 547 Highfin Drive, Winter Haven, FL 33881 (MLS # S5110172)
    547 Highfin Drive, Winter Haven, FL
    547 Highfin Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,004 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  24. Photo of 205 Avenue U NW, Winter Haven, FL 33881 (MLS # P4931646)
    $300,000
    Photo of 205 Avenue U NW, Winter Haven, FL 33881 (MLS # P4931646)
    Photo of 205 Avenue U NW, Winter Haven, FL 33881 (MLS # P4931646)
    205 Avenue U NW, Winter Haven, FL
    205 Avenue U NW
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,588 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  25. Photo of 1995 Helena Road, Winter Haven, FL 33884 (MLS # T3548619)
    $325,000
    Photo of 1995 Helena Road, Winter Haven, FL 33884 (MLS # T3548619)
    Photo of 1995 Helena Road, Winter Haven, FL 33884 (MLS # T3548619)
    35
     
    1995 Helena Road, Winter Haven, FL
    1995 Helena Road
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,108 Home (sqft)
    • 2 Baths
    • 25,701 Lot (sqft)
  26. Photo of 602 Taylor Boulevard, Winter Haven, FL 33880 (MLS # L4946859)
    $264,500
    Photo of 602 Taylor Boulevard, Winter Haven, FL 33880 (MLS # L4946859)
    Photo of 602 Taylor Boulevard, Winter Haven, FL 33880 (MLS # L4946859)
    602 Taylor Boulevard, Winter Haven, FL
    602 Taylor Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,242 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  27. Photo of 1077 Medinah Way, Winter Haven, FL 33884 (MLS # K4902611)
    $244,000
    Photo of 1077 Medinah Way, Winter Haven, FL 33884 (MLS # K4902611)
    Photo of 1077 Medinah Way, Winter Haven, FL 33884 (MLS # K4902611)
    1077 Medinah Way, Winter Haven, FL
    1077 Medinah Way
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,563 Home (sqft)
    • 2 Baths
    • 2,178 Lot (sqft)
  28. Photo of 150 El Dorado #107, Winter Haven, FL 33884 (MLS # P4931642)
    $151,000
    Photo of 150 El Dorado #107, Winter Haven, FL 33884 (MLS # P4931642)
    Photo of 150 El Dorado #107, Winter Haven, FL 33884 (MLS # P4931642)
    150 El Dorado #107, Winter Haven, FL
    150 El Dorado #107
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,372 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  29. Photo of 1905 Manor Circle SE, Winter Haven, FL 33880 (MLS # O6232532)
    $355,000
    Photo of 1905 Manor Circle SE, Winter Haven, FL 33880 (MLS # O6232532)
    Photo of 1905 Manor Circle SE, Winter Haven, FL 33880 (MLS # O6232532)
    1905 Manor Circle SE, Winter Haven, FL
    1905 Manor Circle SE
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,067 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
  30. Photo of 450 Avenue B NE, Winter Haven, FL 33881 (MLS # T3548780)
    $299,900
    Photo of 450 Avenue B NE, Winter Haven, FL 33881 (MLS # T3548780)
    Photo of 450 Avenue B NE, Winter Haven, FL 33881 (MLS # T3548780)
    450 Avenue B NE, Winter Haven, FL
    450 Avenue B NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,624 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
Previous Page 14 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 10:13 AM PST.

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