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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 108 5th Jpv Street, Winter Haven, FL 33880 (MLS # O6246683)
    $249,900
    Photo of 108 5th Jpv Street, Winter Haven, FL 33880 (MLS # O6246683)
    Photo of 108 5th Jpv Street, Winter Haven, FL 33880 (MLS # O6246683)
    108 5th Jpv Street, Winter Haven, FL
    108 5th Jpv Street
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 900 Home (sqft)
    • 1 Bath
    • 10,455 Lot (sqft)
  2. Photo of 3329 Royal Tern Drive, Winter Haven, FL 33881 (MLS # S5113265)
    $320,000
    Photo of 3329 Royal Tern Drive, Winter Haven, FL 33881 (MLS # S5113265)
    Photo of 3329 Royal Tern Drive, Winter Haven, FL 33881 (MLS # S5113265)
    3329 Royal Tern Drive, Winter Haven, FL
    3329 Royal Tern Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,867 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  3. Photo of 1864 Avenue Q SW #1864, Winter Haven, FL 33880 (MLS # R4908365)
    $129,900
    Photo of 1864 Avenue Q SW #1864, Winter Haven, FL 33880 (MLS # R4908365)
    Photo of 1864 Avenue Q SW #1864, Winter Haven, FL 33880 (MLS # R4908365)
    1864 Avenue Q SW #1864, Winter Haven, FL
    1864 Avenue Q SW #1864
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 992 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  4. Photo of 2258 Firestone Place, Winter Haven, FL 33884 (MLS # P4932267)
    $229,900
    Photo of 2258 Firestone Place, Winter Haven, FL 33884 (MLS # P4932267)
    Photo of 2258 Firestone Place, Winter Haven, FL 33884 (MLS # P4932267)
    2258 Firestone Place, Winter Haven, FL
    2258 Firestone Place
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,439 Home (sqft)
    • 2 Baths
    • 2,178 Lot (sqft)
  5. Photo of 208 Shelley Drive, Winter Haven, FL 33884 (MLS # TB8309001)
    $279,900
    Photo of 208 Shelley Drive, Winter Haven, FL 33884 (MLS # TB8309001)
    Photo of 208 Shelley Drive, Winter Haven, FL 33884 (MLS # TB8309001)
    208 Shelley Drive, Winter Haven, FL
    208 Shelley Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,364 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  6. Photo of 142 Morning Glory Circle, Winter Haven, FL 33884 (MLS # P4932234)
    $340,000
    Photo of 142 Morning Glory Circle, Winter Haven, FL 33884 (MLS # P4932234)
    Photo of 142 Morning Glory Circle, Winter Haven, FL 33884 (MLS # P4932234)
    142 Morning Glory Circle, Winter Haven, FL
    142 Morning Glory Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,887 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  7. Photo of 235 24th Court SW, Winter Haven, FL 33880 (MLS # L4947875)
    $320,000
    Photo of 235 24th Court SW, Winter Haven, FL 33880 (MLS # L4947875)
    Photo of 235 24th Court SW, Winter Haven, FL 33880 (MLS # L4947875)
    235 24th Court SW, Winter Haven, FL
    235 24th Court SW
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,713 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  8. Photo of 1512 Avenue F NE, Winter Haven, FL 33881 (MLS # P4932240)
    $239,000
    Photo of 1512 Avenue F NE, Winter Haven, FL 33881 (MLS # P4932240)
    Photo of 1512 Avenue F NE, Winter Haven, FL 33881 (MLS # P4932240)
    1512 Avenue F NE, Winter Haven, FL
    1512 Avenue F NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,389 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  9. Photo of 3029 Royal Tern Drive, Winter Haven, FL 33881 (MLS # TB8308367)
    $315,000
    Photo of 3029 Royal Tern Drive, Winter Haven, FL 33881 (MLS # TB8308367)
    Photo of 3029 Royal Tern Drive, Winter Haven, FL 33881 (MLS # TB8308367)
    3029 Royal Tern Drive, Winter Haven, FL
    3029 Royal Tern Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,867 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  10. Photo of 1910 Avenue O SW, Winter Haven, FL 33880 (MLS # P4932233)
    $259,900
    Photo of 1910 Avenue O SW, Winter Haven, FL 33880 (MLS # P4932233)
    Photo of 1910 Avenue O SW, Winter Haven, FL 33880 (MLS # P4932233)
    44
     
    1910 Avenue O SW, Winter Haven, FL
    1910 Avenue O SW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,094 Home (sqft)
    • 2 Baths
    • 20,038 Lot (sqft)
  11. Photo of 1990 5th Street NE, Winter Haven, FL 33881 (MLS # L4947961)
    $185,000
    Photo of 1990 5th Street NE, Winter Haven, FL 33881 (MLS # L4947961)
    Photo of 1990 5th Street NE, Winter Haven, FL 33881 (MLS # L4947961)
    1990 5th Street NE, Winter Haven, FL
    1990 5th Street NE
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 928 Home (sqft)
    • 1 Bath
    • 6,534 Lot (sqft)
  12. Photo of 212 Towhee Road, Winter Haven, FL 33881 (MLS # L4947956)
    $304,000
    Photo of 212 Towhee Road, Winter Haven, FL 33881 (MLS # L4947956)
    Photo of 212 Towhee Road, Winter Haven, FL 33881 (MLS # L4947956)
    212 Towhee Road, Winter Haven, FL
    212 Towhee Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,624 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
  13. Photo of 345 Escambia Drive, Winter Haven, FL 33884 (MLS # W7868737)
    $339,000
    Photo of 345 Escambia Drive, Winter Haven, FL 33884 (MLS # W7868737)
    Photo of 345 Escambia Drive, Winter Haven, FL 33884 (MLS # W7868737)
    345 Escambia Drive, Winter Haven, FL
    345 Escambia Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,809 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
  14. Photo of 960 Drexel Avenue NE, Winter Haven, FL 33881 (MLS # P4932223)
    $235,000
    Photo of 960 Drexel Avenue NE, Winter Haven, FL 33881 (MLS # P4932223)
    Photo of 960 Drexel Avenue NE, Winter Haven, FL 33881 (MLS # P4932223)
    960 Drexel Avenue NE, Winter Haven, FL
    960 Drexel Avenue NE
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 828 Home (sqft)
    • 1 Bath
    • 11,326 Lot (sqft)
  15. Photo of 3113 Elm Street, Winter Haven, FL 33881 (MLS # P4932213)
    $212,500
    Photo of 3113 Elm Street, Winter Haven, FL 33881 (MLS # P4932213)
    Photo of 3113 Elm Street, Winter Haven, FL 33881 (MLS # P4932213)
    3113 Elm Street, Winter Haven, FL
    3113 Elm Street
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,340 Home (sqft)
    • 1 Bath
    • 13,068 Lot (sqft)
  16. Photo of 12 Enclave Drive, Winter Haven, FL 33884 (MLS # P4932115)
    $280,000
    Photo of 12 Enclave Drive, Winter Haven, FL 33884 (MLS # P4932115)
    Photo of 12 Enclave Drive, Winter Haven, FL 33884 (MLS # P4932115)
    12 Enclave Drive, Winter Haven, FL
    12 Enclave Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,526 Home (sqft)
    • 2 Baths
    • 2,178 Lot (sqft)
  17. Photo of 355 Winter Ridge Boulevard #355, Winter Haven, FL 33881 (MLS # O6245592)
    $195,000
    Photo of 355 Winter Ridge Boulevard #355, Winter Haven, FL 33881 (MLS # O6245592)
    Photo of 355 Winter Ridge Boulevard #355, Winter Haven, FL 33881 (MLS # O6245592)
    355 Winter Ridge Boulevard #355, Winter Haven, FL
    355 Winter Ridge Boulevard #355
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,073 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  18. Photo of 296 Krenson Bay Loop, Winter Haven, FL 33881 (MLS # P4932072)
    $309,909
    Photo of 296 Krenson Bay Loop, Winter Haven, FL 33881 (MLS # P4932072)
    Photo of 296 Krenson Bay Loop, Winter Haven, FL 33881 (MLS # P4932072)
    296 Krenson Bay Loop, Winter Haven, FL
    296 Krenson Bay Loop
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,846 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  19. Photo of 251 Lake Howard Drive SW, Winter Haven, FL 33880 (MLS # L4947902)
    $345,000
    Photo of 251 Lake Howard Drive SW, Winter Haven, FL 33880 (MLS # L4947902)
    Photo of 251 Lake Howard Drive SW, Winter Haven, FL 33880 (MLS # L4947902)
    251 Lake Howard Drive SW, Winter Haven, FL
    251 Lake Howard Drive SW
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,060 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  20. Photo of 2927 Walnut Street, Winter Haven, FL 33881 (MLS # L4947907)
    $195,000
    Photo of 2927 Walnut Street, Winter Haven, FL 33881 (MLS # L4947907)
    Photo of 2927 Walnut Street, Winter Haven, FL 33881 (MLS # L4947907)
    2927 Walnut Street, Winter Haven, FL
    2927 Walnut Street
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,512 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  21. Photo of 6304 Red Herring Drive, Winter Haven, FL 33881 (MLS # TB8307326)
    $295,000
    Photo of 6304 Red Herring Drive, Winter Haven, FL 33881 (MLS # TB8307326)
    Photo of 6304 Red Herring Drive, Winter Haven, FL 33881 (MLS # TB8307326)
    23
     
    6304 Red Herring Drive, Winter Haven, FL
    6304 Red Herring Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,592 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  22. Photo of 3978 Warbler Drive, Winter Haven, FL 33880 (MLS # O6241997)
    $265,000
    Photo of 3978 Warbler Drive, Winter Haven, FL 33880 (MLS # O6241997)
    Photo of 3978 Warbler Drive, Winter Haven, FL 33880 (MLS # O6241997)
    3978 Warbler Drive, Winter Haven, FL
    3978 Warbler Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,555 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  23. Photo of 202 4th Wahneta Street E, Winter Haven, FL 33880 (MLS # L4947931)
    $114,999
    Photo of 202 4th Wahneta Street E, Winter Haven, FL 33880 (MLS # L4947931)
    Photo of 202 4th Wahneta Street E, Winter Haven, FL 33880 (MLS # L4947931)
    202 4th Wahneta Street E, Winter Haven, FL
    202 4th Wahneta Street E
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 576 Home (sqft)
    • 1 Bath
    • 6,534 Lot (sqft)
  24. Photo of 6048 Forest Ridge Lane, Winter Haven, FL 33881 (MLS # TB8307402)
    $320,000
    Photo of 6048 Forest Ridge Lane, Winter Haven, FL 33881 (MLS # TB8307402)
    Photo of 6048 Forest Ridge Lane, Winter Haven, FL 33881 (MLS # TB8307402)
    6048 Forest Ridge Lane, Winter Haven, FL
    6048 Forest Ridge Lane
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,788 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  25. Photo of 3337 Raleigh Drive, Winter Haven, FL 33884 (MLS # P4932189)
    $250,000
    Photo of 3337 Raleigh Drive, Winter Haven, FL 33884 (MLS # P4932189)
    Photo of 3337 Raleigh Drive, Winter Haven, FL 33884 (MLS # P4932189)
    3337 Raleigh Drive, Winter Haven, FL
    3337 Raleigh Drive
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,275 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  26. Photo of 1700 6th Street NW #C7, Winter Haven, FL 33881 (MLS # P4932186)
    $82,500
    Photo of 1700 6th Street NW #C7, Winter Haven, FL 33881 (MLS # P4932186)
    Photo of 1700 6th Street NW #C7, Winter Haven, FL 33881 (MLS # P4932186)
    1700 6th Street NW #C7, Winter Haven, FL
    1700 6th Street NW #C7
    Winter Haven, FL
    • 1 Bed
    • 1 Bath
    • 640 Home (sqft)
    • 1 Bath
    • 436 Lot (sqft)
  27. Photo of 1086 Pelham Court, Winter Haven, FL 33884 (MLS # P4932161)
    $240,000
    Photo of 1086 Pelham Court, Winter Haven, FL 33884 (MLS # P4932161)
    Photo of 1086 Pelham Court, Winter Haven, FL 33884 (MLS # P4932161)
    1086 Pelham Court, Winter Haven, FL
    1086 Pelham Court
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,563 Home (sqft)
    • 2 Baths
    • 2,178 Lot (sqft)
  28. Photo of 551 Lake Dexter Boulevard, Winter Haven, FL 33884 (MLS # P4932182)
    $232,900
    Photo of 551 Lake Dexter Boulevard, Winter Haven, FL 33884 (MLS # P4932182)
    Photo of 551 Lake Dexter Boulevard, Winter Haven, FL 33884 (MLS # P4932182)
    551 Lake Dexter Boulevard, Winter Haven, FL
    551 Lake Dexter Boulevard
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,131 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  29. Photo of 4070 Island Lakes Drive, Winter Haven, FL 33881 (MLS # O6244811)
    $370,000
    Photo of 4070 Island Lakes Drive, Winter Haven, FL 33881 (MLS # O6244811)
    Photo of 4070 Island Lakes Drive, Winter Haven, FL 33881 (MLS # O6244811)
    4070 Island Lakes Drive, Winter Haven, FL
    4070 Island Lakes Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,860 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  30. Photo of 5850 Cypress Gardens Boulevard #103, Winter Haven, FL 33884 (MLS # O6244686)
    $152,500
    Photo of 5850 Cypress Gardens Boulevard #103, Winter Haven, FL 33884 (MLS # O6244686)
    Photo of 5850 Cypress Gardens Boulevard #103, Winter Haven, FL 33884 (MLS # O6244686)
    5850 Cypress Gardens Boulevard #103, Winter Haven, FL
    5850 Cypress Gardens Boulevard #103
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,324 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
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