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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 2076 Whispering Trails Blvd, Winter Haven, FL 33884 (MLS # P4931329)
    $267,900
    Photo of 2076 Whispering Trails Blvd, Winter Haven, FL 33884 (MLS # P4931329)
    Photo of 2076 Whispering Trails Blvd, Winter Haven, FL 33884 (MLS # P4931329)
    2076 Whispering Trails Blvd, Winter Haven, FL
    2076 Whispering Trails Blvd
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,432 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  2. Photo of 1414 Avenue H SW, Winter Haven, FL 33880 (MLS # P4931229)
    $359,900
    Photo of 1414 Avenue H SW, Winter Haven, FL 33880 (MLS # P4931229)
    Photo of 1414 Avenue H SW, Winter Haven, FL 33880 (MLS # P4931229)
    1414 Avenue H SW, Winter Haven, FL
    1414 Avenue H SW
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,050 Home (sqft)
    • 1 Bath
    • 10,890 Lot (sqft)
  3. Photo of 399 Lake Daisy Drive, Winter Haven, FL 33884 (MLS # L4946324)
    $299,900
    Photo of 399 Lake Daisy Drive, Winter Haven, FL 33884 (MLS # L4946324)
    Photo of 399 Lake Daisy Drive, Winter Haven, FL 33884 (MLS # L4946324)
    399 Lake Daisy Drive, Winter Haven, FL
    399 Lake Daisy Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,431 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  4. Photo of 1001 Harold Pass, Winter Haven, FL 33884 (MLS # T3542957)
    $272,045
    Photo of 1001 Harold Pass, Winter Haven, FL 33884 (MLS # T3542957)
    Photo of 1001 Harold Pass, Winter Haven, FL 33884 (MLS # T3542957)
    1001 Harold Pass, Winter Haven, FL
    1001 Harold Pass
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,444 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  5. Photo of 1038 Brimstone Circle, Winter Haven, FL 33884 (MLS # T3542617)
    $394,995
    Photo of 1038 Brimstone Circle, Winter Haven, FL 33884 (MLS # T3542617)
    Photo of 1038 Brimstone Circle, Winter Haven, FL 33884 (MLS # T3542617)
    1038 Brimstone Circle, Winter Haven, FL
    1038 Brimstone Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,810 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  6. Photo of 2056 Marigold Alley, Winter Haven, FL 33884 (MLS # T3542614)
    $365,995
    Photo of 2056 Marigold Alley, Winter Haven, FL 33884 (MLS # T3542614)
    Photo of 2056 Marigold Alley, Winter Haven, FL 33884 (MLS # T3542614)
    2056 Marigold Alley, Winter Haven, FL
    2056 Marigold Alley
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,423 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  7. Photo of 1536 Hummingbird Road, Winter Haven, FL 33884 (MLS # T3542606)
    $325,995
    Photo of 1536 Hummingbird Road, Winter Haven, FL 33884 (MLS # T3542606)
    Photo of 1536 Hummingbird Road, Winter Haven, FL 33884 (MLS # T3542606)
    1536 Hummingbird Road, Winter Haven, FL
    1536 Hummingbird Road
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,794 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  8. Photo of 2052 Marigold Alley, Winter Haven, FL 33884 (MLS # T3542608)
    $315,995
    Photo of 2052 Marigold Alley, Winter Haven, FL 33884 (MLS # T3542608)
    Photo of 2052 Marigold Alley, Winter Haven, FL 33884 (MLS # T3542608)
    2052 Marigold Alley, Winter Haven, FL
    2052 Marigold Alley
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,794 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  9. Photo of 2064 Marigold Alley, Winter Haven, FL 33884 (MLS # T3542588)
    $300,995
    Photo of 2064 Marigold Alley, Winter Haven, FL 33884 (MLS # T3542588)
    Photo of 2064 Marigold Alley, Winter Haven, FL 33884 (MLS # T3542588)
    2064 Marigold Alley, Winter Haven, FL
    2064 Marigold Alley
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,680 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  10. Photo of 2200 Starboard, Winter Haven, FL 33881 (MLS # P4931241)
    $219,000
    Photo of 2200 Starboard, Winter Haven, FL 33881 (MLS # P4931241)
    Photo of 2200 Starboard, Winter Haven, FL 33881 (MLS # P4931241)
    2200 Starboard, Winter Haven, FL
    2200 Starboard
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,290 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  11. Photo of 4917 Kaia Avenue, Winter Haven, FL 33884 (MLS # O6223813)
    $335,305
    Photo of 4917 Kaia Avenue, Winter Haven, FL 33884 (MLS # O6223813)
    Photo of 4917 Kaia Avenue, Winter Haven, FL 33884 (MLS # O6223813)
    4917 Kaia Avenue, Winter Haven, FL
    4917 Kaia Avenue
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,988 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  12. Photo of 333 Lake Howard Drive NW #202C, Winter Haven, FL 33880 (MLS # B4901659)
    $109,950
    Photo of 333 Lake Howard Drive NW #202C, Winter Haven, FL 33880 (MLS # B4901659)
    Photo of 333 Lake Howard Drive NW #202C, Winter Haven, FL 33880 (MLS # B4901659)
    333 Lake Howard Drive NW #202C, Winter Haven, FL
    333 Lake Howard Drive NW #202C
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,030 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  13. Photo of 520 Avenue L SE, Winter Haven, FL 33880 (MLS # O6224009)
    $244,900
    Photo of 520 Avenue L SE, Winter Haven, FL 33880 (MLS # O6224009)
    Photo of 520 Avenue L SE, Winter Haven, FL 33880 (MLS # O6224009)
    520 Avenue L SE, Winter Haven, FL
    520 Avenue L SE
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,346 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  14. Photo of 167 Fall Glo Road, Winter Haven, FL 33880 (MLS # O6224115)
    $279,900
    Photo of 167 Fall Glo Road, Winter Haven, FL 33880 (MLS # O6224115)
    Photo of 167 Fall Glo Road, Winter Haven, FL 33880 (MLS # O6224115)
    167 Fall Glo Road, Winter Haven, FL
    167 Fall Glo Road
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,867 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  15. Photo of 4230 Roberta Drive, Winter Haven, FL 33881 (MLS # T3541665)
    $342,000
    Photo of 4230 Roberta Drive, Winter Haven, FL 33881 (MLS # T3541665)
    Photo of 4230 Roberta Drive, Winter Haven, FL 33881 (MLS # T3541665)
    4230 Roberta Drive, Winter Haven, FL
    4230 Roberta Drive
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,577 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  16. Photo of 333 Lake Howard Drive NW #314D, Winter Haven, FL 33880 (MLS # U8246538)
    $124,900
    Photo of 333 Lake Howard Drive NW #314D, Winter Haven, FL 33880 (MLS # U8246538)
    Photo of 333 Lake Howard Drive NW #314D, Winter Haven, FL 33880 (MLS # U8246538)
    333 Lake Howard Drive NW #314D, Winter Haven, FL
    333 Lake Howard Drive NW #314D
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,226 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  17. Photo of 1719 Durden Drive, Winter Haven, FL 33880 (MLS # T3541864)
    $349,900
    Photo of 1719 Durden Drive, Winter Haven, FL 33880 (MLS # T3541864)
    Photo of 1719 Durden Drive, Winter Haven, FL 33880 (MLS # T3541864)
    1719 Durden Drive, Winter Haven, FL
    1719 Durden Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,842 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  18. Photo of 642 Lake Dexter Circle, Winter Haven, FL 33884 (MLS # P4930974)
    $239,900
    Photo of 642 Lake Dexter Circle, Winter Haven, FL 33884 (MLS # P4930974)
    Photo of 642 Lake Dexter Circle, Winter Haven, FL 33884 (MLS # P4930974)
    642 Lake Dexter Circle, Winter Haven, FL
    642 Lake Dexter Circle
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,320 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  19. Photo of 326 Sand Pine Trail, Winter Haven, FL 33880 (MLS # L4946173)
    $245,000
    Photo of 326 Sand Pine Trail, Winter Haven, FL 33880 (MLS # L4946173)
    Photo of 326 Sand Pine Trail, Winter Haven, FL 33880 (MLS # L4946173)
    326 Sand Pine Trail, Winter Haven, FL
    326 Sand Pine Trail
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,012 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  20. Photo of 101 Sugar Creek Road, Winter Haven, FL 33880 (MLS # P4931054)
    $369,900
    Photo of 101 Sugar Creek Road, Winter Haven, FL 33880 (MLS # P4931054)
    Photo of 101 Sugar Creek Road, Winter Haven, FL 33880 (MLS # P4931054)
    101 Sugar Creek Road, Winter Haven, FL
    101 Sugar Creek Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,581 Home (sqft)
    • 2 Baths
    • 25,701 Lot (sqft)
  21. Photo of 1187 Normandy Heights Circle, Winter Haven, FL 33880 (MLS # O6223183)
    $329,900
    Photo of 1187 Normandy Heights Circle, Winter Haven, FL 33880 (MLS # O6223183)
    Photo of 1187 Normandy Heights Circle, Winter Haven, FL 33880 (MLS # O6223183)
    1187 Normandy Heights Circle, Winter Haven, FL
    1187 Normandy Heights Circle
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,018 Home (sqft)
    • 3 Baths
    • 9,584 Lot (sqft)
  22. Photo of 544 Terranova Circle, Winter Haven, FL 33884 (MLS # S5108623)
    $315,000
    Photo of 544 Terranova Circle, Winter Haven, FL 33884 (MLS # S5108623)
    Photo of 544 Terranova Circle, Winter Haven, FL 33884 (MLS # S5108623)
    544 Terranova Circle, Winter Haven, FL
    544 Terranova Circle
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,673 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  23. Photo of 290 36th Street NW, Winter Haven, FL 33880 (MLS # P4931230)
    $255,000
    Photo of 290 36th Street NW, Winter Haven, FL 33880 (MLS # P4931230)
    Photo of 290 36th Street NW, Winter Haven, FL 33880 (MLS # P4931230)
    290 36th Street NW, Winter Haven, FL
    290 36th Street NW
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,580 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  24. Photo of 474 Honey Bell Road, Winter Haven, FL 33880 (MLS # T3541093)
    $285,000
    Photo of 474 Honey Bell Road, Winter Haven, FL 33880 (MLS # T3541093)
    Photo of 474 Honey Bell Road, Winter Haven, FL 33880 (MLS # T3541093)
    474 Honey Bell Road, Winter Haven, FL
    474 Honey Bell Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,690 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  25. Photo of 427 Lake Daisy Drive, Winter Haven, FL 33884 (MLS # T3540006)
    $274,900
    Photo of 427 Lake Daisy Drive, Winter Haven, FL 33884 (MLS # T3540006)
    Photo of 427 Lake Daisy Drive, Winter Haven, FL 33884 (MLS # T3540006)
    15
     
    427 Lake Daisy Drive, Winter Haven, FL
    427 Lake Daisy Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,120 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  26. Photo of 803 Orchid Springs Drive, Winter Haven, FL 33884 (MLS # L4945993)
    $139,900
    Photo of 803 Orchid Springs Drive, Winter Haven, FL 33884 (MLS # L4945993)
    Photo of 803 Orchid Springs Drive, Winter Haven, FL 33884 (MLS # L4945993)
    803 Orchid Springs Drive, Winter Haven, FL
    803 Orchid Springs Drive
    Winter Haven, FL
    • 1 Bed
    • 1 Bath
    • 621 Home (sqft)
    • 1 Bath
    • 436 Lot (sqft)
  27. Photo of 400 El Camino Dr #111, Winter Haven, FL 33884 (MLS # P4931161)
    $109,900
    Photo of 400 El Camino Dr #111, Winter Haven, FL 33884 (MLS # P4931161)
    Photo of 400 El Camino Dr #111, Winter Haven, FL 33884 (MLS # P4931161)
    400 El Camino Dr #111, Winter Haven, FL
    400 El Camino Dr #111
    Winter Haven, FL
    • 1 Bed
    • 2 Baths
    • 768 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  28. Photo of 3780 Avenue T NW, Winter Haven, FL 33881 (MLS # S5108186)
    $230,000
    Photo of 3780 Avenue T NW, Winter Haven, FL 33881 (MLS # S5108186)
    Photo of 3780 Avenue T NW, Winter Haven, FL 33881 (MLS # S5108186)
    3780 Avenue T NW, Winter Haven, FL
    3780 Avenue T NW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,012 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  29. Photo of 2470 Avenue E SW, Winter Haven, FL 33880 (MLS # L4946181)
    $220,000
    Photo of 2470 Avenue E SW, Winter Haven, FL 33880 (MLS # L4946181)
    Photo of 2470 Avenue E SW, Winter Haven, FL 33880 (MLS # L4946181)
    2470 Avenue E SW, Winter Haven, FL
    2470 Avenue E SW
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,082 Home (sqft)
    • 1 Bath
    • 6,534 Lot (sqft)
  30. Photo of 3931 Avenue R NW, Winter Haven, FL 33881 (MLS # O6219688)
    $219,900
    Photo of 3931 Avenue R NW, Winter Haven, FL 33881 (MLS # O6219688)
    Photo of 3931 Avenue R NW, Winter Haven, FL 33881 (MLS # O6219688)
    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)
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