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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 3109 Avenue R NW, Winter Haven, FL 33881 (MLS # O6240356)
    $219,900
    Photo of 3109 Avenue R NW, Winter Haven, FL 33881 (MLS # O6240356)
    Photo of 3109 Avenue R NW, Winter Haven, FL 33881 (MLS # O6240356)
    3109 Avenue R NW, Winter Haven, FL
    3109 Avenue R NW
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 951 Home (sqft)
    • 1 Bath
    • 13,504 Lot (sqft)
  2. Photo of 3324 Fox Ridge Drive, Winter Haven, FL 33884 (MLS # L4947501)
    $299,000
    Photo of 3324 Fox Ridge Drive, Winter Haven, FL 33884 (MLS # L4947501)
    Photo of 3324 Fox Ridge Drive, Winter Haven, FL 33884 (MLS # L4947501)
    3324 Fox Ridge Drive, Winter Haven, FL
    3324 Fox Ridge Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,422 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  3. Photo of 312 Lee Avenue NE, Winter Haven, FL 33881 (MLS # O6240874)
    $154,990
    Photo of 312 Lee Avenue NE, Winter Haven, FL 33881 (MLS # O6240874)
    Photo of 312 Lee Avenue NE, Winter Haven, FL 33881 (MLS # O6240874)
    312 Lee Avenue NE, Winter Haven, FL
    312 Lee Avenue NE
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 784 Home (sqft)
    • 1 Bath
    • 5,663 Lot (sqft)
  4. Photo of 268 Oleander Street, Winter Haven, FL 33881 (MLS # O6240493)
    $249,900
    Photo of 268 Oleander Street, Winter Haven, FL 33881 (MLS # O6240493)
    Photo of 268 Oleander Street, Winter Haven, FL 33881 (MLS # O6240493)
    268 Oleander Street, Winter Haven, FL
    268 Oleander Street
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,450 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  5. Photo of 1208 W Lake Buckeye Drive, Winter Haven, FL 33881 (MLS # P4931952)
    $384,500
    Photo of 1208 W Lake Buckeye Drive, Winter Haven, FL 33881 (MLS # P4931952)
    Photo of 1208 W Lake Buckeye Drive, Winter Haven, FL 33881 (MLS # P4931952)
    1208 W Lake Buckeye Drive, Winter Haven, FL
    1208 W Lake Buckeye Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,097 Home (sqft)
    • 2 Baths
    • 14,375 Lot (sqft)
  6. Photo of 555 Alachua Drive, Winter Haven, FL 33884 (MLS # TB8301662)
    $399,000
    Photo of 555 Alachua Drive, Winter Haven, FL 33884 (MLS # TB8301662)
    Photo of 555 Alachua Drive, Winter Haven, FL 33884 (MLS # TB8301662)
    555 Alachua Drive, Winter Haven, FL
    555 Alachua Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,286 Home (sqft)
    • 3 Baths
    • 11,762 Lot (sqft)
  7. Photo of 821 Sun Burst Road, Winter Haven, FL 33880 (MLS # O6239172)
    $380,000
    Photo of 821 Sun Burst Road, Winter Haven, FL 33880 (MLS # O6239172)
    Photo of 821 Sun Burst Road, Winter Haven, FL 33880 (MLS # O6239172)
    821 Sun Burst Road, Winter Haven, FL
    821 Sun Burst Road
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,601 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  8. Photo of 693 Peyton Brooke Way, Winter Haven, FL 33881 (MLS # O6239397)
    $299,990
    Photo of 693 Peyton Brooke Way, Winter Haven, FL 33881 (MLS # O6239397)
    Photo of 693 Peyton Brooke Way, Winter Haven, FL 33881 (MLS # O6239397)
    693 Peyton Brooke Way, Winter Haven, FL
    693 Peyton Brooke Way
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,867 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  9. Photo of 606 Holt Circle, Winter Haven, FL 33880 (MLS # TB8301601)
    $219,900
    Photo of 606 Holt Circle, Winter Haven, FL 33880 (MLS # TB8301601)
    Photo of 606 Holt Circle, Winter Haven, FL 33880 (MLS # TB8301601)
    606 Holt Circle, Winter Haven, FL
    606 Holt Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,194 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  10. Photo of 2272 Rose Boulevard, Winter Haven, FL 33881 (MLS # TB8301410)
    $319,000
    Photo of 2272 Rose Boulevard, Winter Haven, FL 33881 (MLS # TB8301410)
    Photo of 2272 Rose Boulevard, Winter Haven, FL 33881 (MLS # TB8301410)
    2272 Rose Boulevard, Winter Haven, FL
    2272 Rose Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,690 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  11. Photo of 408 Patrick Avenue, Winter Haven, FL 33880 (MLS # L4948998)
    $189,000
    Photo of 408 Patrick Avenue, Winter Haven, FL 33880 (MLS # L4948998)
    Photo of 408 Patrick Avenue, Winter Haven, FL 33880 (MLS # L4948998)
    408 Patrick Avenue, Winter Haven, FL
    408 Patrick Avenue
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,534 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  12. Photo of 135 Eloise Oaks Drive, Winter Haven, FL 33884 (MLS # P4931900)
    $388,000
    Photo of 135 Eloise Oaks Drive, Winter Haven, FL 33884 (MLS # P4931900)
    Photo of 135 Eloise Oaks Drive, Winter Haven, FL 33884 (MLS # P4931900)
    28
     
    135 Eloise Oaks Drive, Winter Haven, FL
    135 Eloise Oaks Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,866 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  13. Photo of 905 14th Street NE, Winter Haven, FL 33881 (MLS # B4901706)
    $263,900
    Photo of 905 14th Street NE, Winter Haven, FL 33881 (MLS # B4901706)
    Photo of 905 14th Street NE, Winter Haven, FL 33881 (MLS # B4901706)
    905 14th Street NE, Winter Haven, FL
    905 14th Street NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,330 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  14. Photo of 1100 Martinique Drive #208, Winter Haven, FL 33884 (MLS # P4931920)
    $137,500
    Photo of 1100 Martinique Drive #208, Winter Haven, FL 33884 (MLS # P4931920)
    Photo of 1100 Martinique Drive #208, Winter Haven, FL 33884 (MLS # P4931920)
    1100 Martinique Drive #208, Winter Haven, FL
    1100 Martinique Drive #208
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,024 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  15. Photo of 5801 Forest Ridge Drive, Winter Haven, FL 33881 (MLS # O6238884)
    $288,900
    Photo of 5801 Forest Ridge Drive, Winter Haven, FL 33881 (MLS # O6238884)
    Photo of 5801 Forest Ridge Drive, Winter Haven, FL 33881 (MLS # O6238884)
    5801 Forest Ridge Drive, Winter Haven, FL
    5801 Forest Ridge Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,788 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  16. Photo of 1475 Haines Drive, Winter Haven, FL 33881 (MLS # O6238736)
    $309,990
    Photo of 1475 Haines Drive, Winter Haven, FL 33881 (MLS # O6238736)
    Photo of 1475 Haines Drive, Winter Haven, FL 33881 (MLS # O6238736)
    1475 Haines Drive, Winter Haven, FL
    1475 Haines Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,722 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  17. Photo of 247 Lake Lucerne Way, Winter Haven, FL 33881 (MLS # S5111884)
    $285,000
    Photo of 247 Lake Lucerne Way, Winter Haven, FL 33881 (MLS # S5111884)
    Photo of 247 Lake Lucerne Way, Winter Haven, FL 33881 (MLS # S5111884)
    247 Lake Lucerne Way, Winter Haven, FL
    247 Lake Lucerne Way
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,627 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  18. Photo of 264 Spirit Landings Circle, Winter Haven, FL 33880 (MLS # TB8301138)
    $289,900
    Photo of 264 Spirit Landings Circle, Winter Haven, FL 33880 (MLS # TB8301138)
    Photo of 264 Spirit Landings Circle, Winter Haven, FL 33880 (MLS # TB8301138)
    264 Spirit Landings Circle, Winter Haven, FL
    264 Spirit Landings Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,541 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  19. Photo of 752 Reggie Road, Winter Haven, FL 33884 (MLS # TB8301180)
    $325,000
    Photo of 752 Reggie Road, Winter Haven, FL 33884 (MLS # TB8301180)
    Photo of 752 Reggie Road, Winter Haven, FL 33884 (MLS # TB8301180)
    752 Reggie Road, Winter Haven, FL
    752 Reggie Road
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,216 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  20. Photo of 3815 Avenue R NW, Winter Haven, FL 33881 (MLS # S5111841)
    $215,000
    Photo of 3815 Avenue R NW, Winter Haven, FL 33881 (MLS # S5111841)
    Photo of 3815 Avenue R NW, Winter Haven, FL 33881 (MLS # S5111841)
    3815 Avenue R NW, Winter Haven, FL
    3815 Avenue R NW
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 810 Home (sqft)
    • 1 Bath
    • 10,455 Lot (sqft)
  21. Photo of 3184 Royal Tern Drive, Winter Haven, FL 33881 (MLS # S5111840)
    $299,995
    Photo of 3184 Royal Tern Drive, Winter Haven, FL 33881 (MLS # S5111840)
    Photo of 3184 Royal Tern Drive, Winter Haven, FL 33881 (MLS # S5111840)
    3184 Royal Tern Drive, Winter Haven, FL
    3184 Royal Tern Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,725 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  22. Photo of 61 Winter Ridge Road #54, Winter Haven, FL 33881 (MLS # P4931817)
    $165,000
    Photo of 61 Winter Ridge Road #54, Winter Haven, FL 33881 (MLS # P4931817)
    Photo of 61 Winter Ridge Road #54, Winter Haven, FL 33881 (MLS # P4931817)
    61 Winter Ridge Road #54, Winter Haven, FL
    61 Winter Ridge Road #54
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,073 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  23. Photo of 276 Black Skimmer Lane, Winter Haven, FL 33880 (MLS # S5111106)
    $305,000
    Photo of 276 Black Skimmer Lane, Winter Haven, FL 33880 (MLS # S5111106)
    Photo of 276 Black Skimmer Lane, Winter Haven, FL 33880 (MLS # S5111106)
    276 Black Skimmer Lane, Winter Haven, FL
    276 Black Skimmer Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,475 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  24. Photo of Winter Haven, FL 33881 (MLS # S5111816)
    $220,000
    Photo of Winter Haven, FL 33881 (MLS # S5111816)
    Photo of Winter Haven, FL 33881 (MLS # S5111816)
    MLS # S5111816, Winter Haven, FL
    MLS # S5111816
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,148 Home (sqft)
    • 1 Bath
    • 6,970 Lot (sqft)
  25. Photo of 2554 Salzburg Loop, Winter Haven, FL 33884 (MLS # P4931895)
    $359,900
    Photo of 2554 Salzburg Loop, Winter Haven, FL 33884 (MLS # P4931895)
    Photo of 2554 Salzburg Loop, Winter Haven, FL 33884 (MLS # P4931895)
    2554 Salzburg Loop, Winter Haven, FL
    2554 Salzburg Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,687 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  26. Photo of 2158 Mirasol Drive, Winter Haven, FL 33881 (MLS # P4931859)
    $349,000
    Photo of 2158 Mirasol Drive, Winter Haven, FL 33881 (MLS # P4931859)
    Photo of 2158 Mirasol Drive, Winter Haven, FL 33881 (MLS # P4931859)
    2158 Mirasol Drive, Winter Haven, FL
    2158 Mirasol Drive
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,062 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  27. Photo of 426 Lanier Lane, Winter Haven, FL 33884 (MLS # P4931927)
    $285,500
    Photo of 426 Lanier Lane, Winter Haven, FL 33884 (MLS # P4931927)
    Photo of 426 Lanier Lane, Winter Haven, FL 33884 (MLS # P4931927)
    426 Lanier Lane, Winter Haven, FL
    426 Lanier Lane
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,897 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  28. Photo of 815 Hillside Court N, Winter Haven, FL 33881 (MLS # L4947278)
    $399,000
    Photo of 815 Hillside Court N, Winter Haven, FL 33881 (MLS # L4947278)
    Photo of 815 Hillside Court N, Winter Haven, FL 33881 (MLS # L4947278)
    815 Hillside Court N, Winter Haven, FL
    815 Hillside Court N
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,860 Home (sqft)
    • 2 Baths
    • 22,216 Lot (sqft)
  29. Photo of 333 Lake Howard Drive NW #204D, Winter Haven, FL 33880 (MLS # P4931875)
    $139,000
    Photo of 333 Lake Howard Drive NW #204D, Winter Haven, FL 33880 (MLS # P4931875)
    Photo of 333 Lake Howard Drive NW #204D, Winter Haven, FL 33880 (MLS # P4931875)
    333 Lake Howard Drive NW #204D, Winter Haven, FL
    333 Lake Howard Drive NW #204D
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,226 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  30. Photo of 119 Lantern Lane, Winter Haven, FL 33884 (MLS # P4931811)
    $259,900
    Photo of 119 Lantern Lane, Winter Haven, FL 33884 (MLS # P4931811)
    Photo of 119 Lantern Lane, Winter Haven, FL 33884 (MLS # P4931811)
    119 Lantern Lane, Winter Haven, FL
    119 Lantern Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,434 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
Previous Page 12 of 17 Next
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