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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 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)
  2. Photo of 362 Alexzander Way, Winter Haven, FL 33881 (MLS # S5111653)
    $279,990
    Photo of 362 Alexzander Way, Winter Haven, FL 33881 (MLS # S5111653)
    Photo of 362 Alexzander Way, Winter Haven, FL 33881 (MLS # S5111653)
    362 Alexzander Way, Winter Haven, FL
    362 Alexzander Way
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,725 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  3. Photo of 158 Andreas Street, Winter Haven, FL 33881 (MLS # O6236993)
    $325,000
    Photo of 158 Andreas Street, Winter Haven, FL 33881 (MLS # O6236993)
    Photo of 158 Andreas Street, Winter Haven, FL 33881 (MLS # O6236993)
    158 Andreas Street, Winter Haven, FL
    158 Andreas Street
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,959 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  4. Photo of 523 Eagle Landing Boulevard, Winter Haven, FL 33880 (MLS # O6237751)
    $300,000
    Photo of 523 Eagle Landing Boulevard, Winter Haven, FL 33880 (MLS # O6237751)
    Photo of 523 Eagle Landing Boulevard, Winter Haven, FL 33880 (MLS # O6237751)
    523 Eagle Landing Boulevard, Winter Haven, FL
    523 Eagle Landing Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,292 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  5. Photo of 6750 Winterset Gardens Road, Winter Haven, FL 33884 (MLS # P4931474)
    $380,000
    Photo of 6750 Winterset Gardens Road, Winter Haven, FL 33884 (MLS # P4931474)
    Photo of 6750 Winterset Gardens Road, Winter Haven, FL 33884 (MLS # P4931474)
    6750 Winterset Gardens Road, Winter Haven, FL
    6750 Winterset Gardens Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,874 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  6. Photo of 3726 Plymouth Drive, Winter Haven, FL 33884 (MLS # P4931706)
    $369,000
    Photo of 3726 Plymouth Drive, Winter Haven, FL 33884 (MLS # P4931706)
    Photo of 3726 Plymouth Drive, Winter Haven, FL 33884 (MLS # P4931706)
    3726 Plymouth Drive, Winter Haven, FL
    3726 Plymouth Drive
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,797 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  7. Photo of 2662 San Marco Way, Winter Haven, FL 33884 (MLS # L4947214)
    $359,900
    Photo of 2662 San Marco Way, Winter Haven, FL 33884 (MLS # L4947214)
    Photo of 2662 San Marco Way, Winter Haven, FL 33884 (MLS # L4947214)
    2662 San Marco Way, Winter Haven, FL
    2662 San Marco Way
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,004 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  8. Photo of 1865 4th Street SE, Winter Haven, FL 33880 (MLS # O6237323)
    $265,000
    Photo of 1865 4th Street SE, Winter Haven, FL 33880 (MLS # O6237323)
    Photo of 1865 4th Street SE, Winter Haven, FL 33880 (MLS # O6237323)
    1865 4th Street SE, Winter Haven, FL
    1865 4th Street SE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,540 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  9. Photo of 419 Avenue M NE, Winter Haven, FL 33881 (MLS # L4947240)
    $249,900
    Photo of 419 Avenue M NE, Winter Haven, FL 33881 (MLS # L4947240)
    Photo of 419 Avenue M NE, Winter Haven, FL 33881 (MLS # L4947240)
    419 Avenue M NE, Winter Haven, FL
    419 Avenue M NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,232 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  10. Photo of 2014 Bardmoor, Winter Haven, FL 33884 (MLS # P4931902)
    $317,000
    Photo of 2014 Bardmoor, Winter Haven, FL 33884 (MLS # P4931902)
    Photo of 2014 Bardmoor, Winter Haven, FL 33884 (MLS # P4931902)
    2014 Bardmoor, Winter Haven, FL
    2014 Bardmoor
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,880 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  11. Photo of 610 20th Street SW, Winter Haven, FL 33880 (MLS # O6236439)
    $298,000
    Photo of 610 20th Street SW, Winter Haven, FL 33880 (MLS # O6236439)
    Photo of 610 20th Street SW, Winter Haven, FL 33880 (MLS # O6236439)
    610 20th Street SW, Winter Haven, FL
    610 20th Street SW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,181 Home (sqft)
    • 2 Baths
    • 16,989 Lot (sqft)
  12. Photo of 2205 9th Court NE, Winter Haven, FL 33881 (MLS # T3552067)
    $235,000
    Photo of 2205 9th Court NE, Winter Haven, FL 33881 (MLS # T3552067)
    Photo of 2205 9th Court NE, Winter Haven, FL 33881 (MLS # T3552067)
    2205 9th Court NE, Winter Haven, FL
    2205 9th Court NE
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 928 Home (sqft)
    • 1 Bath
    • 6,970 Lot (sqft)
  13. Photo of 287 Cherry Laurel Lane, Winter Haven, FL 33880 (MLS # O6237283)
    $260,000
    Photo of 287 Cherry Laurel Lane, Winter Haven, FL 33880 (MLS # O6237283)
    Photo of 287 Cherry Laurel Lane, Winter Haven, FL 33880 (MLS # O6237283)
    287 Cherry Laurel Lane, Winter Haven, FL
    287 Cherry Laurel Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,224 Home (sqft)
    • 2 Baths
    • 18,296 Lot (sqft)
  14. Photo of 324 Corso Loop, Winter Haven, FL 33884 (MLS # O6235877)
    $344,900
    Photo of 324 Corso Loop, Winter Haven, FL 33884 (MLS # O6235877)
    Photo of 324 Corso Loop, Winter Haven, FL 33884 (MLS # O6235877)
    324 Corso Loop, Winter Haven, FL
    324 Corso Loop
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,867 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  15. Photo of 1730 Avenue C NE, Winter Haven, FL 33881 (MLS # S5111409)
    $162,000
    Photo of 1730 Avenue C NE, Winter Haven, FL 33881 (MLS # S5111409)
    Photo of 1730 Avenue C NE, Winter Haven, FL 33881 (MLS # S5111409)
    1730 Avenue C NE, Winter Haven, FL
    1730 Avenue C NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,400 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  16. Photo of 6162 Grey Heron Drive, Winter Haven, FL 33881 (MLS # A4621768)
    $311,999
    Photo of 6162 Grey Heron Drive, Winter Haven, FL 33881 (MLS # A4621768)
    Photo of 6162 Grey Heron Drive, Winter Haven, FL 33881 (MLS # A4621768)
    6162 Grey Heron Drive, Winter Haven, FL
    6162 Grey Heron Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,872 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  17. Photo of 1145 Brimstone Circle, Winter Haven, FL 33884 (MLS # O6236878)
    $309,990
    Photo of 1145 Brimstone Circle, Winter Haven, FL 33884 (MLS # O6236878)
    Photo of 1145 Brimstone Circle, Winter Haven, FL 33884 (MLS # O6236878)
    1145 Brimstone Circle, Winter Haven, FL
    1145 Brimstone Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,672 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  18. Photo of 904 15th Street NE, Winter Haven, FL 33881 (MLS # O6236266)
    $310,000
    Photo of 904 15th Street NE, Winter Haven, FL 33881 (MLS # O6236266)
    Photo of 904 15th Street NE, Winter Haven, FL 33881 (MLS # O6236266)
    904 15th Street NE, Winter Haven, FL
    904 15th Street NE
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,743 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  19. Photo of 5104 Sylas Jax Avenue, Winter Haven, FL 33884 (MLS # L4947179)
    $338,700
    Photo of 5104 Sylas Jax Avenue, Winter Haven, FL 33884 (MLS # L4947179)
    Photo of 5104 Sylas Jax Avenue, Winter Haven, FL 33884 (MLS # L4947179)
    5104 Sylas Jax Avenue, Winter Haven, FL
    5104 Sylas Jax Avenue
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,744 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  20. Photo of 3824 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232781)
    $306,280
    Photo of 3824 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232781)
    Photo of 3824 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232781)
    3824 Giorgio Drive, Winter Haven, FL
    3824 Giorgio Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,988 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  21. Photo of 4945 Kaia Avenue, Winter Haven, FL 33884 (MLS # O6234828)
    $348,710
    Photo of 4945 Kaia Avenue, Winter Haven, FL 33884 (MLS # O6234828)
    Photo of 4945 Kaia Avenue, Winter Haven, FL 33884 (MLS # O6234828)
    4945 Kaia Avenue, Winter Haven, FL
    4945 Kaia Avenue
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,387 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  22. Photo of 3777 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232784)
    $278,470
    Photo of 3777 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232784)
    Photo of 3777 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232784)
    3777 Giorgio Drive, Winter Haven, FL
    3777 Giorgio Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,695 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  23. Photo of 3816 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232786)
    $275,120
    Photo of 3816 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232786)
    Photo of 3816 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232786)
    3816 Giorgio Drive, Winter Haven, FL
    3816 Giorgio Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,607 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  24. Photo of 3821 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232787)
    $286,385
    Photo of 3821 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232787)
    Photo of 3821 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6232787)
    3821 Giorgio Drive, Winter Haven, FL
    3821 Giorgio Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,483 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  25. Photo of 415 Flagler Road, Winter Haven, FL 33884 (MLS # A4621547)
    $395,000
    Photo of 415 Flagler Road, Winter Haven, FL 33884 (MLS # A4621547)
    Photo of 415 Flagler Road, Winter Haven, FL 33884 (MLS # A4621547)
    415 Flagler Road, Winter Haven, FL
    415 Flagler Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,893 Home (sqft)
    • 2 Baths
    • 14,375 Lot (sqft)
  26. Photo of 555 Heather Glen Drive, Winter Haven, FL 33884 (MLS # O6236159)
    $300,000
    Photo of 555 Heather Glen Drive, Winter Haven, FL 33884 (MLS # O6236159)
    Photo of 555 Heather Glen Drive, Winter Haven, FL 33884 (MLS # O6236159)
    555 Heather Glen Drive, Winter Haven, FL
    555 Heather Glen Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,514 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  27. Photo of 2153 Abbey Road, Winter Haven, FL 33880 (MLS # T3551529)
    $159,000
    Photo of 2153 Abbey Road, Winter Haven, FL 33880 (MLS # T3551529)
    Photo of 2153 Abbey Road, Winter Haven, FL 33880 (MLS # T3551529)
    25
     
    2153 Abbey Road, Winter Haven, FL
    2153 Abbey Road
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,252 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  28. Photo of 256 Lake Smart Circle, Winter Haven, FL 33881 (MLS # L4946974)
    $369,000
    Photo of 256 Lake Smart Circle, Winter Haven, FL 33881 (MLS # L4946974)
    Photo of 256 Lake Smart Circle, Winter Haven, FL 33881 (MLS # L4946974)
    256 Lake Smart Circle, Winter Haven, FL
    256 Lake Smart Circle
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,302 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  29. Photo of 828 27th Street NW, Winter Haven, FL 33881 (MLS # O6235962)
    $249,900
    Photo of 828 27th Street NW, Winter Haven, FL 33881 (MLS # O6235962)
    Photo of 828 27th Street NW, Winter Haven, FL 33881 (MLS # O6235962)
    828 27th Street NW, Winter Haven, FL
    828 27th Street NW
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,220 Home (sqft)
    • 1 Bath
    • 8,712 Lot (sqft)
  30. Photo of 2370 Brassie Court, Winter Haven, FL 33884 (MLS # O6236082)
    $387,900
    Photo of 2370 Brassie Court, Winter Haven, FL 33884 (MLS # O6236082)
    Photo of 2370 Brassie Court, Winter Haven, FL 33884 (MLS # O6236082)
    2370 Brassie Court, Winter Haven, FL
    2370 Brassie Court
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,168 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
Previous Page 13 of 17 Next
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