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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 1712 Lime Drive, Winter Haven, FL 33881 (MLS # O6227523)
    $365,000
    Photo of 1712 Lime Drive, Winter Haven, FL 33881 (MLS # O6227523)
    Photo of 1712 Lime Drive, Winter Haven, FL 33881 (MLS # O6227523)
    1712 Lime Drive, Winter Haven, FL
    1712 Lime Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,218 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  2. Photo of 1067 Haines Drive, Winter Haven, FL 33881 (MLS # O6228199)
    $293,900
    Photo of 1067 Haines Drive, Winter Haven, FL 33881 (MLS # O6228199)
    Photo of 1067 Haines Drive, Winter Haven, FL 33881 (MLS # O6228199)
    1067 Haines Drive, Winter Haven, FL
    1067 Haines Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,708 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  3. Photo of 15 Winterset Drive, Winter Haven, FL 33884 (MLS # P4931480)
    $369,900
    Photo of 15 Winterset Drive, Winter Haven, FL 33884 (MLS # P4931480)
    Photo of 15 Winterset Drive, Winter Haven, FL 33884 (MLS # P4931480)
    15 Winterset Drive, Winter Haven, FL
    15 Winterset Drive
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,936 Home (sqft)
    • 2 Baths
    • 17,860 Lot (sqft)
  4. Photo of 4651 Ostero Street, Winter Haven, FL 33884 (MLS # O6228904)
    $293,580
    Photo of 4651 Ostero Street, Winter Haven, FL 33884 (MLS # O6228904)
    Photo of 4651 Ostero Street, Winter Haven, FL 33884 (MLS # O6228904)
    4651 Ostero Street, Winter Haven, FL
    4651 Ostero Street
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,665 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  5. Photo of 3409 Costello Circle, Winter Haven, FL 33884 (MLS # O6228809)
    $324,990
    Photo of 3409 Costello Circle, Winter Haven, FL 33884 (MLS # O6228809)
    Photo of 3409 Costello Circle, Winter Haven, FL 33884 (MLS # O6228809)
    3409 Costello Circle, Winter Haven, FL
    3409 Costello Circle
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,828 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  6. Photo of 3985 Jaclyns Jetty, Winter Haven, FL 33884 (MLS # O6228355)
    $260,000
    Photo of 3985 Jaclyns Jetty, Winter Haven, FL 33884 (MLS # O6228355)
    Photo of 3985 Jaclyns Jetty, Winter Haven, FL 33884 (MLS # O6228355)
    3985 Jaclyns Jetty, Winter Haven, FL
    3985 Jaclyns Jetty
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,495 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  7. Photo of 4420 Glenns Landing, Winter Haven, FL 33884 (MLS # P4931461)
    $264,500
    Photo of 4420 Glenns Landing, Winter Haven, FL 33884 (MLS # P4931461)
    Photo of 4420 Glenns Landing, Winter Haven, FL 33884 (MLS # P4931461)
    4420 Glenns Landing, Winter Haven, FL
    4420 Glenns Landing
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,560 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  8. Photo of 2310 Isle Royale Court SE, Winter Haven, FL 33880 (MLS # P4931456)
    $239,900
    Photo of 2310 Isle Royale Court SE, Winter Haven, FL 33880 (MLS # P4931456)
    Photo of 2310 Isle Royale Court SE, Winter Haven, FL 33880 (MLS # P4931456)
    2310 Isle Royale Court SE, Winter Haven, FL
    2310 Isle Royale Court SE
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,312 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  9. Photo of 110 Berry Road, Winter Haven, FL 33880 (MLS # L4946526)
    $255,000
    Photo of 110 Berry Road, Winter Haven, FL 33880 (MLS # L4946526)
    Photo of 110 Berry Road, Winter Haven, FL 33880 (MLS # L4946526)
    110 Berry Road, Winter Haven, FL
    110 Berry Road
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,800 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  10. Photo of 5850 Cypress Gardens Boulevard #105, Winter Haven, FL 33884 (MLS # P4931458)
    $179,900
    Photo of 5850 Cypress Gardens Boulevard #105, Winter Haven, FL 33884 (MLS # P4931458)
    Photo of 5850 Cypress Gardens Boulevard #105, Winter Haven, FL 33884 (MLS # P4931458)
    5850 Cypress Gardens Boulevard #105, Winter Haven, FL
    5850 Cypress Gardens Boulevard #105
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,324 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  11. Photo of 1422 Grand Cayman Circle, Winter Haven, FL 33884 (MLS # U8252012)
    $295,000
    Photo of 1422 Grand Cayman Circle, Winter Haven, FL 33884 (MLS # U8252012)
    Photo of 1422 Grand Cayman Circle, Winter Haven, FL 33884 (MLS # U8252012)
    1422 Grand Cayman Circle, Winter Haven, FL
    1422 Grand Cayman Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,615 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  12. Photo of 2040 SE San Marcos Drive #205, Winter Haven, FL 33880 (MLS # L4945032)
    $129,500
    Photo of 2040 SE San Marcos Drive #205, Winter Haven, FL 33880 (MLS # L4945032)
    Photo of 2040 SE San Marcos Drive #205, Winter Haven, FL 33880 (MLS # L4945032)
    2040 SE San Marcos Drive #205, Winter Haven, FL
    2040 SE San Marcos Drive #205
    Winter Haven, FL
    • 1 Bed
    • 1 Bath
    • 666 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  13. Photo of Winter Haven, FL 33880 (MLS # S5109425)
    $149,995
    Photo of Winter Haven, FL 33880 (MLS # S5109425)
    Photo of Winter Haven, FL 33880 (MLS # S5109425)
    MLS # S5109425, Winter Haven, FL
    MLS # S5109425
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,050 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  14. Photo of 485 Lanham Drive, Winter Haven, FL 33881 (MLS # O6227432)
    $379,000
    Photo of 485 Lanham Drive, Winter Haven, FL 33881 (MLS # O6227432)
    Photo of 485 Lanham Drive, Winter Haven, FL 33881 (MLS # O6227432)
    485 Lanham Drive, Winter Haven, FL
    485 Lanham Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,834 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  15. Photo of 8 Casarena Court, Winter Haven, FL 33881 (MLS # P4931417)
    $299,900
    Photo of 8 Casarena Court, Winter Haven, FL 33881 (MLS # P4931417)
    Photo of 8 Casarena Court, Winter Haven, FL 33881 (MLS # P4931417)
    8 Casarena Court, Winter Haven, FL
    8 Casarena Court
    Winter Haven, FL
    • 2 Beds
    • 3 Baths
    • 2,045 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  16. Photo of 1760 Carnostie Road, Winter Haven, FL 33884 (MLS # O6227116)
    $330,000
    Photo of 1760 Carnostie Road, Winter Haven, FL 33884 (MLS # O6227116)
    Photo of 1760 Carnostie Road, Winter Haven, FL 33884 (MLS # O6227116)
    1760 Carnostie Road, Winter Haven, FL
    1760 Carnostie Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,634 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  17. Photo of 2451 Mary Jewett Circle, Winter Haven, FL 33881 (MLS # L4946420)
    $325,000
    Photo of 2451 Mary Jewett Circle, Winter Haven, FL 33881 (MLS # L4946420)
    Photo of 2451 Mary Jewett Circle, Winter Haven, FL 33881 (MLS # L4946420)
    2451 Mary Jewett Circle, Winter Haven, FL
    2451 Mary Jewett Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,870 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  18. Photo of 339 Lake Smart Circle, Winter Haven, FL 33881 (MLS # P4931342)
    $334,000
    Photo of 339 Lake Smart Circle, Winter Haven, FL 33881 (MLS # P4931342)
    Photo of 339 Lake Smart Circle, Winter Haven, FL 33881 (MLS # P4931342)
    339 Lake Smart Circle, Winter Haven, FL
    339 Lake Smart Circle
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,173 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  19. Photo of 123 Ruby Lake Drive, Winter Haven, FL 33884 (MLS # L4946415)
    $399,999
    Photo of 123 Ruby Lake Drive, Winter Haven, FL 33884 (MLS # L4946415)
    Photo of 123 Ruby Lake Drive, Winter Haven, FL 33884 (MLS # L4946415)
    123 Ruby Lake Drive, Winter Haven, FL
    123 Ruby Lake Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,919 Home (sqft)
    • 2 Baths
    • 18,296 Lot (sqft)
  20. Photo of 300 Lake Smart Circle, Winter Haven, FL 33881 (MLS # O6223653)
    $307,100
    Photo of 300 Lake Smart Circle, Winter Haven, FL 33881 (MLS # O6223653)
    Photo of 300 Lake Smart Circle, Winter Haven, FL 33881 (MLS # O6223653)
    300 Lake Smart Circle, Winter Haven, FL
    300 Lake Smart Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,500 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  21. Photo of 4639 Mandolin Loop, Winter Haven, FL 33884 (MLS # S5108932)
    $280,000
    Photo of 4639 Mandolin Loop, Winter Haven, FL 33884 (MLS # S5108932)
    Photo of 4639 Mandolin Loop, Winter Haven, FL 33884 (MLS # S5108932)
    4639 Mandolin Loop, Winter Haven, FL
    4639 Mandolin Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,228 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  22. Photo of 3309 Queens Cove Loop, Winter Haven, FL 33880 (MLS # L4946171)
    $285,000
    Photo of 3309 Queens Cove Loop, Winter Haven, FL 33880 (MLS # L4946171)
    Photo of 3309 Queens Cove Loop, Winter Haven, FL 33880 (MLS # L4946171)
    3309 Queens Cove Loop, Winter Haven, FL
    3309 Queens Cove Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,411 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  23. Photo of 2877 Attwater Loop, Winter Haven, FL 33884 (MLS # O6226451)
    $235,000
    Photo of 2877 Attwater Loop, Winter Haven, FL 33884 (MLS # O6226451)
    Photo of 2877 Attwater Loop, Winter Haven, FL 33884 (MLS # O6226451)
    2877 Attwater Loop, Winter Haven, FL
    2877 Attwater Loop
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,385 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
  24. Photo of 720 Avenue H NE, Winter Haven, FL 33881 (MLS # S5109030)
    $254,000
    Photo of 720 Avenue H NE, Winter Haven, FL 33881 (MLS # S5109030)
    Photo of 720 Avenue H NE, Winter Haven, FL 33881 (MLS # S5109030)
    720 Avenue H NE, Winter Haven, FL
    720 Avenue H NE
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,626 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  25. Photo of 2336 Whispering Trails Place, Winter Haven, FL 33884 (MLS # O6226724)
    $287,000
    Photo of 2336 Whispering Trails Place, Winter Haven, FL 33884 (MLS # O6226724)
    Photo of 2336 Whispering Trails Place, Winter Haven, FL 33884 (MLS # O6226724)
    2336 Whispering Trails Place, Winter Haven, FL
    2336 Whispering Trails Place
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,237 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  26. Photo of 2856 San Marco Way, Winter Haven, FL 33884 (MLS # L4946388)
    $340,385
    Photo of 2856 San Marco Way, Winter Haven, FL 33884 (MLS # L4946388)
    Photo of 2856 San Marco Way, Winter Haven, FL 33884 (MLS # L4946388)
    2856 San Marco Way, Winter Haven, FL
    2856 San Marco Way
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,996 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  27. Photo of 1407 Avenue D NE, Winter Haven, FL 33881 (MLS # P4931215)
    $285,000
    Photo of 1407 Avenue D NE, Winter Haven, FL 33881 (MLS # P4931215)
    Photo of 1407 Avenue D NE, Winter Haven, FL 33881 (MLS # P4931215)
    1407 Avenue D NE, Winter Haven, FL
    1407 Avenue D NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,344 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
  28. Photo of 3719 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # P4931371)
    $319,900
    Photo of 3719 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # P4931371)
    Photo of 3719 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # P4931371)
    3719 Julius Estates Boulevard, Winter Haven, FL
    3719 Julius Estates Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,750 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  29. Photo of 700 Mirror Ter Ter NW #702, Winter Haven, FL 33881 (MLS # P4931264)
    $124,400
    Photo of 700 Mirror Ter Ter NW #702, Winter Haven, FL 33881 (MLS # P4931264)
    Photo of 700 Mirror Ter Ter NW #702, Winter Haven, FL 33881 (MLS # P4931264)
    700 Mirror Ter Ter NW #702, Winter Haven, FL
    700 Mirror Ter Ter NW #702
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,029 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  30. Photo of 333 Lake Howard Drive NW #204C, Winter Haven, FL 33880 (MLS # U8249519)
    $105,000
    Photo of 333 Lake Howard Drive NW #204C, Winter Haven, FL 33880 (MLS # U8249519)
    Photo of 333 Lake Howard Drive NW #204C, Winter Haven, FL 33880 (MLS # U8249519)
    333 Lake Howard Drive NW #204C, Winter Haven, FL
    333 Lake Howard Drive NW #204C
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,330 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
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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 4:13 PM PST.

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