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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 pool 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 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)
  2. Photo of 201 6th Jpv Street, Winter Haven, FL 33880 (MLS # G5085673)
    $249,989
    Photo of 201 6th Jpv Street, Winter Haven, FL 33880 (MLS # G5085673)
    Photo of 201 6th Jpv Street, Winter Haven, FL 33880 (MLS # G5085673)
    201 6th Jpv Street, Winter Haven, FL
    201 6th Jpv Street
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,096 Home (sqft)
    • 1 Bath
    • 11,762 Lot (sqft)
  3. Photo of 135 Majestic Gardens Court, Winter Haven, FL 33880 (MLS # T3548327)
    $305,000
    Photo of 135 Majestic Gardens Court, Winter Haven, FL 33880 (MLS # T3548327)
    Photo of 135 Majestic Gardens Court, Winter Haven, FL 33880 (MLS # T3548327)
    135 Majestic Gardens Court, Winter Haven, FL
    135 Majestic Gardens Court
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,721 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  4. Photo of 706 Canberra Road, Winter Haven, FL 33884 (MLS # P4931554)
    $364,900
    Photo of 706 Canberra Road, Winter Haven, FL 33884 (MLS # P4931554)
    Photo of 706 Canberra Road, Winter Haven, FL 33884 (MLS # P4931554)
    706 Canberra Road, Winter Haven, FL
    706 Canberra Road
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,114 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  5. Photo of 1423 Grand Cayman Circle, Winter Haven, FL 33884 (MLS # T3544655)
    $299,900
    Photo of 1423 Grand Cayman Circle, Winter Haven, FL 33884 (MLS # T3544655)
    Photo of 1423 Grand Cayman Circle, Winter Haven, FL 33884 (MLS # T3544655)
    1423 Grand Cayman Circle, Winter Haven, FL
    1423 Grand Cayman Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,588 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  6. 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)
  7. 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)
  8. 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)
  9. Photo of 2200 Starboard, Winter Haven, FL 33881 (MLS # P4931241)
    $215,000
    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)
  10. 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)
  11. Photo of 600 Sunway Lane, Winter Haven, FL 33880 (MLS # L4945998)
    $360,000
    Photo of 600 Sunway Lane, Winter Haven, FL 33880 (MLS # L4945998)
    Photo of 600 Sunway Lane, Winter Haven, FL 33880 (MLS # L4945998)
    600 Sunway Lane, Winter Haven, FL
    600 Sunway Lane
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,798 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
  12. Photo of 525 Avenue O SE, Winter Haven, FL 33880 (MLS # P4931133)
    $250,000
    Photo of 525 Avenue O SE, Winter Haven, FL 33880 (MLS # P4931133)
    Photo of 525 Avenue O SE, Winter Haven, FL 33880 (MLS # P4931133)
    525 Avenue O SE, Winter Haven, FL
    525 Avenue O SE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,428 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  13. Photo of 102 Jardin Lane, Winter Haven, FL 33884 (MLS # P4930688)
    $397,500
    Photo of 102 Jardin Lane, Winter Haven, FL 33884 (MLS # P4930688)
    Photo of 102 Jardin Lane, Winter Haven, FL 33884 (MLS # P4930688)
    21
     
    102 Jardin Lane, Winter Haven, FL
    102 Jardin Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,172 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  14. Photo of 2410 Salzburg Loop, Winter Haven, FL 33884 (MLS # P4930700)
    $300,000
    Photo of 2410 Salzburg Loop, Winter Haven, FL 33884 (MLS # P4930700)
    Photo of 2410 Salzburg Loop, Winter Haven, FL 33884 (MLS # P4930700)
    2410 Salzburg Loop, Winter Haven, FL
    2410 Salzburg Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,930 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  15. Photo of 305 Eagle Pond Drive #305, Winter Haven, FL 33884 (MLS # P4929571)
    $194,900
    Photo of 305 Eagle Pond Drive #305, Winter Haven, FL 33884 (MLS # P4929571)
    Photo of 305 Eagle Pond Drive #305, Winter Haven, FL 33884 (MLS # P4929571)
    305 Eagle Pond Drive #305, Winter Haven, FL
    305 Eagle Pond Drive #305
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,017 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  16. Photo of 3181 Royal Tern Drive, Winter Haven, FL 33881 (MLS # S5100366)
    $359,900
    Photo of 3181 Royal Tern Drive, Winter Haven, FL 33881 (MLS # S5100366)
    Photo of 3181 Royal Tern Drive, Winter Haven, FL 33881 (MLS # S5100366)
    3181 Royal Tern Drive, Winter Haven, FL
    3181 Royal Tern Drive
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,616 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  17. Photo of 8208 Waterview Way #8208, Winter Haven, FL 33884 (MLS # P4927867)
    $149,900
    Photo of 8208 Waterview Way #8208, Winter Haven, FL 33884 (MLS # P4927867)
    Photo of 8208 Waterview Way #8208, Winter Haven, FL 33884 (MLS # P4927867)
    8208 Waterview Way #8208, Winter Haven, FL
    8208 Waterview Way #8208
    Winter Haven, FL
    • 1 Bed
    • 1 Bath
    • 559 Home (sqft)
    • 1 Bath
    • 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 12/22/24 6:20 PM PST.

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