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    • 100 Dutch Hill Rd Suite 260
      Orangeburg, NY 10962
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    Chain of Lakes City

    Townhouses & Duplexes in Winter Haven, FL

    Welcome to Winter Haven, the Polk County "Chain of Lakes City" between Tampa and Orlando, home to Legoland Florida and dozens of canal-connected lakes.

    Winter Haven is a mid-sized city in Polk County, Florida, positioned in the center of the state between Tampa and Orlando along the Interstate 4 corridor. Its defining geographical feature is water: the city is touched by dozens of lakes, with more than 20 of them linked by navigable canals to form the celebrated Chain of Lakes. That interconnected waterway, unusual among Florida cities, has shaped the community's identity, economy, and housing patterns for more than a century. The city's modern history is closely tied to tourism. Cypress Gardens, founded in 1936, became one of Florida's signature mid-century attractions, famous for its botanical gardens and pioneering water ski shows. Although the theme park closed in 2009, its legacy endures: the gardens were preserved within Legoland Florida, which opened on the site in 2011 and now anchors the area's tourism economy. The Cypress Gardens Water Ski Team continues to perform on Lake Eloise, keeping a piece of the city's heritage alive. Winter Haven's economy extends beyond tourism to healthcare, agriculture, and logistics, with the city serving as a commercial hub for eastern Polk County. Its population has grown steadily, drawing families, retirees, and commuters who appreciate the lakeside lifestyle and the city's position between two major metros. For residents, Winter Haven offers a distinctive combination: genuine lake living with public water access, a major family attraction in Legoland, and convenient highway connections to Tampa, Orlando, and Lakeland. It is a city where recreation on the water is woven into everyday life rather than reserved for vacations.

    Population 64,648
    County Polk County
    Active Listings 1431
    Browse by Listing Type
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    Frequently Asked Questions

    What county is Winter Haven in?

    Winter Haven is located in Polk County, Florida, in the central part of the state between Tampa and Orlando. It sits within the Interstate 4 corridor, one of Florida's busiest growth areas.

    Why is Winter Haven called the Chain of Lakes City?

    Winter Haven is called the Chain of Lakes City because dozens of lakes touch the city, with more than 20 connected by navigable canals. The city maintains boat ramps, waterfront parks, and public docks that make the chain central to boating, fishing, and daily life.

    What is Legoland Florida?

    Legoland Florida is a large theme park and resort that opened in 2011 on the historic grounds of Cypress Gardens. It preserved the original botanical gardens, which have been a Florida attraction since 1936, and offers themed rides, water park attractions, and family entertainment.

    What school district serves Winter Haven?

    Winter Haven is served by the Polk County Public School District, one of the largest districts in Florida with about 160 school sites. Winter Haven Senior High School is among the district's campuses serving the city.

    How far is Winter Haven from Tampa and Orlando?

    Winter Haven sits roughly midway between Tampa and Orlando, with Lakeland about 19 miles to the west. U.S. Highways 27 and 17 and State Roads 540 and 544 serve the city, placing both metropolitan areas within a short drive.

    MARKET SNAPSHOT

    The Market at a Glance

    How homes have been selling here over the last 90 days.

    home_work New This Week 50
    Went Under Contract 3
    trending_down Price Reductions 0
    payments Median Sale Price $281,000 -1.7%
    square_foot Price per Sq Ft $133
    schedule Avg Days on Market 86
    sell Homes Sold 364
    percent Sale-to-List Ratio 99.0%
    inventory_2 Months of Inventory 8.3

    Price & Sales History

    Market data reflects closed sales over the last 90 days and is provided for informational purposes.

    BROWSE BY ZIP

    Zip Codes

    Browse listings by postal code in this area.

    010 homes for saleMedian sale$295K1 sale in the last 90 days
    003 homes for saleMedian sale$295K
    0001 home for saleMedian sale$295K
    00006 homes for saleMedian sale$295K
    0000029 homes for saleMedian sale$370KPer sq ft$199 sales in the last 90 days
    0060225 homes for saleMedian sale$417.5KPer sq ft$3124 sales in the last 90 days
    0060322 homes for saleMedian sale$235KPer sq ft$7273 sales in the last 90 days
    0061228 homes for saleMedian sale$160KPer sq ft$1685 sales in the last 90 days
    0062359 homes for saleMedian sale$240KPer sq ft$19214 sales in the last 90 days
    006418 homes for saleMedian sale$262KPer sq ft$1762 sales in the last 90 days
    00646141 homes for saleMedian sale$1.5MPer sq ft$59625 sales in the last 90 days
    0066239 homes for saleMedian sale$463KPer sq ft$2939 sales in the last 90 days
    View All Zip Codes
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    1507 7TH STREET SW #1511 For Rent
    $1,150
    1507 7TH STREET SW #1511Winter Haven, FL 33880
    • 2 bd
    • 1 ba
    • 1860 sqft
    • Built 1948
    • MFRS5155819
    2318 W CANNON TERRACE NW #B For Rent
    $1,675
    2318 W CANNON TERRACE NW #BWinter Haven, FL 33881
    • 3 bd
    • 2 ba
    • 1040 sqft
    • Built 2022
    • MFRO6434361
    504 ORANGE BLOSSOM DRIVE For Rent
    $1,850
    504 ORANGE BLOSSOM DRIVEWinter Haven, FL 33880
    • 2 bd
    • 2.5 ba
    • 1924 sqft
    • Built 1993
    • MFRP4939612
    2500 21ST STREET NW #44 For Rent
    $1,500
    2500 21ST STREET NW #44Winter Haven, FL 33881
    • 2 bd
    • 2.5 ba
    • 1828 sqft
    • Built 1975
    • MFRL4964002
    2463 AVENUE C SW #A For Rent
    $1,275
    2463 AVENUE C SW #AWinter Haven, FL 33880
    • 2 bd
    • 1 ba
    • 854 sqft
    • Built 1978
    • MFRTB8533906
    139 AVENUE D SW For Rent
    $1,350
    139 AVENUE D SWWinter Haven, FL 33880
    • 2 bd
    • 1 ba
    • 1082 sqft
    • Built 1972
    • MFRP4939394
    1484 32ND STREET NW For Rent
    $1,100
    1484 32ND STREET NWWinter Haven, FL 33881
    • 2 bd
    • 1 ba
    • 950 sqft
    • Built 1985
    • MFRS5152662
    3022 FIREBRUSH LANE For Sale
    $254,900
    3022 FIREBRUSH LANEWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1673 sqft
    • Built 2026
    • MFRO6425598
    2765 GLADIOLA ROAD For Sale
    $263,990
    2765 GLADIOLA ROADWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1673 sqft
    • Built 2026
    • MFRO6425596
    2759 GLADIOLA ROAD For Sale
    $263,990
    2759 GLADIOLA ROADWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1673 sqft
    • Built 2026
    • MFRO6425591
    2753 GLADIOLA ROAD For Sale
    $263,990
    2753 GLADIOLA ROADWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1673 sqft
    • Built 2026
    • O6425589
    2747 GLADIOLA ROAD For Sale
    $263,990
    2747 GLADIOLA ROADWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1673 sqft
    • Built 2026
    • MFRO6425585
    4 ENCLAVE DRIVE For Sale
    $240,000
    4 ENCLAVE DRIVEWinter Haven, FL 33884
    • 3 bd
    • 2 ba
    • 2149 sqft
    • Built 1995
    • MFRP4939268
    532 WINTER TERRACE For Sale
    $164,000
    532 WINTER TERRACEWinter Haven, FL 33881
    • 3 bd
    • 2 ba
    • 1073 sqft
    • Built 1996
    • O6376627
    2723 GLADIOLA ROAD For Sale
    $263,990
    2723 GLADIOLA ROADWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1673 sqft
    • Built 2026
    • O6424234
    2771 GLADIOLA ROAD For Sale
    $273,990
    2771 GLADIOLA ROADWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1758 sqft
    • Built 2026
    • O6424150
    2741 GLADIOLA ROAD For Sale
    $273,990
    2741 GLADIOLA ROADWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1758 sqft
    • Built 2026
    • O6424142
    1507 7TH STREET SW #1507 For Rent
    $1,049
    1507 7TH STREET SW #1507Winter Haven, FL 33880
    • 1 bd
    • 1 ba
    • 620 sqft
    • Built 1948
    • S5153118
    702 AVENUE H NE For Rent
    $2,000
    702 AVENUE H NEWinter Haven, FL 33881
    • 3 bd
    • 2 ba
    • 1900 sqft
    • Built 1955
    • P4939213
    308 AVE P NW For Rent
    $1,650
    308 AVE P NWWinter Haven, FL 33881
    • 2 bd
    • 2 ba
    • 1071 sqft
    • Built 2025
    • O6420616
    2711 GLADIOLA ROAD For Sale
    $254,900
    2711 GLADIOLA ROADWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1673 sqft
    • Built 2026
    • O6420341
    501 AVENUE G SE #A For Rent
    $1,595
    501 AVENUE G SE #AWinter Haven, FL 33880
    • 3 bd
    • 1 ba
    • 1234 sqft
    • Built 1955
    • O6419533
    3025 CAPTAIN JAX WAY For Sale
    $239,990
    3025 CAPTAIN JAX WAYWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1623 sqft
    • Built 2026
    • O6419265
    664 CLUBHOUSE ROAD For Sale
    $235,000
    664 CLUBHOUSE ROADWinter Haven, FL 33884
    • 2 bd
    • 2 ba
    • 1458 sqft
    • Built 1981
    • P4939078
    117 NEMO LANE For Sale
    $249,900
    117 NEMO LANEWinter Haven, FL 33881
    • 3 bd
    • 2.5 ba
    • 1942 sqft
    • Built 2026
    • L4962759
    5657 STRUTHERS COURT For Rent
    $1,475
    5657 STRUTHERS COURTWinter Haven, FL 33884
    • 2 bd
    • 1 ba
    • 1890 sqft
    • Built 1984
    • O6415136
    209 AVENUE B SE For Rent
    $1,500
    209 AVENUE B SEWinter Haven, FL 33880
    • 2 bd
    • 1 ba
    • 993 sqft
    • Built 1977
    • S5151255
    3032 CAPTAIN JAX WAY For Sale
    $219,990
    3032 CAPTAIN JAX WAYWinter Haven, FL 33884
    • 3 bd
    • 2.5 ba
    • 1586 sqft
    • Built 2026
    • O6412165
    1830 2ND STREET NW #B For Rent
    $1,575
    1830 2ND STREET NW #BWinter Haven, FL 33881
    • 3 bd
    • 1 ba
    • 1075 sqft
    • Built 2006
    • O6411725
    1830 2ND STREET NW #A For Rent
    $1,575
    1830 2ND STREET NW #AWinter Haven, FL 33881
    • 3 bd
    • 1 ba
    • 1075 sqft
    • Built 2006
    • O6411721
    2097 AVENUE H NW For Sale
    $315,000
    2097 AVENUE H NWWinter Haven, FL 33881
    • 4 bd
    • 2 ba
    • 1893 sqft
    • Built 1952
    • L4962122
    245 WINTER RIDGE BOULEVARD For Rent
    $1,450
    245 WINTER RIDGE BOULEVARDWinter Haven, FL 33881
    • 2 bd
    • 2 ba
    • 1140 sqft
    • Built 1992
    • S5150403
    154 2ND STREET SW #Unit 7 For Sale
    $495,000
    154 2ND STREET SW #Unit 7Winter Haven, FL 33880
    • 2 bd
    • 2.5 ba
    • 2080 sqft
    • Built 2015
    • L4961765
    5667 STRUTHERS COURT For Rent
    $1,300
    5667 STRUTHERS COURTWinter Haven, FL 33884
    • 2 bd
    • 1 ba
    • 1646 sqft
    • Built 1983
    • P4938716
    10 ENCLAVE DRIVE For Sale
    $214,900
    10 ENCLAVE DRIVEWinter Haven, FL 33884
    • 2 bd
    • 2 ba
    • 2072 sqft
    • Built 1996
    • P4938719
    3023 CANEEL STREET For Sale
    $235,000
    3023 CANEEL STREETWinter Haven, FL 33884
    • 2 bd
    • 2 ba
    • 1773 sqft
    • Built 2020
    • TB8504638
    606 ORANGE BLOSSOM DRIVE For Sale
    $224,900
    606 ORANGE BLOSSOM DRIVEWinter Haven, FL 33880
    • 3 bd
    • 2 ba
    • 1407 sqft
    • Built 1994
    • P4938640
    2330 SE ROYAL ISLE For Sale
    $215,000
    2330 SE ROYAL ISLEWinter Haven, FL 33880
    • 2 bd
    • 2.5 ba
    • 1872 sqft
    • Built 1996
    • O6402947
    324 AVENUE Y NE #B For Rent
    $1,550
    324 AVENUE Y NE #BWinter Haven, FL 33881
    • 2 bd
    • 2 ba
    • 904 sqft
    • Built 2024
    • O6402503
    139 WODEN WAY For Sale
    $429,500
    139 WODEN WAYWinter Haven, FL 33884
    • 4 bd
    • 3.5 ba
    • 3572 sqft
    • Built 1994
    • P4938404
    321 ORANGE BLOSSOM DRIVE For Sale
    $199,950
    321 ORANGE BLOSSOM DRIVEWinter Haven, FL 33880
    • 2 bd
    • 2.5 ba
    • 1924 sqft
    • Built 2001
    • S5146754
    28 CASARENA COURT For Sale
    $155,000
    28 CASARENA COURTWinter Haven, FL 33881
    • 2 bd
    • 2.5 ba
    • 2045 sqft
    • Built 1989
    • S5146381
    1502 NE BUCKEYE ROAD NE #2 For Sale
    $279,900
    1502 NE BUCKEYE ROAD NE #2Winter Haven, FL 33881
    • 3 bd
    • 3 ba
    • 2731 sqft
    • Built 1974
    • O6389762
    503 AVENUE B NW #503 For Sale
    $325,000
    503 AVENUE B NW #503Winter Haven, FL 33881
    • 2 bd
    • 2.5 ba
    • 1408 sqft
    • Built 1982
    • P4938108
    137 NEMO LANE For Sale
    $259,900
    137 NEMO LANEWinter Haven, FL 33881
    • 3 bd
    • 2.5 ba
    • 1942 sqft
    • Built 2026
    • L4959021
    133 NEMO LANE For Sale
    $249,900
    133 NEMO LANEWinter Haven, FL 33881
    • 3 bd
    • 2.5 ba
    • 1942 sqft
    • Built 2026
    • L4959017
    2739 RUTLEDGE COURT For Sale
    $215,000
    2739 RUTLEDGE COURTWinter Haven, FL 33884
    • 3 bd
    • 2 ba
    • 1789 sqft
    • Built 2006
    • P4936870
    5850 CYPRESS GARDENS BOULEVARD #304 For Sale
    $139,000
    5850 CYPRESS GARDENS BOULEVARD #304Winter Haven, FL 33884
    • 2 bd
    • 1.5 ba
    • 1332 sqft
    • Built 1975
    • O6266648
    11 CASARENA COURT For Sale
    $230,000
    11 CASARENA COURTWinter Haven, FL 33881
    • 2 bd
    • 2.5 ba
    • 2500 sqft
    • Built 1985
    • S5132611
    49

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