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  • 118 South Fremont Avenue
    Tampa, FL 33606
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Miami Association of REALTORS®

MIAMI ASSOCIATION OF REALTORS® All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Multiple Listing Service. Real estate listings held by brokerage firms other than Marjo Realty Co. may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS.

My Florida Regional MLS DBA Stellar MLS

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website. Listing Information presented by local MLS brokerage: Renaissance Realty Group

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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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homeHouses apartmentCondos & Apartments holiday_villageTownhouses & Duplexes crop_landscapeLots & Land parkFarms & Ranches

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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