Winter Haven
Life In Winter Haven

Winter Haven known as the Chain of Lakes City, boasts stunning residential properties and outstanding quality of life, among many other admirable qualities. Here is everything you need to know about living in Winter Haven.
History
Prior to Winter Haven's incorporation as a city in 1923, the area was settled by different groups throughout history. First were the Calusa and the Timucua, both of which are considered Winter Haven's earliest inhabitants. These two groups were severely affected by war and disease during the 16th century when the Spanish came. They were followed by the Seminole and the Creek in the 19th century. In this time period, Florida became part of the United States. The 20th century saw Winter Haven's incorporation and expansion. More and more people came to the city to establish their roots. Most of Winter Haven's historic Colonial Revival homes were built during this period. Winter Haven's growth continued to become the city we all know and love today.

Location
Winter Haven is located in Polk County in Central Florida. It is a part of the Lakeland-Winter Haven metropolitan area. Additionally, Winter Haven is considered the second most populous city in Polk County, with a population of approximately 38,900 residents according to 2016 estimates. One of Winter Haven's most distinctive features is a large number of lakes within its boundaries. According to official records, there are about 50 lakes within the city, including Lake Howard, Lake Eloise, and Lake Lulu. Aside from being a hotbed of outdoor recreation and water activities, these lakes and their surrounding areas are thriving with wildlife. Winter Haven is located adjacent to Lakeland. Tampa is situated approximately 50 miles west of Winter Haven. Surrounding communities include Lake Alfred, Haines City, Bartow, Lake Wales, Auburndale, Davenport, Dundee, and Lakeland.
Winter Haven has many meanings to many people. For some it’s as literal as it sounds . . . it’s the perfect haven from the harsh Winter months up North. To others, Winter Haven means experiencing the lakeside lifestyle – pontoon boat tours, paddle-boarding, wake-boarding, water skiing, kayak tours and fishing.
Then there’s the more relaxed way of enjoying our lakes – watch vibrant orange and pink sunsets from a dock while sipping on a glass of wine or a Winter Haven brewed craft beer.
Winter Haven is home to LEGOLAND® Florida Resort and more. Get on Winter Haven’s Chain of Lakes or experience the city’s award winning community theatre, lakeside restaurants and local(kid-friendly) brewerys
LEGOLAND Florida Resort
To children, or even just the child within, Winter Haven is home to the most beautiful, entertaining and interactive theme park, hotel and beach resort in the world, LEGOLAND Florida Resort, Pirate Island Hotel, LEGOLAND Hotel and LEGOLAND Beach Retreat. And opening just steps from LEGOLAND in February 2022 will be the Peppa Pig Theme Park, especially designed for pre-schoolers.
Activities
Golf - There are several golf courses located in Winter Haven, such as The Country Club of Winter Haven, Cypresswood Golf Course and Country Club, Willowbrook Golf Course, and Lake Bess Golf Club. Each of these golf facilities offers a number of amenities and promise great tee times, whether you're a golf beginner or a seasoned player
Outdoor recreation - When you live in an area as beautiful as Winter Haven, there's little reason to stay indoors. Outdoor recreation is a popular pastime in Winter Haven. Winter Haven is also a short drive from a couple of wildlife preserves, such as Hilochee Wildlife Management Area, Upper Hillsborough Preserve, Colt Creek State Park, and Green Swamp Wilderness Preserve.
The Water Ski Capital of the World
For water skiers, no location is as storied as the banks of Lake Eloise, the home of Cypress Gardens in Winter Haven. It is fitting that the central point in the sport’s centennial celebration is here in Florida’s Sweetest Spot. Learn all about how we are celebrating the 100th Anniversary of the Sport of Water Ski throughout 2022
Wildlife observation - Winter Haven's lake areas are teeming with wildlife, making Winter Haven also a desired destination for wildlife enthusiasts, especially bird watchers. Animal species that have been spotted in Winter Haven include great blue herons, egrets, bald eagles, and alligators.
Shopping and dining - Downtown Winter Haven is home to a string of shopping and dining opportunities, from national retailers to local businesses and independent boutiques. Every Saturday, you will find a weekend market that sells a variety of goods, from local artisanal products to fresh produce.
Arts & Culture
Winter Haven is a place of varied arts and cultural experiences from multiple art galleries, locally-owned artisan restaurants and shopping, a restored historic downtown business district and the revival of locally-grown music at Gram Parson’s Derry Down and the historic Ritz Theatre. It’s also home to the one of Florida’s best community theaters, Theatre Winter Haven.
Downtown Winter Haven also hosts a number of community events throughout the year, such as Oktoberfest, Carols in the Park, and the annual tree lighting ceremony. What's most exciting about Downtown Winter Haven is the continuous growth and expansion of the area. In 2018, the neighborhood underwent a massive redevelopment project that made Main Street more bicycle- and pedestrian-friendly. A new park is also currently being developed as of the time of writing.
Schools in Winter Haven
Winter Haven's family-friendliness is further boosted by its well-performing schools. Public schools in and around the city, such as Jewett Academy Middle School, Winter Haven Senior High School, and Lake Region High School, are managed by Polk County Public Schools. There are also several private schools that serve Winter Haven. Explore Winter Haven real estate and homes for sale by getting in touch with us today at 863-875-5583
Made with love in Winter Haven, Florida.
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Copyright © MFRMLS.com 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 consumers 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 on this site was last updated Last updated on September 25, 2026 7:16 PM UTC The listing information on this page last changed on Last updated on September 25, 2026 7:16 PM UTCd. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of MFR MLS.
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 consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Updated on September 25, 2026 7:16 PM UTC