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Life in Winter Haven

Winter Haven, Florida

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.


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.


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.


  • 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. Popular spots include Paradise Island RV Park, Circle B Bar Reserve in nearby Lakeland, Chain O’ Lakes Complex, and Winter Haven Recreational and Cultural Center.

    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.

  • Water sports – With so many lakes to explore in and around Winter Haven, there is a wide variety of water sports to enjoy. Go on a kayak or paddleboat, or try out wakeboarding and water skiing!
  • 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.
  • Bass fishing – Over the years, Winter Haven has built a reputation as a world-class destination for bass fishing. And why not? Winter Haven’s lakes are well-stocked with healthy populations of bass and other fish species for most of the year.
  • 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.

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 or