Winter Haven, FL 4-10
Often overshadowed by its larger neighbors Orlando and Tampa, Winter Haven, FL has been quietly transforming itself into one of Florida’s most appealing destinations.
Known as the “Chain of Lakes City,” Winter Haven boasts a unique aquatic network that defines its character. While locals proudly dubbed it the “City of 100 Lakes,” the reality is slightly more modest but no less impressive—55 lakes dot the landscape, with 24 connected by navigable canals. This distinctive feature creates a waterway system that allows residents and visitors to traverse significant portions of the city entirely by boat, canoe, or kayak.
The city’s history is deeply rooted in Florida’s agricultural past. The first settlers arrived in the 1860s, with the village officially named by P.D. Eychleshimer in 1885. The famous canal system, now a recreational treasure, was originally constructed between 1915 and the early 1920s to transport citrus crops—a testament to Winter Haven’s innovative spirit even a century ago. Read another article.
Perhaps Winter Haven’s most significant claim to fame came in 1936 when Dick Pope opened Cypress Gardens on Lake Eloise. For 73 years, this botanical wonderland entertained more than 50 million visitors before closing its doors. The legacy continues today as LEGOLAND Florida Resort now occupies this historic site, maintaining the beautiful botanical gardens while adding colorful building blocks to Winter Haven’s tourism portfolio. In 2022, the Peppa Pig Theme Park joined LEGOLAND, further cementing Winter Haven’s place on Florida’s tourism map.
The economic landscape of Winter Haven reflects remarkable growth and diversity. Part of the Winter Haven-Lakeland Metropolitan Statistical Area, the region was the second-fastest growing in the United States in 2020, with a growth rate of 45% from 2010 to 2020. The city itself now boasts nearly 50,000 residents within its limits.
What sets Winter Haven apart from many Florida communities is its economic self-sufficiency. Rather than functioning as a bedroom community for larger cities, Winter Haven has cultivated a diverse economic ecosystem built on small businesses, entrepreneurs, and larger industries. The city strategically focuses on six target sectors: agribusiness, business development, freight transportation and logistics, healthcare, technology and innovation, and tourism and hospitality.
Downtown Winter Haven has experienced a renaissance in recent years, with a walkable core featuring locally-owned shops, innovative restaurants, and cultural venues. The historic Ritz Theatre has found new life under local leadership, adding to the city’s growing arts scene.
The natural environment remains central to Winter Haven’s identity. Beyond the lakes, residents enjoy Florida’s characteristic sunshine and mild climate most of the year, with occasional afternoon showers providing perfect opportunities to explore indoor attractions and cultural venues.
As Winter Haven continues to evolve, it maintains a delicate balance between growth and preserving its lakeside lifestyle. The community prides itself on offering “something for everyone”—whether you’re raising a family, starting a business, enjoying retirement, or simply visiting. This versatility, combined with a lower cost of living than neighboring metropolitan areas, makes Winter Haven not just a destination but increasingly a destination of choice for those seeking Florida living without the crowds and costs of bigger cities.
In the heart of what locals call “Florida’s Super Region,” Winter Haven embodies the best of Central Florida—water, sunshine, opportunity, and community—all wrapped in a package that remains refreshingly authentic.
Additional information about Winter Haven, FL.
POI #1 – Lake Shipp Park, 1649 Lake Shipp Dr, Winter Haven, FL 33880’
POI #2 – Lake Shipp Elementary School, 250 Camellia Dr, Winter Haven, FL 33880
POI #3 – Harborside, 2435 7th St SW, Winter Haven, FL 33880