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Winter Haven, FL Homes for Sale

Winter Haven is known as the “Chain of Lakes City” and “City of 100 Lakes.” And while the official count is only about 55, there’s no doubt that the beautiful lakes dotting the area are its defining feature.

More than 30% of Winter Haven’s total surface area is water. This includes the famed Chain of Lakes, a series of freshwater lakes connected by canals that wind through various neighborhoods.

There are two chains of lakes in Winter Haven, the northern chain and the southern chain. The northern chain encompasses two other cities in Polk County, but the southern chain is found almost entirely in Winter Haven. In 2011, these two chains were connected with the opening of a canal lock system in the city.

Winter Haven FL Waterfront Homes For Sale

With its many lakes, Winter Haven has become one of the most popular destinations in all of Florida, particularly in the winter months. The lakes offer myriad opportunities for fun water-based activities, including waterskiing, wakeboarding, kayaking, boating, or simply gazing at the beautiful pink and orange sunsets by the beach.

The lakes are also the natural habitats of various species of fish and wildlife, making them the perfect spots for world-class fishing, wildlife viewing, and bird watching.

Winter Haven offers plenty of fun and recreation on land, too. The city is home to the world’s biggest LEGOLAND, as well as to many restaurants, retail shops, and entertainment venues. It also boasts several scenic and challenging golf courses.

The pleasures of living in Winter Haven don’t end with its bountiful attractions. The city enjoys a strong business climate, thanks to the many tech companies that have made their home here. The recent opening of the CSX Intermodal Logistics Center has also given Winter Haven’s economy a strong boost.

Real estate in Winter Haven

Winter Haven offers something for everyone – from starter homes and condos to executive homes and grand estates.

With the city’s numerous lakes, you get plenty of options for waterfront living. You will find excellent choices in various neighborhoods, including in lakeside developments that offer luxurious pool homes with top-of-line finishes and appointments, as well as smaller single-family homes updated with the latest features.

Some of the finest homes and the most desirable vacant lots are found in exclusive gated communities, including:

  • Wyndsor Oaks
  • Eloise Pointe
  • Wyndham
  • Hamilton Pointe
  • Eloise Pointe
  • Interlochen

Golf communities like Renaissance and Cypress Wood offer gorgeous single-family homes in expansive lots with great access to the water and top-rated golf courses.

Neighborhoods like The Gates of Lakes offer homes in a wide range of sizes and prices, including affordable homes ideal for starting families.

With its relaxing natural surroundings, Winter Haven is also the perfect place for retirement communities like Traditions at Lake Ruby, offering resort-style amenities and tranquil lakeside living.

Condos and townhomes are also popular in Winter Haven. A good number are waterfront developments, providing affordable options for that coveted lakeside living.

Attractions and Amenities

    • Winter Haven’s Chain of Lakes makes the city a boating mecca. You can paddle your way from one lake to another, navigating through the canals that connect them. On the lakes, you will find various rentals, including paddleboards, jet skis, kayaks and pontoon boats.


    • The city offers the finest places for waterfront dining and after-hours fun, with lakeside restaurants and bars like Harborside Restaurant, Tanner’s Lakeside and Idle Zone Bar & Grill.


    • Sport and recreational fishing are popular in Winter Haven. The Chain of Lakes teems with prized catch, including largemouth bass, sunshine bass, bluegill and crappie.


    • Downtown Winter Haven is a beautifully landscaped Main Street town, showcasing historical landmarks and a wide variety of restaurants, shops, and entertainment venues.


    • In addition to amazing LEGO displays, LEGOLAND Resort also features waterslides, fun rides and other attractions.


  • Winter Haven is home to several public and private golf courses, including Lake Bess Golf Club, East Course at Lake Ashton Golf Club and Four Lakes Golf Club.

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