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Living a Boating Lifestyle in Winter Haven, Florida

If you have been looking for a great lake boating town, look no further than Winter Haven, FL. The former home of Cypress Gardens and its famous waterskiers, Winter Haven boasts over 50 lakes within the city limits, many of which areconnected by canals. When you are tired of boating or fishing,  the excellent parks await your recreation needs.  There is a four year college, Polk State College.  you can get more information by contacting our Greater Winter Haven Chamber of Commerce. The city is a little over one hours drive from Atlantic or Gulf beaches.  We love it here.  Our condo is 1400 sq.ft. overlooking the chain of lakes and we can walk to many things including grocery and restaurants. There is a city park 8 acres in size with wonderful walking trails, exercise equipment and lots of shade.  Photos courtesy of Winter Haven Chamber of Commerce.

Where to Retire in Winter Haven and Home Prices

There are active adult communities in the area (link at top left).

The National Association of Realtors reports the median sale price to be $343,000 during the 2nd quarter of 2022, in the Lakeland-Winter Haven area, up over 30% from a year earlier.

What Is Special about Winter Haven

Winter Haven was formerly the home of Cypress Gardens, the theme park that has since closed.   "Legoland Florida", a 150 acre theme park opened in 2011, and is on the site of the original Cypress Gardens theme park, although 30 acres of the original cypress Gardens is preserved with this change for historic continuity.  Because of its many lakes, Winter Haven has been the home of several water skiing schools. There is a public library built from scratch 10 years ago, which is an anchor for our downtown area and its Main Street Program.  The chain of lakes trail goes through the city and is excellent for walking.

What Is Not Special about Winter Haven

The crime rate is above average.

Climate and Physical Environment

There is a very large number of lakes in the area, which is in central Florida. The average January temperature is above 60 degrees.

Restaurants & Cultural Scene

Winter Haven boasts many buildings designed by Gene Leedy, one of the founders of the Sarasota School of Architecture. Polk State College offers some cultural programs. 


According to the crime rate (455) is well above the U.S. average (301).

Medical Facilities

500 bed Winter Haven Hospital not for profit with national recognition for programs in heart and stroke care.


There is an Amtrak stop 1/2 mile from downtown with 2 trains going North and 2 trains going South daily.  Interstate 4 is nearby, and the huge Orlando Airport is not too far.

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