Winter Haven : Florida


What It Is Like to Retire in Winter Haven

WinterHaven, FL is located midway between Orlando and Tampa off I-4 and is a small city of 49,219 (2020 Census).  Winter Haven is the chain of lakes city with over 50 lakes within the city limits with many connected by canals.  There is a four year college located here, Polk State College. The city is a little over one hours drive from Atlantic or Gulf beaches.  

Watch this short Youtube video prepared by WinterHavenChamber:

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.

Who Will Like Retirement in Winter Haven

Winter Haven is definitely a popular retirement spot with an average age of 44.

Local Economy Is Driven by

Retirement and tourism have been traditional staples of the economy.

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.

Valuable Links

Winter Haven website
Winter Haven NewsChief
Winter Haven Videos


What people are saying about Winter Haven

We love Winter Haven
This comment came in from David, who loves Winter Haven: We as residents and retirees are sold on this place and so glad that we found it. Winter Haven has to be Florida's best kept secret. I realize many of your readers are looking for the massive gated retirement communities. We have some of those in Winter Haven too. But there are also many, and a growing number, who would be far better served in a small city like Winter Haven in established housing with manageable fees, taxes etc. If you have a few minutes go to and type in Winter Haven, FL. Hundreds of places will pop up with prices way, way, way below what you would expect including many with water, golf and park views. I think you will be amazed. When you see the prices and the quality of what's available here you may even want to get a place and come yourself!!!
Posted by topretirementseditor on January 14, 2011

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