New 55+ Communities in Winter Haven

Located just 50 miles east of Tampa and about the same distance southwest of Orlando, Winter Haven is the perfect location for retirees who are looking to get away from the big cities but still be close enough to visit whenever they want.

Winter Haven is also home to exciting outdoors and water sports opportunities, an award-winning community theater program, some of the best antique shopping in Florida, and a wide range of excellent dining options for all occasions.

Where to Retire in Winter Haven

Winter Haven has a wide variety of community and housing types to offer, but currently only one new 55+ community is being developed:

Lake Ashton – Winter Haven, FL

Set on over 1,200 scenic acres, amongst three spectacular lakes and nature preserves, Lake Ashton offers a great retirement lifestyle in the heart of Florida. This award-winning, 24-hour manned gated community is tucked between Tampa and Orlando.

Lake Ashton has two 18-hole golf courses, a 26,000 sq. ft. main clubhouse, a 30,000 sq. ft. fitness center, community pools, pickleball, and tennis courts, and so much more.

New homes and resales are available from the $300k's.

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Other Winter Haven 55+ Communities

Other popular 55+ communities include Traditions at Lake Ruby, Vienna Square, and several more. Here are some homes in various Winter Haven 55+ communities currently on the market:

For more information on what options might be available in your desired price range, just fill out this form:

Getting to Winter Haven

As I mentioned, Winter Haven is pretty much equidistant to Tampa and Orlando, so you could potentially fly into either Orlando International Airport or Tampa International Airport.

It's a pretty easy drive from anywhere within Central Florida to get to Winter Haven, as it sits about 10 miles south of I-4.

Winter Haven History

The area that would eventually become known as Winter Haven was originally home to the Timucua and Calusa tribes. It was also inhabited by various Seminole tribes throughout the 19th century. Railroad expansion in the middle of that century brought the first settlers to the area which was eventually named Winter Haven because of its comfortable year-round climate.

While there was some growth in the area during the early 1900s, things really began to take off in Winter Haven following World War II. During this century, the town welcomed the very first Publix supermarket, a large citrus packing plant, and the visually stunning Cypress Gardens, which would eventually become today's Legoland.

Winter Haven Cost of Living

With a cost of living index of 88.1, Winter Haven is quite a bit under the national average (100) in this department, and even further under Florida's cost of living index of 102.8.

A large component of the cost of living index is an area's median home sales price. While the median sales price for Florida as a whole in 2021 was $348,000, the median home sales price in the Lakeland-Winter Haven Metropolitan Statistical Area for the same time period was $270,000.

So if you are trying to figure out where in Florida you can get the most bang for your buck housing-wise, and also be able to stretch a dollar further once you get here, you can't do too much better right now than the Winter Haven area.

Winter Haven Healthcare

Admittedly you won't find as many healthcare options in Winter Haven as you would in bigger cities like Orlando, Tampa, or Jacksonville. But there are some decent options available, including Winter Haven Hospital, and Lakeland Regional Health Medical Center is about 30 minutes away in Lakeland.

Winter Haven Weather

As the name suggests, it's a Haven in the Winter. Here’s a look at the average low and high temperatures in Winter Haven throughout the year:

Month	Avg. Low	Avg. High
January	51	73
February	52	76
March	57	80
April	60	84
May	66	89
June	71	91
July	73	92
August	73	92
September	72	90
October	66	86
November	59	79
December	53	75

Winter Haven Lifestyle

The Winter Haven lifestyle is all about getting out on the water and enjoying more than 55 lakes that you will find across the region. That means that everything from waterskiing and wakeboarding to kayaking and standup paddleboarding is available here throughout the year.

Tripadvisor has a good list of the best things to do in Winter Haven.

Winter Haven Culture

Theatre Winter Haven has long been the heart of the cultural side of the community. Here you will find one of the most decorated community theatre organizations in all of Florida, and just wait until you see what they have planned for their brand new Chain O' Lakes Complex!

There is also the Polk Theatre located right down the road in Lakeland, which almost always has an old film or live musical performance on its calendar.

Nearby Lakeland is also the home of Florida Southern College, which houses the largest single-site collection of Frank Lloyd Wright designs, and you can find some exciting vintage aircraft restoration projects happening at The Fantasy of Flight.

Winter Haven Dining

If delicious food in a casual environment is what you are looking for, Nutwood should be at the top of your bucket list for dining in Winter Haven. This modern American restaurant boasts some high-end menu items at mid-range prices that keep your palate coming back for more. And since the weather is always great in Winter Haven, you can usually make use of their lovely patio seating.

Another favorite restaurant in the area is Harry's Old Place, which is the classic Florida seafood restaurant that offers the perfect combination of a casual environment and stunning views of the water. Their fried fish “blackboard” changes every day, and you can get their fresh catches prepared just about any way you like.

When you are ready for a special meal in Winter Haven, Arabellas is the ultimate destination. This high-end Italian restaurant offers all of your favorite dishes prepared perfectly in an environment that just screams “special occasion.”

With everything that Winter Haven has to offer, it is no surprise that it has developed a reputation as one of the best destinations for retirees. If you are looking for an option between Tampa and Orlando, this lovely town offers a unique hybrid combination of both.