Best Places to Retire in Florida: Winter Haven

Winter Haven bird eye view

The dozens of retirement communities dotting its landscape are proof that Winter Haven is one of the best places to retire in Florida. Its central location between two major Florida cities, incredible natural beauty, the 50 lakes that give it the nickname Chain of Lakes City, and endless dining, shopping, entertainment, and outdoor activities make this small city a true haven, not just for snowbirds but also for retirees looking for the best Florida living for seniors.

What to Expect

Winter Haven Downtown


Winter Haven is a small city of about 45,000 that is located almost exactly 50 miles from both Orlando and Tampa. Its central location makes it perfect for retirees, because it offers peaceful lakeside living within reach of big-city appeal. Add in a low-cost of living and some world-renowned attractions, and there is a reason this city has grown more than 30 percent over the last 10 years.


Winter Haven originally earned its name because of its pleasant year-round climate that does make it a true retreat from the harsher winters of more northern states. If you can handle a little bit of mugginess in the middle of the year, you can enjoy balmy temperatures that make living in this city, and state, a truly enjoyable experience.

The city enjoys an average January high of 73 degrees, but summers do not get much hotter than the rest of the state, with average highs topping out in the low 90s. Add in an impressive 242 days of sunshine and no snow, and Winter Haven truly lives up to its name. Retire here, and you can say goodbye to winter driving, snow shoveling, and bitter cold days.


During retirement, you want to fewinel secure so you can enjoy all of the amenities and recreation available in your chosen city. Winter Haven, despite having a slightly higher crime rate than average, still only experiences a crime rate of 4.16 crimes per 1,000 residents. The city also experiences a lower crime rate than average in areas such as motor vehicle theft and burglary.

Life in Winter Haven is particularly safe in the eastern and southwestern parts of the city, which is where Bedrock Communities’ Cypress Harbor 55+ community is located. Here, you can live in security and confidence for a truly peaceful retirement.

Practical Living

City skylineAirport

Winter Haven has a general aviation airport, which may be of interest if you wish to do your own flying during your retirement. If you are looking for air transportation in and out of Winter Haven, however, you have multiple options available in the major cities surrounding the city.

The closest major airport to the city is Orlando International Airport (MC), which is less than 40 miles and about an hour’s drive from Winter Haven. Other airports a little further away include Tampa International Airport (TPA) and Orlando Sanford Airport (SFB).

Depending upon your time and budget, you can make your way to these airports by car, bus, or even shuttle. That makes getting into and out of your retirement retreat, and welcoming guests into your home, simple and relatively fast.

Getting Around

Because Winter Haven possesses a suburban atmosphere, you should plan to bring your own vehicle to help you get around. However, there are some areas of the city that are intentionally walkable.

In particular, the newly revitalized downtown area is designed to be pedestrian-friendly and give you easy access to its numerous restaurants and shops. In addition, some communities, such as our Cypress Harbor community, allow you to walk safely and conveniently to visit neighbors and access amenities.

Winter Haven also possesses its own bus transit system, called Winter Haven Area Transit, which operates 9 buses. An additional 4 buses operate from the Polk County Citrus Connection transit system, so you can get to important areas of the city without needing to take a car.


The many stores in Winter Haven cluster primarily in the downtown area, where you can find numerous specialty and gift shops, such as antique shops, a Lego store, and vintage stores. In addition, you can do all of your major grocery and retail shopping right in the city, where box stores such as Walmart are also plentiful.


The nearby big cities of Orlando and Tampa make access to big-name hospitals and cutting-edge healthcare a matter of a short drive out of Winter Haven. However, Winter Haven itself also offer numerous healthcare options, including the following:

  • Home health care
  • Women and children healthcare
  • AdventHealth Centra
  • Rehabilitation center
  • Nursing homes
  • Surgery facilities
  • And more

The abundance of medical care options in Winter Haven make it easy and convenient to get good healthcare, regardless of your specific medical needs.


Completing your banking errands is convenient in Winter Haven, thanks to the presence of numerous financial institutions. From credit unions to banks, lenders, and regional institutions, your preferred bank is probably nearby. That makes doing everything from withdrawing cash to getting a loan easy to do locally so you can successfully manage your retirement finances.


All of your postal needs can also be fulfilled in Winter Haven. The city has a post office, as well as several UPS stores and FedEx locations. If you choose to live in a retirement community, such as Cypress Harbor, you can also complete some of your post office transactions right within your community.

Things to Do


Winter Haven could hardly call itself a Florida city if it did not have access to beaches. The city’s renowned chain of 50 lakes makes numerous beaches a reality right within the city limits. Try any of the following:

  • Winter Haven Park
  • Max Beach
  • Lake Shipp Park
  • Lake Roy Beach
  • Lakefront Beach

In addition, you can access some of Florida’s most beautiful and famous ocean beaches, such as Clearwater Beach, within a drive of about an hour and a half. That makes sunbathing, fishing, kayaking, sailing, swimming, and more an integral part of a truly enjoyable Florida retirement.


While Legos may not be a central part of your retirement, it is one of the most famous attractions in Winter Haven. Built on the site of the former renowned Cypress Gardens, LEGOLAND provides endless entertainment for kids from 2-12. That means that your retirement home could become a destination for grandkids who want to explore the wonders of Lego with you.

Vintage Explorations

Vintage and antiques are abundant in Winter Haven, so if antiquing is your thing, you may want to enjoy Florida living for seniors right here. The city is part of Florida’s Antique Loop, where numerous antique shops provide endless opportunities to explore, learn about, and purchase parts of the past.

In addition, Winter Haven is home to the world’s largest collection of vintage aircraft. Housed at The Fantasy of Flight in the Central Florida Air Museum, this collection actively restores these aircraft and is always willing to give you a tour.

Outdoor Fun

The great outdoors are right at your fingertips when you live in Winter Haven. The height of places to retire in Florida, this city provides 13 miles of biking trails, numerous parks, and of course, endless lakeside activities to enjoy within the city limits.

Arts and Culture

If you prefer shows and art, you can still enjoy Winter Haven. The area is home to many theatres, shows, and art displays. Fulfill your arts and culture cravings at any of the following locations:

  • Gram Parson’s Derry Down
  • Theatre Winter Haven – One of the nation’s best community theatres.
  • Ritz Theatre

Water Activities

Winter Haven makes the most of its many lakes. Here you can kayak, canoe, swim, fish, and more in any of the area’s beautiful lakes. In addition, Winter Haven puts on some pretty amazing water-based fun, including the following:

  • Pontoon boat cruises
  • Waterski team performances
  • Paddleboard tours
  • And more

Find a Home

Cypress Harbor in Winter HavenBedrock Communities Living

Winter Haven’s median home price of about $241,000, the area might not be the friendliest to retirement budgets. The good news, however, is that Bedrock Communities’ Cypress Harbor offers attainable and quality mobile home options for far less than the average home price in the city. That means you can enjoy the best in Florida living while staying within your budget.


Our Cypress Harbor community is built with your retirement needs in mind. The goal is to give you a home that matches your lifestyle and your taste. Join our community, and discover all of the following features:

  • A short drive from shops, dining, entertainment, beaches, and big cities
  • Beautiful mobile homes for an affordable price
  • Pet-friendly policies
  • An active and friendly 55+ community


Our Cypress Harbor community also boasts many amenities right within our community. These amenities give you the chance to relax, have fun, and connect with your neighbors in a relaxed environment. Find all of the following in Cypress Harbor:

  • Shuffleboard court
  • Clubhouse
  • Lake access
  • Fire pit

If you are looking for great Florida living for seniors, look no further than Winter Haven. Our beautiful community and great homes make the perfect location to enjoy everything Winter Haven has to offer you. Contact us today to learn more!

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