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Top 5 Cities to Retire to in Florida

Judith Weiniger

After successfully growing her own brand and team under a national brand’s shingle since 2003, Judy Weiniger knew it was time to step out on her own...

After successfully growing her own brand and team under a national brand’s shingle since 2003, Judy Weiniger knew it was time to step out on her own...

Jan 24 6 minutes read

For those who are looking for fabulous 55+ communities to retire to, the Sunshine State is a popular choice with New Jersey residents, and with good reason: Its warm, tropical climate, dynamic culture, long list of attractions and the fact that it's a short flight from the northeast all make Florida a highly desired destination! 

The top cities to retire to in Florida include Tampa, Sarasota, Naples, Key West, and Boca Raton, and we explored what makes each place so special in addition to what 55+ communities are available.

Join us as we take a look at each city and what it can offer retirees:


Tucked on sunny Florida’s west coast right on Tampa Bay, Tampa is the second largest metropolitan area in Florida. Ranked as one the best outdoor cities by Forbes, Tampa is popular for its tropical climate, beautiful parks and public outdoor spaces, rich history, and long list of attractions and things to do! 

Stroll along the new Curtis Hixon Park on the waterfront, and visit the Children’s Museum, Tampa Art Museum, the amazing Florida Aquarium, eclectic restaurants, and more when family comes to visit. Many unique neighborhoods—including the historic Ybor City, settled in the late 1880s—are just waiting to be explored!

As a top choice for many in retirement, Tampa offers several 55+ communities. Sprawling luxury retirement resorts with thousands of homes, smaller golf and country clubs with hundreds of homes, and exclusive retreats along the water are all available. Homes range from under $100s all the way up to the high $700s. The eclectic selection ensures that there’s a little something for every lifestyle!

Interested in learning more about retirement communities in Tampa? Contact Judy Weiniger here!

2. Sarasota

A city just south of Tampa, Sarasota is well known for its fabulous beaches, resorts, and rich cultural scene. Home to the Sarasota Orchestra, the Sarasota Ballet, the Sarasota Opera, several theatre companies, the annual Sarasota Film Festival and a myriad of other opportunities to enjoy and participate in the performing arts, Sarasota is truly a vibrant community! Also a popular golfing and fishing destination, Sarasota has many outdoor attractions, making it easy to stay busy, entertained, and active.

When it comes to finding a 55+ community in Sarasota, there are several exclusive, resort-like options. Most of their 55+ communities have fewer than 1,000 homes, and homes in these communities typically range from the low $200s to the high $700s. Ranging from ranch settings to yacht clubs, there is a little something for every lifestyle.

Interested in learning more about retirement communities in Sarasota? Contact Judy Weiniger here!

3. Naples

Located in southern Florida, Naples is an affluent, prosperous city filled with scenic attractions, especially incredible outdoor opportunities. Home to the Everglades National Park, the Corkscrew Swamp Sanctuary, Big Cypress National Preserve, Ten Thousand Islands National Wildlife Refuge, the Naples Zoo, and several more state parks, fabulous beaches filled with white sand and stunning views!

Naples is a top-choice for many looking to retire in comfort, surrounded by natural beauty! Tropical and beautifully manicured 55+ communities range from country clubs and golf clubs to bay-side resorts. As far as size, there are smaller communities with as few as 400 homes, and large communities with thousands of residences! Price range from the mid-$100s to the high $1Ms.

Interested in learning more about retirement communities in Naples? Contact Judy Weiniger here!

4. The Villages

Located just northwest of Orlando in central Florida, The Villages is an active adult retirement community. Known as “Florida’s Friendliest Hometown,” this dynamic, sprawling community of over 50,000 residents offers the opportunity for a fabulous retirement lifestyle filled with fun, learning, activity, and social opportunities! If you’re interested in giving The Villages lifestyle a try, you can even take part in a Villages Vacation.

The community includes 3 town squares filled with shopping, restaurants, movie theaters, and nightly entertainment, fitness centers and healthcare facilities, several churches, a Lifelong Learning College and more. Staying active and getting out and about is made easy with the community’s recreation centers, which includes softball fields, polo grounds, pools, recreation rooms, and even a woodworking shop! There’s also a whopping 36 nine-hole beautifully maintained golf courses!

Interested in learning more about retirement communities in The Villages? Contact Judy Weiniger here!

5. Boca Raton

Just 43 miles north of Downtown Miami, Boca Raton is a coastal city with many outdoor attractions that nature lovers are sure to find fascinating! In addition to fabulous beaches, Boca Raton is also home to Red Reef Park and South Inlet Park, excellent snorkeling destinations. The Gumbo Limbo Nature Center is another highlight—this dynamic attraction features a butterfly garden, boardwalk trail, observation tower, and is even a research facility. Boca Raton’s outdoors attracts many, and it’s known for having some of the most beautiful, affluent gated communities in the country.

55+ communities in Boca Raton range from small, exclusive communities with as few as 30 residences, to larger 55+ communities with thousands of homes. Prices range from under the $100s all the way up to the $1Ms to suit a wide range of needs.

Would you like to learn more about downsizing and retirement living in Florida? Contact Judith Weiniger to connect you to a top agent in each of these locations!

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