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We Beg to Differ: Florida Has Some of the Best Places to Retire

Category: Best Retirement Towns and States

November 26, 2019 — Are you in the camp of retirees who “hate” Florida, or are you among those that “love” it? Most folks thinking about the best place to retire in Florida seem to fall into one of those divisions; not so many have no opinion. In our view, Florida is filled with many great retirement towns, and it is diverse in more ways than you might think. This article will tell you a bit about this very large and populous state, plus give you a list of 12 Florida towns we think make for a great place to retire.

First, a few facts
Florida’s 2018 estimated population was 21,300,000, the 4th most populous in the nation. Some 19% of the population is 65 and over, compared to 15% nationwide.

Geographically speaking, the State has a very unusual shape – it is both tall and wide. So tall and wide that it takes over a day to drive from Pensacola to Key West (832 miles). Florida is the 22nd largest state, has the longest coastline in the contiguous states, and the only state to have a coastline on the Atlantic and the Gulf of Mexico. It is a very flat state, which is one of the things that people tend not to like about it (Mount Dora, at 185′ is one of its highest towns).

Florida’s median home value in late 2019 was $237,900 – up from $120,600 in 2012 (Zillow), just slightly lower than the U.S. median ($231,000 – Zillow, or $163,500 – NAR). According to the priciest metro in the state for homes is Naples ($329,100) and the most inexpensive is Pensacola ($132,100).

From a tax viewpoint Florida is very friendly to retirees. There is no state income tax. Sales tax is 6%. Florida has a homestead law, Save Our Homes, that protects full-time residents from property taxes above the rate of inflation. One of the few economic negatives about Florida is that in many areas near the coast, property insurance is very expensive. Many private insurers have pulled out of the market after several bad hurricane seasons, leaving the non-profit Citizens Insurance Co. as the insurer of last resort. You can find more facts about Florida in our FL Mini-Retirement Guide.

12 Best Places to Retire in Florida

There are multiple ways to come up with the 10 Best Places to Retire in Florida. One way would be popularity at Topretirements: on that basis the leading contenders in 2019 would be Pensacola, Sarasota, St. Petersburg, Fort Myers, Venice, and Jupiter – all of these towns made our recent “20 Most Popular Places to Retire in the Southeast“. But based on some other rating factors – location/geography, charm, walkability/traffic, cultural resources – this a sampler of our top choices, in no particular order.

Downtown Sarasota

Sarasota, FL. Some consider Sarasota to be the cultural capital of Florida, after Miami. It has one of Florida’s best walkable downtowns with many interesting neighborhoods. An impressive array of cultural facilities are available in Sarasota, along with high-rise, luxury hotels and apartments. The barrier islands have great beaches and developments where retirees can live.

Courthouse in Vero Beach

Vero Beach. Located in the middle of Florida’s Atlantic Coast, the town is in several parts – a long ‘beach” area on the barrier island with a resort feel, and a large downtown across the bay on the mainland. There are types of interesting active adult and 55+ communities offering an array of lifestyles. The Zillow Home Value Index was $214,100. One potential drawback is Vero is relatively far from a big airport. On the other hand, it doesn’t have the congestion of some bigger places.

Downtown Delray Beach

Delray Beach
We love Delray Beach for so many reasons. At the end of the main street is an amazing stretch of public beaches and dunes. Take a boat tour on the Intracoastal…Enjoy the interesting restaurants filled with interesting people of all ages…Live downtown in a condo above the many cool shops… or take in a concert or a museum. Above all you can walk anywhere with ease. Surprisingly, the Zillow Home Value Index was only $209,800, making it a much more attractive alternative than Fort Lauderdale, Boca Raton, or Miami. Properties near the water will be much more.

Welcome to Dunedin

This great little town (pronounced Due need’ an) just north of Tampa and St Petersburg still celebrates its Scottish heritage. It has a concentrated and interesting downtown that is easy to walk through. In a State known for its beaches, its easily accessible public beaches are some of the best. There is a 39 mile bike/walk trail system running through town.

Winter Park

Winter Park

The heart of this walkable town near Orlando is Park Avenue. It is aptly named, as Winter Park claims it has more park space than any town in Florida. The walkable main street includes retail and public civic buildings, art galleries, a private liberal arts college (Rollins), museums, a park, a train station, a golf course country club, a historic cemetery, and a beach and boat launch. The Zillow Home Value Index in Winter Park is $402,700, higher than we expected to see.

Scene on Amelia Island

Fernandina Beach
Situated at the very top of Florida on the Atlantic Ocean (just above Amelia Island), this town has a wonderful and walkable downtown. There are great restaurants and shops. Best of all if you live in one of the cute neighborhoods you can be downtown with just a few steps.

The Hollywood Beach

Hollywood Beach.
Hollywood is just south of Fort Lauderdale. It enjoys about 60 parks, seven golf courses, and beaches that run for miles. Hollywood Beach is famous for the great boardwalk that extends about 2.5 miles along the Atlantic Ocean.

Home in Key West

Key West. Once the wealthiest city in Florida, Key West citizens have created fortunes over the centuries from shipwreck treasures, turtles, sponges fishing, and cigars. Most recently its economy is based on the tourist trade and folks looking for a warm and artsy place to spend the winter. You can walk or bike anywhere on this small island with nice bike lanes and drivers who look out for pedestrians. “The Conch Republic” attracts artists, musicians, and people of every type under the rainbow.

Home in Mount Dora

Mount Dora. This central Florida lakefront community is nestled in gentle hills and orange groves. Its elevation of 184 feet makes it one of the higher communities in Florida. It features active shopping, excellent antiquing, a rich cultural life, and recreation. Many festivals and community events attract residents and tourists. See the article we wrote on Mount Dora.


St. Petersburg has long been a synonym for retirement community, which does not tell the real story. This city on a long peninsula has a lot going for it. For one, it has a bustling, big city downtown with thriving businesses and lots to do. For another, it’s a peninsula with beaches and water just about everywhere. Then it has many funky neighborhoods and villages, like definitely funky Gulfport and its famous dancehall Casino.

Great mural in Tarpon Springs
Great mural in Tarpon Springs

Tarpon Springs is a fascinating little town on the West Coast above Tampa and St. Pete. What makes it unique is its Greek heritage – descendants of earlier immigrants who came here for sponge gathering are still here fishing and operating Greek restaurants for tourists. Another unique feature of Tarpon Springs is that is has 2 downtowns. The main one has a nice area with shops, restaurants, and the old train station. It is charming, but a bit frayed around the edges like a funky town should be. The waterfront area a mile away offers an array of Greek restaurants and views of fishing and shrimp boats.

Jacksonville Skyline

Jacksonville. You might not think you want to retire in the 12th largest  city in the country.  But this huge city has many very different neighborhoods and areas to retire in – from little beach communities, to an urban setting, to sophisticated new urban style communities. An historic neighborhood that gets a lot of favorable press is the Riverside and Avondale area. Surrounding towns like Orange Park and Fleming Island offer many interesting options.

Bottom line. We hope this whets your appetite for a possible Florida retirement, because there are a lot more towns like these if you get out and explore the Sunshine State. Please let us know your favorite towns in the State in the Comments section below.

For further reading:

Posted by Admin on November 26th, 2019


  1. The Villages should be listed among the best places in Florida. It is a thriving, growing community with the most clubs and activities on this Earth. With over 700 holes of golf, over 180 pickleball courts, nearly 40 recreation centers, and over 80 pools it is a great place to stay active. Currently there are over 3000 clubs and activities for the 130,000+ residents.

    by Bart — November 27, 2019

  2. We spent years visiting family in Florida as well as “touristing” and looking around for possible new home areas. For me personally, Florida’s worst aspect is simply that it has become “too” popular. Heat and humidity don’t bother me, the “warmth” aspect is a major draw (“I wanna go where it’s WARM!” — Jimmy Buffet). Hurricanes are something you better learn to live with — find some area less likely to be severely impacted by things like evacuation. (Mt. Dora was of interest, but we have yet to visit there.) Since we already live in the Southern woods, bugs and critters etc. are just another minor nuisance. Where have we been that I liked enough to explore purchase options and will continue to visit for vacations or snowbirding? The Keys, St. Augustine area, mid-Florida Atlantic coast, Ft Myers/Cape Coral area stand out — we’ve spent at least two weeks in all those places.

    by RichPB — November 27, 2019

  3. I meant to add to the above what I have said in other posts — we have decided there is no better place for us than our current home of 26 years in central NC. So the “vacations or snowbirding” applies. Why stay here? So many reasons — we have built and fostered our personal “paradise”, the financial benefits of downsizing from here are basically minor, don’t like even the mild NC winters but can put up with it, snowbirding out of the cold is a fine option over the hassles of moving which would entail the loss of those aspects of our home that make it our view of “paradise”.

    by RichPB — November 27, 2019

  4. Some of us are already living in our own personal paradise and just don’t realize it. With all the global warming going on in our world, I feel it is safer to stay in Connecticut for now. I thought I would move to California or Florida but with all the fires, hurricanes, and flooding going on, I would rather stay in Connecticut and take long vacations or snowbird to warmer locations without moving my primary residence. Global Warming is unfortunately making my dream of a safe beachfront cottage retirement a fantasy.

    by Jasmine — November 29, 2019

  5. We ended up in Ponte Vedra Beach south of JAX, but discovered that that is not the place to be. PVB has nothing other than country clubs and nothing else is close since JAX is so spread out. JAX also has some areas to be avoided. So we relocated to Lakewood Ranch in the Sarasota area. Everything is well planned, everything is convenient and lots of activities. We also looked at Naples and Miami areas but stayed away because of 60% snowbirds in some areas, which means that summers are boring with not much going on.

    by AndyR — November 29, 2019

  6. Sorry, but global warming is the least worry since that will disappear once none of the “predictions” come true. As recently as in the 1970s all kinds of predictions were about the next ice age around the corner, now it is global warming. So much for that. They can’t even predict the weather for the next month, or which way a typical tropical storm will go in a couple of days. But they “can predict the global temp for the next 100 years”. Come on, cool off. The thing is that the climate has always changed and will continue to change as long as the sun shines, no matter what we do or don’t.

    by AndyR — November 29, 2019

  7. Agree with Andy R.. And, there are various weather tendencies, in no matter what area of our country one lives in. After many Fla trips over the years, on both coasts, have pretty much settled on the Panhandle for retirement. Would absolutely live in the Keys, our most relaxing place ever, but, it’s a long drive for family and friends to get to,for visits..30a, here we come..

    by Gigi P — November 29, 2019

  8. The focus of this article is most definitely not about climate change and whether you believe in it or not. According to NASA, “the vast majority of actively publishing climate scientists – 97 percent – agree that humans are causing global warming and climate change.” You can either agree with them or think your science is better.
    But the issue is relevant if you believe rising sea levels and other climate related changes might affect where you choose to retire. The evidence is pretty compelling that there are problems coming down the pike (in fact already here) for a lot of Florida towns, especially the Keys and the Miami area. This article in the Washington Post explains how three top Florida Republicans, Gov. DeSantis, former Gov. Rick Scott, and Sen Marco Rubio are starting to take action to protect Floridians from what appear to be serious problems. The problems might not be meaningful in our retirements, but for our children.

    Now, let’s move on to our favorite and least favorite places to retire in Florida. Gigi, we agree with you, the Keys are wonderful! We think there are a lot of good ones – for now anyway.

    by Admin — November 29, 2019

  9. Well, since Mt Dora might end up being beachfront in 50 years, might just head there now, beat the rush. And it’s close to Disney World…

    by Daryl — November 30, 2019

  10. Seriously, we changed our mind about the southwest coast of Florida after the recent scourge of red tide, areas south of Vero beach (our second choice) were afflicted with the blue-green algae, both causing human problems in addition to the fish and animal kills. Little a River SC, our next choice had the thousand year flood, along with flooding in St Augustine (another favorite.) California was a dream now dashed by drought, then landslides, wildfires, earthquakes. Even our paradise of Hawaii was sideswiped by two hurricanes. Farther north saw flooding on the rise in coastal Virginia. Things are definitely changing. I don’t want to live in a place requiring evacuation. Right now I’d be happy with more sunshine, less pollution and snow. I’m seeing more “southern” birds at my feeder each year. I might not be moving south, but south is moving north.

    by Daryl — November 30, 2019

  11. I think I’ll stick with my little class b RV since I can keep rolling, rolling, rolling!

    by Bob — November 30, 2019

  12. I moved to FL from Westchester County in NY in 1970, only because my husband at the time was sick of the snow. Lived in Ft Ldle on the east coast and St. Pete and Clearwater on the west coast. Visited every one of the places on your list many times. Up until this past year I lived in Vero Beach for the past 44 years, and recently sold my home and moved to SC. In my opinion IF you want to live in FL , Vero Beach is by far the best! And one of the big reasons why I left, ……(not to mention losing two roofs over the years to hurricanes and the cleanup afterwards). Now, too many people have discovered Vero and snowbird season which gets longer every year is unbearable with traffic and restaurant waits, etc. Honestly, I do not know who wrote your piece on Vero Beach…..and chose to show a pic of the Courthouse? Vero Beach has miles of beautiful beaches, with resort style shopping beachside and just across the Indian River a SMALL “artsy “downtown area. Lots of great restaurants on both sides of the river and downtown. A large boating community with both the Indian River and ocean access, beautiful walking trails along the river and Riverside Theatre with Broadway productions, not to forget the Vero Beach Museum of Art…fantastic ! Former winter home of the Dodgers and many first class golf courses, home of Piper Aircraft and Cleveland Clinic, and too many millionaires to count. Elite Air flies to northern cities as well as Asheville NC from Vero Beach airport, and Palm Beach Airport is just a little more than an hour south and Melbourne airport is less than an hour north. SO, if it’s so great, why did I leave? I have always missed the change of seasons, the winding roads, the hills, the beautiful Fall leaves. I moved 7 hours north to a small town in SC, midstate…(and NO hurricane insurance). I can get to the mountains in 3 hours north and if I ever want to see a beach again 2 hours to the east. Yes, summers are hot here, but not as humid as FL is 10 months of the year…the winter months here are very mild and just 2 months long…..and the people here are SO friendly! My children and grandchildren still live in Vero Beach and we have all been able to make the drive back and forth in 7 hours for holidays, etc. Having grown up in FL they are ready for change also and after they retire I believe they will be leaving also. So many times over the years while living in Vero Beach a “snowbird” would relate to me how wonderful Vero was and how happy they were that they found it…..and I would reply “yes, and please don’t tell anyone!” LOL Obviously they didn’t listen to me and they own the town from October to May?

    by Diane Greto — December 1, 2019

  13. Daryl, I’ve come to agree with you. Here in central NC, we live on a ridge at about 500 ft above sea level. (Interestingly, our 600 foot plus well draws from BELOW sea level.) Nearby Jordan Lake is at roughly 240 ft and we like to joke that it’s beaches may some day be “beach front” property. Hey, with a drop of 100 ft in elevation on just our 11 acres, WE too might be beach front! (Seriously, this is truly a major problem looming and I feel for those in coastal plain areas that will be affected and are currently affected with every passing hurricane.)

    by RichPB — December 2, 2019

  14. Diane, thanks for the wonderful informative post about Vero Beach, Florida. I have not yet visited Vero Beach but look forward to visiting. I love seeing posts like yours. So very helpful!

    by Jasmine — December 3, 2019

  15. We are with Jasmine in our thinking. After actually living in the South for five years, we returned to Massachusetts (Cape Cod) for good. We know all the pluses and minuses of living in a northern state, and we decided we would rather deal with the known than the unknown. We make occasional trips to the South and Southwest. The high quality way of life, the healthcare, the attitudes in New England make this, for us, the best choice for retirement.

    by Thom — December 5, 2019

  16. We love the Florida Keys, and judging from what others have posted here, we are not the only ones. Unfortunately, rising sea levels show the perils of living in a low elevation location. This story, ,reports how just one 3 mile stretch in the Keys could cost $3 million per home (there are 24 homes on the road) to keep the road dry in 2025 – $7 million each to keep it dry for the year 2060. The local authorities are not expected to approve the project. Unfortunately, there are a lot more roads that also need to be raised so they are passable during king tides and big storms.

    by Admin — December 5, 2019

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