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The Five Best Small Towns in Florida

Florida sunset

Florida is best known for its year-round sunny weather and sandy beaches. It’s no wonder that 126.1 million out-of-state visitors traveled to the Sunshine State in 2018, setting a tourism record for the eighth consecutive year. 

For the lucky ones, Florida is a place to call “home.” We get to live where others vacation. Residents also have greater accessibility to some of the small towns in Florida that make it so great. These pockets of Florida are better known for their pristine beaches, lakes and nature preserves than for their amusement parks. In these parts, it’s common to find people fishing, meandering in and out of the downtown boutiques, or strolling along the beach, with no particular place to be or time to be there.

Here are five small towns in Florida that will make you want to visit — and stay for good.   

  1. Mount Dora – Just 30 minutes north of Orlando, Mount Dora is located within Lake County — perfectly named for its 1,400 lakes. Among them is the prestigious Lake Dora, which was named after Dora Ann Drawdy in 1846. Visitors and residents alike enjoy fishing its tranquil waters for largemouth bass. Sitting 184 feet above sea level, Mount Dora is an official “mount” — a departure from Florida’s typically flat landscape. The city is also known for its collection of artsy boutiques, city parks and restaurants.  Real estate in Mount Dora, Fla., offers a wide variety of homes, from historic vintage homes and charming cottages to lakefront estates, condominiums and new communities.  
     
  2. Harmony – If you prefer small-town living with big-town activities, Harmony is the place to be. Residents shop, eat and meet in Harmony’s Town Square. Its lined with shops, restaurants, a doctor’s office, and a market, where you can pick up fresh fruit, vegetables, or a nice wine to pair with a homemade dinner. There’s also an amphitheater, open space and park benches, inviting you to sit and be present in the moment. Golf is another popular pastime, especially at the Harmony Golf Preserve — a Johnny Miller signature designed course. Those with an active lifestyle will also love the roughly 12.5 miles of walking, hiking or biking trails — free from street traffic. There’s a healthy mix of housing options, including single-family homes and multigenerational homes. 
     
  3. Winter Park – Old-world charm runs deep along the brick-lined streets of Winter Park. Downtown, you’ll find upscale shopping, restaurants, and wine rooms, offering a taste of the good life. It’s a popular place on the weekends, especially during the farmers market on Saturdays from 7 a.m. to 1 p.m. The only weekend it doesn’t run is on the third Saturday of March each year, which is when Winter Park hosts its annual sidewalk art festival. You can find condos, townhouses and homes in just about any setting, whether you’re looking for a lakefront property — where you may encounter bald eagles, red foxes and osprey — or a spacious home nestled among the old oaks, just walking distance from the renowned Park Ave.
     
  4. Anna Maria Island – Long ago, the island was used for hunting and fishing by Indian tribes — and the only way on or off the island was by boat. Today, the city is still well-preserved and loved, with strict regulations governing the types of buildings and businesses allowed. Anna Maria Island is known for its turquoise waters, freshly-caught seafood, antique shopping, and art galleries. You can even ride a free trolley, which runs from 6 a.m. to 10 p.m. every day. One thing you won’t find? A plethora of high rises and fast-food restaurants. Instead, you might invest in a quaint cottage by the sea, deluxe suite or million-dollar villa, depending on your price range.
     
  5. Captiva Island – Water activities abound on Captiva Island. There, you can spend the day boating on the water or go below sea level on a snorkeling or scuba diving trip. The island also offers numerous family activities — from sailing school and mermaid- and pirate-play sessions to on-the-beach day camps and a popular catch-and-release fishing program. Their property types are as varied as their outdoor activities, from golf-view condos to bay-front homes with docks. 

Whether you decide to visit or stay, you’ll treasure all the memories made in these five small towns in Florida. 

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