What It’s Like to Live in … Clearwater

Clearwater, Florida. Kurdistan Photography

Some places can convince even the most grounded visitors that they really ought to up and move. Clearwater, especially its Gulf-front barrier island, is one of those places. Though most know the area by the sand and surf that is Clearwater Beach, the city limits extend inland to Tampa Bay, encompassing a 26- mile sweep of barrier islands, a mainland down- town atop a bay-front bluff, a historic neighbor- hood and the commercialized corridor of State Road 60 and Highway 19.

But it’s the beach that wows most folks, including Shari Asti, who fell in love after topping the last of the causeway bridges. “I moved here three months later,” she says. Asti, whose lifestyle includes riding a purple bicycle around town, has yet to buy a home since moving here three years ago. So far, Asti and her husband have rented a house on Clearwater Bay, where she often saw dolphins and once caught a stone crab right from the dock. Now they’re awaiting the chance to enjoy a rental on the beach, frequently rated among the best in the world.

Clearwater is a town of skateboarders, beachcombers, entrepreneurs and tourists. Everyone is quite welcome here, and the shops and restaurants embody that philosophy. The town’s a mixed demo- graphic of full- and part-time residents, retirees, families and wintertime Northerners who take advantage of their good fortune to live here.


“You find every kind of person here,” says Michael “Frenchy” Preston, a 1970s transplant who’s built a restaurant empire and recently opened Frenchy’s Oasis boutique motel. Paul Gibson, a realtor with Re/Max Action First, describes Clearwater as “almost ‘classless.’” There’s no restaurant where one has to be seen, though many enjoy Casanova in downtown’s revitalized Cleveland Street District — a favorite pit stop for racecar driver Mario Andretti, who owns a home in Clearwater. Beachside, Shor and Caretta on the Gulf rate among the finest. Same goes for cars, except that Jaguars seem to be the luxury vehicle of choice.

Notoriety and change are headed Clearwater’s way, thanks to September’s big-screen release of Dolphin Tale, the true life story of Winter, Clearwater Marine Aquarium’s tailless dolphin. “This movie will put us on the map,” says the aquarium’s CEO, David Yates, who’s portrayed by Morgan Freeman. The film will likely generate interest from first-time visitors, who, like Asti, may have that flash of belonging. The same thing happened to Gibson, who now sells the Clearwater dream. About 75 percent of his clients are second-home buyers, many taking advantage of prices that reflect a boom gone bust — 50 percent of what they were just a few years ago. “They’re buying now and are going to move in when they retire in five to six years,” he says.

Many of Clearwater’s waterfront homes and condos are found along the island’s extreme southern and northern boundaries. Condo prices have already edged up 15 percent, especially in newer luxury towers on Clearwater Beach and nearby Sand Key, Gibson says. Listings range from $43,000 for a spit of a space on the beach to $3.7 million for a penthouse in the Grande on Sand Key. Clearwater Bay properties tempt with boats-in-the-backyard opportunities. North Beach, where you’ll find Sandpearl Residences and its sister resort, has a commercial and residential mélange of 1950s-era beach cottages, motels and newer Old Florida-style homes. Island Estates, between Clearwater Beach and the mainland, boasts mid-rise condos. In Harbor Oaks, a bluff-top historic district overlooking Clearwater Harbor, giant live oaks filter sunlight above century-old homes like one 14,912-square- foot mansion, priced at $14.9 million. Farther inland, older subdivisions like Countryside deliver prices in the $400,000s, reflecting the distance from the water.


One striking reason for Clearwater’s appeal is its sense of community, which is evident even in the casual, friendly greeting from a fellow pedestrian. Most of Clearwater Beach’s restaurants and businesses are locally owned; some are now run by second or third generations. The Palm Pavilion Beachside Grill & Bar has had just two owners since opening in 1926 as a burger joint, bathhouse and Skee-Ball hangout. Today, it’s a bar, restaurant and gift shop. “My dad grew up coming to the Palm and always told the owner he would buy it,” says Hoyt Hamilton, a former city commissioner who now co-owns the Palm with his brothers. Throughout Clearwater Beach, old melds with new. Hold- outs like the two-story Tropic Isle Motel brush against the Sandpearl. At 65 years old, the ivy- covered Bob Heilman’s Beachcomber is an icon. “Their fried chicken is legendary,” Hamilton says.

Clearwater’s commitment to tourism — its largest industry — is reflected in the $30 million Beach Walk, part of an ongoing project that attracted the Hyatt and Sandpearl. A low wall snaking along the nearly mile-long promenade provides a perch for people-watching and leads to Pier 60. Echoing the city’s promotion of all that Clearwater has to offer, Gibson says, “We have the beach, boating and warm weather. It’s the package everyone wants.”


Email Newsletters and Special Offers

Sign up for Florida Travel + Life emails to receive features on travel destinations, event listings and product reviews as well as special offers on behalf of FTL’s partners.
By signing up you agree to receive communications from Florida Travel + Life and select partners in accordance with our Privacy Policy. You may opt out of email messages/withdraw consent at any time.