Joe Lombardi strolled through the packed Field 5 parking lot outside the Jones Beach amphitheater on Long Island—past the men dressed as pirates, the boat parked atop a party bus, the cornhole players and the silver-haired tailgaters pedaling tandem bikes. The diehards had arrived at dawn, and by midafternoon, some had crashed out in the shade of inflatable palm trees, napping away the hours before Jimmy Buffett would take the stage.

“A certain segment of his fans would like to live in Margaritaville,” said Lombardi, who serves as president the local chapter of the Parrot Heads in Paradise, a Buffett fan club with 25,000 members around the world.

It wasn’t an idle observation. Over the past two decades, Buffett has built a licensing and hospitality empire on the back of his most ubiquitous hit, selling everything from hotel rooms to deck chairs and frozen shrimp through his company, Margaritaville Holdings.

Now he’s slapping his brand on 55-and-older communities in a novel bid to sell homes to boomers who are ready to kick back—just not in the same way their parents did. In February, the company said it was partnering with a Canadian homebuilder called Minto Communites to build 7,000 homes in Daytona Beach, Fla., in an age-restricted development called Latitude Margaritaville.

“The last thing anyone wants is to go someplace where people are living out their last years.”

Buffett has a loyal fan and consumer base, but aging homebuyers may prove to be a tricky market. Boomers are working longer and moving less often than their parents, preferring to renovate their homes so they can age in place. For some, the snowbird lifestyle their parents’ generation invented might look like one last tradition against which to rebel. Others might just not want to admit they’re getting old.

“We have people who are really into the lifestyle. They can’t wait,” said Lombardi. Other fans worry the communities could resemble theme parks, or worse: “The last thing anyone wants is to go someplace where people are living out their last years.”

Forty years ago, long before it became a microwave dinner or real-estate development, Margaritaville was a 1977 hit that saw Buffett playing his trademark role of everyman in paradise, bemused at his circumstances but determined to live in the present, cocktail in hand, not dwell on the half-remembered past.

Buffett turned Margaritaville into an actual place with the opening of his first restaurant in Key West in 1987, but it wasn’t until the late-’90s that he kicked his branding operation into gear. Today, the singer’s website offers an astounding array of branded consumer goods, including LandShark Lager, rum and tequila, chips and salsa, pool floats, beachwear, and a selection of souped-up blenders sold under the heading of party machines.

Margaritaville’s hospitality business has become an even bigger draw, with 70 restaurants and a string of hotels in resort towns dotting the Gulf of Mexico and the Caribbean Sea. In all, its revenue topped $1.5 billion in 2015, and more than 20 million guests walked into a Margaritaville establishment last year, according to John Cohlan, the company’s chief executive officer.

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