The vintage postcard beach cottage—the kind of cozy, wood-frame home near the water that appeals to your inner Jimmy Buffett—still exists. Just ask Jack Hamlin, who found his humble dream home on Siesta Key last year. Less than 1,000 square feet in size, the home had been neglected for years, but after Hamlin’s thorough remodel, it’s ready for its close-up. 

Located in the Sea Club community on the east side of the key, the home is part of a collection of condos and a handful of cottages from 1978 that share a pool and boat basin. It’s “kind of stuck in time,” says Hamlin, 46, who lives in Denver, Colorado, but is selling his home there to move back to Florida. As a remote worker in the engineering industry, he has options.

The home is a transplant and was originally a tar paper pilot’s barracks at the Venice Army Air Base, where roughly 20,000 pilots trained during World War II. “In 1943, this building was on that base, which housed P-51 Mustangs,” Hamlin says. “The base was decommissioned in 1947 after the war, and many of the barracks were demolished. In the mid-’60s, this one was brought to Siesta Key.” It’s not the only barracks that survived; others are still standing, scattered around the region.

Hamlin has been visiting the area for 25 years, and for years had his heart set on living in a cottage by the water. He scanned Sarasota’s shores for three years before he bought unit #1A at 5955 Midnight Pass Road. “I always had this dream,” says Hamlin, “I was picky about it being old and pretty and not new and modern.”

Hamlin doesn’t like what he calls “the cube-everything look” or “the Mediterranean Revival craze.” He says he’s always just wanted “somewhere where I could park a boat and live like Ernest Hemingway.”

Before that, though, he had to battle rot and decay. The home had previously been used as a short-term rental. The doors were falling off hinges, and the roof was leaking and ready to collapse. “It should have been condemned,” he admits.

With the help of Patrick Murphy, the president of Sarasota’s PJM Construction, the house got a total gut job that included removing the roof. Like Hamlin, Murphy is partial to historic Florida homes and said he would do the job on one condition. “Jack wanted to drywall the pecky cypress walls and I talked him into keeping it,” Murphy says. “I refused to do the job otherwise.” The ultimatum worked, but every slat had to be extracted, planed down and sanded before being put back up, “even if we sometimes had to relocate them,” Murphy says.

Behind the walls, Hamlin and Murphy found failed beams, structural problems and dead animals. The house got new plumbing, wiring, flooring and roofing, and was fumigated. It also had to be jacked up to make it level because it was caving in. Footers were added to evenly ​​distribute the structure’s weight so that it doesn’t sink into the ground and to protect the foundation from water damage. In the process, the house was also brought up to current hurricane safety codes.

“Too many people see this type of project as too much of a financial burden, and it’s sometimes cheaper to tear down and build new,” Murphy says. “Especially with the rapid changes happening here, I like to see some pieces of history given this kind of appreciation.”

Hamlin estimates that he put about $310,000 into the project, amounting to almost 50 percent of the property’s original cost. That total doesn’t include legal fees, which he racked up when he had to go head-to-head with the homeowners association over tearing down his roof. He won, but the battle delayed the project. “It was the nightmare HOA you hear about,” he says.

Different outdoor areas add up to roughly the same square footage you find indoors. A front door patio faces west for sunset views, while the north end faces the pool and feels like a private oasis. Then there’s the paver patio right off the kitchen, perfect for a barbecue

For the finish work, Hamlin and his wife used Buster + Punch lighting for vintage toggle switches to maintain the old-school feeling. Furniture picks are earthy-toned and organic, with leather, seagrass, mango wood and jute rope chairs.

But Hamlin’s favorite spot is the covered patio in the back where he can stare at the Intracoastal and his ride: a 21-foot Scout boat. “That’s the dream,” he says. “You get in a boat, not a car."