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Enjoy the Castaway Life on a Marooned Houseboat in the Florida Keys

Enjoy the Castaway Life on a Marooned Houseboat in the Florida Keys

It isn’t unusual for boats to wash ashore in the Florida Keys, but it is unusual for a beached houseboat to find a new life as a private residence.

Enter the Gilmore Estate. Listed for $ 5,950,000, this 959-square-foot home in Islamorada, FL, is a bright and cheery little home with a hint of Art Deco style. As you look at the two-bedroom, two-bathroom home perched on the sand, however, you might start to suspect that its nautical lines are not just for flair.

“It is an actual 60-foot, 1948 Chris-Craft houseboat,” said listing agent Cheri Tindall.

Even stranger—and cooler—is how the boat found its way there.

In 1948, the houseboat was custom-made for the hotel king Conrad Hilton. In the 1950s, ownership of the boat went to a newly married couple, Jim and Diana Gilmore, according to the Wall Street Journal. The Gilmores had docked the vessel at the nearby Cheeca Lodge, but when Hurricane Donna slammed the Florida Keys in 1960, the houseboat broke away and wound up beached on U.S. Highway 1.

The Gilmores found the houseboat and used telephone poles to roll it back to where it sits today, permanently anchored, on the beach, surrounded by white sand, palm trees, and ocean views.

It may be getting on in years, but the houseboat is in pristine condition inside and out. The first deck has a salon with wall-to-wall windows overlooking the water. There is also a galley-style kitchen, a stateroom, and two bathrooms.

The top deck, accessible only by exterior stairs, consists of a master stateroom with four bunk beds. Adjacent to the stateroom is a private patio facing the ocean.

Despite making some upgrades, the Gilmores kept the style of the houseboat intact. No matter where you step in the home, you’ll feel like the captain of your own ship.

You might also feel like you’ve landed on your own private island—the property is massive.

“The 5-plus acres offer lush tropical landscaping that cocoons all who enter from the sandy driveway down to the oceanfront houseboat,” Tindall said. In fact, despite being situated in downtown Islamorada, Tindall says, the property is “one of the last few large parcels left on the ocean.”

And if a houseboat isn’t enough space for you, there is room to grow.

“The property can be expanded. Actually, you can move the houseboat and use it as a guesthome and build a main residence,” Tindall said.

And like any good sea captain, you’ll also have fascinating stories about your vessel. According to the owners, the houseboat has hosted some famous guests. President Harry Truman composed much of the Truman Letters while staying on the boat. More recently, President George H.W. Bush was also a guest.

Anchors aweigh, captain!

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