A 10-acre-plus waterfront resort and marina in the Florida Keys that once hosted actor Paul Newman and gonzo journalist Hunter S. Thompson is listed for sale for $45 million, The Real Deal has learned.
Sugarloaf Lodge & Marina, near mile marker 17, consists of 31 hotel rooms and commercial space. The site at 17001 Overseas Highway comes with development rights to rebuild 24 hotel keys lost in Hurricane Wilma in 2005, according to listing broker Lisa Swanson.
Swanson, of The Agency Florida Keys, is listing the property with Jamie Bederak, of The Agency Miami.
The asking price amounts to $1.45 million per hotel key.
Sugarloaf Lodge was built in the late 1950s by the Pennsylvania strip mining company that dredged and developed much of Sugarloaf Key. Additions were built in the 1960s. In 1973, husband-and-wife Lloyd and Miriam Good bought the property and moved to Sugarloaf Key to run the resort with their four children.
The property is now owned by entity Miriam BG, led by John Good and Caren Ward, children of the late Lloyd and Miriam Good. The entity also is led by Jessica Duncan Wex and Katchen Elizabeth Duncan, John Good’s nieces.
Sugarloaf spans nearly 10.6 acres and includes a 12,700-square-foot hotel and a 5,300-square-foot restaurant leased to South of the Seven, plus a tiki bar and events venue. It includes office space, some of it leased to kayak and boat rental firms and a solar energy company, and it also has an apartment, marinas, a pool and tennis courts, according to Swanson and John Good.
The owners have preserved much of the property’s original look, including Mid-Century Modern decor in the hotel rooms.
The property can be entirely redeveloped, though it would mean bigger setbacks from the bay, especially for the restaurant that now juts into the water atop stilts, due to changes in construction regulations. The development potential for 24 hotel keys is legally vested with the property.
Monroe County caps heights to 38 feet, with officials considering legislation to increase this to 42 feet for residential uses.
Good, who grew up on the property and hosted the 5 p.m. daily dolphins shows, recalled some of its history.
Dolly, a “very smart” dolphin that escaped the U.S. Navy was a common visitor when the Good family arrived at Sugarloaf Lodge. The Goods removed any nets keeping her within the bay, and Dolly eventually swam away, as she wasn’t too keen on doing the shows, Good said.
Jacques Cousteau had studied Dolly for her intelligence and featured her in one of his books. Sugar, the other bottlenose dolphin there, enjoyed performing, sticking around until her death in 1997, Good said.
Newman was fun to talk with, Good said, and imparted some insight on his alma mater Kenyon College, where Good was headed at the time. Thompson “was kind of part of our family for a couple of years,” Good said. A pig prank involving Thomson and Lloyd Good made it into Thomspon’s “Songs of the Doomed.”
“Crazy times,” John Good said. “It was the ’70s and ’80s … a lot of characters.”
The Florida Keys are quieter than bustling Miami to the north, though the Keys also attracted some investment during South Florida’s commercial and residential real estate boom of recent years.
In Islamorada, Barstool Sports owner Dave Portnoy bought the 1.7-acre waterfront mansion at 76180 Overseas Highway for $27.8 million in October.
Also in Islamorada, Frisbie Group sold the Islands of Islamorada resort consisting of 22 villas and an eight-key hotel for $72 million in 2024. Buyer Wills Companies launched sales of the villas last year.
In 2023, The Ardid family’s Brickell-based Key International paid more than $37.6 million for the 100-key Perry Hotel at 7001 Shrimp Road in Key West, and Miami-based Integra Investments paid about $29.7 million for the adjacent 288-slip, 35-acre Perry Marina at 7005 Shrimp Road.
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