Real Estate News

Want to buy an island? At least eight are for sale in the Florida Keys

In 2017, Realtor Patti Stanley sold a 40-acre private island off Lower Matecumbe Key for $13.8 million.

Parmelee Key, a horseshoe shaped island that juts out into Florida Bay at mile marker 75, had been privately owned since the 1950s. It had a moment of fame when it was chosen as one of the music video locations for Jennifer Lopez’s 2017 hit “Ni Tú Ni Yo.”

That same year, the Islamorada Village Council and the state Department of Economic Opportunity cleared the way for 10 houses on the island. Developers are now in the process of building homes there, Stanley said.

Now, another one of Stanley’s listings is making a splash: a 16-acre island connected to Upper Matecumbe Key by a 2,000-foot driveway. It’s known as Terra’s Key and has been on the market since May, with an asking price of $17 million.

Terra’s Key, a 16-acre island off Upper Matecumbe Key, has one five-bedroom, four-bathroom house. Courtesy of Patti Stanley

Terra’s Key has one five-bedroom, four-bathroom house, but any developer hoping to buy the island and build a subdivision is out of luck. The five-member Village Council years ago restricted zoning to one single-unit home.

“The village put a quash on developing anything more back in the day,” Stanley said this week.

The property, whose listing was reported in the South Florida Sun Sentinel, also has a 40-foot dock, tennis court and a swimming pool.

It hadn’t been for sale since the early 1990s, when Chicago businessman James Terra bought it for $3.1 million, according to Monroe County property records.

Stanley said she gets lots of calls about the island from potential buyers — but many have sticker shock.

“They say, ‘Oh, $17 million,’ “ she said.

The property is one of at least eight small islands for sale up and down the Keys, according to

Islands for sale include:

Pumpkin Key, a 26-acre island in north Key Largo in Card Sound Bay, listed for $95 million.

The four-acre Palm Island near Marathon, listed for $15.5 million.

Tavernier Key, a 31-acre island off Plantation Key, listed for more than $10 million.

Just outside of Key West, the five-acre Thompson Island, along with its 8,700-square feet mansion once owned by philanthropist and developer Edward B. Knight, sold for $8 million in March this year.

Before he died last year, Key West developer David Wolkowsky agreed to donate his private island, Ballast Key. The 14-acre island will be preserved as part of the Key West National Wildlife Refuge. But a few years ago, he decided to test the market and put it up for sale for more than $15 million.

Like many places in the Keys, Terra’s Key has a storied history, said Brad Bertelli, historian and curator of the Keys History and Discovery Center in Islamorada.

The first recorded name of the island was in 1772, when it was called Boys Kay, Bertelli said. British mapmaker and military engineer George Gauld identified the island on his chart as Umbrella Kay.

“The small key off the west end of New Matecumbe has a remarkable single tree at the south end of it like an umbrella,” Gauld wrote, according to Bertelli.

Lemeul Otis, who the Monroe County Sheriff’s Office identifies as the Keys’ first sheriff, farmed the island as early as 1828 when it was called Tea Table Key, Bertelli said.

The island also has a military history.

“In 1838, Fort Paulding, a naval depot and hospital, is established on the island,” Bertelli said, noting it was named after James Paulding, then secretary of the U.S. Navy.

The fort was moved to nearby Indian Key after an attack by local Native Americans on Aug. 7, 1840, Bertelli said.

“From that point, Tea Table is used for small arms drills for the soldiers,” he said.

Now, you can have a piece of history. For 17 million bucks.

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David Goodhue covers the Florida Keys and South Florida for and the Miami Herald. Before joining the Herald, he covered Congress, the Environmental Protection Agency and the Department of Energy in Washington, D.C. He is a graduate of the University of Delaware.