3 famed Florida Keys resorts change hands in $500M buying spree. What’s next?

Business admin August 25, 2026 0 Comments

3 famed Florida Keys resorts change hands in $500M buying spree. What’s next?

Investors and developers are pouring nearly half a billion dollars into some of the Florida Keys’ most coveted properties, buying three of the islands’ famed luxury resorts in just three months.

The latest big buy is the legendary Pier House resort in Key West, which sold for $190 million in mid-August.

That followed the sale of the iconic Cheeca Lodge & Spa in Islamorada in June for an undisclosed amount said to be more than $300 million.

And in July, the newer, luxury gated Islands of Islamorada resort, a seven-acre oceanfront property with 22 private villas and eight hotel suites was purchased for $38 million by Mast Capital and Koch Real Estate Investments.

Taken together, the three deals offer a snapshot of a Florida Keys luxury market increasingly defined by one thing: scarcity.

There is little room to build, development is tightly controlled by the state, and county and waterfront property cannot be expanded.

But that restriction makes the Keys increasingly attractive to investors and high-end buyers looking for something they can’t create elsewhere — a piece of a paradise where supply is limited and privacy is part of the deal, according to real estate experts.

The new owners of Pier House and Cheeca have not unveiled their plans for the properties, but the owners of the Islands of Islamorada are already selling the waterfront villas, with prices starting at $3.8 million each.

A market built on scarcity

Unlike much of South Florida, where developers can continue building luxury towers and large residential communities. The Keys’ growth plan is based on the need to quickly evacuate residents via a two-lane highway in case of a hurricane.

“It’s not like they’re going to buy a special property and watch another special property go up next door,” said Will Langley, principal broker for Berkshire Hathaway Keys Real Estate. Langley said high-end buyers view properties such as Pier House and Cheeca as world-class assets in a market that is difficult to enter.

Langley described the resorts as “trophy assets in the Florida Keys.”

Wealthy buyers are also drawn to the Keys for the privacy.

“Billionaires enjoy the Florida Keys,” Langley said. “They come here nobody recognizes them. They can put on their flip-flops and fit in like Jimmy Buffett.”

But high-end buyers shouldn’t expect bargains.

“No one is going to come here and get a steal,” Langley said.

Following the money

The same dynamic is increasingly reflected in the residential market, too.

But it’s not just wealthy buyers driving demand. More people are coming to the Florida Keys.

Key West International Airport reached a million passengers in July for the first time in the airport’s history, another sign of the growing popularity of Keys, according to KeysWeekly, a community publication in Monroe County.

“More and more the Florida Keys are turning into the Hamptons of Florida,” Langley said.

Before the pandemic, homes in the Florida Keys were selling for about $700,000. Today, the average sale for a home across Monroe County is about $1.2 million, according to Realtor.com. The comparison prices explode in the luxury market.

“We have seen more $10 million to $20 million home sales in the last two years than we have ever seen,” Langley said. “And builders are following the money.”

At the very top of the market, prices can be dramatically higher.

A waterfront Islamorada property that sold for $12 million in February returned to the market in July for $13.75 million.

Realtor.com reported that the listing agent attributed some of the renewed interest in the community to the attention generated by Barstool Sports founder Dave Portnoy’s $27.75 million purchase of an Islamorada estate.

In March, a mansion on Sunset Key, a small residential island about 400-yards off Key West accessible only by ferry, sold for $22 million, setting a record for the highest price ever paid for a home on the island.

Before then, in 2024, one of the most expensive home sales in the Keys belonged to actress Sydney Sweeney, who paid $13.5 million for a six-bedroom mansion on Summerland Key.

The three resorts are not interchangeable luxury properties. Each has a history that helped shape the Florida Keys’ tourism industry.

Cheeca Lodge & Spa

Cheeca Lodge’s history stretches back to the late 1800s, but the property became a resort in 1946 when Clara May Downey purchased it and renamed it the Olney Inn. Its first guest was President Harry S. Truman, beginning a long tradition of attracting presidents and wealthy anglers.

Perhaps Cheeca’s most famous longtime guest was President George H.W. Bush, an avid fisherman who was a regular visitor starting in the early 1970s and returned during his presidency.

In June, outdoor gear retail giant Bass Pro Shops acquired Cheeca Lodge & Spa. The buyer and seller didn’t disclose the purchase price, but the resort had been marketed for $300 million before the sale.

“We’re humbled and honored to have the opportunity to help protect Cheeca Lodge and carry that story forward,” Bass Pro Shops founder Johnny Morris said in announcing the acquisition.

Pier House

Pier House, which opened in 1968, played a similar role in transforming Key West’s tourism industry. The resort was developed by David Wolkowsky, a Key West native, preservationist and businessman who helped transform the city’s neglected waterfront.

Before Pier House, accommodations in Key West were largely island hotels, motels and guest houses. Pier House helped establish the western tip of Duval Street and the waterfront around Mallory Square as a luxury destination.

Pier House quickly became a gathering place for celebrities, writers and musicians. Truman Capote and Tennessee Williams were among the writers associated with the property, while the tiny Chart Room bar became part of Key West music lore.

Jimmy Buffett played there in the 1970s, reportedly working for drinks while developing songs that would become some of his biggest hits.

Sixth Street, a San Francisco-based global investment firm, acquired the prestigious gulf-front, 142-room Pier House in mid-August. The company described the acquisition as an opportunity to own a rare piece of Key West

“We believe Pier House represents an opportunity to acquire a historic luxury resort in one of the country’s most supply-constrained and sought-after tropical leisure markets,” Aman Gupta, a Sixth Street principal, said in announcing the deal.

The Islands of Islamorada

The newest addition to the group is the Islands of Islamorada, a seven-acre oceanfront resort with 22 private villas and eight hotel suites, which opened in 2020 on Upper Matecumbe Key before Wills Companies sold it to a joint venture between Mast Capital and Koch Real Estate Investments in July

What happens to the Keys?

The three resort acquisitions show investors are betting not merely on another season of strong tourism but on the long-term value of owning scarce pieces of the Florida Keys.

The challenge now is whether the Keys can absorb the money without losing the character that made the string of islands a low-key, low-stress, tropical destination.