Real Estate News Florida Keys luxury resorts sell for nearly $500 million. Here’s what to know By Produced using AI, based on original work by Luisa Yanez August 26, 2026 8:12 AM Opened in 1968, Pier House introduced a luxury destination to the tip of Key West. The resort was sold in August 2026. Three of the Florida Keys’ most famous luxury resorts have changed hands in just three months, drawing nearly half a billion dollars from investors betting on a market defined by scarcity. The deals were for the historic Pier House in Key West, the celebrity-favored Cheeca Lodge & Spa in Islamorada, and the newer Islands of Islamorada. FULL STORY: 3 famed Florida Keys luxury resorts change hands in $500M buying spree. What’s next? Here are key takeaways: The deals: Pier House sold in mid-August for $190 million to San Francisco-based Sixth Street. Cheeca Lodge & Spa was acquired in June by Bass Pro Shops for an undisclosed sum after being marketed at $300 million. Islands of Islamorada went to Mast Capital and Koch Real Estate Investments for $38 million in July. Why now: Development in the Keys is tightly restricted by state and county rules tied to hurricane evacuation on a two-lane highway, meaning waterfront property cannot be expanded. Will Langley, principal broker for Berkshire Hathaway Keys Real Estate, called the resorts “trophy assets in the Florida Keys.” A booming residential market: Keys homes previously sold for about $700,000 and the average Monroe County home now goes for about $1.2 million, according to Realtor.com. Barstool Sports founder Dave Portnoy recently paid $27.75 million for an Islamorada estate, and a Sunset Key mansion sold for a record $22 million in March. Storied histories: Pier House, opened in 1968, hosted Truman Capote, Tennessee Williams and a young Jimmy Buffett. Cheeca Lodge welcomed President Harry S. Truman as its first guest in 1946 and later became a favorite of President George H.W. Bush. Tourism surge: Key West International Airport hit 1 million passengers in July for the first time, according to KeysWeekly. This report was produced with the assistance of a proprietary tool powered by artificial intelligence and using our own originally reported, written and published content. It was reviewed and edited by our journalists. Luisa Yanez Miami Herald Email this person Luisa Yanez covers real estate and the impact of wealth migration in South Florida for the Miami Herald. In her work, she will be using both traditional reporting and AI tools.
Curated by Taleb Kabbara · Source: www.miamiherald.com