Islamorada's Iconic Cheeca Lodge Could Sell for $300 Million

Every January since 1990, a fleet of charter boats has assembled off Cheeca Lodge's 525-foot fishing pier for the Presidential Sailfish Tournament, an event George H.W. Bush helped launch that grew into a cornerstone of the Islamorada Charter Boat Association's calendar and a fixture of the Florida Keys Gold Cup Series. That tournament, along with three on-site restaurants, a Jack Nicklaus-designed nine-hole golf course, a full-service spa, and the Camp Cheeca kids program, has woven the resort into the economic fabric of Islamorada for eight decades. Now, Northwood Investors is quietly testing whether that footprint has a price: roughly $300 million.

Northwood, the Denver-based investment firm led by former Blackstone executive John Kukral, tapped Jones Lang LaSalle as its adviser to approach potential buyers for the 27-acre oceanfront property at 81801 Overseas Highway. People familiar with the effort asked not to be named because the process is private, and no formal asking price has been confirmed, but market sources indicated the valuation could approach $300 million.

That figure would nearly triple what Northwood paid when it acquired the resort in August 2011: $102 million. The long-range trajectory is more striking still. In 1983, the property was valued at roughly $4 million. By the time Northwood closed its purchase following a full rebuild of the main lodge in 2009 and extensive renovations through 2010, the price already reflected a transformed asset. A decade later, Baker's Cay Resort in Key Largo, a 200-room property, sold for $200 million, establishing a new benchmark for oceanfront resort transactions in Monroe County and signaling where Keys valuations were heading.

Northwood continued adding to the Cheeca footprint during its ownership. In 2020, the firm acquired an adjacent parcel containing 11 private oceanfront casitas, a private pool, and two additional restaurants, bringing the total to 243 rooms across 26 buildings. The resort's main dining venues, Atlantic's Edge, Limoncello, and Nikai Sushi, sit alongside six lighted tennis courts, a saltwater lagoon, and more than 1,200 linear feet of beachfront, all of which require a workforce and vendor network that has sustained Islamorada's hospitality economy for generations.

Charter captains and fishing guides with ties to the Cheeca tournaments have the most direct stake in what comes next. The Islamorada Charter Boat Association, a 501(c)(3) focused on fisheries conservation, receives support through the Presidential Sailfish Tournament's entry fees. The separate George Bush/Cheeca Lodge Bonefish Tournament ran from 1994 through 2003 and further cemented the resort's role as the hub of the Upper Keys sportfishing circuit. A buyer who repositions the brand away from its fishing identity, restructures tournament programming, or raises room rates beyond what the current clientele can absorb would send ripple effects through the charter operators, tackle shops, and marine service providers whose annual calendars are built around Cheeca's event schedule.

The property opened in 1946 as the Islamorada Olney Inn, with President Harry S. Truman as its first guest, and became Cheeca Lodge when Carl and Cynthia Twitchell combined their names to brand the rebuilt resort after a 1960 hurricane leveled the original. It has since survived hurricanes, ownership transfers, and a complete reconstruction. Whether a buyer at $300 million sustains the fishing tournaments, preserves public access to the pier, and holds the workforce in place will determine whether this transaction is a routine capital rotation or a genuinely consequential moment for Islamorada.