A private land trust has assembled roughly 18.5 acres along Gordon Drive in Naples’ Port Royal neighborhood through purchases totaling about $311 million. The transactions include a record-setting three-property sale and a later, previously overlooked acquisition. Demolition permits point to a major redevelopment, but the buyers and their plans remain largely unknown.
Key takeaways
- The trust paid $225 million for three properties in April 2025 and $86 million for a neighboring property in June 2026.
- The combined holdings encompass about 18.5 acres of Gulf-front land.
- A separate trust acquired one of the original properties for $84 million in September, with the same attorney named as trustee.
- Demolition is underway or approved at several addresses, while new-home plans remain under review.
A record-setting purchase, followed by another acquisition
The original three properties—2170, 2200 and 2340 Gordon Drive—were part of a longtime compound owned by the DeGroote family. Their $225 million sale in April 2025 set a Florida record for a residential property transaction. The largest parcel, 2200 Gordon Drive, sold for $133 million.
In June 2026, the same 2200 Gordon Drive Land Trust bought 2100 Gordon Drive for $86 million, adding approximately 3.4 acres. Public records list Naples attorney Kevin Coleman as trustee. The buyer’s identity has not been publicly established, and the acquisition was not widely marketed.
A separate trust and a notable transfer
On Sept. 11, records show that 2340 Gordon Drive changed hands for $84 million through a different trust, also listing Coleman as trustee. The property had been included in the 2025 package at a reported $46.9 million. Broker Michael McCumber said the transaction took place within the trust rather than on the open market and said he did not know the reason for the change. He said the property would remain part of the broader compound.
McCumber, who handled the 2026 purchase, said he dealt with representatives and attorneys rather than meeting the buyers. He described the added property as a way to increase privacy around the larger holding.
Demolition signals a major redevelopment
Naples approved a demolition permit for 2100 Gordon Drive on Sept. 25. The work covers a two-story house and guesthouse, along with a pond, rockwork, walkways and driveways. Demolition at 2170 and 2200 has also been approved, while work at 2340 is listed as complete. Applications for new construction, including a main residence, remain under city review.
The broker has observed firms including Stofft Cooney Architects and Newbury North Associates at the properties, but details of the eventual development have not been disclosed. He said some mature landscaping appeared to be preserved.
Why Port Royal commands a premium
Port Royal’s limited supply of large Gulf-front parcels, navigable waterways and proximity to Old Naples help explain the prices, according to local luxury real estate specialist Matt Brown. Membership eligibility at the neighborhood’s private beach club is another draw; the club is undergoing a roughly $100 million reconstruction after Hurricane Ian damage. Combined, the purchases rank among the country’s largest residential land assemblies.