Woodbox Sold By Blue Flag Partners, Ending Its Bid To Resurrect Historic Inn

The former Woodbox Inn was sold last week for $2.4 million by Blue Flag Partners, the Boston-based real estate private equity firm, ending its years-long bid to resurrect the historic lodging establishment.

Property records show the property, located at 29 Fair Street, was sold to 21A Pleasant Street LLC, a limited liability company registered to island developer Chris Skehel, of The Castle Group, and Virginia residents Thomas and Katherine Anderson. The deal does not include the neighboring property at 27 Fair Street, which Blue Flag will retain, according to co-founder Brad Guidi.

"We are all currently traveling with families for the holidays, but I can confirm that the sale was just for the Woodbox, not 27 Fair," Guidi told the Current over the weekend. "As of right now, we are going to hold onto 27 Fair."

Skehel did not return several messages seeking comment about the acquisition. In addition to running The Castle Group, Skehel owns Hotel Pippa in downtown Nantucket, currently manages Crosswinds restaurant at Nantucket Memorial Airport, and owns numerous other residential properties around the island. 

The sale ends Blue Flag's effort to restore the historic property to its former glory after acquiring the Woodbox in 2021 for $2.8 million. It is one of the oldest and most historic structures on Nantucket, dating back to 1709 – making it just slightly younger than the Oldest House.

When it purchased the Woodbox four-plus years ago, Blue Flag set out to resurrect the inn and restaurant with an ambitious expansion and redevelopment project. But those plans were met with immediate opposition by a group of neighbors.

After a protracted dispute with those neighbors in 2022, the Planning Board approved a scaled-back plan to reopen the historic property that included 17 guest rooms and a private restaurant available only for guests of the inn.

But Blue Flag waited more than a year to officially file the Planning Board's approval with the Town Clerk. With the structure falling into disrepair, Blue Flag faced complaints to the Historic District Commission that it was allowing Woodbox to deteriorate in violation of the town's so-called minimum maintenance bylaw. The law requires the owners of historic properties to "provide sufficient minimum maintenance...to the minimum extent necessary to keep such buildings from falling into a state of poor repair." In her November 2024 complaint to the HDC, island resident Emmy Kilvert stated that Blue Flag had not done any maintenance at the Woodbox since it purchased the property in 2021 and that it is now "deteriorating rapidly due to lack of care, maintenance, and attention by the owner."

In response, Blue Flag and Guidi vowed to prevent the Woodbox from decaying any further and were emphatic that demolition was never considered. But Guidi also claimed that economic conditions and the limitations of the approval granted by the Planning Board due to concerns raised by neighbors had left the project "not financially viable."

"During the course of the entitlement process, the neighbors hired Attorney Arthur Reade resulting in a Planning Board approval of 17 guest rooms and a 'guest-only' restaurant," Guidi wrote in an email that was entered into the HDC record. "For countless years, the Summer House ran the property with 24 bedrooms and a restaurant open to the public. The Woodbox restaurant was a beloved part of the island and the approval we received essentially ceased its operations. As you can imagine, losing seven bedrooms and making the restaurant only available to guests - combined with a hyper-inflationary environment and rising construction costs - has left the project, as it stands now, as not financially viable. We would love nothing more than to preserve and restore this building but without the ability to have a public restaurant (of note, this was the oldest restaurant in Nantucket) the numbers simply don't work."

The sale of the Woodbox last week marked the second high-profile property that Blue Flag has disengaged from over the past two months. After attempting to sell the former Surfside Lifesaving Station and Star of the Sea Hostel to the town, it was sold by its owners in mid-November for $4.5 million to an unknown buyer, officially ending Blue Flag's ambitious plan to convert the property into a luxury hotel.

Over the past five years, Blue Flag has assembled a sprawling real estate portfolio on Nantucket that now features residential, lodging, and restaurant properties. They include the Faraway Nantucket hotel (the former Roberts House Collection), The Pearl and Boarding House restaurants, the former Century House Inn, the Beachside hotel, the Pineapple Inn (now the Blue Iris), the Brass Lantern Inn, and the residential developments at Cannonbury Lane and Hawthorne Park. Blue Flag also owns properties on Martha's Vineyard, in Jackson Hole, Wyoming, Sag Harbor, New York, and Montauk, NY.