Another Chatham Hotel Sold: Seafarer Goes For $4.4M

By: Alan Pollock

The Chatham Seafarer. ALAN POLLOCK PHOTO

CHATHAM — For the third time in less than four months, a longstanding Chatham hotel property has changed hands. This time, it’s the Chatham Seafarer at 2079 Main St., which sold in late June for $4.4 million.

The buyer is identified as Melissa Leonard, whose partners are listed as Robert Cochran and Antonino Scimeca. Leonard said she is planning some renovations at the Seafarer, and is interested in keeping it as a hotel. In the past, other small hotel properties have been converted to residences, including the former Ridgevale Motel on the opposite side of Ridgevale Road.

“We have no plans in doing that. We love hospitality,” Leonard said. In her youth, she traveled Europe and stayed in hostels, and started her hospitality career managing the hostels across the Cape and Islands for some time. Later, she was managing owner of the Penny House Inn in Eastham and owned and operated Cliff Lodge, a 12-room inn on Nantucket. She and Cochran sold their properties on the island and looked for something on the mainland.

“We love Chatham and knew we wanted to be in Chatham,” she said. In 2020, her commercial real estate investment firm, Oceanview Holdings, LLC, purchased the Chatham Highlander for $2.3 million. “It wasn’t for sale, but we saw the potential in it,” Leonard said. They made renovations and intended to keep the Highlander, but couldn’t ignore a $7.7 million offer from Rhode Island-based Procaccianti Companies, which purchased it last month.

Working with real estate broker Nicholas Herz of Boston Realty Advisors, Oceanview sought out another property to purchase, and found the Seafarer.

The sale of the Highlander and the purchase of the Seafarer were part of a single real estate investment strategy known as a “1031 exchange,” named after the IRS code that allows it. Under the rule, an investor is allowed to essentially swap one qualifying property for another, allowing capital gains taxes to be deferred. The tax strategy is complex and highly regulated, but essentially allows capital gains taxes to be put off for many years, with some investors using the technique many times in serial property swaps.

“We’re a family-run business, so it’s us and our family,” Leonard said. The staff from the Highlander was brought over to the Seafarer, she said. They have planned a number of upgrades to the 22-room Seafarer, which was built in 1958 and renovated several times. She said there’s a strong demand for lodging rooms in town.

“Chatham is such a lovely town, and I think we need all of the hotel rooms we can get,” Leonard said.

Is Oceanview on the market to acquire additional properties?

“If something comes up, we don’t ever close the door,” she said.

In addition to the Seafarer and the Highlander, the iconic Chatham Wayside Inn also changed ownership this year; it was purchased by Procaccianti Companies from longtime owner David Oppenheim in late March for $18 million.