The building that housed Pittsfield's Highland Restaurant for 90 years is officially on the market, listed for $975,000 just weeks after the family-run eatery served its last meal. The 12,786-square-foot property at 100 Fenn Street sits right next to Pittsfield City Hall, and its new owner will inherit two existing tenants along with a full commercial kitchen still fitted out for service.
Real estate agent Jim Thurston, who is handling the sale, told The Berkshire Eagle that the Arace brothers — Pasquale, Gerardo and Dario, who inherited the business and building after their father Leone died in 1996 — had discussed selling for several years but wanted to wait for the right moment and close the restaurant first. According to Thurston, the brothers decided they were ready to close and move on, and the Highland served its final meals on August 27 after running out of food just three days before its last day in business.
A Building With Tenants Already in Place
Whoever buys 100 Fenn Street won't be starting from scratch on income. The Pittsfield Retirement Board rents first-floor space under a lease that runs through 2029, while the Cantarella School of Dance occupies the second floor on a month-to-month basis. Thurston did not disclose how much rent either tenant pays, but he said the rental income will help carry the building for a new owner.
The listing describes the property as suitable for restaurant, retail, hospitality, residential or mixed-use redevelopment, and the former restaurant space still comes stocked with a full kitchen, walk-in cooler, dining area, tables, chairs and a bar. Thurston said that if a buyer doesn't want the equipment, the owners would get rid of it. Berkshire County Multiple Listing Service records reviewed by Coldwell Banker show the building sits on a 0.17-acre lot and was originally constructed in 1900.
The Highland's Name and Recipes Stay With the Family
One thing not included in the sale: the Highland name itself. Jim Thurston said the brothers did not explain why the name and recipes weren't for sale, leaving that piece of the restaurant's legacy out of the deal even as the physical space changes hands. Thurston called the brothers' decades of work at the Highland a point of pride, saying they cherished the restaurant and did a great job running it.
The site's dining history stretches back even further than the Highland itself. Marty's Luncheonette opened as the first known eatery there in 1926, a decade before Dominick Sondrini and Angelo Balardini founded The Highland Restaurant in 1936. Sondrini's son Rudolph Sondrini and partner Leone Arace took over ownership in 1972, according to the Devanny-Condron Funeral Home. Leone Arace had started at the restaurant as a chef in the 1950s before becoming co-owner, a connection that led his three sons to join the restaurant's operations in 1992, per the Berkshire Eagle's earlier reporting.
Structurally Sound, But Needs Updating
Thurston describes the building as structurally sound, and it received a new roof in 2023, though the former restaurant space itself needs upgrading. He said he plans to advertise the listing nationally soon, and he has already shown the space to one potential buyer interested in renovating the entire building after the local listing went up the prior week. “Every property has a story,” Thurston said.
When the Arace family announced the closure on social media on August 2, they noted that some staff members had worked at the Highland for more than 50 years, according to iBerkshires. The building's position next to City Hall made the restaurant a longtime gathering spot for civic officials and downtown workers for decades.
Zoning Could Open the Door to Housing
The property falls within Pittsfield's Downtown Creative District, a form-based zoning designation the City Council ordained in April 2021 to streamline permitting and encourage mixed-use and residential redevelopment downtown, replacing older and more restrictive overlay rules. Any residential conversion would need to account for the district's inclusionary housing rule, which requires multi-unit developments to set aside 20 percent of units as affordable housing or pay into the city's Affordable Housing Trust.
Separately, Elyse Harney Real Estate listing records show the property carries an annual property tax liability of $13,202 for 2025, based on a tax-assessed valuation of $347,800.
Whether 100 Fenn Street's next chapter involves another restaurant, apartments, or something else entirely remains up to whoever decides to take on a 126-year-old address with nine decades of Highland history baked into its walls.
