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Vermont residents purchase two prime North Street properties

Greystone Building Photo

The Greystone Building at North Street and Maplewood Avenue in Pittsfield has been sold for $4.7 million to two Vermont residents who also spent $1.5 million for the Lloyd Building across the street. 

PITTSFIELD — Two Vermont residents recently became the owners of a sizable chunk of prime downtown real estate located in the 400 block of North Street.

Dennis McIntosh and Catherine Kupperstock, who live in Wilmington, Vt., spent over $6 million to purchase the Greystone Building on the corner of North Street and Maplewood Avenue and the Lloyd Building on the other side of Pittsfield’s main downtown thoroughfare at 391-401 North St.

The couple paid $4.75 million for the Greystone Building, which contains a mix of apartments and commercial enterprises, and $1.5 million for the Lloyd Building, which is also a residential/commercial complex. The Lloyd Building is on the corner of Bradford and North streets, and also includes a residential entrance at 28 Bradford St.

McIntosh and Kupperstock have obtained a $3.1 million mortgage on both properties from NBT Bank, according to documents filed at the Middle Berkshire Registry of Deeds in Pittsfield.

The two transactions are listed separately at the registry, and will be run by two different limited liability companies. Both properties were previously owned by William Gioielli and Cole Ungar, of Skytop Properties in Pittsfield. Both men originally worked for a New York City-based real estate firm before forming their own Berkshire-based company, which owns several properties in Pittsfield and the Berkshires.

Earlier this year, Ungar and Gioielli sold a residential/commercial building on Wendell Avenue Extension in Pittsfield that was originally the Wendell Hotel for $3.3 million to two residents of Brooklyn, New York.

Ungar, who is originally from the Berkshires, said that neither North Street property had been for sale, but that Skytop decided to sell them after receiving an “unsolicited offer” from McIntosh and Kupperstock.

“They called us on another deal that we already had in contract with a different buyer,” Ungar said. “We said we don’t have anything else available, but they said do you have any other property? They gave us an offer and it worked out.

“They’re great people. They were really easy to work with and we’re excited to have them in the community."

Ungar and Gioielli originally paid $2.27 million for the Greystone Building when they bought it from Whaling Properties in December 2018. According to Ungar, Skytop has invested $1 million in the structure since then.

“We’re value-add investors as sort of a general practice,” Ungar said. “So our main thesis whenever we’re looking at anything is how we can improve the building, improve the quality of living and ultimately improve rents, minimize expenses and increase revenue. That is something we did with both properties.”

At the Greystone, Ungar said Skytop improved the structure’s 18 upper-floor apartments and renegotiated and extended the leases with the building’s three ground-floor commercial tenants — Dottie’s Coffee Lounge, Mission Bar + Tapas, and Circa, a retro furnishings store.

“So when we bought the property to when we sold it I think we doubled the net operating income through improvement,” Ungar said.

The Lloyd Building’s commercial tenants include Methuselah Bar and Lounge, Shire Glass smoke shop, Allstars Cuts barber shop, Radiance Yoga and Terpiscore Dance Center.

Tony Dobrowolski can be reached at tdobrowolski@berkshireeagle.com or 413-496-6224.

Business writer

Tony Dobrowolski's main focus is on business reporting. He came to The Eagle in 1992 after previously working for newspapers in Connecticut and Montreal. He can be reached at tdobrowolski@berkshireeagle.com or 413-496-6224.

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