Best places to buy in the Berkshires in 2026

Best places to buy in the Berkshires in 2026

Home Buying

Real estate professionals share where home buyers can find the most value right now in this Western Mass. region.

Adobe, Ally Rzesa/Globe Staff

It’s a place people go to find inspiration, renewal, and/or a fabulous spa weekend.

Yes, the Berkshires have always run at a different speed than the rest of Massachusetts, and that includes its real estate. A house can sit out here for months without anyone panicking, and winter is treated as a selling point. But the region’s reputation as a place to find a deal is getting harder to live up to, and where the value is hiding has shifted.

The median single-family home in Berkshire County sold for $372,500 in April, up nearly 12 percent from a year earlier, according to the Berkshire County Board of Realtors. But inventory is scarce: The county is sitting on roughly three months of supply, down from almost six months a year ago, a level that still tilts toward sellers.

Corey Bishop, the board’s president, said the squeeze is producing the kind of activity that would have been unthinkable a few years back. He recently listed a split-level ranch in Pittsfield for $349,900 and had three offers within two days, two of them above asking with escalation clauses, where a buyer agrees to raise their offer on a home if the seller receive a higher competing offer. A duplex with a pool drew the same frenzy.

“Our limited inventory is really driving this,” he said.

That’s not the whole picture, though.

Thom Garvey, an agent with William Pitt Sotheby’s International Realty, sees a market that has cooled from its pandemic peak even as it stays active. Prices jumped 30 percent to 40 percent during COVID and have largely held, he said, but multiple offers are now rare outside of exceptional, sharply priced properties. By Garvey’s own count, the average days on the market in Berkshire County runs around 178 — what might seem like an eternity in Greater Boston, but is the usual routine in Western Mass.

The difference comes down to who’s buying. The Berkshires are, as Garvey put it, a second-homeowner-driven market, and second-home buyers behave nothing like the primary-residence shoppers who fuel bidding wars closer to Boston or even the second-home seekers on Cape Cod and the Islands.

“We don’t have that urgency and necessity, so buyers can afford to wait,” he said.

Sellers, often calling the shots from suburbs of Boston, New Jersey, and New York, expect the speed of their home markets and are routinely surprised. When a house is overpriced, both the buyers and their agents know it, and they simply wait the seller out.

So where should a buyer look? Both agents point north and to the edges.

Pittsfield, Adams, and North Adams remain the county’s most affordable footholds, Bishop said; North Adams, anchored by Mass MoCA and the Greylock Works mill, is where Bishop said buyers have typically found the most value when purchasing a home in the region.

The house at 24 Temple St. in Adams is on the market for $309,900. – John M. Ciepiela
The living room of 24 Temple St. in Adams faces the residential street. – John M. Ciepiela

The median single-family home sale price was $230,000 in North Adams last year; $257,500 in Adams; and $293,000 in Pittsfield, according to data from real estate tracker The Warren Group — all below the county’s roughly $360,000 median. But affordability is relative and shrinking. Pittsfield and North Adams median home prices are up 65 percent and 67 percent, respectively, since 2019, and smaller towns have run hotter as buyers chase what’s left. Clarksburg, north of North Adams, has nearly tripled its median since 2019, to $349,000; Cheshire, between Adams and Pittsfield, has more than doubled, to roughly $380,000.

The house at 24 Temple St. in Adams is 1,341 square feet. – John M. Ciepiela
The house at 24 Temple St. in Adams sits on 0.16 acres. – John M. Ciepiela

Hinsdale, where the median sat at $354,000 last year, is the move for buyers chasing a lake at a discount. Garvey said a nice house there on Ashmere Lake can still be had in the high five to low seven hundreds, while tear-down lots on more sought-after waters in other municipalities — Otis Reservoir, Goose Pond, Pittsfield’s Onota and Pontoosuc — can run $600,000 on their own.

The far end of the price spectrum holds few surprises. In Great Barrington, where you can find multimillion-dollar mansions, the median reached $575,000 last year. In Lenox, it reached $605,000, while Williamstown — buoyed by Williams College — jumped 33 percent in a single year to nearly $500,000, per The Warren Group (even though North Adams sits five minutes down the road at less than half that).

The view of downtown Great Barrington from Mooncloud cocktail bar. – Lidia Ryan

But both agents shared a word of caution before you fall for the local Berkshires charm. Most homes here are on private wells and septic systems — much of the housing stock dates to the 18th and 19th centuries — and disclosures pile up fast. Bishop is also seeing the first signs of buyer’s remorse from the pandemic rush: homes bought sight unseen, without inspections, now turning up with foundation problems.

But in a market with this little inventory and this many discretionary buyers, the right house at the right price still moves fast.

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