Upstate House

Berkshires Gold: Your Guide to Great Barrington MA

By Jamie Larson  |  Photos by David McIntyre  |  Winter 2022   |  Community Spotlight

The secret’s out about living in Great Barrington. The town is full of art and culture, creative business, restaurants, shopping, natural outdoor attractions, a civically engaged community, good schools—the works. Unsurprisingly, now everyone wants to live here. “Having real estate in the Southern Berkshires is like having gold. It’s never going to depreciate,” says Great Barrington resident Claudia Laslie, founder of Berkshire Rental Properties and certified broker with Lance Vermeulen Real Estate. “The market during the first year of COVID was insane. The second year was even crazier. People wanted to get into the Berkshires at all costs.” 

The Great Barrington Scene

Great Barrington boasts a destination business district and a notable restaurant scene that includes fine dining treasures like Prairie Whale, Number Ten steakhouse, Cafe Adam, and Bizen, as well as casual favorites like Baba Louie’s, Fuel Bistro, and Momma Lo’s BBQ. Shopping is getting more and more high end, with home goods and fashion from stores like Hammertown, Scout, and Artemisa, coming to define the rural Berkshire aesthetic. 

There are art galleries and boutiques dotting the downtown. A thriving arts district is anchored by the Mahaiwe Performing Arts Center. Productions can also be taken in at the Daniel Art Center on the Bard College’s Simon’s Rock campus. Just a short drive away, North Adams is home to Mass MoCA, one of the absolute best modern art museums in the country, and just south of Great Barrington is the world-renowned Jacob’s Pillow Center for Dance.

The second annual Berkshire Busk event series ran in town throughout the summer and Betsy Andrus, Southern Berkshires Chamber of Commerce Executive Director, says the outdoor music, arts, and commerce programming proved to be both a great attraction for visitors and a block party for the local community.

For all the attractions Great Barrington has built, nothing rivals the natural splendor that surrounds it. Recreation opportunities abound, with Monument Mountain, the Catamount and Ski Butternut areas, the Pfeiffer Arboretum, and much more within a stone’s throw. You are never far from nature here and there’s an ever-present calming quality to the clean, crisp air. 

“Great Barrington is safer, cleaner, greener, and close to New York and Boston,” says Laslie. “The buyers we are seeing are young families from the city and climate refugees from the West Coast. With all the new residents, what I’m hoping is that in the next five years we see a dramatic increase in services.”

While the influx of new residents and capital has brought growth, stakeholders are working to make sure the community culture that drew people here in the first-place perseveres. Community organizations creating opportunities for children and underserved residents like the Railroad Street Youth Project, Elizabeth Freeman Center, and Multicultural BRIDGE, see strong local support. “I moved with my young kids to Great Barrington in 2003,” Laslie recalls. “I thought I’d only be here a few years. Then I woke up, like the rest of the world. I wake up every morning and I can’t believe I live in this place. I am profoundly grateful. The abundance of beauty here is off the charts, all four seasons.”  

Great Barrington Real Estate Market

The real estate market was strong in Great Barrington pre-pandemic but once COVID hit, there was an avalanche of demand. Metropolitan refugees paid big for anything they could get their hands on in the civilized, modern mountain town. The market is slowing a bit now but not much, and really only due to lack of inventory. There’s next to nothing available under $1 million and Laslie says what there is over $1 million still sells pretty quick and often for cash. 

“I think the reason people feel this area is so appealing is because everyone is open and very welcoming,” says Andrus. “We have some problems to work out but people see us as a safe haven.”

Prices are inflated here but for those who regularly peruse listings, it’s clear you get what you pay for: charming architecture, fresh remodels, bucolic properties, and proximity to one of the most appealing town centers in the Northeast. 

Just three blocks from the center of Great Barrington there is an 1861 Colonial with five bedrooms, two-and-a-half baths, and 3,400 square feet on the market (likely not for long) for $1,695,000. It’s got a carriage house and is set back from the road. 

Perhaps a more down-to-earth example in close proximity is a 1973 bungalow up on scenic Castle Hill Avenue. The entirety of the three-bedroom, two-bath, 1,600-square-foot home has been renovated and it’s on the market for $795,000. 

In an attempt to maintain character while the town grows so quickly, the Selectboard recently passed strict short-term rental regulations that limit a property to only 150 days of short-term rental a year. While the move intends to disincentivize corporations from buying up real estate and turning neighborhoods into Airbnb motels, critics of the move say it’s also devastating to established local hosts who have relied on rental properties for needed income. 

Laslie says her business, which primarily brokers long-term seasonal rentals (over 30 days), is unaffected by the ruling but she was a part of the local pushback on the legislation. The ban had initially limited short-term rentals to just 90 days a year. 

While opportunities to buy your own piece of Great Barrington are few these days, agents say there are deals out there on great properties, if you are willing to be patient or just drive a few minutes out of town to Pittsfield or North Adams. These towns are still in the active stages of their come-ups and offer copasetic vibes. And they’re just a short drive away from the full package.   

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