5 houses for sale in Great Barrington, Massachusetts
Escape from New York

5 houses for sale in Great Barrington, MA, for outdoorsy people

Austin Havens-Bowen
By Austin Havens-Bowen  |
October 1, 2021 - 10:30AM

This four-bedroom, two-bath Victorian is listed for $799,000 after a recent $36,000 price cut.

If you want to move to the Berkshires—like many other New Yorkers did during the pandemic—or buy a vacation home, Great Barrington is a good place to consider. It's easy to enjoy the outdoors here with hiking at Fountain Pond State Park and Monument Mountain, fishing at Lake Mansfield, and skiing at Ski Butternut. 

You also won’t miss out on a walkable downtown: Main Street and the surrounding area are home to Mahaiwe Performing Arts Center (listed on National Register of Historic Places) plus there are lots of local stores and restaurants like Barrington Outfitters, The Prairie Whale, Siam Square, and Baba Louie’s. Berkshires Botanical Garden and Tanglewood are in nearby Stockbridge and the area is about a three-hour drive to New York City.

There are only about 42 houses currently listed on Zillow. Despite the small number of listings, you’re likely to find a house for a bit less than similar towns in the Hudson Valley: The current median listing price is $535,000. On the market currently are houses within walking distance of Main Street and some farther out in more rural areas.

So if you’re looking to buy a place in the Berkshires, check out these five houses in Great Barrington including a 1900 Victorian with a wraparound porch.

31 Hillside Ave.

This four bedroom, three bath is listed for $619,000. The renovated house features wood siding, a new roof, hardwood floors, recessed lighting, stainless steel appliances, quartz countertops, a laundry room, finished basement, deck, and large backyard. Dewey Park is nearby. 

75 Taconic Ave. 

This four bedroom, two bath is listed for $799,000 after a recent $36,000 price cut. The 1900 Victorian has a wraparound porch, a fireplace, hardwood floors, moldings, built-ins, stainless steel appliances, arched doorways, a home office, patio, and large backyard. Downtown Great Barrington is within walking distance.

97 Castle St.  

This three bedroom, two and a half bath is listed for $849,000. It has high ceilings, original woodwork, hardwood floors, moldings, built-ins, stainless steel appliances, a fireplace, wraparound porch, finished attic, basement, landscaped yard, and all new wiring and mechanical systems. Great Barrington Town Hall is nearby. 

22 East Mountain Rd.

This five bedroom, four bath is listed for $1,275,000. The cabin-style house has vaulted ceilings, wood walls, oversized windows, a stone fireplace, moldings, ceiling fans, stainless steel appliances, a deck, screened-in porch, and tennis/basketball court. Ski Butternut is nearby. 

112 Brush Hill Rd.

This five bedroom, five bath is listed for $2,995,000. The custom-built house has high ceilings, two fireplaces, hardwood floors, recessed lighting, stainless steel appliances, central air, ceiling fans, a basement, sunroom, two-car garage with a studio above, deck, patio, inground heated pool, and a tennis/basketball court. It sits on eight acres of land.


Austin Havens-Bowen

Austin Havens-Bowen


Austin Havens-Bowen is a writer and reporter. He previously covered local news for the Queens Ledger and The Hunts Point Express in the Bronx. He graduated from Hunter College with a BA in media studies. He rents a one-bedroom apartment in Astoria with his boyfriend and their two cats.

Brick Underground articles occasionally include the expertise of, or information about, advertising partners when relevant to the story. We will never promote an advertiser's product without making the relationship clear to our readers.