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With culture and wilderness, you don’t have to settle for less in the Berkshires
The quaint towns of Western Mass. are more affordable than homes in Greater Boston.
Berkshire County is the mountainous region in westernmost Massachusetts that has it all: relatively low property taxes, great skiing, hiking trails, restaurants, museums, Mount Greylock, historic homes, and as much privacy as you want. Herman Melville wrote “Moby-Dick” and several other novels from his home in Pittsfield, called Arrowhead. James Taylor lives in Lenox and has been performing at Tanglewood for 50 years.
Home prices in the northernmost towns are more affordable, and as you head south on US Route 7 (or Mass. Route 8), home prices go north.
Northern Berkshire County is anchored by Williams College in Williamstown and the Massachusetts Museum of Contemporary Art in North Adams. It tends to attract educators and artists and is primarily occupied by year-round homeowners, with a growing appeal to second-home buyers.
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The majority of homes here sell for between $200,000 and $400,000, according to the Berkshire County Board of Realtors.
Andy Perenick is a broker/associate with Lamacchia Realty‘s Dalton office. He’s also the 2025 president of the Berkshire County Board of Realtors. He grew up in Winchester, but his parents, siblings, and wife were all born in the Berkshires, so it felt natural for him to raise his family there.
“The Berkshires has something for everybody,” he said. “I moved here to have a better quality of life. And compared to home prices in and around Boston, it’s very affordable. And if you want to go to the city, you’re only a two-hour drive from Boston, a little longer to New York City, and Albany is only 55 minutes away.”
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He described northern Berkshire County as more rustic than the rest of the county.
“I have cousins who live on a mountain in Florida, Mass., [near North Adams],” he said. “If you want to be more in the boondocks and have a little bit of a rugged experience, you can get a little shack up there in the woods. … If you like hunting and fishing and not a lot of neighbors and very reasonable prices.”
The Berkshire County Board of Realtors calls central Berkshire County the region’s commercial hub, comprised primarily of year-round residents. Here, most homes sell for between $250,000 and $500,000, according to the realtor group.
Cameron Volastro is a real estate agent with Stone House Properties. His YouTube channel is filled with videos highlighting the best the Berkshires have to offer.
“The Berkshires offer many different attractive lifestyles,” he said. “There’s the waterfront living lifestyle, the historic walk to town properties are very appealing, and also the privacy of something tucked away in the woods. It’s also incredible for anyone who’s into any sort of arts and culture and wants to go see dance at Jacob’s Pillow or art at Mass MoCA.”
Volastro said people are drawn to the Berkshires for its natural beauty and quaint towns. “Take Stockbridge, for example,” he said. “So much effort goes into preserving that town to keep it like when Norman Rockwell was alive and painting there, it’s why they recreate a picture of the town every year in the same fashion of one of the paintings. It’s just incredible how little has changed there. People really love that the museum is right there and the Berkshire Botanical Garden. And about half of the homes there are second homes. It’s a good mix.”
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Historically, most people buying property in the Berkshires are moving from Greater Boston and New York, but he said he’s recently been seeing more people relocate from much farther away.
“I see a lot of people relocating from California and Texas,” he said. “I hear a lot about how people are moving here because of climate change. This area is a haven for people who are concerned in places like [the state of] Florida, they look to the Berkshires, and they love that they don’t have to worry about rising sea levels and damage from crazy storms here.”
Southern Berkshire County is known for its luxury market. Single-family homes in this area sell for between $500,000 and $2 million-plus, according to the realtor group. Home to Tanglewood, the summer home of the Boston Symphony Orchestra, as well as both Mirival and Kripalu health and wellness resorts, towns like Lenox, Stockbridge, and Great Barrington are increasingly magnets for celebrities.
Will Shillinger owns Pilot Recording Studios in Great Barrington. Musicians and actors come from all over the world to work with him in the former church near the banks of the Housatonic River, which he bought in 2011 and opened as the studio in 2012. Born and raised in New York City, he went to college at Simon’s Rock in Great Barrington in 1975 and fell in love with the area. As an adult living and working in the city, he bought a vacation home in the 90s.
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He and his partner, Beth Rose, are building a sustainable home in nearby Monterey. They enjoy the outdoors, going out to local restaurants, and seeing live music.
“I do an annual multiday trip on the Appalachian Trail,” Shillinger said. “I’m getting into hiking and cycling and skiing and all the other outdoor activities that go on around here. For live music, the Egremont Barn is one of our favorite hangs. And we love the food at the Heirloom Lodge.”
When the population swells in the summer, he sometimes jokingly refers to the Berkshires as the “Hamptons on the Housatonic.” But what he loves most about the area is its inescapable beauty.
“One of the things about this area is it has a really special light,” he said. “Nothing against Woodstock, but I feel like when you go over the hills and you’re in the Hudson Valley, that valley, it’s always shaded, and there’s something sort of vibrant and magical about the light in the Berkshires.
“I’ve felt that way since I was a kid. There’s so many amazing places to hike that are just absolutely gorgeous. It really is an idyllic place to live.”
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