Fifteen years ago, Julia Kaplan left New Jersey to escape its notoriously high property taxes and settled in the small city of Pittsfield, Mass., in the Berkshire Mountains.
Over the years, Ms. Kaplan updated and renovated her historic, six-bedroom home in Pittsfield, which had plenty of space for her two college-age children when they returned home for summers. But every year, she’d watch as the property taxes crept upward. By the summer of 2025, the rate had doubled since her arrival in 2011, to about $12,740.
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“I had been thinking of listing my house for over a year before that,” said Ms. Kaplan, 67. “But when I got my tax bill that summer, I said, ‘That’s it, I’m done.’ I’m not against paying taxes, but when they get out of control and you don’t need those services, it’s time to move on.”
Ms. Kaplan, a former commercial real estate developer who now runs an event photography business, did not want to leave the Berkshires. She loved the arts and culture in the area, as well as the active Jewish community. Instead, she wanted to find a property with lower carrying costs, but still enough space for her children and their families to visit. She also wanted to move southward toward Connecticut, where one of them lives, and Great Barrington, where she has photographed several arts groups.
Among her “must-haves” were a ground-level primary bedroom suite and laundry room, and a garage attached to the house. With that in mind, Ms. Kaplan and her broker, Carrie Lobovits Wright of William Pitt Sotheby’s International Realty, began a six-month search for a new home.
Ms. Kaplan’s budget ranged up to about $800,000, but she knew that the market remained tight in Berkshire County, with inventory lagging behind demand. That meant adjusting expectations during the search. “We homed in,” Ms. Lobovits Wright said. “We started very broad and then she figured out what she wanted, after seeing what was on the market.”

This three-bedroom, two-and-a-half-bath Cape with nearly 2,500 square feet was well located in Sheffield, Mass., close to the Connecticut border and Route 7. Set on a flat acre of land, the 1950 home was also in good condition, with hardwood floors, large windows, built-ins, an updated kitchen and bathrooms, and space for a laundry room. There was a bedroom suite on the first floor, plus two bedrooms and a bathroom upstairs. The ceilings were a bit low and the garage was not attached, though “it was close enough, and it had a loft,” Ms. Kaplan said. The property came with an in-ground pool and was surrounded by a farm. The price was $895,000, eventually reduced to $845,000, with annual property taxes of about $7,500.


Also close to Route 7, this four-bedroom, two-and-a-half-bath house from 1984 had nearly 2,400 square feet. Its open layout, cathedral ceilings and wood detailing gave it a rustic feel. Ms. Kaplan loved the primary bedroom suite, which offered a separate office space and outdoor area. The garage was accessible through the basement, which was partially finished, and there was an open kitchen and dining area that stepped out to a sunroom and rear deck. Built in 1984, the post-and-beam-style house was set on 1.9 wooded acres next to the Appalachian Trail corridor, which is protected from development. The home was also powered by a nearby solar farm, so Ms. Kaplan could see energy savings. The price was $765,000, with taxes of about $8,385.


Farther from the Connecticut border but still close to a highway, this four-bedroom, five-bath house from 1989 in the town of Becket had 1,776 square feet. There were primary bedroom suites on both the ground and second floors, the former with a walk-in closet and private patio. A ground-floor bathroom doubled as a laundry room. Another post-and-beam-style residence with wood everywhere, it had an open design with a tiled fireplace, a cozy kitchen, a screened-in sunroom and a wraparound porch. The two-car garage, with a bonus room and full bath, was connected to the house. The 3.3-acre property was a bit more rural than the other options, but a grocery store was within a 12-minute drive. The price was $699,000, with annual property taxes of around $6,000.

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