The five highest-priced home sales reported in Berkshires, Massachusetts for the week ending November 1, 2026, came to a combined $4.21 million. All five are single-family homes in Berkshire County, spread from Williamstown in the north to Great Barrington in the south, with stops in Richmond and Pittsfield along the way.
Williamstown accounts for two of the five, which together sold for $1,665,000. The group spans nearly two centuries of building, from a home dating to 1830 to a Contemporary finished in 1986, and runs from a third of an acre on a lake to almost 20 acres of pasture along a river.
No. 1 — $965,000 · 295 Blair Rd, Williamstown, Massachusetts
The oldest home in this week’s group sits on the largest piece of land: 19.94 acres along the Green River in Williamstown, with ponds, pasture, barns and an outbuilding. Built in 1830, the property sold for $965,000.
There is room here to farm or keep livestock, and the grounds also include an in-ground pool and an outdoor hot tub, with a second hot tub indoors. Views take in the river, the ponds and the open pasture.
The home has seven bedrooms, five bathrooms (four full and one half) and 5,104 square feet, the most living area of the five. There is also an attached guest house with its own bedrooms and baths, suited to visiting family or a multigenerational household. The kitchen has granite counters, stainless steel appliances and a fireplace of its own, and looks out toward the side porch, a screened room and the pastures beyond. Two more living rooms on the first floor each have a fireplace and French doors opening onto porches, and a mudroom at the back entrance handles boots and coats. On the second floor are the primary suite with a walk-in closet, two more bedrooms and a laundry room. Two further bedrooms sit on the third floor. There is also a sun room.
The property last sold for $340,000 in 1998, 28 years ago.
Erin M. Scott and Dante Cellana, both of BURNHAM GOLD REAL ESTATE, LLC, were the listing agents for the week’s top sale, and Wayne Santelli of KEMPF-VANDERBURGH REALTY CONSULTANTS, INC. represented the buyer.
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No. 2 — $946,000 · 261 Osceola Rd, Richmond, Massachusetts
From its deck, 261 Osceola Road in Richmond looks west over preserved meadow to the lower Taconic Mountains. The home is in Osceola Notch, a community with shared preserved common land and a tennis court, where the association helps keep the landscape open.
The Colonial was built in 1975 and sits on 1.55 acres. It has three bedrooms, three bathrooms (two full and one half), 2,064 square feet and an attached two-car garage. The kitchen was renovated in 2023 with KraftMaid cabinets, Brazilian silver soapstone counters, open shelving and a large island, and sliding doors open from it onto a deck with cable railings that leave the view clear. The living room has hardwood floors, a wood-burning fireplace and wide windows facing the meadow and mountains.
The land has been managed for native plants, pollinators and birds, and a kestrel nesting box in the meadow is monitored through the Berkshire Bird Observatory. In winter the fields are open for cross-country skiing.
The home sold for $946,000, $61,000 above its asking price of $885,000. It last sold for $560,000 in 2019. Selina Lamb of Birch Properties was the listing agent.
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No. 3 — $874,000 · 10 Club Cir, Pittsfield, Massachusetts
The home at 10 Club Circle in Pittsfield has 115 feet of frontage on Pontoosuc Lake, close enough to swim and launch a boat from its own shoreline. Out on the open water there are views of Mount Greylock, and sunrises come up over the hills across the lake. It sold for $874,000 after going under contract 30 days after it was listed.
Built in 1967 and offered for sale by its original owner, the Cape Cod still has its original walnut woodwork. The living area has a fireplace, the kitchen has stone counters and a covered porch looks over the water. The primary suite is on the first floor, with the other bedrooms and a large bath upstairs. In all, the home has three bedrooms, three bathrooms (two full and one half) and 2,228 square feet on 0.33 acres, the smallest lot of the five. A full, partially finished basement has a walk-out.
Tiffany Roberts of TIFFANY ROBERTS PROPERTIES LLC was the listing agent, and Elisha Poirier of STONE HOUSE PROPERTIES, LLC represented the buyer.
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No. 4 — $725,000 · 1 Cornwall Dr, Great Barrington, Massachusetts
Cornwall Estates in Great Barrington is a small community of eight homes, and 1 Cornwall Drive sits on a quiet cul-de-sac there, on a level, wooded lot of 2.43 acres. It sold for $725,000.
The Cape Cod was built in 1985 and has three bedrooms, three bathrooms and 2,008 square feet. The primary bedroom and its bathroom are on the first floor, and the living room has a vaulted ceiling. A screened porch opens onto a large backyard that is partly fenced. Within the last three years the kitchen and bathrooms have been updated. The community has a heated pool nearby, and Great Barrington is minutes away.
The property last sold for $525,000 in 2022.
Stephen R. Schoenfeld of WILLIAM PITT SOTHEBY’S – GT BARRINGTON and Thom Garvey of WILLIAM PITT SOTHEBY’S – LENOX were the listing agents. Martha Piper of THE KINDERHOOK GROUP represented the buyer.
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No. 5 — $700,000 · 1030 Simonds Rd, Williamstown, Massachusetts
The second Williamstown sale of the week, 1030 Simonds Road, is the newest home in the group: a Contemporary built in 1986 on 7.59 private acres. It sold for $700,000 and last sold for $430,000 in 1996.
Inside, exposed wood beams cross the ceilings and natural light fills the rooms. The home has five bedrooms, five bathrooms (four full and one half) and 4,102 square feet, including a new, private primary suite with a soaking tub and a second primary suite. A third-floor room can serve as a bedroom or a loft. Two woodstoves and a wood-burning fireplace heat the home, and there is a sauna in the basement. Outside are two large decks, a garden area and a two-car garage with loft space above it.
Carrie Swift Heck of COMPASS MASSACHUSETTS , LLC GB was the listing agent, and Gintare Everett of ALTON & WESTALL REAL ESTATE AGENCY, LLC represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, November 1, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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