The five highest-priced home sales reported in Berkshires, Massachusetts for the week ending November 8, 2026, came to a combined $8.69 million. Williamstown had two of them, and Monterey, Southfield and Pittsfield had one each. Four were single-family homes and one was a condominium, and the group ran from a country estate with ponds and trails to a college-town Colonial with a presidential family history.
No. 1 — $3,065,000 · 161 Beartown Mountain Rd, Monterey, Massachusetts
The top sale of the week is a New England farmhouse-style home on 30 acres that border Beartown State Forest in Monterey. Clark + Green designed it, Jess Cooney did the interiors and 377 Builders built it. Finished in 2018, it is the newest of the five homes and, at 4,702 square feet, the largest. It has four bedrooms, five bathrooms and a three-car garage. The property last sold for $1.325 million in 2015, before the current house was built.
Inside are vaulted ceilings, a sun room and floors of reclaimed wood. The kitchen has countertops of Vermont Danby marble, a large pantry and a breakfast nook that opens to the living spaces around it. There is also an indoor hot tub, and the walk-out basement is partly finished.
Outside, a heated gunite pool and spa are set among lawns and open fields. The land has miles of private trails, and there are spring-fed ponds, a brook, gardens and old stone walls. An old horse barn stands at the edge of the meadow. The views take in water, pasture and distant hills. For all its privacy, the property is about 15 minutes from shops, restaurants and cultural attractions.
The home sold for $3.065 million, $70,000 above its asking price of $2.995 million. Katie Williams of STONE HOUSE PROPERTIES, LLC was the listing agent, and Cameron Volastro of WILLIAM PITT SOTHEBY’S – LENOX represented the buyer in the week’s highest-priced sale.
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No. 2 — $2,300,000 · 294 Bulkley St, Williamstown, Massachusetts
Bulkley Street in Williamstown climbs to an estate near the top of the hill that is made up of three separate parcels on 11.35 acres. Hopkins Memorial Forest, a 2,600-acre ecological reserve, is close by, and Williams College, the Clark Art Institute and Williamstown center are minutes away.
The home dates to 1870 and has been updated while keeping its character. It has five bedrooms, four full baths and one half bath, and 4,027 square feet, with public rooms that range from intimate to open. A four-season sunporch looks out over the gardens, the sweeping grounds and the distant ridgeline.
Behind the main home is a separate carriage house. Its apartment above has a kitchenette, a great room and a bedroom, the last two under beamed cathedral ceilings, and an exercise room is on the level below. A bit down the hill, on a lower parcel of six acres, stands a second residence from the early twentieth century that is waiting to be renovated. The property last sold for $456,000 in 1991.
The same agent was on both sides of the $2.3 million sale: Maureen Dietze of ALTON & WESTALL REAL ESTATE AGENCY, LLC was the listing agent and also represented the buyer. The brokerage also listed the No. 3 home, on South Street in Williamstown.
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No. 3 — $1,400,148 · 115 South St, Williamstown, Massachusetts
The listing traces this South Street home to Harry A. Garfield, a president of Williams College and the son of President James Garfield, who gave it to his daughter. Built in 1932, the Colonial has 4,386 square feet on 1.20 acres and a three-car garage. Its six bedrooms and six bathrooms, five full and one half, are the most of the five homes.
The entrance hall leads on one side to a wood-paneled library with built-in bookshelves and a corner fireplace on a slate hearth. The living room has a second fireplace, this one framed by pilasters over a marble hearth, and it opens to a covered slate terrace at the side of the home. The formal dining room has a third fireplace and a china cabinet with glass doors. Latson & Latson custom designed the kitchen, which has a large cherry island and green marble countertops and leads to a wood-paneled family room. Oak floors, floor-to-ceiling windows, six-panel doors and crown moldings appear throughout.
The home is near the Clark Art Institute, whose 140-acre campus has trails through meadows and woodlands, and close to the Williams College campus and the shops and restaurants of Spring Street. The property last sold for $585,000 in 1994.
It sold for $1.4 million, $105,148 over its asking price of $1.295 million. Maureen Dietze of ALTON & WESTALL REAL ESTATE AGENCY, LLC was the listing agent, and Matthew Chow, also of ALTON & WESTALL REAL ESTATE AGENCY, LLC, represented the buyer.
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No. 4 — $1,172,000 · 1001 Canaan Southfield Rd, Southfield, Massachusetts
The oldest home of the five is a Colonial built in 1797 on 23.60 acres in Southfield. The Umpachene River winds through the land, and the grounds include two ponds with fountains, more than 300 feet of stone walls and stone patios. The landscaping is mature. The home has four bedrooms, among them a large primary suite, along with four bathrooms, three full and one half, and 3,389 square feet. Slate and wood floors run through the rooms, and there is an outbuilding as well as a one-car garage. The property includes three separate parcels, and an additional lot is across the street.
Suzann Laverack Ward of HOUSATONIC REAL ESTATE was the listing agent for the $1.172 million sale, and Molly Thomas of COMPASS MASSACHUSETTS , LLC GB represented the buyer.
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No. 5 — $750,000 · 101 Alpine Trl, Pittsfield, Massachusetts
The week’s only condominium is an end unit on Alpine Trail in Pittsfield, near Bousquet Mountain. Built in 2006 on several levels, it has three bedrooms, three bathrooms and 2,381 square feet. The ceilings are vaulted, and there is a fireplace. The primary suite is on the first floor, while the second level has two guest bedrooms, a full bath and a loft that overlooks the great room. The unit has a screened porch and a deck, and its views are of the woods. The walkout lower level is unfinished, and residents can use the association’s pool. The property last sold for $420,000 in 2022.
The condominium sold for $750,000, above its asking price of $729,000. Cortney K Dupont of COHEN & WHITE ASSOCIATES was the listing agent, and Matt Carlino of MACCARO REAL ESTATE represented the buyer.
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