The five highest-priced home sales reported in Berkshires, Massachusetts for the week ending October 25, 2026, came to a combined $6.685 million. Stockbridge accounted for two of them, and the rest were spread across South Egremont, Egremont and Lenox.
All five are single-family homes in Berkshire County, and most sit on generous land, from just under an acre to nearly ten. Their ages run from a Cape Cod built in 1950 to a contemporary finished in 2021, and between them they take in lake and mountain views, a post-and-beam barn, a private beach and a heated pool.
No. 1 — $1,985,000 · 60 Mahkeenac Rd, Stockbridge, Massachusetts
The week’s top sale was a 1952 Contemporary on Mahkeenac Road in Stockbridge, which sold for $1,985,000. At 9.71 acres, it is the largest property in this Top 5. The irregular lot is landscaped and shaded by deciduous trees, and it offers privacy.
The property has views of water, including a lake, along with distant views of the hills and mountains. There is a deck. Inside, the home has four bedrooms and four baths, three full and one half, in 2,800 square feet, with wood, ceramic tile and carpeted floors. A full finished basement has walk-out access, and the three-car garage is the largest among the five sales. The property last sold for $1.21 million in 2003.
The record names no listing agent who can be credited for this sale. Selina Lamb of BIRCH PROPERTIES represented the buyer.
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No. 2 — $1,700,000 · 14 Old Tree Farm Rd, Stockbridge, Massachusetts
Set on 8.67 acres of meadow and woodland in Stockbridge, the home at 14 Old Tree Farm Road sold for $1,700,000. Built in 1986 in a center-hall Colonial form with contemporary touches, it is the largest home in this Top 5 at 3,000 square feet, with three bedrooms and four baths, three full and one half.
Life in the home centers on an open kitchen with an island, soapstone counters, a breakfast nook and a sitting area. That end of the home is lined with glass, and French doors lead out to a stone patio set among landscaped gardens with a waterfall. A dining room adjoins the kitchen, and the living room runs from the front of the home to the back under a cathedral ceiling, with a fireplace and hardwood floors. The grounds look west to the mountains, and there is an outdoor hot tub.
Apart from the main residence stands a renovated post-and-beam barn of about 1,800 square feet with cathedral ceilings, suited to a studio, an office or guest space. Tanglewood and the villages of Stockbridge, Lenox and West Stockbridge are a short drive away. The property last sold for $796,000 in 2002.
The home went under contract 25 days after it was listed. Maureen White-Kirkby of BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY was the listing agent, and Paula J. McLean of PAULA MCLEAN REALTORS INC. represented the buyer.
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No. 3 — $1,175,000 · 9 Prospect Lake Rd, South Egremont, Massachusetts
The oldest home in this Top 5 is a 1950 Cape Cod at 9 Prospect Lake Road in South Egremont, which sold for $1,175,000. It sits back from the road on 3.69 landscaped acres, with lake privileges and a private beach, and a short walk brings residents to French Park, where there are tennis and pickleball courts, a basketball court, a playground, a dog park and hiking trails.
With four bedrooms and five baths, three full and two half, the home has more bathrooms than any other in the group, in 2,524 square feet. It was built for accessibility: it can be used from a wheelchair, and the primary bathroom has a roll-in shower with grab bars. A separate apartment within the home can serve as guest quarters or a professional office. A steel roof and a 10kW generator round out the practical side.
Catamount Ski Area is minutes away, and Tanglewood is within half an hour. The property last sold for $175,000 in 1996.
George Cain of WILLIAM PITT SOTHEBY’S – GT BARRINGTON was the listing agent, and Robin Ban of COMPASS MASSACHUSETTS , LLC GB represented the buyer. The brokerage also listed the No. 4 sale this week.
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No. 4 — $975,000 · 10 Terra Ferma Dr, Egremont, Massachusetts
At the end of a private road in Egremont, the newest home in the group was finished in 2021 and sold for $975,000. Its step-free floor plan is built around a chef’s kitchen that opens to the main living space, with stone countertops and wood floors.
The home has three bedrooms, among them a generous primary suite with a walk-in closet, and three baths, two full and one half, in 1,782 square feet, along with a home office. Outdoors, a front porch and a wide stone patio look over 1.87 landscaped acres, and wooded hiking trails begin close by. The property last sold for $919,000 in 2025.
The home went under contract 20 days after it was listed and sold at its full asking price. Antonio M Segalla of WILLIAM PITT SOTHEBY’S – GT BARRINGTON was the listing agent, giving the firm a second listing in this Top 5 after the No. 3 sale, and Judi Panzano of HOUSATONIC REAL ESTATE represented the buyer.
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No. 5 — $850,000 · 22 Post Rd, Lenox, Massachusetts
Behind a hemlock hedge on a cul-de-sac in Lenox, the 1960 Colonial at 22 Post Road sold for $850,000. The backyard is the heart of the property: the fenced, professionally landscaped yard has a heated in-ground saltwater pool, a deck, a patio, a built-in swing set and a shed.
Inside, an open floor plan with wood floors centers on a living area with a gas fireplace and a kitchen with modern appliances. The home has three bedrooms, plus an extra room that can work as a home office, and three baths, two full and one half, in 2,262 square feet. A full basement lies below, and there is an attached two-car garage. The property, on just under an acre, is moments from downtown Lenox and Tanglewood. It last sold for $465,500 in 2008.
The Allain Group of Compass and India Ward were the listing agents.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 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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