6 spacious homes in the Berkshires

Great Barrington

Set on 120 woodland acres, this seven-bedroom modern home is 10 minutes from one of the iconic towns in this Massachusetts mountain region famed for its beauty and lively arts scene. The 2007 house features sliding glass walls and extensive decking with panoramic views, and an airy great room with fireplace, dining space, and open chef’s kitchen. 

Outside are a sweeping lawn, picturesque rock outcroppings, 25-meter heated saltwater pool, hot tub, stone firepit, barn, and two-bedroom guesthouse. $6,800,000. Mary Jane White, Cohen + White Assocs., (413) 429-7611.

Lenox

Historic Winthrop Estate, just outside of downtown near shops, restaurants, and cultural institutions, has been a country home, offices, and events venue. Restored as a 10-bedroom private house, this 1929 Tudor Revival of stone, stucco, and elaborate brickwork has high ceilings, crown molding, wood paneling, nine fireplaces, and formal rooms including a library and a conservatory. 

Subscribe to The Week

Escape your echo chamber. Get the facts behind the news, plus analysis from multiple perspectives.

SUBSCRIBE & SAVE

Sign up for The Week's Free Newsletters

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

Sign up

On the 45-acre mountain view property are terraces, gardens, woods, a carriage barn, and a three-bedroom midcentury-modern additional house. $5,500,000. Selina Lamb, Birch Properties, (413) 331-7483.

Egremont

This farmhouse-style five-bedroom home is walking distance to shops and a pond, and a short drive to Great Barrington. The 1950 structure includes a 1540s English post-and-beam barn added as a great room, with 28-foot-high ceilings, exposed timbers, brick fireplace and windows framing mountain views; a large kitchen opening to a screened porch; and a pine-paneled den with a fireplace. 

On the 5.73-acre lot are a patio, pool, lawns, trees and a spring- fed pond. $1,295,000. Maureen Kirkby, Berkshire Hathaway HomeServices Barnbrook Realty, (413) 446-5634.

Stockbridge

Minutes from downtown, this seven-bedroom home is also a short drive from Lake Mahkeenac and the Tanglewood music festival. Designed by modernist architect John Rogers, the 1968 house features vaulted wood-clad ceilings, wide-plank floors, and floor-to-ceiling windows; a living-dining room with double-sided fireplace; an eat-in chef’s kitchen with attached greenhouse; a gym and indoor pool; and a catering kitchen. 

The 57-acre wooded property includes landscaped grounds with professionally curated gardens, outdoor pool, tennis court and playground. $4,750,000. Nancy Cole, Compass, (978) 402-5790.

Richmond

Just over the hill from Tanglewood, this three-bedroom lodge is also less than 10 minutes by car from downtown Lenox. The 1989 house has a main living area with exposed-truss cathedral ceiling, wall of glass doors and whitewashed-brick fireplace; a skylit galley kitchen with rustic cabinets and granite counters; and upstairs and downstairs decks with views of green lawns and mature trees. 

The 10-acre forested property comes with deeded access to Fairview Pond. $995,000. Martha Piper, William Pitt Sotheby’s International Realty, (413) 627-4599.

Sheffield

This three-bedroom home abutting a wildlife area is a short drive from the shops, dining and Mahaiwe Performing Arts Center of Great Barrington. The 1955 midcentury-modern, open-plan ranch features wood and concrete floors, built-ins, a great room with floor-to-ceiling stone fireplace, a pass-through kitchen with penny tile backsplash, and a seasonal screened porch. 

The 1.29-acre wooded lot includes yards, trees, a shed and access to Berkshire Trout Pond. $549,000. Karen Climo, William Pitt Sotheby’s International Realty, (413) 429-6732.

This article was first published in the latest issue of The Week magazine. If you want to read more like it, you can try six risk-free issues of the magazine here.