The Berkshires

Get to know the Berkshires and Columbia County, New York. We’ll help match you with your ideal home in the town that’s the best fit for you, your family, and your lifestyle.
Alford

Alford

Originally settled in 1750, Alford is one of the best-kept secrets of the Berkshires. The population remains steady around 500 people, and second-home owners and retirees make up a large percentage of the population...
Becket & Otis

Becket & Otis

The southeastern towns of Becket and Otis represent some of the best values in Berkshire County homes. With their close distance to Springfield and other large Western and Central Massachusetts cities, they’re also...
Egremont

Egremont

Quiet yet never sleepy, Egremont—comprised of North Egremont and South Egremont—is nestled in the southwestern Berkshire Hills, close to both Great Barrington and the New York State line. A former stagecoach stop on the...
Great Barrington

Great Barrington

Big-city culture and ideas with a small-town, friendly vibe—that’s the essence of Great Barrington. Named one of the 20 Best Small Towns in America by Smithsonian Magazine and one of the top 25 Dream Towns in Massachusetts...
Housatonic

Housatonic

Housatonic is technically a small village located at the northeastern tip of Great Barrington, but what it lacks in size in makes up for in attitude. Once a booming mill town that experienced a period of decline following the mill closing...
Lee

Lee

Once a bustling mill town, Lee has undergone one of the most dramatic transformations in all of the Berkshires. A downtown revitalization project not only helped to preserve Main Street’s antique brick and clapboard buildings...
Lenox

Lenox

Known for its profusion of inimitable, late-nineteenth-century Berkshire “cottages,” Lenox is the cultural heart of the Berkshires and one of the region’s most-visited towns. And no wonder, thanks to its picturesque New England streets...
Monterey

Monterey

Small in size but big in stature, Monterey is located on the Mill River in the southern Berkshires. This peaceful little town is ideal for lovers of wildlife, camping, and the outdoors. From the Monterey overlook at Beartown State Forest, you can...
New Marlborough

New Marlborough

While New Marlborough was one of the first towns to be settled in the Berkshires in the early 1700s, in modern times, its peaceful, noncommercial atmosphere and location on the southern tip of the county have earned it hidden-gem status...
Pittsfield

Pittsfield

If Lenox is the cultural heart of the Berkshires, Pittsfield is the region’s commercial, business, and arts lifeblood. Through a variety of downtown-focused initiatives, this proud city has transformed itself from an industrial mecca into a lively...
Richmond

Richmond

Just south of Pittsfield and north of West Stockbridge, and tucked along the border of Canaan, New York, Richmond represents rural living at its most spectacular. Its remarkable beauty comes courtesy of its rolling hills, wide-open fields...
Stockbridge

Stockbridge

Stockbridge is one of the oldest and best-known towns in the Berkshires, thanks to famous residents like sculptor Daniel Chester French, artist Norman Rockwell, former slave and civil rights activist Mumbet, diplomat Jospeh Choate...
Sheffield

Sheffield

Scenic and sophisticated, Sheffield lies in the Housatonic River valley, between Mount Everett (part of the Taconic Range) and Mount Washington, along the southern border of the Berkshires and Litchfield County, Connecticut...
West Stockbridge

West Stockbridge

West Stockbridge, on the western border of the Berkshires and New York State, may not have the historic renown of its big sister, Stockbridge, but in recent years it has gained a reputation as a hip, up-and-coming Berkshire town with an...
Columbia County

Columbia County

Just over the state line from the Berkshires, Columbia County has been a favorite getaway and second-home spot for city dwellers for decades. Rich in rural beauty, arts, and culture, Columbia County consists of 18 towns...
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