Westhampton
Westhampton is a charming small town near Northampton. It features Outlook Farm and Steve's Sugar Shack. The highly-rated Westhampton Elementary School and natural areas like Lynes Woods Wildlife Sanctuary enhance its appeal.
Average Value
$497K
List Price
$296K - $2.3M
For Sale
Homes For Sale
5 Listings
Conway
Conway, a western Massachusetts hill town, spans 40 square miles of farms and forests. Residents visit Chapel Brook Trail and Conway Community Swimming Pool. The highly rated Frontier Regional schools serve the area.
Average Value
$485K
List Price
$325K - $920K
For Sale
Homes For Sale
3 Listings
Ashfield
Ashfield is a rural New England town in the Berkshire foothills. It features Ashfield Lake, hiking trails, and the DAR State Forest. The community includes a golf course, local theater, and an annual Fall Festival.
Average Value
$435K
List Price
$361K - $1.2M
For Sale
Homes For Sale
2 Listings
Huntington
Huntington in Western Massachusetts provides rural living with access to city amenities. Attractions include hiking at Knightville Dam Recreation Area and Huntington State Forest, along with swimming and fishing at Norwich Pond.
Average Value
$349K
List Price
$161K - $478K
For Sale
Homes For Sale
4 Listings
Goshen
Settled in 1761, the rural town of Goshen hasn’t changed much throughout the centuries, with dense maple and birch forests that produce colorful fall foliage. In fact, the area’s main attraction is a state forest, where many go swimming and hiking. Residents in this community live a secluded lifestyle in the remote foothills of the Berkshire
Average Value
$426K
List Price
$249K - $1.6M
For Sale
Homes For Sale
7 Listings
Alford
Alford is a small, rural community of under 500 people, offering wooded lots and forested trails where locals go hiking or cross-country skiing. “Alford is very rural and picturesque with low taxes,” says Stephen Schoenfeld, a real estate agent with William Pitt Sotheby’s International Realty and resident of the Berkshires region for over 30
Average Value
$1.08M
List Price
$629K - $5.6M
For Sale
Homes For Sale
4 Listings
Monterey
Hiking trails and fishing lakes have drawn residents to Monterey since President James A. Garfield visited relatives here in the mid-19th century. This mountain town in the southern Berkshires has a rural feel, but nearby cultural activities such as orchestra concerts are another draw for seasonal and full-time residents. While gathering spaces
Average Value
$925K
List Price
$415K - $5.1M
For Sale
Homes For Sale
6 Listings
Stockbridge
Sweeping mountain vistas, secluded historic estates, a vibrant art scene and a quaint Main Street brimming with local businesses define life in Stockbridge, a seasonal community in the Berkshires. "Stockbridge is a quintessential, charming New England town," says Lori Rose, a broker and partner at Stone House Properties, who has been in the
Average Value
$884K
List Price
$241K - $3.1M
For Sale
Homes For Sale
11 Listings
Egremont
Egremont is a community of over 1,000 on the New York border, near the tourist and outdoor attractions in southern Berkshire County. Settled in the 1720s by Dutch settlers from New York, this area quickly became known as a small farming community. They saw activity here during the Revolutionary War, with American General Henry Knox passing
Average Value
$881K
List Price
$367K - $3.3M
For Sale
Homes For Sale
11 Listings
Richmond
Bordering Upstate New York in the Berkshires of Western Massachusetts, Richmond serves as a permanent escape for locals and a peaceful getaway for city dwellers. “We have a very high population of second homers,” says Cindy Welch, a Realtor with LandVest Inc., who has lived in Richmond for more than a decade. “People who work and live in Manhattan
Average Value
$780K
List Price
$229K - $3.3M
For Sale
Homes For Sale
10 Listings
West Stockbridge
Straddling the border between Massachusetts and New York, Western Stockbridge is Stockbridge's quieter, more rural counterpart in the Southern Berkshires. "I always say Stockbridge is near and dear to my heart, but I absolutely love living in West Stockbridge," says Lori Rose, a West Stockbridge resident and broker and partner at Stone House
Average Value
$760K
List Price
$369K - $2.6M
For Sale
Homes For Sale
11 Listings
Tyringham
Tucked between the Beartown State Forest and October Mountain State Forest, Tyringham is a rural town known for its tranquil landscapes, historic charm and 13-mile strip of the Appalachian Trail in the Southern Berkshires. "Tyringham offers a bucolic, country setting and is more rural than the surrounding towns. But it's just outside Lee, so
Average Value
$746K
List Price
$421K - $2.2M
For Sale
Homes For Sale
2 Listings
Lenox
Once a summer retreat for the Gilded Age elite, Lenox remains an upscale and highly sought-after destination in the Berkshire mountains of Western Massachusetts. This town of about 5,000 residents is the summer home of the Boston Symphony Orchestra. Summertime concerts, internationally renowned spas and ski resorts draw hundreds of thousands of
Average Value
$729K
List Price
$190K - $4.1M
For Sale
Homes For Sale
16 Listings
New Marlborough
In southern Berkshire County, the rural town of New Marlborough is a historic community with just over 1,500 residents. Incorporated in 1759, New Marlborough spent its first two centuries heavily involved in the manufacturing and farming industries. These industries gradually faded during the latter half of the 20th century; today, the town is
Average Value
$719K
List Price
$418K - $5.9M
For Sale
Homes For Sale
14 Listings
Great Barrington
Great Barrington is a community known for its surrounding landscape, set in the Berkshire Mountains of western Massachusetts with the Housatonic River winding through its center. Here, historic homes and quiet neighborhoods blend with a steady flow of visitors—some arriving to hike Monument Mountain or catch a show at the Mahaiwe Performing Arts
Average Value
$716K
List Price
$253K - $4M
For Sale
Homes For Sale
38 Listings
Mount Washington
Mount Washington is a high-altitude community in the Taconic Mountains that rises nearly 2,000 feet above sea level. With less than 200 full-time residents, Mount Washington has the lowest town population in Berkshire County and the third lowest in Massachusetts. The town anchors the state’s southwestern corner, bordering New York to the west and
Average Value
$693K
List Price
$301K - $565K
For Sale
Homes For Sale
0 Listings
Sheffield
Bordering Connecticut and about 9 miles from the New York state line lies the rural community of Sheffield. Here in southwest Massachusetts, locals can expect peace, quiet and hikers traversing the Appalachian Trail. Within the Berkshires, Sheffield sits amongst the rolling green hills and winding creeks of the Housatonic River Valley. “I really
Average Value
$609K
List Price
$227K - $4.8M
For Sale
Homes For Sale
28 Listings
Williamstown
Hidden within the northwest corner of Massachusetts, Williamstown is a small town surrounded by the Berkshires expansive mountain ranges and just miles from the borders of Vermont and New York. Williamstown is nearly inseparable from Williams College, an elite, private liberal arts school that anchors the community. Williamstown was founded in the
Average Value
$591K
List Price
$255K - $1.9M
For Sale
Homes For Sale
25 Listings
Otis
Woodlands cover almost all of Otis, a small rural community scattered across nearly 40 square miles. Its 1,600 residents enjoy plenty of nature as mountains and mature trees surround several lakes in the southeast corner of the Berkshires. “I have a friend who can walk to the reservoir, but she’s tucked away in the woods. That’s very typical for
Average Value
$564K
List Price
$138K - $2.1M
For Sale
Homes For Sale
26 Listings
Sandisfield
Sandisfield, Massachusetts, is secluded in the forested mountains of southern Berkshire County. Despite its rural location, it has become a popular outdoor escape for residents of the Northeast’s large coastal cities. “A lot of buyers from the bigger cities have found this area because of its accessibility,” says Realtor Jeff Wilkinson with Stone
Average Value
$524K
List Price
$141K - $1.9M
For Sale
Homes For Sale
9 Listings
Williamsburg
Williamsburg, or “Burgy” as it’s known locally, is one of 28 bucolic Western Massachusetts Hilltowns. It was a busy industrial settlement until a dam burst and destroyed much of the town in 1874, leading to its transformation into the scenic small town it is today, more suburban than commercial. “It’s very rural and peaceful, surrounded by
Average Value
$468K
List Price
$219K - $1.2M
For Sale
Homes For Sale
8 Listings
New Ashford
New Ashford is a small Berkshire County town that lines U.S. Route 7 along a flat pass between the Greylock and Taconic Mountain ranges. And “small” might be an understatement to describe the size of New Ashford; according to the U.S. Census Bureau, the town reported a population of only 250 residents in 2020. But what it lacks in size and
Average Value
$465K
For Sale
Homes For Sale
0 Listings
Lee
The town of Lee, located in western Massachusetts, got its nickname “The Gateway to the Berkshires” because Interstate 90 runs through it, and anyone headed to the popular New England vacation spot must drive right through town to get where they’re going. While similarly charming to other towns in the Berkshires, Lee is smaller, with about 6,000
Average Value
$460K
List Price
$263K - $4.3M
For Sale
Homes For Sale
16 Listings
Montgomery
The town of Montgomery is made for country living. But while this community, set about 20 miles north of the Massachusetts-Connecticut border, is surrounded by the mountains and waterways of the Berkshires, it is not far from modern conveniences. “You’re a mere 15-, 20-minute drive from shopping centers and hospitals, yet you’re up on a little
Average Value
$449K
List Price
$280K - $630K
For Sale
Homes For Sale
1 Listing
Shelburne
Nestled among the Berkshire Mountains' foothills and Franklin County farmlands, the Town of Shelburne is a rural New England community incorporated in 1775. “People are here because they want to be, not because they have to be,” says Cathy Roberts, a longtime resident and local Realtor with Cohn & Company Real Estate Agency. “They’ll say that they
Average Value
$444K
List Price
$350K - $753K
For Sale
Homes For Sale
2 Listings
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