Berkshire County · Massachusetts
Stockbridge, MA Homes for Sale & Real Estate
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Stockbridge is a classic Berkshire village set along the Housatonic River, with a Main Street of white clapboard buildings that Norman Rockwell made famous. Settled in the 1730s as a mission town, it later became a summer retreat for writers, artists and Gilded Age estate builders. Today museums, historic houses and gardens are woven through the village and the smaller centers of Glendale and Interlaken.
From village colonials within walking distance of Main Street to hillside homes overlooking the Stockbridge Bowl, the housing here carries a lot of history. You will also find farmhouses on country roads and a range of second homes and condominiums. When you are weighing an antique house or a second home here, Dolan O’Rourke can walk you through historic details, inspections and seasonal-use questions.
Living in Stockbridge
Norman Rockwell Museum
The Norman Rockwell Museum holds a major collection of the illustrator’s original work, along with his relocated studio, on a hillside campus overlooking the Housatonic River.
Main Street
Stockbridge’s Main Street, with its historic inn, shops and the Mission House, is the scene captured in Rockwell’s well-known holiday painting.
Naumkeag and Chesterwood
Naumkeag’s terraced gardens and Chesterwood, the summer home and studio of sculptor Daniel Chester French, are two of the area’s most visited historic estates.
Berkshire Botanical Garden
The Berkshire Botanical Garden, at the junction of Routes 102 and 183, offers display gardens, classes and a popular annual harvest festival.
Berkshire County · Massachusetts
Homes for sale in Stockbridge, MA
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Getting around and the outdoors
Getting around
Route 7 runs through the village between Great Barrington and Lenox, and Route 102 links Stockbridge to Lee and the Massachusetts Turnpike. Route 183 heads south through Glendale toward Housatonic. Pittsfield’s Amtrak and bus connections are a short drive north, and Albany and Hartford are within reach for longer trips.
Parks and recreation
The Stockbridge Bowl offers boating and swimming, and the Ice Glen and Laura’s Tower trails climb from the village to a ravine and a lookout over the valley. Monument Mountain’s summit trail is just south, and summer brings performances at the Berkshire Theatre Group’s Stockbridge stages and Tanglewood next door.
Villages and neighborhoods in Stockbridge
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Buying or selling in Stockbridge?
Whether you are buying your first home, moving up, downsizing or investing, our agents will guide you from the first conversation to the closing table.
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- Home value: Find out what your Stockbridge home is worth.
Client reviews
What our clients say
I had the absolute pleasure of working with John Dolan and Dolan O’Rourke Real Estate Services while selling my mother’s home. We were going through an extremely difficult transition. We were both unfamiliar with the process of selling a home. From day one, John made himself readily available and kindly explained every part of the process to my mother, always making sure she understood each detail. His knowledge and expertise goes far and above what we expected. His constant communication never left us guessing – we felt very involved in every part of the process. I was caring for my mother on my own and he did everything in his power to ease the burden of selling her property. John knew I had great anxiety over our difficult situation and would always tell me not to worry. He always found a resolution to every bump in the road- and now I am finally worry free! John made us feel cared for and safe. We cannot thank him enough for his hard work. He helped us find a deal that we never could’ve imagined and changed our life for the better!
John was amazing with helping us in our home buying journey! His knowledge and patience made things very easy for us as first time home buyers. I highly recommend John to anyone who wants professionalism and someone who’s gonna get the job done! Thanks John!
We worked with John of Dolan O’Rourke Real Estate Services to purchase our first home in the Greater Boston area. As first time home buyers, John invested a lot of time early on to educate us about what to expect and strategies to consider. Throughout the process John had great communication, listening and advice as we navigated a challenging market. John was approachable, knowledgeable and always fun to be around as we looked at numerous houses, and helped us shape our conversations to really dial in to what we were looking for. We would love to recommend John for future real estate services and are so appreciative of his hard work.
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