Stockbridge, MA Real Estate & Homes For Sale

Stockbridge is the quintessence of small-town New England charm, untainted by large-scale development. It is also the blueprint for small-town America as represented on the covers of the Saturday Evening Post by painter Norman Rockwell (the official state artist of Massachusetts). From 1953 until his death in 1978, Rockwell lived in Stockbridge and painted the simple charm of its buildings and residents. James Taylor sang about the town in his hit “Sweet Baby James,” as did balladeer Arlo Guthrie in his famous Thanksgiving anthem “Alice’s Restaurant,” in which he tells what ensued when he tossed some garbage out the back of his Volkswagen bus down a Stockbridge hillside. Search new real estate in the Berkshires town of Stockbridge, MA. Discover hundreds of current listings, including single-family homes, luxury estates, and residential land. Love what you see? Register with us to save your favorites, and receive notifications when similar properties are listed. Contact us to see any of the homes below!

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Stockbridge MA

44 Main St, Stockbridge, Massachusetts 01262

Beautiful Storefront (Unit 1A) with 1,337 SF in historic Main Street building. Recently renovated and in pristine condition. Available immediately. Next door to Stockbridge Library and just up the street from the Red Lion Inn, this is an ideal location for a retail or public facing office space. It has been a real estate office and, more recently a high end chocolate shop.
MLS Number 240550

West Stockbridge MA

0 Lot 5 Pond View Dr, West Stockbridge, Massachusetts 01266

MLS Number 240539

West Stockbridge MA

0 Lot 6 Pond View Dr, West Stockbridge, Massachusetts 01266

MLS Number 240538

Stockbridge MA

23 Prospect Hill Rd, Stockbridge, Massachusetts 01262

Legacy property of culturally influential family retained under their stewardship since 1968 is a rare offering. This truly generational, Mid-Century Modern masterpiece prominently sited on 57+ acres on prestigious Prospect Hill Rd, is close to the Stockbridge Bowl and quaint downtown Stockbridge.
MLS Number 240500

Stockbridge MA

30 Mahkeenac Rd, Stockbridge, Massachusetts 01262

Situated just steps from the magical Stockbridge Bowl, this Unique Contemporary home is architect-designed with a focus on light and passive energy.Enjoy your morning coffee from the outdoor enclosed porch, lakeside or venture into the water and swim to Kwuniikwat Island across from the beach.
MLS Number 240484

Stockbridge MA

8 Quiet Knoll Rd, Stockbridge, Massachusetts 01262

Charming Stockbridge contemporary ranch with the convenience of one-level living! There is so much to appreciate with this immaculately maintained property. For starters: a convenient circular flow for entertaining with spacious dining room and open kitchen/family room with fireplace. A large/private rear deck adds to the ease of summer entertaining.
MLS Number 240475

West Stockbridge MA

28 Oak St, West Stockbridge, Massachusetts 01266

Super spacious 3 bedroom 2 bathroom ranch with tons of bonus space on lower level. Hardwood floors, newer roof, bathrooms, over sized trex decking, attached 2 car garage, sunroom, skylights, wood fireplace.Lower walk out has 6 extra rooms, a custom built bar and a cold storage room, 2 guests rooms, 2 offices and an exercise room.
MLS Number 240459

Stockbridge MA

Ice Glen Rd, Stockbridge, Massachusetts 01262

Triangular shaped parcel overlooking the Marsh and mountains in the distance. Peaceful and serene with gently sloping lawn, and a wooded area above. Lovely sunny spot for gardening, bird watching, bee keeping, or what have you.
MLS Number 240447

Stockbridge MA

16 Yale Hill Rd, Stockbridge, Massachusetts 01262

The combination of a gracious and meticulous Federal style home, antique barn, frontage on the Kampoosa brook and privacy is rare in this coveted neighborhood in Stockbridge. Light and airy, the generous foyer is flanked by a living room with wood burning fireplace, and a library.
MLS Number 240423

West Stockbridge MA

181 West Center Rd, West Stockbridge, Massachusetts 01266

Lots of preparation work went into this building lot with a handsome meadow and dramatic ledge formations with large pockets of cool ferns. Some western views and a north east field stone wall. Almost 2 acres. Old well in place. Excellent percolation test results with 1 inch per min. Curb cut. Ready to build.
MLS Number 240422

West Stockbridge MA

4 Stockbridge Rd, West Stockbridge, Massachusetts 01266

Be on the lawn at Tanglewood in 9 minutes from this charming period home in sought after downtown West Stockbridge. Nearly 200 years old, this stately , well maintained Federal/Greek revival home is the perfect combination of original details and modern improvements.Set back from the road and nestled among beautiful landscaped gardens with 3,128 sqft there's plenty of space to live and play.
MLS Number 240392

Lenox MA

238 Old Stockbridge Rd, Lenox, Massachusetts 01240

First time on the market! This immaculate deck home was built in 1961 with three bedrooms, each with hard wood floors, and one and a half bathrooms. The property sits on .36 acres in Lenox with an additional 6.5 acres located in Stockbridge directly behind the house and leading right to Lily Pond. What an ideal location! Close to Lenox, Stockbridge and everything cultural.
MLS Number 240386
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