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!
Stockbridge MA
44 Main St, Stockbridge, Massachusetts 01262
2Bathroom(s)
3Parking(s)
16Picture(s)
1,337Sqft
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.
$44
MLS Number 240550
$229,000
MLS Number 240539
$229,900
MLS Number 240538
Stockbridge MA
23 Prospect Hill Rd, Stockbridge, Massachusetts 01262
7Bedroom(s)
7Bathroom(s)
8.00Parking(s)
29Picture(s)
8,200Sqft
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.
$4,899,000
MLS Number 240500
Stockbridge MA
30 Mahkeenac Rd, Stockbridge, Massachusetts 01262
4Bedroom(s)
2Bathroom(s)
2Parking(s)
26Picture(s)
1,374Sqft
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.
$831,000
MLS Number 240484
Stockbridge MA
8 Quiet Knoll Rd, Stockbridge, Massachusetts 01262
4Bedroom(s)
3Bathroom(s)
35Picture(s)
1,991Sqft
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.
$724,900
MLS Number 240475
West Stockbridge MA
28 Oak St, West Stockbridge, Massachusetts 01266
3Bedroom(s)
2Bathroom(s)
45Picture(s)
1,772Sqft
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.
$539,000
MLS Number 240459
Stockbridge MA
Ice Glen Rd, Stockbridge, Massachusetts 01262
5Picture(s)
1.18Acre
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.
$225,000
MLS Number 240447
Stockbridge MA
16 Yale Hill Rd, Stockbridge, Massachusetts 01262
4Bedroom(s)
2Bathroom(s)
55Picture(s)
2,112Sqft
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.
$975,000
MLS Number 240423
West Stockbridge MA
181 West Center Rd, West Stockbridge, Massachusetts 01266
14Picture(s)
1.98Acre
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.
$210,000
MLS Number 240422
West Stockbridge MA
4 Stockbridge Rd, West Stockbridge, Massachusetts 01266
5Bedroom(s)
6Bathroom(s)
42Picture(s)
3,128Sqft
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.
$827,750
MLS Number 240392
Lenox MA
238 Old Stockbridge Rd, Lenox, Massachusetts 01240
3Bedroom(s)
2Bathroom(s)
2Parking(s)
38Picture(s)
1,825Sqft
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.
$575,000
MLS Number 240386
