Communities – West Stockbridge

Welcome to the Town of West Stockbridge. They are a small community with a population of approximately 1650 full time Residents. The town is located in the Southern Berkshires of Western Massachusetts and has a small, attractive downtown retail center, which serves residents, tourists and adjacent communities.

West Stockbridge is a beautiful, hilly town with many ponds, streams, wetlands and open fields that make it a very desirable place to live. The Williams River is a picturesque waterway that flows through the town providing residents and tourists with excellent opportunites for angling and canoeing.

Search new real estate in the Berkshire town of West Stockbridge, MA. Discover hundreds of current listings, including beautiful antique properties and single-family homes. Like what you see? Register with us to save your favorites, and receive notifications with similar properties are listed. Contact us today to see any of the homes below!

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8 Meadow Rd, Stockbridge, Massachusetts 01262

Residential For Sale

4Bedroom(s)
4Bathroom(s)
44Picture(s)
4,282Sqft
Spacious contemporary located on 10+ acres with deeded Stockbridge Bowl lake access. This tucked away gem is located down a long driveway for absolute privacy in a park like setting. First floor has radiant heat, a living room with fireplace, library with built ins, bedroom, full bath and a spacious great room with cathedral ceilings & loft. This light filled home boasts 4200 square feet.
$1,500,000

76 Gt Barrington Rd, West Stockbridge, Massachusetts 01266

Residential For Sale

3Bedroom(s)
2Bathroom(s)
34Picture(s)
1,984Sqft
Private and peaceful setting surrounded by State land and the Williams River. Mountain views hiking trails your own private forest. Includes a potential building lot to add another home to make your own compound. 2 car garage has a workshop as well as an up stairs potential studio space/home office. 1 mile from south of Mass Pike and town center. Home offers 3 bedrooms 2 baths.
$569,000

2 Wallace Rd, Stockbridge, Massachusetts 01262

Condominium For Sale

2Bedroom(s)
2Bathroom(s)
32Picture(s)
1,647Sqft
Spacious and charming condo with picturesque views, situated on the beautiful grounds at Heron Pond. Centrally located in the Berkshires, around the corner from Main St.
$449,000

2 Wallace Rd, Stockbridge, Massachusetts 01262

Residential For Sale

2Bedroom(s)
2Bathroom(s)
32Picture(s)
1,647Sqft
Spacious and charming condo with picturesque views, situated on the beautiful grounds at Heron Pond. Centrally located in the Berkshires, around the corner from Main St.
$449,000

27 Glendale Rd, Stockbridge, Massachusetts 01262

Residential For Sale

3Bedroom(s)
1Bathroom(s)
2Parking(s)
31Picture(s)
1,287Sqft
This vintage Sears and Roebuck craftsman bungalow sits on one sunny acre, perched above the Housatonic River in the village of Glendale. Relax on the front porch, or enjoy the south facing deck with views of the gardens and generous yard. A well-groomed private path beckons down a gentle slope to the riverbank.
$389,000

15 Lakeview Dr, Stockbridge, Massachusetts 01262

Residential For Sale

2Bedroom(s)
1Bathroom(s)
31Picture(s)
832Sqft
Rarely available Waterfront! Beautifully situated in the sought after Beachwood community on the Stockbridge Bowl Outlet with direct, tranquil water views and access from the private dock. The existing cottage is comprised of a living room/dining room with fireplace, kitchen, screened in porch, small deck, 2 comfortable bedrooms and one bathroom.
$579,000

8 Prospect Hill Rd, Stockbridge, Massachusetts 01262

Residential For Sale

5Bedroom(s)
6Bathroom(s)
60Picture(s)
5,765Sqft
In 1737 Ephraim Williams chose a special setting on Prospect Hill to build his home. Through many iterations, Windermere has become an exceptional home. Beautiful porches wrap around two sides. The interior is bathed in natural light. The first floor is graced by an entry parlor, living room and fabulous music room. Great updated kitchen has an exceptional butler's pantry and breakfast room.
$1,865,000

35 Nielsen Ln, Stockbridge, Massachusetts 01262

Residential For Sale

3Bedroom(s)
2Bathroom(s)
32Picture(s)
2,394Sqft
Walking distance to the center of Lenox ! Totally private as it sits on over 3 acres of land in Stockbridge but only 1 mile to the center of Historic Lenox. This 3 bedroom 2 full bath home has so much potential with some updates and TLC. Enjoy the screened porch and sounds of nature. Or sit on the deck with views into your own private paradise.
$550,000

3 West Dale Rd, Stockbridge, Massachusetts 01262

Residential For Sale

5Bedroom(s)
5Bathroom(s)
5Parking(s)
38Picture(s)
4,174Sqft
Your Berkshires Paradise Awaits! Magnificent 5 BR Stockbridge colonial on 18 spectacular acres w/ swimming/skating pond. Huge 1st floor master suite w/ fireplace. Great room w/ cathedral, coffered ceilings, fireplace & walls of windows.
$1,695,000

18 Hill Rd, Stockbridge, Massachusetts 01262

Residential For Sale

2Bedroom(s)
1Bathroom(s)
19Picture(s)
1,015Sqft
The most adorable log home in the woods, and only 3 miles to Tanglewood! Privately situated on two acres. Completely renovated and upgraded in the last couple years. Extremely well maintained inside and out. New kitchen with quartz counters, lots of cabinet space, stainless appliances and Pecan floors.
$409,900

5 Cone Hill Rd, West Stockbridge, Massachusetts 01266

Residential For Sale

3Bedroom(s)
2Bathroom(s)
22Picture(s)
1,821Sqft
Solid and well built post and beam home. Lovingly cared for inside and out. Open Kitchen and dining with a really great open living room and sun room. First floor bedroom and bath with two bedrooms and a bath on the second floor. Excellent location just 1 mile to the village. Yard has producing apple trees and lots of quiet spots to sit in the shade and enjoy the environment.
$649,000

31 Glendale Rd, Stockbridge, Massachusetts 01262

Residential For Sale

3Bedroom(s)
1Bathroom(s)
1Picture(s)
1,560Sqft
Complete renovation project! A very special location overlooking the Housatonic river waterfall. Close to the very best attractions the Berkshires has to offer, including The Norman Rockwell Museum, Tanglewood, Stockbridge Bowl and more. Imagine the possibilities. Work on this charmer through the winter and be ready for the spring market! Great for second home owner, artist studio or Airbnb.
$95,000
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