Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

West Stockbridge MA Homes for Sale

West Stockbridge, Massachusetts is home to a small, walkable town center with several coffee shops, delicious restaurants, shops, and more. West Stockbridge is perfect for those who want to be close to Tanglewood and Bard College at Simon’s Rock. In the warmer months, residents enjoy hiking its many trails and attending the farmer’s market.

Browse current homes for sale in West Stockbridge, MA. Don't hesitate to contact us with any of your questions.

Search SimplerRegister now to save your favorite listings and custom searches. Best of all, we'll email you when new properties that match your criteria hit the market.

55 Maple Hill, West Stockbridge, MA 01266

Price$1,900,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 209797

  • Listings
  • Beds 6
  • Baths 8
  • Sq Ft 9744
  • Acres 68.61

Exciting opportunity to customize this grand property in West Stockbridge. Acknowledging the renovations a new buyer may wish to take on, the seller will offer a $500,000 credit at closing to be applied to those changes. Take this estate and make it yours. Luxury B&B and Airbnb or not profit potential. Surrounded by 578 acres of Wildlife Management Protection.Beautiful grounds in a private setting. 68+/- magnificent acres overlooking a pristine swimming pond, rolling lawns, an orchard, and mountain views. This credit makes this a tremendous opportunity for a discerning buyer. The additional lot makes subdivision a possibility. Minutes from Tanglewood, hiking trails, the desirable village of West Stockbridge, and Great Barrington.

Listing courtesy of Lori J Rose and Martha Piper of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

26 Austerlitz, West Stockbridge, MA 01266

Price$1,490,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222426

  • Listings
  • Beds 4
  • Baths 5
  • Sq Ft 3792
  • Acres 9.01

With spring comes the opportunity to own this stunning Contemporary with incredible living/entertaining spaces both inside and out overlooking a private pond surrounded by beautiful gardens and mature landscaping. Luxurious first floor master bedroom en suite with three additional guest bedrooms en suites accommodate a few or many. Impeccably maintained and move in ready with the acreage/frontage for another potential building site....BERKSHIRE PERFECT!

Listing courtesy of Mary Jane White of COHEN & WHITE ASSOCIATES

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

24 Red Rock, West Stockbridge, MA 01266

Price$1,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220785

  • Listings
  • Beds 4
  • Baths 5
  • Sq Ft 3442
  • Acres 19

Enjoy all the recent renovations to this privately set home on 19 acres, land in both MA and NY. In-ground propane heated pool, gardens, mature landscaping, bi level decking for great outside entertaining space. Enter the house from a walk way to the main door and foyer or thru the oversized two car attached garage: a convenient mud room and laundry area is also found on the main level. The interior has been tastefully renovated with a fabulous new kitchen, large island, stainless appliances, and wood floors that gleam. The living room with fireplace and dining room overlook the private yard. The main level master suite offers an updated jet tub and glass and tiled shower. The second floor offers an additional master suite and two guest bedrooms that share a full bath. Love where you li

Listing courtesy of Patrice C. Melluzzo and Karen Climo of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

20 Glendale, West Stockbridge, MA 01266

Price$1,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222773

  • Listings
  • Beds 2
  • Baths 3
  • Sq Ft 3028
  • Acres 12.28

If a PANORAMIC VIEW with privacy is what you are looking for this sophisticated Adirondack Lodge, on a back country road, minutes from everywhere you want to be in the Berkshires is the house for you. Rustic, contemporary open plan living with two-story stone fireplace, screened porch, extensive decking, lots of glass for natural light & views, two-car garage, permitted for a guest house (total of 5 bedrooms for main residence & guest house), 12 + acres of privacy and a MOST spectacular sweeping view.......paradise in the Berkshires!

Listing courtesy of Brandon White and Mary Jane White of COHEN & WHITE ASSOCIATES

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

55 Maple Hill, West Stockbridge, MA 01266

Price$1,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 223034

  • Listings
  • Beds 6
  • Baths 8
  • Sq Ft 9744
  • Acres 62.6

Somerset is a premier property with potential for Air BnB, a Luxury B&B, or a non profit entity. Beautiful grounds in a private Berkshire setting. Sited in the middle of 62 +/- acres overlooking a pristine swimming pond, rolling lawns, perennial gardens, orchards, and mountain views, the property abuts 578 acres of protected land. The main house has dramatic features including a handsome grand entrance foyer, a large formal dining room with fireplace and a spacious living room/music room, also with a fireplace. 6 bedrooms, 4 en suite, plus a 1 bedroom apartment. Several outbuildings including a stable and a 3 story equipment barn. Close to Tanglewood, skiing, hiking, West Stockbridge & a short drive to Great Barrington. Addt'l land available which would make subdivision possible.

Listing courtesy of Lori J Rose and Martha Piper of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3 Jada Spring, West Stockbridge, MA 01266

Price$1,149,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222689

  • Listings
  • Beds 4
  • Baths 4
  • Sq Ft 4323
  • Acres 5.15

This spectacular contemporary enjoys an equally spectacular westerly view over Tom Ball Mountain with beautiful, colorful sunsets. The new great room with a soaring fieldstone fireplace and full bank of windows takes in the view as do most of the rooms in the house as well as the beautifully landscaped patio with its Goshen stone walkway and stairs. Central air conditioning, 3 car garage, and room for everyone and every need. Perfectly located just 10 minutes to Great Barrington, Stockbridge and West Stockbridge town centers.

Listing courtesy of Suzanne Crerar of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

15 Maple View, West Stockbridge, MA 01266

Price$929,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222003

  • Listings
  • Beds 4
  • Baths 5
  • Sq Ft 2941
  • Acres 5.9

Enjoy country living at its best! This extraordinary property offers privacy, gorgeous views, comfortable accommodations for family & guests, & 5.9 acres to delight you in all seasons. The updated, well-maintained, center-entrance Colonial offers three levels of living space. On the first floor: a living room with FP, family room with woodstove, designer kitchen with propane FP, TV room, study, sitting room, & screened porch. Upstairs: a master suite & two bedrooms, each with bath. On the 3rd floor: bonus space & a yoga room. The barn features a guest suite with kitchenette, great studio/office, & workroom. Outdoors is a paradise of native perennials, shrubs, fruit & other trees, plus three acres of pretty fields. Prime location, convenient to the Taconic Parkway & all Berkshire amenities!

Listing courtesy of Gladys Montgomery and Maggie Barry of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

30 Alford, West Stockbridge, MA 01266

Price$895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222898

  • Listings
  • Beds 4
  • Baths 4
  • Sq Ft 3281
  • Acres 7.67

Living is easy in this light-filled Contemporary on 7.8 country acres, in a prime location affording privacy, gorgeous mountain views & proximity to Berkshire culinary, cultural & recreational attractions. This beautiful home offers three levels of living space. On the first floor, an open floor plan encompasses a great room with cathedral ceiling & wood burning fireplace, dining room with sliders to the deck, kitchen with granite counter-tops, sun room, half bath & laundry room, & first floor master with walk-in closet & master bath. On the second floor: two bedrooms, a bath, & study/office. The walk-out lower level contains a guestroom with bath, family room, & billiard room with full bar, perfect for entertaining. There's also a bonus room above the two-car oversize garage. A must see!

Listing courtesy of Maggie Barry and Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

21 Alford, West Stockbridge, MA 01266

Price$889,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218290

  • Listings
  • Beds 4
  • Baths 4
  • Sq Ft 4000
  • Acres 4

Exceptional custom built home located on private 4 acres. The great location is close to all Berkshire attractions. Enter from a sweeping stair reminiscent of many fine Charleston homes. A spacious Great Room combines the gourmet kitchen, dining area and living room and boasts high ceilings abd skylights. Windows and a large slider open to the raised wood paneled year round solarium that offers views of the pond. The Master bedroom with a luxurious bathroom, private office behind custom glass doors, two guest bedrooms and a full bath and laundry room complete the main floor. The lower level includes family room and private guest suite with glass doors to the Goshen stone steps that lead to the heated Pebble Tec pool with extensively landscaping Included is a 2 car garage and utility room

Listing courtesy of Patrice C. Melluzzo and Karen Climo of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

66 Maple Hill, West Stockbridge, MA 01266

Price$689,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222763

  • Listings
  • Beds 3
  • Baths 4
  • Sq Ft 3061
  • Acres 10.87

This beautifully maintained home was designed with an iconic classic contemporary style. With strong lines and smooth forms, there is an abundance of open space and natural light. Most rooms take in the mountain VIEWS and the night skies are dramatic. The handsome stone fireplace is the focal point of the gathering areas and the floor plan allows for easy entertaining. There are 3 large, airy bedrooms, including a first floor master bedroom suite. There is also a nicely sized den, which could serve as a 4th bedroom. The screened porch is welcoming on warm summer evenings and the open deck runs the length of the house. The property offers privacy and there are walking paths to a nice babbling brook. Adjacent 5 acre building lot available. Great West Stockbridge location!

Listing courtesy of Lori J Rose and Martha Piper of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

128 Center, West Stockbridge, MA 01266

Price$675,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222776

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 2208
  • Acres 3.57

Renovated country home. Enter from a large mud room with storage into a renovated kitchen with large island, laundry room located off of kitchen. The open floor plan includes kitchen, dining room and 3 season room. Living room with fireplace is spacious and overlooks the rear yard and sun filled deck. A full bath and spacious office or master complete the main floor. Second floor with two bedrooms and full bath. The area above the 3 car garage is semi finished space ready to become your home studio, office, yoga studio, music room, compose your next song or write your memoirs....great space move right in!

Listing courtesy of Patrice C. Melluzzo and Samantha A. Homeyer of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

86 Maple Hill, West Stockbridge, MA 01266

Price$598,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 221648

  • Listings
  • Beds 3
  • Baths 4
  • Sq Ft 2381
  • Acres 0.58

Beautifully inspired Modern Barn Living.Featuring 3 bedrooms, 4 bathrooms, stone patio screened back porch retreat and radiant heat. Designed by Clark & Green, exceptional indoor/outdoor flow with a cool interior design. Mix of natural wood and Local Alford marble. Warm, cozy, colorful and very open to nature inside. Exceptional Value!Grass landscape design. Floor to ceiling light.Stone walls, stairs, charming spaces with a beautiful layout.

Listing courtesy of Maggie C Merelle and Steven J. Weisz of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.