West Stockbridge Real Estate

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!

20 Cobb Road West Stockbridge MA 01266

West Stockbridge, MA20 Cobb Road

Price$4,650,000

Est. Mortgage: $/month

MLS Number 242589

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 6,200
  • Acreage 66

The beauty of nature surrounds on a sleepy winding country road, this new and truly one-of-a-kind single level home-blends modern & rustic seamlessly inside and out. 66 magical acres w/views in every direction. Beautiful inside and outdoor spaces include a gunite pool, sauna, outdoor shower, and patio with firepit, 4 beds plus office, 5 baths an open concept filled with natural light. 3 stunning living rooms, pool house/guest wing plus a 3 car garage, all with metal roofing. Plenty of spaces for work or meditation to meet everyones needs. Live in paradise, amazing setting, gently sloping meadow, beautiful flower beds, quiet, peaceful, private with abundant wildlife. A nature lover's dream abutting the williams river. Build a family compound or guest home on the extra lot.

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

180 West Center Road West Stockbridge MA 01266

MLS Number 243861

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,468
  • Acreage 25.36

Follow a pastoral and tree lined driveway to a hidden gem in the heart of west stockbridge. This light filled home in the park like setting offers plenty of room to entertain a crowd, and yet it is perfect for those seeking peace and quiet. Multiple levels offer 5+ bedrooms and/or sleeping areas, 4.5 bathrooms, home office, playroom and much more. Great room overlooks the heated in-ground gunite pool and it leads to three separate blue stone patios. Breathtaking views of tom ball mountain in the distance. Situated on over 25 acres, this property also offers you your own tennis court, a small pond and plenty of mature landscaping.

Listed by Stephen R. Schoenfeld and Michael Linden of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

176 West Center Road West Stockbridge MA 01266

MLS Number 244212

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 3,354
  • Acreage 21.69

The lovely approach to this gorgeous estate property ensures serenity, privacy, and the beauty of living in the country and includes a 3 bed 2 1/2 bath main house and a gorgeous architect designed guest house. Offering 2 ensuite bedrooms with balconies, dramatic exposed beams, vaulted ceilings, and gas fireplace the guest house is an extraordinary place to host family and friends both winter and summer. With views of tom ball mountain, this 21 acre property is a combination of gardens, fields, forest, and offers several outdoor living spaces, including a stone patio off the kitchen. Super location, too; close to tanglewood, six depot,for coffee and performing arts at the foundry. Also convenient to great barrington for shops, restaurants and so much more.

Listed by Lori J Rose of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

45 Swamp Road West Stockbridge MA 01266

West Stockbridge, MA45 Swamp Road

Price$2,100,000

Est. Mortgage: $/month

MLS Number 243556

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,956
  • Acreage 30.92

It was 1930 when will rogers told americans to buy land 'cause they aren't making any more of it.Well,he likely would have been interested in this except it wasn't available for sale until now. For well more than 150 years the same family has held this property....Until now...More than 30 acres of amazing land with pasture, woods, water frontage and views.This property stretches with approx 2000' frontage on swamp road (#35-#57) all the way to shaker mill pond and did we mention that cone brook runs right through it!! With a gentle slope to the south west, if you walk these fields you will fall in love with the ''berkshire life''. With an older four bedroom two bath family home along with barns, run in shed, improved interior road. 3.5 mi to tanglewood .5 mi to ws village

Listed by Juanita O'Rourke of JUANITA O'ROURKE REALTY ((518) 325-1059)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

76 Lenox Road West Stockbridge MA 01266

West Stockbridge, MA76 Lenox Road

Price$1,950,000

Est. Mortgage: $/month

MLS Number 243832

  • Residential
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 5,115
  • Acreage 3.76

New world meets old in this impeccably designed and elegant french country inspired estate nestled perfectly on the hillside, affording gorgeous westerly mountain and sunset views. Situated on 3.76 acres, the home offers ample privacy, yet it is just a stone's throw from tanglewood and downtown lenox and west stockbridge. Designed for hosting extended family and friends, it offers generously proportioned rooms and seamlessly blends indoor and outdoor entertainment for year-round enjoyment. With six bedrooms and seven bathrooms, including one primary suite and three additional en-suite bedrooms, this residence is designed for comfort and style. Entering through the wisteria draped antique door into the foyer, the discerning buyer will appreciate the impeccable craftsmanship throughout.

Listed by Maggie Gavin and Danielle Giulian of WILLIAM PITT SOTHEBY'S - LENOX ((413) 637-4402)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

29 Main Street West Stockbridge MA 01266

West Stockbridge, MA29 Main Street

Price$1,675,000

Est. Mortgage: $/month

MLS Number 244497

  • MultiFamily
  • Acreage 0.3
  • Year Built 1900
  • Parking Spaces 12

Step into a piece of history with the once iconic card lake inn tavern, now transformed into a stunning residential haven in the heart of downtown west stockbridge. This property offers not only a prime location but also an exceptional living experience, combining modern amenities with charming historic character. The building houses six completely renovated high-end apartments, each thoughtfully designed to meet the needs of modern living. These units feature elegant wood floors and come equipped with all necessary appliances, including dishwashers and in-unit laundry facilities. Central air conditioning ensures comfort year-round, while tiled double-sink bathrooms add a touch of luxury. Ample storage space is available in each unit, allowing residents to keep their living areas tidy.

Listed by Suzann Laverack Ward of HOUSATONIC REAL ESTATE ((413) 274-5065)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

2 Oak Street West Stockbridge MA 01266

MLS Number 242358

  • Commercial
  • Acreage 1.7

Successful, turnkey inn located in the picturesque village of west stockbridge, walking distance to shops, restaurants, and galleries. This unique property boasts nine spacious, well-appointed guest rooms, most with private outdoor entrances. Each room has a kitchenette and ensuite bathroom. Most rooms have gas fireplaces and private balconies, overlooking the manicured grounds. The greylock suite is perfectly set up for long term stays, with a full kitchen, living room, and separate bedroom. For the innkeeper, there is a spacious owner's quarters, privately located on the top level of the inn, with its own separate entrance, full kitchen, laundry, and lots of charm.Close to all that the berkshires have to offer, this is a great live/work opportunity in a highly desirable area.

Listed by Lance Vermeulen and Lauren Rosen of LANCE VERMEULEN RE,INC ((413) 528-6011)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

5 Water Street West Stockbridge MA 01266

West Stockbridge, MA5 Water Street

Price$1,350,000

Est. Mortgage: $/month

Pending

MLS Number 243388

  • Residential
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 3,136
  • Acreage 1.22

Welcome to your dreamy mini-estate, complete with main house, barn, and heated pool located in the heart of the berkshires! This stunning 6 bedroom, 5 bath residence is nestled into a tranquil 1+ acre lot, on a quiet cul-de-sac! Nicely updated, this home offers wood floors, central ac, fully fenced heated pool, stone patio, mature gardens, dynamic screen porch, stainless appliances, and high-efficiency boiler. This lovely colonial offers plenty of space for friends and family to gather with several light-filled nooks to explore. The gorgeous barn offers storage below and a finished apartment above! With 1 bedroom, full bath, full kitchen, den, and its own deck overlooking the pool and gardens + outdoor shower and 1/2 bath off the pool-this is one that should not be missed!

Listed by Sarah Dixon and Claudia Laslie of LANCE VERMEULEN RE,INC ((413) 528-6011)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

258 Great Barrington Road West Stockbridge MA 01266

MLS Number 244685

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 3,963
  • Acreage 5.01

Sanctuary ! Modern contemporary home, bathed in natural light, nestled on 5 acres. This 3 bedroom, all with ensuite baths, and a 1st floor half bath residence is perfect for outdoor enthusiasts-whether you're a hiker, birder, or gardener. Conveniently located less than 10 minutes from great barrington, west stockbridge, stockbridge and lenox, this property offers both seclusion and accessibility. The mature gardens, meticulously maintained, are featured in the book ''great gardens of the berkshires''. Extensive hiking trails begin right outside your back door, allowing you to lose yourself in nature. A koi pond with a cascading waterfall adds a serene touch to the land scape.

Listed by William Morrow of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

30 Great Barrington Road West Stockbridge MA 01266

MLS Number 242088

  • Residential
  • Bathroom 2
  • Bedrooms 1
  • Square Feet 3,810
  • Acreage 1.39

New master builder's home with a wide opulent wrap-around porch welcomes you into the immense open floor plan bathed in sun-filled light from the wall of glass overlooking a terraced lawn. Entertainment begins here with the fully equipped high-end chef's kitchen with a butler's pantry including its own dishwasher and sink. A magnificent curved staircase leads to the king's pine flooring of the primary suite with two balconies. Located in the heart of the berkshires just minutes from the mass pike, ny state thruway and taconic parkway. This custom house was designed with luxury and comfort in mind, including built in sound system, central vac, full house generator, dual head shower, hydrotherapy massage tub, and 4 fireplaces.

Listed by Austin Choquette of GALLAGHER REAL ESTATE ((413) 536-7232)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

5 Stockbridge Road West Stockbridge MA 01266

MLS Number 244396

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,356
  • Acreage 0.28

Enjoy the very best of town and country living in this jewel of a home located in the heart of the village- and only 7 minutes to tanglewood! This handsome, traditional colonial has a spacious, airy layout with 8 well-proportioned rooms and two full baths. The first floor features an eat-in kitchen, dining room, living room, office, full bath, and a mudroom with laundry. Upstairs are 4 generous bedrooms and the second full bath. One of the highlights of this property is the stunning back yard with babbling brook and lovely winter views of lenox mountain. There are outdoor living spaces on 3 levels to relax and enjoy the lush, verdant countryside: a bluestone patio and garden off the basement, a covered porch off the living room and a deck on the second floor with private access from the

Listed by Ellen Lomaglio of KEY REALTY ((413) 329-5209)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

278 Great Barrington Road West Stockbridge MA 01266

MLS Number 244691

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,672
  • Acreage 4.85

Charming dutch colonial on the prettiest piece of land. On the first floor is a bedroom, dining room with wood fireplace, eat-in kitchen with large pantry, half bath. Upstairs are two large bedrooms with full bath. Partially finished basement with two usable rooms and laundry in the utility room. Breezeway/mudroom to attached 2-car garage. Outside is a pool, barn and children's play shed. Solar panels provide electricity. Title v has passed.

Listed by Kristin P. Piasecki of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of October 10, 2024 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.