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West Stockbridge Homes for Sale

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  • /58

    $1,595,000

    • 6 Beds
    • 3.5 Baths
    • 3,905 Sq Ft

    21 Stockbridge Rd, West Stockbridge, MA 01266

    Tucked away on a private 2.35-acre knoll, this beautifully updated residence offers a rare blend of antique charm and modern ease in one of the Berkshires' most sought-after villages. With six generously sized bedrooms, a chef's kitchen designed for entertaining, and multiple inviting living spaces with fireplaces, the home is ideal for gatherings or quiet retreats alike. A stunning contemporary

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 675-5317

    21 Stockbridge Rd, West Stockbridge, MA 01266
  • /61

    $1,280,000

    • 3 Beds
    • 3 Baths
    • 2,002 Sq Ft

    276 Great Barrington Rd, West Stockbridge, MA 01236

    Price Improvement! Motivated Seller!This 52-acre homestead blends early American heritage with modern sustainability and self-sufficiency. Originally built in 1802, this stunning property offers privacy, fertile farmland, and breathtaking mountain views-including Monument Mountain/Flag Rock. Mature fruit orchard with over 15 trees, 30-tree sugar bush with a sugarhouse for maple syrup

    Agent Photo

    Keytoria Jenkins

    THE KINDERHOOK GROUP - PITTSFIELD

    (413) 675-5502

    276 Great Barrington Rd, West Stockbridge, MA 01236
  • /7

    $109,900

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    27 Gwenn Ln, West Stockbridge, MA 01266

    Agent Photo

    John Ciepiela

    BISHOP WEST REAL ESTATE

    (413) 323-3952

    27 Gwenn Ln, West Stockbridge, MA 01266
  • /5

    $129,900

    • 3 Beds
    • 2 Baths
    • 1,000 Sq Ft

    11 Jennifer Ln, West Stockbridge, MA 01266

    Spacious 1998 Titan double-wide with 3 bedrooms, 2 baths, cathedral ceilings, and an open living area. Features a cozy fireplace and efficient pellet stove. The primary suite includes a private bath and ample closet space. Bright kitchen and dining area with plenty of storage. Great layout for comfortable living in a peaceful setting.

    Agent Photo

    John Ciepiela

    BISHOP WEST REAL ESTATE

    (413) 414-5197

    11 Jennifer Ln, West Stockbridge, MA 01266
  • /61

    $1,790,000

    • 6 Beds
    • 6.5 Baths
    • 5,115 Sq Ft

    76 Lenox Rd, West Stockbridge, MA 01266

    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

    Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

    76 Lenox Rd, West Stockbridge, MA 01266
  • /49

    $949,000

    • 1 Bed
    • 1.5 Baths
    • 3,810 Sq Ft

    30 Great Barrington Rd, West Stockbridge, MA 01266

    The renovation of this 1930's Cape Cod by a master craftsman and his designer wife into the stunning modern day Contemporary it is today, while preserving some of the original highlights,is nothing short of a design miracle. The immense Great Room with the 60 foot wall of glass overlooking the terraced stone wall that leads to a stream and pine forest is the focal point of this special home. The

    Cortney Dupont COHEN & WHITE ASSOCIATES

    30 Great Barrington Rd, West Stockbridge, MA 01266
  • /71

    $2,200,000

    • 5 Beds
    • 4.5 Baths
    • 3,354 Sq Ft

    176 W Center Rd, West Stockbridge, MA 01266

    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

    Lori Rose STONE HOUSE PROPERTIES, LLC

    176 W Center Rd, West Stockbridge, MA 01266
  • /49

    $1,875,000

    • 5 Beds
    • 5.5 Baths
    • 3,225 Sq Ft

    5 Easland Rd, West Stockbridge, MA 01266

    A Home Designed for Living and RetreatNestled at the base of Tom Ball Mountain on over 10 private acres, 5 Easland Road is a custom-designed contemporary sanctuary where nature, luxury, and thoughtful craftsmanship come together in perfect harmony.This 5-bedroom, 5.5-bath home features soaring vaulted ceilings, dramatic walls of glass, and gleaming hardwood floors throughout. Each of the three

    Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    5 Easland Rd, West Stockbridge, MA 01266
  • /56

    $1,395,000

    • 4 Beds
    • 2 Baths
    • 2,058 Sq Ft

    45 Swamp, West Stockbridge, MA 01266

    1950s retro home, rich with family history, situated on 30+ acres of land & offering expansive westerly views & gentle sloping fields. Pathways lead to Shaker Mill Pond & Cone Brook which run the entire length of the property. Interior features include 2 BRs, office & full bath on the main level, 2 BRs & full bath on the second floor, a quaint kitchen, & living room. Additionally, a fully heated

    Paige Paluch LANCE VERMEULEN RE, INC

    45 Swamp, West Stockbridge, MA 01266
  • /37

    $289,000

    • 2 Beds
    • 1 Bath
    • 1,155 Sq Ft

    19 Great Barrington Rd, West Stockbridge, MA 01266

    Two to three bedroom country colonial just minutes from West Stockbridge Village. Large 1.26 acre level lot is perfect for entertaining and relaxation day or night! Direct access to Card Pond; close proximity to Tanglewood, shopping, dining, galleries, theatre, hiking/biking, boating and all the cultural and recreational amenities of South Berkshire County and beyond. Bring your vision and

    Amy Wood STEEPLEVIEW REALTY - N. ADAMS

    19 Great Barrington Rd, West Stockbridge, MA 01266
  • /58

    $635,000

    • 3 Beds
    • 3 Baths
    • 2,476 Sq Ft

    4 Main St, West Stockbridge, MA 01266

    Don't miss this one-of-a-kind opportunity to own a commercially zoned, mixed-use property offering exceptional live/work potential in a prime in-town location along the Williams River. This uniquely designed 3-bedroom, 3-bath home includes a versatile accessory apartment, making it ideal for those seeking a combination of residential comfort and business flexibility. Enjoy water views from two

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    4 Main St, West Stockbridge, MA 01266
  • /19

    $775,000

    • 8 Beds
    • 4 Baths
    • 3,192 Sq Ft

    35 Main St, West Stockbridge, MA 01266

    Introducing a beautiful in-town 4-family investment opportunity on the picturesque Main St, offering separate utilities for each unit. With a new roof, fresh paint, and renovations completed in units, 1,2 &3 all in 2023.

    Matt Carlino MACCARO REAL ESTATE

    35 Main St, West Stockbridge, MA 01266
  • /43

    $640,000

    • 2 Beds
    • 1 Bath
    • 1,688 Sq Ft

    3 & 5 Swamp Rd, West Stockbridge, MA 01266

    Historic Greek Revival & Grange Hall, a unique residence for the next owner. In-town privacy overlooking stunning Shaker Mill Pond. Enjoy private backyard, patio with water views, glorious sunsets, canoeing & even ice skating in the winter. Within walking distance to restaurants & markets. The house, c1840, has two bedrooms, formal dining room, eat-in country kitchen, living room with fireplace &

    Scott Sawyer STONE HOUSE PROPERTIES, LLC

    3 & 5 Swamp Rd, West Stockbridge, MA 01266
  • /23

    $792,500

    • 3 Beds
    • 2 Baths
    • 2,620 Sq Ft

    9 Iron Mine Rd, West Stockbridge, MA 01266

    Located in the town of West Stockbridge just 1 1/2 miles from the village center home to an eclectic array of shops, restaurants, a very cool bookstore, No. Six Depot Roastery & Cafe and the annual West Stockbridge Zucchini Festival is this contemporary style home. With smart planting the home on 2+ acres feels totally private. Enjoy the great outdoors from the spacious deck or lawn. Inside

    Deborah Mielke CORASHIRE REALTY

    9 Iron Mine Rd, West Stockbridge, MA 01266
  • /3

    $325,000

    • Land
    • 15 Acres
    • $22,049 per Acre

    0 E Alford Rd, West Stockbridge, MA 01266

    Beautiful and pristine 14.7 acre lot, family owned since 1963. 3-4 acres are an open field; a former Christmas tree farm. Rear portion of property is largely wooded with a stream. This area of East Alford Road has many million dollar plus homes. Perfect lot to build your tranquil dream home. Lot was perc tested in 2007. 10 Minutes to the center of West Stockbridge, 15 minutes to Great

    Matt DeLucia William Pitt Sotheby's International Realty

    0 E Alford Rd, West Stockbridge, MA 01266
  • /3

    $975,000

    • Land
    • 132 Acres
    • $7,404 per Acre

    0 Lenox Rd Unit 246122, West Stockbridge, MA 01266

    This is a generous hillside parcel with a perc and potential views to the west. It is just over the hill from Stockbridge Bowl and Tanglewood, in an area of fine homes.

    Jim Stark L. J. STARK AND CO.

    0 Lenox Rd Unit 246122, West Stockbridge, MA 01266
  • /53

    $615,000

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    6 Bryan Rd, West Stockbridge, MA 01266

    Nature Lover's Paradise on 17+ Acres - Private Forests, Manicured Lawns, and Protected Wetlands!Centrally located to all Berkshire attractions. Easy access to NY and Boston higway exits, yet quiet and peaceful.Entirely private, 6 Bryan Road features spectacular wetland vistas, green meadows, and serene untouched woods.Stunning west-facing views from your deck overlook 8+ acres of protected

    Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

    6 Bryan Rd, West Stockbridge, MA 01266
  • /12

    $212,900

    • Land
    • 4.00 Acres
    • $53,225 per Acre

    0 Cross Rd, West Stockbridge, MA 01266

    Spectacular 4+/- acre partial in a peaceful setting. This beautiful parcel is perfectly cleared and ready for your new home! Nestled in a tranquil area this property boasts the ideal combination of privacy and natural beauty. The land has a recent perk test and a survey. Come develop your dream home on this beautiful parcel that is next to a conservatory which means there will be no future

    Kimber Bradley Robin Delaney Real Estate

    0 Cross Rd, West Stockbridge, MA 01266
  • /52

    $1,675,000

    • 12 Beds
    • 7 Baths
    • 8,881 Sq Ft

    29 Main St, West Stockbridge, MA 01266

    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

    Suzann Ward HOUSATONIC REAL ESTATE

    29 Main St, West Stockbridge, MA 01266
  • /14

    $219,000

    • Land
    • 3.62 Acres
    • $60,497 per Acre

    7 Silver Mine Ln, West Stockbridge, MA 01266

    This parcel of land is located off the beaten path yet very near civilization. Set in an area of fine homes offering casual elegance. This parcel has 3.62 acres, its southern boundary is Cone Brook and has lovely views to the south. The building area is level, the utilities (electric and internet) are underground, this property is on Town water. There is a 2004 percolation report. Homeowner

    Laurie Nikituk RED HORSE REAL ESTATE, LLC

    7 Silver Mine Ln, West Stockbridge, MA 01266
  • /28

    $425,000

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft

    3 van Schaack Rd, West Stockbridge, MA 01266

    Charming property in a private setting! Newly refinished wood flooring on main level, higher ceilings and lovely natural light. Great room, dining and kitchen on the first level with a beautiful large front porch; two bedrooms, full bath and laundry on the second level. Third level offers character, separate room for storage and many possibilities. Gracious deck, out building, large yard and

    Cortney Dupont COHEN & WHITE ASSOCIATES

    3 van Schaack Rd, West Stockbridge, MA 01266
  • /17

    $229,000

    • Land
    • 4.63 Acres
    • $49,460 per Acre

    0 Pixley Hill Rd, West Stockbridge, MA 01266

    Great opportunity to build on Pixley Hill Road in the desirable town of West Stockbridge. Recently surveyed and perc'd, this lot is ready to go. This 4.6 acre parcel has stone walls, a gentle slope - perfect for a home design incorporating a walk out lower level - and direct access to the old rail bed walking trail that allows for gorgeous views of the Williams River. Private and Peaceful

    Lori Rose STONE HOUSE PROPERTIES, LLC

    0 Pixley Hill Rd, West Stockbridge, MA 01266
  • /14

    $250,000

    • Land
    • 1.98 Acres
    • $126,262 per Acre

    181 W Center Rd, West Stockbridge, MA 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.

    Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    181 W Center Rd, West Stockbridge, MA 01266

Frequently Asked Questions Why Live in West Stockbridge

Is West Stockbridge a good place to live?
West Stockbridge is a good place to live. West Stockbridge is considered very car-dependent and somewhat bikeable. West Stockbridge is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. West Stockbridge has 1 park for recreational activities. It has a median age of 54. The average household income is $110,981 which is above the national average. College graduates make up 66.7% of residents. A majority of residents in West Stockbridge are home owners, with 14.4% of residents renting and 85.6% of residents owning their home. A local real estate agent serving West Stockbridge can help you decide if this neighborhood is the right one for you. Learn more on our West Stockbridge neighborhood guide.
Is West Stockbridge, MA a safe neighborhood?
West Stockbridge, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
What are the best public schools in West Stockbridge?
The best public schools that serve West Stockbridge are:
What are the best private schools in West Stockbridge?
The best private schools that serve West Stockbridge are:
What are the most popular zip codes in West Stockbridge, West Stockbridge, MA?
The most popular zip codes in West Stockbridge, West Stockbridge, MA include 01266, 01236, 01262, 12017 and 01254.
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