20

West Stockbridge, MA Homes for Sale

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  • /58

    $1,300,000

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

    276 Great Barrington Rd, West Stockbridge, MA 01236

    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: apples, peaches, pears, cherries, plums.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
  • /43

    $1,499,000 Open Sat 10AM - 12PM

    • 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
  • /58

    $1,795,000

    • 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

    Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

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

    $1,950,000

    • 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
  • /57

    $2,950,000

    • 5 Beds
    • 4.5 Baths
    • 4,468 Sq Ft

    180 W Center Rd, West Stockbridge, MA 01266

    Experience serene living at the end of a picturesque tree-lined driveway in a secluded family estate in the heart of West Stockbridge. Crafted as a berm home artfully built into the rolling hillside, this turnkey residence glows with natural light in its park-like setting. Ideal for both grand entertaining and quiet retreats, the multi-level home features over five bedrooms or flexible sleeping

    Stephen Schoenfeld WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    180 W Center Rd, West Stockbridge, MA 01266
  • /53

    $1,075,000

    • 4 Beds
    • 2.5 Baths
    • 1,986 Sq Ft

    12 Harrison Calkins Rd, Alford, MA 01266

    Enjoy the magic of living in Alford in this Contemporary Cape surrounded by 8+ acres of privacy and the enjoyment of the sound of Scribner Brook running through the front yard from the spacious screened porch. This 4 br, 2.5 bath turn key property is ready for you to walk in and begin your most perfect life in the country. Gather in the Great Room with vaulted ceiling to enjoy the surrounding

    Brandon White COHEN & WHITE ASSOCIATES

    12 Harrison Calkins Rd, Alford, MA 01266
  • /43

    $1,890,000

    • 5 Beds
    • 4.5 Baths
    • 6,000 Sq Ft

    248 East Rd, West Stockbridge, MA 01266

    A luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pastoral acres, with picturesque mountain views. Enter a sun-drenched living room with a soaring cathedral ceiling and an elegant fireplace centerpiece. Enjoy an expansive 3-season porch, with panoramic windows and classic mahogany floors. A recently updated eat-in kitchen features Sub Zero appliances and a

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    248 East Rd, West Stockbridge, MA 01266
  • /23

    $825,000

    • 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
  • /25

    $197,000

    • 2 Beds
    • 1 Bath
    • 1,117 Sq Ft

    17 Swamp Rd, West Stockbridge, MA 01266

    Nestled on serene Shaker Mill Pond, this unique property offers a rare opportunity to own a slice of peaceful paradise with boundless possibilities. The main home, though in need of significant renovation, boasts an unbeatable location with direct water access and panoramic views--perfect for those with a vision to restore or rebuild.Set on over .65 acre, the property includes a charming old barn

    Mary Jane Dunlop BISHOP WEST REAL ESTATE

    17 Swamp 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
  • /49

    $925,000

    • 3 Beds
    • 2.5 Baths
    • 1,979 Sq Ft

    18 Glendale Rd, West Stockbridge, MA 01266

    Architect designed Mid Century home with spectacular western views from every window. Multi level living has been updated with new roof, Pella windows, entry and sliding doors, interior doors, refinished wood floors, modern primary bathroom, heat pump and mini-splits controlled remotely, a whole house generator and recently painted interior and exterior. There is a lovely two sided fireplace

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    18 Glendale Rd, West Stockbridge, MA 01266
  • /47

    $650,000

    • 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!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 wetlands, including a pond frequented by geese, ducks, and blue herons. To the south, the grand lawn is perfect for

    Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

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

    $224,900

    • Land
    • 4.00 Acres
    • $56,225 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
  • /19

    $435,000

    • 3 Beds
    • 1.5 Baths
    • 1,772 Sq Ft

    26 High St, Housatonic, MA 01236

    This charming colonial home is located within walking distance of the quaint center of Housatonic Village. Situated just over the border in West Stockbridge where property taxes are more favorable. Originally constructed as one of the manager's homes for the local mills, this residence has wood floors & high ceilings creating a spacious atmosphere. The first floor features generous living room &

    Molly Thomas COMPASS MASSACHUSETTS , LLC GB

    26 High St, Housatonic, MA 01236
  • /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
  • /23

    $239,000

    • Land
    • 3.00 Acres
    • $79,667 per Acre

    6 Colonial Acres --, West Stockbridge, MA 01266

    This lot offers a wonderful combination of privacy and open space without feeling secluded. Located on a private road at the rear of a cul-de-sac, this 3 acre parcel has been partially cleared and surveyed and with underground electricity in place, it's ready to go. The unique landscape would be ideal for a modern house with lots of glass to capture the natural views and vistas. Access from this

    Lori Rose STONE HOUSE PROPERTIES, LLC

    6 Colonial Acres --, 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
  • /2

    $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 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
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