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West Stockbridge, MA Homes for Sale with Acreage

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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
  • /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
  • /40

    $1,795,000

    • 4 Beds
    • 4 Baths
    • 3,524 Sq Ft

    1 Old Tree Farm Rd, Stockbridge, MA 01262

    Impeccably Renovated Stockbridge Country Retreat. Minutes from Stockbridge, Lenox and Tanglewood, in the heart of the Berkshires cultural corridor, a rare opportunity in a perfect setting on 4.25 level, landscaped acres. Surrounded by mature trees and curated gardens, this home blends classic design with modern updates, offering refined style throughout. White oak floors, three full baths, a gas

    Suzann Ward HOUSATONIC REAL ESTATE

    1 Old Tree Farm Rd, Stockbridge, MA 01262
  • /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
  • /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
  • /47

    $1,575,000 New Construction

    • 1 Bed
    • 2 Baths
    • 3,826 Sq Ft

    293 East Rd, West Stockbridge, MA 01266

    A Hidden Berkshire Gem - With a Cottage, a Dream, and over 30 Acres of PossibilityWelcome to BarKing Cow Farm ! Your future compound that is tucked away on almost 30 private acres of peace and possibility, this rare offering is a true diamond awaiting its final polish. Located in one of the Berkshires' most sought-after townsa"boasting the lowest tax rate in South Countya"this property invites

    William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    293 East Rd, 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
  • /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
  • /48

    $5,775,000

    • 5 Beds
    • 8 Baths
    • 9,400 Sq Ft

    Unlisted Address

    Nestled in the heart of Alford, Massachusetts, this extraordinary 35.6-acre Berkshire County estate offers unparalleled privacy with sweeping western Catskill Mountain views and direct access to conservation land. The impressive 9,400 sq ft main residence, built in 2003 and comprehensively updated beginning in 2020, features 4 bedrooms, 5 full baths, and resort-caliber amenities throughout its

    Elyse Morris ELYSE HARNEY REAL ESTATE

    Unlisted Address
  • /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

    $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
  • /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
  • /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

Home Trends in West Stockbridge, MA

Housing Trends

Median Single Family Sale Price
$1,280,000
Average Price Per Sq Ft
$553
Number of Homes for Sale
3
Last 12 months Home Sales
0
Median List Price
$1,300,000
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