16

West Stockbridge, MA Houses for Sale

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  • /58

    $1,395,000

    • 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
  • /34

    $810,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 1.5 Baths
    • 1,294 Sq Ft

    15 Mahkeenac Heights Rd, West Stockbridge, MA 01266

    Chic and modern Berkshires retreat. Completed in 2022, this fully renovated property is one of only a handful of homes within Mahkeenac Heights to have a rare double lot -- offering space, privacy, and direct connection to nature just moments from Stockbridge Bowl and minutes to Tanglewood.The design is simple, modern, and sophisticated: a wall of glass frames the surrounding woods, with light

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 779-8896

    15 Mahkeenac Heights Rd, West Stockbridge, MA 01266
  • /47

    $1,790,000

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

    76 Lenox Rd, West Stockbridge, MA 01266

    New World charm meets timeless elegance in this thoughtfully designed French Country-style home, perfectly sited to take in stunning westerly mountain and sunset views. Privately nestled on 3.76 manageable acres, it's just minutes to Tanglewood, downtown Lenox, and West Stockbridge.Designed with both comfort and hospitality in mind, the home offers a flexible layout with six bedrooms and seven

    Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

    76 Lenox Rd, West Stockbridge, MA 01266
  • /68

    $1,250,000

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

    276 Great Barrington Rd, West Stockbridge, MA 01236

    A unique farming opportunity on a self-sufficient 51-acre parcel, highlighted by an 1802 antique Colonial exuding historical charm. A thoughtfully conserved agrarian sanctuary with organic soil, a fruit orchard, maple sugar house, trails, gated pastures, and a running brook. The large barn and mature gardens are framed by stone walls and outbuildings. Bright rooms with wood floors, antique beams,

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    276 Great Barrington Rd, West Stockbridge, MA 01236
  • /34

    $1,549,000

    • 4 Beds
    • 3.5 Baths
    • 3,724 Sq Ft

    5 Silver Mine Ln, West Stockbridge, MA 01266

    This must see outstanding, Move-in Ready, Beautifully Upgraded, Open Floor Plan, Country Contemporary is on a cul-de-sac located just minutes from Tanglewood! The main level features an En Suite Primary Bedroom and Bath, with large 2 walk-in closets! The bright spacious Great Room boasts a vaulted ceiling and a propane fireplace. Like to cook? The gourmet kitchen sports stainless appliances

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    5 Silver Mine Ln, West Stockbridge, MA 01266
  • /34

    $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 4.16 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
  • /68

    $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
  • /50

    $1,825,000

    • 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
  • /58

    $855,000

    • 4 Beds
    • 2.5 Baths
    • 2,872 Sq Ft

    51 Albany Rd, West Stockbridge, MA 01266

    Modern updates have turned this beautiful 1850 colonial into a home worthy for today's most discerning buyer. Walking distance to the village of West Stockbridge where you'll find a fabulous coffee shop (6 Depot), public market, restaurants, ice cream shop, and more! The 1st floor has a large kitchen complete with a seating area, dining room that extends to a screened-in room, half bath, and a

    Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

    51 Albany Rd, West Stockbridge, MA 01266
  • /33

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 1,424 Sq Ft

    19 Washington Square, West Stockbridge, MA 01266

    Charm. You'll find it in this 3BR, 2.5BA West Stockbridge home. The charm of a farmhouse fence, lush with white hydrangeas, roses, and day lilies, set along a peaceful street where neighbors jog, push strollers, or walk their dogs. The charm of luminous freshly painted interiors and windows framing views of greenery on all sides--mists atop Lenox Mountain, vivid sunsets, and star-spangled night

    Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    19 Washington Square, 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
  • /41

    $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. Whether you're a small business owner, creative entrepreneur, or someone creating a unique lifestyle setup - this is your opportunity to own a space that works as hard as you do. This efficiently designed

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    4 Main St, West Stockbridge, MA 01266
  • /48

    $5,475,000

    • 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
  • /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
  • /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

Why Live in West Stockbridge

West Stockbridge, Massachusetts, located in the Southern Berkshires near the Massachusetts-New York border, is known for its vibrant art scene and close-knit community. With approximately 1,350 year-round residents, the town features a charming Main Street lined with historic storefronts, small galleries, and essential local businesses such as a bank, hardware store, and public market. Notable attractions include No. Six Depot, a cafe and art gallery housed in a former train station, and TurnPark Art Space, a 16-acre sculpture park and exhibition venue. Dining options range from global cuisine at Truc Orient Express to the historic Charles H. Baldwin & Sons, known for its handcrafted vanilla extracts and spices. The town offers ample recreational opportunities with West Stockbridge Town Park, Card Pond, and nearby nature trails like Stevens Glen. The Maple Hill Wildlife Management Area and nearby state forests provide extensive outdoor activities year-round. The Berkshire Hills Regional School District serves the area, with highly rated schools such as Muddy Brook Regional Elementary and Monument Mountain Regional High. Housing styles in West Stockbridge include late 1800s and early 1900s colonial-style farmhouses, 20th-century ramblers, Cape Cods, and custom-built estates. The town is car-dependent with access to Interstate 90 and U.S. Route 7, making Albany International Airport 45 miles away and nearby towns like Lee and Great Barrington easily reachable.

Home Trends in West Stockbridge, MA

Housing Trends

Median Sale Price
$685,000
Median Single Family Sale Price
$810,000
Median Townhouse Sale Price
$1,395,000
Average Price Per Sq Ft
$396
Number of Homes for Sale
15
Last 12 months Home Sales
19
Months of Supply
9.50
Median List Price
$925,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
10%
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