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Newest Homes for Sale in West Stockbridge, MA

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  • /40

    $419,000

    • 3 Beds
    • 1 Bath
    • 1,269 Sq Ft

    26 Lenox Rd, West Stockbridge, MA 01266

    1900's cottage set above the village of West Stockbridge. Open plan living with updated kitchen and bath, with laundry tucked in below the stairs and second floor has three bedrooms. Fenced yard creating a nice private space with wraparound deck. Shed at the back of the property providing a lovely additional space.

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    26 Lenox Rd, West Stockbridge, MA 01266
  • /52

    $3,750,000

    • 4 Beds
    • 3.5 Baths
    • 3,225 Sq Ft

    40 E Alford Rd, West Stockbridge, MA 01266

    Perched dramatically on a 18 acre very private mountainside, this brand-new modern home overlooks the sweeping beauty of the Berkshire Hills. A long, winding driveway builds anticipation as it ascends, ultimately revealing striking contemporary architecture framed by panoramic sunrise views. Designed to embrace the natural landscape at every turn, this residence delivers a serene, elevated living

    Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    40 E Alford Rd, West Stockbridge, MA 01266
  • /42

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,842 Sq Ft

    16 Swamp Rd, West Stockbridge, MA 01266

    The George Tyler Homestead appears on West Stockbridge maps as early as 1855. This charming 3-bedroom cottage exudes warmth and character with plenty of original details throughout. The wood-paneled living room features a handsome brick hearth with original beehive oven and beautifully aged pine floors. The L-shaped kitchen offers ample storage and opens to a formal dining room, where a large

    Vashti Poor LANCE VERMEULEN RE, INC

    16 Swamp Rd, West Stockbridge, MA 01266
  • /95

    $13,500,000

    • 7 Beds
    • 9 Baths
    • 10,429 Sq Ft

    30 East Rd, West Stockbridge, MA 01266

    Majestic 71 acre Tudor Estate atop Tom Ball Mountain in the quaint hamlet of Alford, MA. Enjoy total privacy and breathtaking views from nearly every room. The main house features 5 en-suite bedrooms, a gourmet kitchen, formal living and dining rooms, den, family room, gym, billiard room and massage room. A separate 2-bedroom guest house offers beamed ceilings and full amenities. Manicured

    Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    30 East Rd, West Stockbridge, MA 01266
  • /17

    $499,000

    • 2 Beds
    • 1 Bath
    • 1,015 Sq Ft

    18 Hill Rd, Stockbridge, MA 01262

    Log Cabin in Stockbridge! Tucked away at the end of a country road, this charming log home offers warmth, privacy, and convenience - and it's close to Tanglewood. Beautifully maintained inside and out, it sits on two wooded acres with a welcoming front porch. Inside you will find a cozy retreat - a living room with cathedral ceilings, pine floors, and a working fireplace. The updated kitchen

    Marie Bourassa SIGNATURE ASSOCIATES

    18 Hill Rd, Stockbridge, MA 01262
  • /10

    $225,000

    • Land
    • 3.26 Acres
    • $69,018 per Acre

    88 Great Barrington Rd, West Stockbridge, MA 01266

    Cleared 3+ acre lot ready to be built in a desirable West Stockbridge location. Wonderful south facing site, set off the road with distant uninterrupted views. Existing driveway presents easy access. Previous owner had percolation tests done which allows for a below grade septic system. Plans for the septic system are included. The site has already be approved by the DEP. Architectural plans for

    Jennifer Capala WILLIAM PITT SOTHEBY'S - LENOX

    88 Great Barrington Rd, West Stockbridge, MA 01266
  • /22

    $849,000

    • Land
    • 29 Acres
    • $29,276 per Acre

    416 West Rd, Alford, MA 01266

    Experience the Berkshires Like Never BeforeNestled on West Road in Alford, this exceptional 29-acre estate offers a rare blend of natural beauty, flexibility, and investment potential. A meandering brook, Alford Brook gently courses through the property, creating serene waterside vistas and the soothing soundtrack of flowing water day and night.From the open meadows and wooded glens, enjoy

    Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    416 West Rd, Alford, MA 01266
  • /49

    $780,000

    • 3 Beds
    • 2 Baths
    • 2,046 Sq Ft

    17 Iron Mine Rd, West Stockbridge, MA 01266

    Designed for country living and entertaining, the heart of the home centers around a sun-filled great room with vaulted ceilings, wood beams, and French doors leading to a private deck. The chic kitchen has marble counters, subway tile, stainless steel appliances, gas stove and a peninsula for prep and dining. The 1st-floor primary suite offers a walk-in closet, updated full bath and deck access.

    Tracy Crawford COMPASS MASSACHUSETTS , LLC GB

    17 Iron Mine Rd, West Stockbridge, MA 01266
  • /15

    $649,000

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    17 Beachwood Dr, Stockbridge, MA 01262

    Discover a truly exceptional opportunity to own a spacious 3-bedroom seasonal cottage on 1.3 acres of uniquely private land in one of the Berkshires' most desirable lakeside enclaves.Nestled in the serene and exclusive Beachwood community on Stockbridge Bowl, this property offers the perfect balance of natural beauty, privacy, and cultural access. Residents enjoy steps to a private beach,

    Franz Forster FRANZ J. FORSTER R. E.

    17 Beachwood Dr, Stockbridge, MA 01262
  • /68

    $1,100,000

    • 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
  • /2

    $289,000

    • Land
    • 3.69 Acres
    • $78,320 per Acre

    0 Interlaken Cross Rd, Stockbridge, MA 01262

    A pristine building lot in the heart of the Berkshires! Parcel B at Echo Valley is a 3.69-acre wooded, buildable lot offering a beautiful blank canvas for your dream home. Located off Interlaken Cross Road in Stockbridge, MA, this level parcel is easy to work with and provides excellent flexibility for siting your house, garage, and outdoor living spaces. Just minutes from Tanglewood, Stockbridge

    Lisa Berry Simply Sell Realty

    0 Interlaken Cross Rd, Stockbridge, MA 01262
  • /3

    $315,000

    • Land
    • 14.74 Acres
    • $21,370 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
  • /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
  • /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
  • /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
  • /60

    $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
  • /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
  • /3

    $975,000

    • Land
    • 131.69 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
  • /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
  • /12

    $212,900

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

    0 Cross Rd, West Stockbridge, MA 01266

    Spectacular 4+/- acre parcel in a peaceful setting. It is backed up to a state conservatory so your privacy will remain in tact! This beautiful parcel is ready for your new home with a recent survey and perc test. Nestled in a tranquil area, that’s close to Card Pond and downtown Lenox. Come develop your dream home on this private parcel, but yet still be near all of the local attractions and

    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
  • /43

    $1,790,000

    • 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
  • /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

What is the average home price in West Stockbridge, MA?
Homes for sale in West Stockbridge, MA have an average home price of $2,144,456.
Are home prices dropping in West Stockbridge?
Yes, home prices in West Stockbridge are down 18% in the last 12 months.
How many homes have sold over the last 12 months in West Stockbridge, MA?
23 homes have sold in West Stockbridge, MA over the last 12 months.
What are the most popular zip codes in West Stockbridge, MA?
The most popular zip codes in West Stockbridge, MA include 01236, 01266, 01262, 12017 and 01254.
How much do you need to make to afford a house in West Stockbridge?
The median home price in West Stockbridge is $814,000. If you put a 20% down payment of $162,800 and had a 30-year fixed mortgage with an interest rate of 6.26%, your estimated principal and interest payment would be $4,010 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $172K a year to afford the median home price in West Stockbridge. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in West Stockbridge, MA?
West Stockbridge, MA has highly rated public and private schools. Some of the best schools in West Stockbridge based on Niche Grades are Muddy Brook Regional Elementary School, Chatham High School and Richmond Consolidated School. Browse all the schools in West Stockbridge, MA to learn more.

Home Trends in West Stockbridge, MA

Housing Trends

Median Sale Price
$685,000
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$1,104,500
Average Price Per Sq Ft
$488
Number of Homes for Sale
12
Last 12 months Home Sales
23
Months of Supply
6.30
Median List Price
$814,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
10%
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