West Stockbridge, MA Homes

/7
$79,900
- 2 Beds
- 1 Bath
- 550 Sq Ft
3 Jennifer Ln, West Stockbridge, MA 01266

Nicely remodeled 2 bedroom trailer with fireplace and 2 baths. Park rent is $399.56 per month.

John Ciepiela

BISHOP WEST REAL ESTATE

(413) 741-1606

3 Jennifer Ln, West Stockbridge, MA 01266
/33
$542,500 Sold Dec 19, 2025

19 Washington Square, West Stockbridge, MA 01266
- 3 Beds
- 2.5 Baths
- 1,424 Sq Ft
- Built 1850
Last Sold Summary
- 9% Below List Price
- $381/SF
- 81 Days On Market
Current Estimated Value $536,293

Last Listing Agent Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

19 Washington Square, West Stockbridge, MA 01266

/21
Est $340,575 Not Listed For Sale

123 State Line Rd, West Stockbridge, MA 01266
- 3 Beds
- 1 Bath
- 1,176 Sq Ft
- Built 1959
123 State Line Rd, West Stockbridge, MA 01266

Last Sold Summary
- 42% Above List Price
- $204/SF
- 120 Days On Market
Last Sold Price $240,000

Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC

/57
$1,895,000
- 6 Beds
- 4.5 Baths
- 4,139 Sq Ft
176 W Center Rd, West Stockbridge, MA 01266

A lovely, winding approach to this gorgeous 21-acre estate ensuring serenity, privacy, and the beauty of living in the country. The main house includes 3-4 bed, 2 1/2 bath. An impressive architect-designed guest house has 2 ensuite bedrooms with balconies, dramatic exposed beams and vaulted ceilings. The guest house is an extraordinary place to host family and friends both winter and summer. With

Randy Thunfors STONE HOUSE PROPERTIES, LLC

176 W Center Rd, West Stockbridge, MA 01266
/34
$885,000 Sold Jun 30, 2025

3 Willard Hill Rd, Stockbridge, MA 01262
- 4 Beds
- 3.5 Baths
- 2,189 Sq Ft
- Built 1996
Last Sold Summary
- $404/SF
- 17 Days On Market
Current Estimated Value $916,062

Last Listing Agent Tom Lynch COMPASS MASSACHUSETTS , LLC GB

3 Willard Hill Rd, Stockbridge, MA 01262

/27
Est $597,264 Not Listed For Sale

14 Interlaken Rd, Stockbridge, MA 01262
- 4 Beds
- 2 Baths
- 2,132 Sq Ft
- Built 1969
14 Interlaken Rd, Stockbridge, MA 01262

Last Sold Summary
- 49% Above List Price
- $188/SF
- 49 Days On Market
Last Sold Price $400,000

Last Listing Agent Patricia Andrew STONE HOUSE PROPERTIES, LLC

/60
$2,185,000
- 3 Beds
- 3.5 Baths
- 4,752 Sq Ft
14 Old Tree Farm Rd, Stockbridge, MA 01262

A rare Berkshire offering w/ space, privacy, & exceptional versatility. Fabulous home & separate studio minutes from Tanglewood & Stockbridge Bowl. Charming 3 BR, 2.5 BA, 2,952 sq ft home - complemented by a beautifully renovated 1,800 sq ft studio barn w/ loft & full BA - rests on 8 picturesque acres with beautiful western views. Perfect for outdoor enthusiasts, culture lovers, or anyone seeking

Claire Pollart WILLIAM RAVEIS - BERKSHIRE

14 Old Tree Farm Rd, Stockbridge, MA 01262
/5
$129,900 Sold Oct 08, 2025

11 Jennifer Ln, West Stockbridge, MA 01266
- 3 Beds
- 2 Baths
- 1,000 Sq Ft
- Built 1998
Last Sold Summary
- $130/SF
- 54 Days On Market
Last Listing Agent John Ciepiela BISHOP WEST REAL ESTATE

11 Jennifer Ln, West Stockbridge, MA 01266

/34
Est $592,738 Not Listed For Sale

20 State Line Rd, West Stockbridge, MA 01266
- 2 Beds
- 2.5 Baths
- 1,596 Sq Ft
- Built 1980
20 State Line Rd, West Stockbridge, MA 01266

Last Sold Summary
- 6% Above List Price
- $350/SF
- 93 Days On Market
Last Sold Price $559,000

Last Listing Agent Lori Rose STONE HOUSE PROPERTIES, LLC

/21
$1,575,000
- 4 Beds
- 4.5 Baths
- 2,835 Sq Ft
130 East Rd, West Stockbridge, MA 01266

Nestled in picturesque Alford, this inviting four-bedroom, 4.5-bath home blends comfort and flexibility in a serene Berkshire setting. The first-floor primary suite features a private ensuite bath, ideal for easy living. Thoughtfully designed spaces offer room for guests, work, or hobbies, while seasonal views bring natural beauty indoors throughout the year. With low Alford taxes and a peaceful

Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

130 East Rd, West Stockbridge, MA 01266
/51
$662,500 Sold Aug 12, 2025

256 Great Barrington Rd, Housatonic, MA 01236
- 4 Beds
- 3 Baths
- 3,095 Sq Ft
- Built 1988
Last Sold Summary
- 4% Below List Price
- $214/SF
- 10 Days On Market
Current Estimated Value $707,213

Last Listing Agent Lori Rose STONE HOUSE PROPERTIES, LLC

256 Great Barrington Rd, Housatonic, MA 01236

/43
Est $1,068,328 Not Listed For Sale

388 West Rd, West Stockbridge, MA 01266
- 3 Beds
- 2 Baths
- 1,966 Sq Ft
- Built 1895
388 West Rd, West Stockbridge, MA 01266

Last Sold Summary
- 11% Below List Price
- $610/SF
- 39 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Jen Harvey COMPASS MASSACHUSETTS , LLC GB

/43
$1,790,000 Pending
- 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
/57
$3,750,000 Sold Jan 16, 2026

20 Cobb Rd, Housatonic, MA 01236
- 5 Beds
- 4.5 Baths
- 5,000 Sq Ft
- Built 2020
Last Sold Summary
- $750/SF
- 86 Days On Market
Current Estimated Value $1,948,483

Last Listing Agent Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

20 Cobb Rd, Housatonic, MA 01236

/25
Est $730,429 Not Listed For Sale

17 Glendale Rd, West Stockbridge, MA 01266
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
- Built 1978
17 Glendale Rd, West Stockbridge, MA 01266

Last Sold Summary
- 16% Above List Price
- $404/SF
- 5 Days On Market
Last Sold Price $630,000

Last Listing Agent Mary Jane Dunlop BERKSHIRE ACCESS REALTY, INC

/73
$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
$814,000 Sold Nov 03, 2025

19 Hawthorne Rd Unit GH 8, West Stockbridge, MA 01266
- 3 Beds
- 2.5 Baths
- 1,922 Sq Ft
- Built 1984
Last Sold Summary
- $424/SF
Last Listing Agent Comparable Listing COMPARABLE LISTING ONLY

19 Hawthorne Rd Unit GH 8, West Stockbridge, MA 01266

/16
Est $445,242 Not Listed For Sale

15 State Line Rd, West Stockbridge, MA 01266
- 3 Beds
- 2 Baths
- 1,532 Sq Ft
- Built 1840
15 State Line Rd, West Stockbridge, MA 01266

Last Sold Summary
- 27% Above List Price
- $228/SF
- 74 Days On Market
Last Sold Price $350,000

Last Listing Agent Helen Mullany HELEN MULLANY REAL ESTATE, LLC

/56
$1,295,000
- 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 WILLIAM RAVEIS - BERKSHIRE

45 Swamp, West Stockbridge, MA 01266
/20
$435,000 Sold Aug 04, 2025

26 High St, Housatonic, MA 01236
- 3 Beds
- 1.5 Baths
- 1,772 Sq Ft
- Built 1920
Last Sold Summary
- 7% Below List Price
- $245/SF
- 134 Days On Market
Current Estimated Value $448,829

Last Listing Agent Molly Thomas COMPASS MASSACHUSETTS , LLC GB

26 High St, Housatonic, MA 01236

/38
Est $1,314,990 Not Listed For Sale

258 East Rd, West Stockbridge, MA 01266
- 4 Beds
- 3.5 Baths
- 1,638 Sq Ft
- Built 1976
258 East Rd, West Stockbridge, MA 01266

Last Sold Summary
- 7% Above List Price
- $748/SF
- 14 Days On Market
Last Sold Price $1,225,000

Last Listing Agent Claudia Crane COMPASS MASSACHUSETTS , LLC GB

/40
$389,000 Pending
- 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
$1,180,000 Sold Jul 11, 2025

46 W Center Rd, West Stockbridge, MA 01266
- 4 Beds
- 3.5 Baths
- 3,642 Sq Ft
- Built 1984
Last Sold Summary
- 9% Below List Price
- $324/SF
- 12 Days On Market
Current Estimated Value $1,180,415

Last Listing Agent Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

46 W Center Rd, West Stockbridge, MA 01266

/25
Est $785,262 Not Listed For Sale

275 East Rd, West Stockbridge, MA 01266
- 2 Beds
- 2 Baths
- 2,400 Sq Ft
- Built 1988
275 East Rd, West Stockbridge, MA 01266

Last Sold Summary
- 9% Above List Price
- $300/SF
- 2 Days On Market
Last Sold Price $720,000

Last Listing Agent Claudia Crane COMPASS MASSACHUSETTS , LLC GB

/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
/34
$840,000 Sold Nov 17, 2025

15 Mahkeenac Heights Rd, West Stockbridge, MA 01266
- 2 Beds
- 1.5 Baths
- 1,294 Sq Ft
- Built 1950
Last Sold Summary
- 4% Above List Price
- $649/SF
- 7 Days On Market
Last Listing Agent Selina Lamb BIRCH PROPERTIES

15 Mahkeenac Heights Rd, West Stockbridge, MA 01266

/41
Est $515,778 Not Listed For Sale

20 Pixley Hill Rd, Housatonic, MA 01236
- 4 Beds
- 3.5 Baths
- 2,128 Sq Ft
- Built 1976
20 Pixley Hill Rd, Housatonic, MA 01236

Last Sold Summary
- 31% Above List Price
- $186/SF
- 26 Days On Market
Last Sold Price $395,000

Last Listing Agent Pamela Roberts ROBERTS & ASSOC. REALTY, INC

/3
$750,000
- Land
- 131.69 Acres
- $5,695 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
$586,500 Sold Sep 26, 2025

6 Bryan Rd, West Stockbridge, MA 01266
- 3 Beds
- 2.5 Baths
- 1,500 Sq Ft
- Built 1875
Last Sold Summary
- 10% Below List Price
- $391/SF
- 143 Days On Market
Current Estimated Value $578,349

Last Listing Agent Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

6 Bryan Rd, West Stockbridge, MA 01266

/30
Est $500,131 Not Listed For Sale

34 W Center Rd, West Stockbridge, MA 01266
- 3 Beds
- 2 Baths
- 2,020 Sq Ft
- Built 1958
34 W Center Rd, West Stockbridge, MA 01266

Last Sold Summary
- 30% Above List Price
- $191/SF
- 102 Days On Market
Last Sold Price $385,000

Last Listing Agent Donna DiGrigoli DIGRIGOLI REAL ESTATE

/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
/58
$825,000 Sold Dec 08, 2025

51 Albany Rd, West Stockbridge, MA 01266
- 4 Beds
- 2.5 Baths
- 2,872 Sq Ft
- Built 1850
Last Sold Summary
- 4% Below List Price
- $287/SF
- 44 Days On Market
Current Estimated Value $831,294

Last Listing Agent Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

51 Albany Rd, West Stockbridge, MA 01266

/42
Est $649,910 Not Listed For Sale

2 Carlotto Rd, Housatonic, MA 01236
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
- Built 1957
2 Carlotto Rd, Housatonic, MA 01236

Last Sold Summary
- 4% Above List Price
- $501/SF
- 2 Days On Market
Last Sold Price $625,000

Last Listing Agent David Graziani BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

/35
$679,000 Under Contract
- 3 Beds
- 2 Baths
- 1,822 Sq Ft
139 W Center Rd, West Stockbridge, MA 01266

Location, location, location - one of the nicest roads in the county, more bicycle riders than cars. Classic NE Farmhouse with many recent updates Energy Efficient Heat and Cooling Electric Pumps, Solar Panels ($114/month), newer kitchen appliances, a cook's designed kitchen with stainless steel counters, two sinks, high ceiling, lots of glass and light overlooking a stream in the back yard,

Susan Baum BERKSHIRE HOMES AND CONDOS

139 W Center Rd, West Stockbridge, MA 01266
/28
$685,000 Sold Sep 12, 2025

52 Lenox Rd, West Stockbridge, MA 01266
- 3 Beds
- 2 Baths
- 1,488 Sq Ft
- Built 1985
Last Sold Summary
- 1% Above List Price
- $460/SF
- 2 Days On Market
Current Estimated Value $686,364

Last Listing Agent Leslie Claus Van Hise BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

52 Lenox Rd, West Stockbridge, MA 01266

/35
Est $843,452 Not Listed For Sale

5 Lenox Rd, West Stockbridge, MA 01266
- 5 Beds
- 2.5 Baths
- 2,578 Sq Ft
- Built 1825
5 Lenox Rd, West Stockbridge, MA 01266

Last Sold Summary
- 4% Below List Price
- $339/SF
- 6 Days On Market
Last Sold Price $875,000

Last Listing Agent Selina Lamb Birch Properties

/53
$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
/23
$525,000 Sold Oct 03, 2025

9 Iron Mine Rd, West Stockbridge, MA 01266
- 3 Beds
- 2 Baths
- 2,620 Sq Ft
- Built 1989
Last Sold Summary
- 36% Below List Price
- $200/SF
- 105 Days On Market
Current Estimated Value $573,301

Last Listing Agent Deborah Mielke CORASHIRE REALTY

9 Iron Mine Rd, West Stockbridge, MA 01266

/38
Est $1,156,043 Not Listed For Sale

258 Great Barrington Rd, Housatonic, MA 01236
- 3 Beds
- 3.5 Baths
- 3,963 Sq Ft
- Built 1987
258 Great Barrington Rd, Housatonic, MA 01236

Last Sold Summary
- 8% Above List Price
- $270/SF
- 7 Days On Market
Last Sold Price $1,070,000

Last Listing Agent William Morrow William Pitt

/40
$384,000
- 3 Beds
- 1.5 Baths
- 1,677 Sq Ft
20 Moscow Rd, West Stockbridge, MA 01266

Short walk to quaint downtown West Stockbridge featuring local coffee shop, variety store, restaurants and shops. Just a few minutes to local theatres, music venues, Tanglewood, historic Stockbridge, and the Mass Pike. Beautiful open yard great for summer entertaining including cookouts, yard games or just relaxing and reading a book! Cozy fireplace for those beautiful snowy New England nights.

Mark Harris SIGNATURE ASSOCIATES

20 Moscow Rd, West Stockbridge, MA 01266

Showing Results 1 - 40, Page 1 of 18

Massachusetts Berkshire County West Stockbridge

Home Trends in West Stockbridge, MA

On average, homes in West Stockbridge, MA sell after 50 days on the market compared to the national average of 55 days. The median sale price for homes in West Stockbridge, MA over the last 12 months is $685,000, down 14% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$685,000

Median Single Family Sale Price

$742,500

Median Townhouse Sale Price

$571,500

Average Price Per Sq Ft

$406

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

4.90

Median List Price

$810,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-14%

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West Stockbridge, MA Homes

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Home Trends in West Stockbridge, MA

Housing Trends