Berkshire, MA Homes

/29
$995,000
- 4 Beds
- 2.5 Baths
- 2,008 Sq Ft
9 Yale Hill Rd, Stockbridge, MA 01262

9 Yale Hill was built c1880 by prominent Berkshire architect Joseph McArthur Vance as a summer cottage for La Chaumiere in the village of Stockbridge, the estate up the hill. Artfully put together, the cottage is incredibly charming in its original details and lovely elements that have been added over the years. The house is tucked in amongst perennial gardens and beautiful neighboring homes. The

Annabel Taylor Four Seasons Sotheby's International Realty

9 Yale Hill Rd, Stockbridge, MA 01262
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/30
$245,000 Sold Feb 18, 2025
- 1,721 Sq Ft
- $142/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1948
44 East St, Stockbridge, MA 01262

True fixer upper on 3.6 acres being sold as is including the unknown condition of the septic system. Known defects are that all of the cooper water lines have been stripped from the house. So, it is unkown if the 2008 oil furnace is operational. There are hardwood floors on the first and second floors. There is one bedroom on the first floor and two on the second floor. Full bathrooms are also on

Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

44 East St, Stockbridge, MA 01262

/31
Est $668,108 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,909 Sq Ft
10 Church St, Stockbridge, MA 01262

10 Church St, Stockbridge, MA 01262

/46
$789,000
- 2 Beds
- 2.5 Baths
- 1,922 Sq Ft
19 Hawthorne Rd Unit GH 4, Stockbridge, MA 01262

This White Pines Garden Unit is a must see if you are considering condominium living in this sought after community. Open living Great Room/kitchen/dining with double volume glass to take in the view, fireplace & guest bath on main level. The lower level greets you with a tiled floor sunroom w/direct access to the spacious decking w/private courtyard outdoor space. The primary ensuite, guest

Mary Jane White COHEN & WHITE ASSOCIATES

19 Hawthorne Rd Unit GH 4, Stockbridge, MA 01262
/12
$145,000 Sold Jan 28, 2025
- Land
- 0.74 Acre
- $195,948 per Acre
- 15 Days On Market
Unlisted Address

GREAT LOCATION JUST UP THE HILL FROM THE TOWN BEACH ON STOCKBRIDGE BOWL Tanglewood is a short 2.5 miles up the road. Nicely situated between the centers of Stockbridge and Lenox. The walk to the Beach is less than a half-mile. Perfect for a vacation or full time home. Almost three quarters of an acre of level land on the corner of Mahkeenac Heights Rd and Yokum Rd. Town sewer is available.

Sheila Thunfors STONE HOUSE PROPERTIES, LLC

Unlisted Address

/26
Est $535,543 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,120 Sq Ft
7 Birch Ln, Stockbridge, MA 01262

7 Birch Ln, Stockbridge, MA 01262

/54
$2,500,000
- 5 Beds
- 5.5 Baths
- 5,233 Sq Ft
55 Main St, Stockbridge, MA 01262

Historic Elegance Reimagined!Wellness-forward design. Artisan craftsmanship. In-town privacy.A Kitchen Rebuilt from the Ground Up: At the heart of the home, a brand-new chef's kitchen makes a bold, refined statement with honed dark gray granite countertops, crisp white shaker cabinetry, and minimalist matte black fixtures. Oversized divided-light windows flood the space with natural light, while

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

55 Main St, Stockbridge, MA 01262
/42
$1,275,000 Sold Jan 16, 2025
- 2,358 Sq Ft
- $541/SF
- 34 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1880
35 Church St, Stockbridge, MA 01262

Experience the perfect blend of historic charm and modern comfort in this stunning Antique Stockbridge Eyebrow Colonial! Nestled on nearly an acre, this 4-bedroom, 3.5-bath gem welcomes you with timeless elegance and contemporary upgrades.Step into a warm, inviting kitchen--the heart of the home--highlighted by gorgeous exposed vintage brick and seamless flow to the sunlit south-facing patio,

Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

35 Church St, Stockbridge, MA 01262

/28
Est $594,494 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,607 Sq Ft
27 Park St, Stockbridge, MA 01262

27 Park St, Stockbridge, MA 01262

/42
$485,000
- 2 Beds
- 2 Baths
- 1,296 Sq Ft
42 East St, Stockbridge, MA 01262

Set on 6.4 scenic acres, this classic New England farmhouse captures the timeless spirit of Stockbridge, a town beloved for its rich history and cultural legacy. This 2-bed 2-bath home offers authentic charm, featuring beautiful hardwood floors, a spacious kitchen, family room + 1st floor full bath, and a welcoming front porch that evokes a slower, simpler time. Thoughtful updates include a newer

Conor Meehan STONE HOUSE PROPERTIES, LLC

42 East St, Stockbridge, MA 01262
/52
$1,350,000 Sold Dec 31, 2024
- 3,891 Sq Ft
- $347/SF
- 49 Days On Market
- 5 Beds
- 4 Baths
- Built 1826
82 E Main St, Stockbridge, MA 01262

Discover a historically significant gem in Stockbridge, nestled on 2 lush acres with Housatonic River frontage. The property, originally landscaped by renowned sculptor Daniel Chester French, features an enchanting garden, a koi pond, a two-car garage with power and water, and a charming potting shed. Inside, five spacious bedrooms and four well-appointed bathrooms retain original features that

Kate Lascar COMPASS MASSACHUSETTS , LLC GB

82 E Main St, Stockbridge, MA 01262

/32
Est $816,019 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,395 Sq Ft
3 Yale Hill Rd, Stockbridge, MA 01262

3 Yale Hill Rd, Stockbridge, MA 01262

/29
$912,000
- 4 Beds
- 4 Baths
- 2,280 Sq Ft
21 East St, Stockbridge, MA 01262

**Price Improvement** Nestled in the heart of the Berkshires, this spaciously built 2003 Colonial sits on over 14 acres, offering privacy, potential, and long-term value. Currently operating as a doggy day care, but you wouldn't know it when you walk inside! Well-maintained & cared for. Recent updates include the kitchen, bathrooms, carpets, back deck, and front landscaping, while still leaving

Brianna Boffoli Cameron Prestige, LLC

21 East St, Stockbridge, MA 01262
/41
$660,000 Sold Dec 10, 2024
- 1,768 Sq Ft
- $373/SF
- 6 Days On Market
- 2 Beds
- 2 Baths
- Built 1986
19 Hawthorne Rd Unit S-2C, Stockbridge, MA 01262

WHITE PINES SINGLE LEVEL TWO BEDROOM 2.5 BATH UNIT! One of only two single level opportunities to buy in the Stables. Open common spaces with wood beam detail, wall of windows for amazing natural light, fireplace in great room open to dining, kitchen and den. Primary bedroom with two walk in closets; ensuite bath with double sinks and separate tub, shower and water closet. Guest bedroom with

Cortney Dupont COHEN & WHITE ASSOCIATES

19 Hawthorne Rd Unit S-2C, Stockbridge, MA 01262

/23
Est $440,538 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 853 Sq Ft
3 Indian Rd, Stockbridge, MA 01262

3 Indian Rd, Stockbridge, MA 01262

/19
$949,000
- 11 Beds
- 6 Baths
- 4,863 Sq Ft
Unlisted Address

Fully Rented In Town 5-Family Investment Opportunity. Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures.

Matt Carlino MACCARO REAL ESTATE

Unlisted Address
/43
$1,200,000 Sold Dec 06, 2024
- 4,057 Sq Ft
- $296/SF
- 678 Days On Market
- 6 Beds
- 4.5 Baths
- Built 1900
2 Cherry St, Stockbridge, MA 01262

A Magnificent 6 bedroom stucco residence less than a mile to the center of Stockbridge. Enjoy views of the golf course and mountains in the distance. Five fireplaces, a beautiful eat in kitchen, stunning butlers pantry with a cozy nook to sit in, and a sun filled spacious dining room. Read a good book in the beautiful library next to one of the five fire places throughout the house. Step out

Patricia Andrew STONE HOUSE PROPERTIES, LLC

2 Cherry St, Stockbridge, MA 01262

/33
Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,360 Sq Ft
17 Christian Hill Rd, Stockbridge, MA 01262

17 Christian Hill Rd, Stockbridge, MA 01262

/24
$299,900
- 1 Bed
- 1 Bath
- 658 Sq Ft
2 Wallace Rd Unit DH-B, Stockbridge, MA 01262

Come experience this charming condo in the beautiful Heron Pond Community in Stockbridge. Thoughtful use of space with large, private front patio facing expansive manicured lawns and gardens. Enjoy 1-level living, (1-bed,1-bath with separate dining room) fully applianced kitchen with pantry and instant boiling water faucet. Washer and Dryer included. Zoned smart heating thermostats.

Susan Calkins STONE HOUSE PROPERTIES, LLC

2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
/57
$1,210,000 Sold Nov 22, 2024
- 3,300 Sq Ft
- $367/SF
- 244 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1824
17 Main St, Stockbridge, MA 01262

CIRCA 1824 GEM on 4.3 ACRES OF MEADOWS AND WOODS IN THE HEART OF THE HISTORIC VILLAGE OF STOCKBRIDGE. Walk to shops, restaurants, town tennis courts, the library, the Stockbridge Golf Club, the Berkshire Theatre Festival and more. The David Dudley Field house is steeped in history remaining in the Field family until 1984. The current owners have lovingly maintained and cherished this exceptional

Randy Thunfors STONE HOUSE PROPERTIES, LLC

17 Main St, Stockbridge, MA 01262

/31
Est $3,013,565 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,400 Sq Ft
3 Mahkeenac Terrace, Stockbridge, MA 01262

3 Mahkeenac Terrace, Stockbridge, MA 01262

/40
$1,995,000
- 6 Beds
- 8 Baths
- 10,507 Sq Ft
14 Pine St, Stockbridge, MA 01262

Prime Owner-User/Investment Property in the heart of historic Stockbridge. Currently an Educational Facility with Retail, Office and Residential Units. Can be combined for Offices, Medical, Educational, Gallery, Apartments/Condos, or any use that demands a location in one of the most well known and loved towns in America. Fully upgraded mechanicals, large Parking facilities and Handicapped

Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

14 Pine St, Stockbridge, MA 01262
/54
$1,900,000 Sold Nov 01, 2024
- 2,600 Sq Ft
- $731/SF
- 8 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2017
1 Lakeview Dr, Stockbridge, MA 01262

Contemporary Stunner on Stockbridge Bowl Outlet!Step into this waterfront home and be wowed. Superbly designed 2017 build with every amenity and gorgeous water views. Located on Lakeview Drive, with kayak, canoe and paddle board access from your back door to the Outlet and Bowl, and access to the private community beach on the Stockbridge Bowl.An open first floor great room with 9' ceilings and

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

1 Lakeview Dr, Stockbridge, MA 01262

/26
Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,240 Sq Ft
11 Mahkeenac Heights Rd, West Stockbridge, MA 01266

11 Mahkeenac Heights Rd, West Stockbridge, MA 01266

/50
$425,000
- 2 Beds
- 2 Baths
- 1,647 Sq Ft
2 Wallace Rd Unit 2E, Stockbridge, MA 01262

Welcome to Heron Pond Condominiums in charming Stockbridge, where comfort meets convenience in a tranquil setting. This beautiful condominium offers an ideal combination of spacious living and cozy charm, featuring 2 or 3 bedrooms and 2 full baths. The screened porch is ideal to relax and enjoy nature without the bugs, a serene space to unwind, whether you're enjoying morning coffee or evening

Paula McLean PAULA MCLEAN REALTORS INC.

2 Wallace Rd Unit 2E, Stockbridge, MA 01262
/31
$500,000 Sold Oct 16, 2024
- 2,502 Sq Ft
- $200/SF
- 103 Days On Market
- 3 Beds
- 3 Baths
- Built 2016
38a Glendale Rd, Stockbridge, MA 01262

Fantastic Location! This property boasts proximity to the Norman Rockwell museum and golf courses. The residence features 3/4 bedrooms and 3 full bathrooms. On the second floor, you'll find a delightful master suite, while a guest bathroom is nestled between two additional bedrooms. The first floor offers a full bathroom and one bedroom, with a relatively open floor plan that seamlessly combines

Clifford Ponte KELLER WILIAMS SOUTH WATTUPA

38a Glendale Rd, Stockbridge, MA 01262

/19
Est $426,667 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,104 Sq Ft
15 Park St, Stockbridge, MA 01262

15 Park St, Stockbridge, MA 01262

/26
$239,000
- Land
- 8 Acres
- $30,508 per Acre
13 Rattlesnake Mountain Rd, Stockbridge, MA 01262

PRIME BERKSHIRE LAND - FEEL 'AWAY FROM IT ALL' YET YOU ARE MOMENTS FROM THE BEST OF THE BERKSHIRES. $158,000+ UNDER ASSESSED VALUESet on a serene & forested country road, this location makes the perfect retreat - yet you are in the heart of the Berkshires just minutes to Stockbridge & Lenox, Tanglewood, The Bowl, The Mount, Kripalu, Great Barrington, the Pike, shopping & more. The single home

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

13 Rattlesnake Mountain Rd, Stockbridge, MA 01262
/25
$500,000 Sold Oct 16, 2024
- 2,502 Sq Ft
- $200/SF
- 341 Days On Market
- 3 Beds
- 3 Baths
- Built 2016
38 Glendale Rd, Stockbridge, MA 01262

Fantastic Location! This property boasts proximity to the Norman Rockwell museum and golf courses. The residence features 3/4 bedrooms and 3 full bathrooms. On the second floor, you'll find a delightful master suite, while a guest bathroom is nestled between two additional bedrooms. The first floor offers a full bathroom and one bedroom, with a relatively open floor plan that seamlessly combines

The Ponte Group Keller Williams South Watuppa

38 Glendale Rd, Stockbridge, MA 01262

/28
Est $592,833 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
12 Beachwood Dr, Stockbridge, MA 01262

12 Beachwood Dr, Stockbridge, MA 01262

/16
$295,000
- Land
- 25 Acres
- $11,697 per Acre
0 Glendale Rd Unit 245211, Stockbridge, MA 01262

Beautiful 25 Acres in Stockbridge. Stockbridge Bowl, Tanglewood, the villages of Stockbridge, Lenox, and Housatonic are all nearby. The property consists of two separate building lots - the south lot with 12.56 acres, and the north lot with 12.66 acres. Potential for mountain views from both lots with some clearing. Many possibilities - build on the north lot and keep the south lot for extra

Sheila Thunfors STONE HOUSE PROPERTIES, LLC

0 Glendale Rd Unit 245211, Stockbridge, MA 01262
/78
$1,221,000 Sold Oct 08, 2024
- 3,100 Sq Ft
- $394/SF
- 7 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1881
1 Laurel Ln, Stockbridge, MA 01262

Exquisite, fully renovated farmhouse on private lane abutting nature reserve in heart of Stockbridge close to Red Lion. Foyer leads into an open plan LR/DR/Kit w/ beamed ceilings, hardwood floors, FP, oak slab island, marble counters, chef's stainless appls. Bright LR w/ floor-ceiling windows & French doors open onto patio w/ dining area. Huge 1st floor main BR suite w/ vltd ceils, walls of

Gary Lazarus COMPASS MASSACHUSETTS , LLC GB

1 Laurel Ln, Stockbridge, MA 01262

/31
Est $1,158,633 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,710 Sq Ft
20 Lake Dr, Stockbridge, MA 01262

20 Lake Dr, Stockbridge, MA 01262

/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
/37
$1,429,000 Sold Oct 07, 2024
- 4,088 Sq Ft
- $350/SF
- 14 Days On Market
- 4 Beds
- 5 Baths
- Built 2003
11a Interlaken Cross Rd, West Stockbridge, MA 01266

Impeccably kept expansive contemporary home on 2 acres near Stockbridge Bowl. 4 bedrooms with bonus bunk room and 5 baths on 3 levels of living area makes it an ideal get away from the city or primary residence located in the heart of the Berkshires. Delicately sited in a very quiet neighborhood offering protected views from your front porch and from your backyard you'll enjoy a shared walking

Altaluxre Group William Pitt Sotheby's International Realty

11a Interlaken Cross Rd, West Stockbridge, MA 01266

/49
Est $714,520 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,012 Sq Ft
2 Meadow Rd, Stockbridge, MA 01262

2 Meadow Rd, Stockbridge, MA 01262

/38
$895,000 Pending
- 5 Beds
- 3.5 Baths
- 3,194 Sq Ft
33 Interlaken Rd, Stockbridge, MA 01262

Enjoy convenient one level living in this expanded contemporary ranch. Super location - Located less than 5 minutest to the main gates of Tanglewood, the Stockbridge Bowl for swimming, and Gould Meadows for a nature lovers hike. Sited at the end of a long winding driveway this 2+ acre parcel is level and sunny (ideal for a pool). 5+ bedrooms and 3 1/2 bathrooms including a suite with a

Lori Rose STONE HOUSE PROPERTIES, LLC

33 Interlaken Rd, Stockbridge, MA 01262
/20
$427,000 Sold Oct 04, 2024
- 1,152 Sq Ft
- $371/SF
- 2 Days On Market
- 2 Beds
- 2 Baths
- Built 1982
3 N Church St, Stockbridge, MA 01262

Charming Single Level Living Home in Stockbridge - A Rare find!! This adorable home promises a ton of potential, perfect for those seeking a cozy yet functional space. Galley kitchen w/ an efficient layout opens to an inviting living room w/ a wood burning fireplace making it perfect for entertaining. Step outside to a spacious deck that overlooks a scenic backyard. This home also offers two

Molly Thomas COMPASS MASSACHUSETTS , LLC GB

3 N Church St, Stockbridge, MA 01262

/67
Est $1,262,158 Not Listed For Sale
- 6 Beds
- 3 Baths
- 3,762 Sq Ft
19 Yale Hill Rd, Stockbridge, MA 01262

19 Yale Hill Rd, Stockbridge, MA 01262

/28
$799,000 Pending
- 3 Beds
- 2 Baths
- 1,773 Sq Ft
11 Prospect Hill Rd Unit 1, Stockbridge, MA 01262

This 3 Bedroom, 2 Bath unit on the historic grounds of Oronoque Estate checks off all the boxes. Only 14 units in complex, this Villa offers one floor living, attached garage, high ceilings, recently renovated natural cherry custom cabinetry, walk in shower in primary bath, low Stockbridge taxes, propane heat, central air conditioning, wood burning fireplace. Two guest bedrooms, a screened in

Susan Baum BERKSHIRE HOMES AND CONDOS

11 Prospect Hill Rd Unit 1, Stockbridge, MA 01262

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