Berkshire, MA Homes

/40
$1,795,000
- 4 Beds
- 3 Baths
- 5,469 Sq Ft
17 East St, Lenox, MA 01240

Nestled just north of Stockbridge, MA, this elegantly expanded brick Federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) Originally built in the 1830s, the Carter Estate has been artfully expanded and renovated and boasts over 5,400sf of light-filled, luxurious living space, ideal for those seeking a private yet gracious lifestyle.As you

Selina Lamb

BIRCH PROPERTIES

(413) 300-6860

17 East St, Lenox, MA 01240
/17
$12,500 per month
- 3 Beds
- 2 Baths
- 1,861 Sq Ft
- House for Rent
5 Beachwood Dr, Stockbridge, MA 01262

Delightful, classic Berkshires summer cottage in the Beachwood enclave. Shares in gorgeous community beach at south end of the Stockbridge Bowl (Lake Mahkeenac.) Enjoy swimming, kayaking, etc. Minutes to Tanglewood and all the cultural delights of the Berkshires. 3BR including primary suite with bath. 1 Queen BR, 1 Br with double bunk beds. Fantastic large screened porch with dining. LR with

Selina Lamb

Birch Properties

(413) 610-3637

5 Beachwood Dr, Stockbridge, MA 01262
/52
$975,000 Sold Jul 25, 2025
- 2,010 Sq Ft
- $485/SF
- 10 Days On Market
- 4 Beds
- 3 Baths
- Built 1948
66 Interlaken Rd, Stockbridge, MA 01262

Handsome redesign and total renovation in 2017. Living space all on one convenient level. Light bright interior. Well-designed kitchen opens to the great room with cathedral ceiling, fireplace and access to the three-season porch. Primary suite privately set at one end of the house and additional 3 bedrooms and 2 baths (1 ensuite) at the other end of the house. Den. Beautiful wood floors.

Sheila Thunfors STONE HOUSE PROPERTIES, LLC

66 Interlaken Rd, Stockbridge, MA 01262

/36
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,269 Sq Ft
4 Lee Rd, Lee, MA 01238

4 Lee Rd, Lee, MA 01238

/6
$425,000
- Land
- 3.30 Acres
- $128,788 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

Birch Properties

(413) 343-5283

9 Wheatleigh Dr, Stockbridge, MA 01262
/40
$660,000 Sold Jul 10, 2025
- 1,853 Sq Ft
- $356/SF
- 133 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1988
176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262

Some of the best views the Berkshires have to offer. One of the ''Great Estates'' conversions, Winden Hill condos are in Stockbridge, but within 1.5 miles of downtown Lenox and a short drive to Tanglewood. Located in the Smith building - this unit features 2 bedrooms each with private bath. Easy entertaining in the great room with fireplace and vaulted ceiling. French door leads to the

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

176 Old Stockbridge Rd Unit Smith 2, Stockbridge, MA 01262

/27
Est $558,038 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,132 Sq Ft
14 Interlaken Rd, Stockbridge, MA 01262

14 Interlaken Rd, Stockbridge, MA 01262

/6
$425,000
- Land
- 3.30 Acres
- $128,788 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

BIRCH PROPERTIES

(413) 722-5098

9 Wheatleigh Dr, Stockbridge, MA 01262
/34
$885,000 Sold Jun 30, 2025
- 2,189 Sq Ft
- $404/SF
- 17 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1996
3 Willard Hill Rd, Stockbridge, MA 01262

LIGHT-FILLED CONTEMPORARY CAPE on a premier road in the historic Interlaken section of Stockbridge. The open-concept first floor includes a living area with a wood-burning fireplace, dining area with a glass door leading to a large deck, and a recently remodeled kitchen. A half bath and a primary bedroom suite with a full bath complete the first floor. Upstairs, is a second primary suite with a

Tom Lynch COMPASS MASSACHUSETTS , LLC GB

3 Willard Hill Rd, Stockbridge, MA 01262

/25
Est $625,912 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,560 Sq Ft
31 Glendale Rd, Stockbridge, MA 01262

31 Glendale Rd, Stockbridge, MA 01262

/6
$650,000
- Land
- 19 Acres
- $34,211 per Acre
0 Mohawk Lake Rd, Stockbridge, MA 01262

Discover a rare opportunity to own a piece of history in Stockbridge, available for the first time in over 120 years. This stunning land offers a private setting perfect for building your dream home, while being just moments away from the renowned Norman Rockwell Museum, Chesterwood, the enchanting Berkshire Botanical Gardens, and the charming downtown Stockbridge, all within a 3-mile radius.

Gary Fuls Jr

RE/MAX TRANSITIONS

(413) 884-5511

0 Mohawk Lake Rd, Stockbridge, MA 01262
/3
$600,000 Sold Jun 25, 2025
- Land
- 35 Acres
- $17,109 per Acre
- 76 Days On Market
0 Interlaken Cross Rd, Stockbridge, MA 01262

Large parcel of land centrally located on a quiet road in Stockbridge. Minutes to the town centers of Stockbridge, Lenox, and West Stockbridge, as well as Tanglewood, Kripalu, the Norman Rockwell Museum, and the Berkshire Botanical Gardens. It is also walking-distance to the Stockbridge Bowl outlet and the Berkshire Art Center.The land is mostly wooded, level, and dry with some open areas. Town

Carole Murko BOULDERWOOD GROUP

0 Interlaken Cross Rd, Stockbridge, MA 01262

/42
Est $820,789 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,014 Sq Ft
16 Interlaken Rd, Stockbridge, MA 01262

16 Interlaken Rd, Stockbridge, MA 01262

/5
$998,000
- Land
- 9 Acres
- $109,670 per Acre
19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

RARE LUXURY: READY-to-BUILD MODERNIST RETREAT on EXCLUSIVE PRIVATE POND minutes to TANGLEWOODWelcome to a once-in-a-lifetime opportunity in the heart of the Berkshires. Set on 9.1 acres approximately acres of pristine land, this exceptional estate parcel offers frontage on tranquil Lily Pond, a private, non-motorized body of water that ensures peace, privacy, nature and views. Comprising the

Selina Lamb

BIRCH PROPERTIES

(413) 343-4919

19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
/12
$371,000 Sold Jun 18, 2025
- 837 Sq Ft
- $443/SF
- 57 Days On Market
- 1 Bed
- 1 Bath
- Built 1850
57 Main St Unit 10, Stockbridge, MA 01262

Beautiful first floor condo that has been rehabbed. This beautiful Knoll Condominium is walk to town in a beautiful lovely setting. Lots of natural light in this unit and it so charming , Laundry room and storage area in the building, Perfect location if you like to walk to the Red Lion Inn and downtown. Close to all the Berkshire attractions. No Pets

Kathleen Hopkins CARRIAGE HOUSE REAL ESTATE

57 Main St Unit 10, Stockbridge, MA 01262

/26
Est $670,849 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,912 Sq Ft
38 Interlaken Rd, Stockbridge, MA 01262

38 Interlaken Rd, Stockbridge, MA 01262

/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
/77
$3,700,000 Sold May 30, 2025
- 2,882 Sq Ft
- $1284/SF
- 4 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2011
25 Mahkeenac Terrace, Stockbridge, MA 01262

Nestled on the shores of the legendary Stockbridge Bowl, this immaculate contemporary lakefront home offers a perfect blend of casual luxury & tranquility. Ideally located moments from Tanglewood & the quintessential Berkshire towns of Lenox & Stockbridge. Cathedral height windows frame breathtaking, unobstructed views of the lake & the majestic Berkshire Hills creating a seamless harmony of

Gary Lazarus COMPASS MASSACHUSETTS , LLC GB

25 Mahkeenac Terrace, Stockbridge, MA 01262

/28
Est $920,140 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,459 Sq Ft
6 Interlaken Rd, Stockbridge, MA 01262

6 Interlaken Rd, Stockbridge, MA 01262

/55
$1,675,000
- 4 Beds
- 2 Baths
- 2,200 Sq Ft
5 Glendale Rd, Stockbridge, MA 01262

Two Dwellings on almost four acres.Just a very special property. Located between the Rockwell Museum and the Botanical Garden. You are moments from Tanglewood. Equidistant from Lenox and Great Barrington providing easy access to the Berkshires wonderful restaurants. The main house has four bedrooms and two baths , while the guest cottage adds another bedroom, bath, and large living room. The

Martha Piper THE KINDERHOOK GROUP - PITTSFIELD

5 Glendale Rd, Stockbridge, MA 01262
/11
$375,000 Sold May 28, 2025
- Land
- 1.50 Acres
- $250,000 per Acre
- 16 Days On Market
14 Partridge Way, Stockbridge, MA 01262

A rare opportunity to own a 1.5-acre parcel on a quiet road in the highly sought-after Beachwood community, available only once in many decades. This property is ideally located in a peaceful, nature-filled setting with deeded rights to the Stockbridge Bowl, and is just minutes from the private Beachwood beach and swimming area and is connected to town sewer. It's also conveniently close to

Gary Lazarus COMPASS MASSACHUSETTS , LLC GB

14 Partridge Way, Stockbridge, MA 01262

/15
Est $640,279 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,430 Sq Ft
58 Interlaken Rd, Stockbridge, MA 01262

58 Interlaken Rd, Stockbridge, MA 01262

/50
$2,250,000
- 4 Beds
- 4 Baths
- 2,738 Sq Ft
8 Yale Hill Rd, Stockbridge, MA 01262

A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

8 Yale Hill Rd, Stockbridge, MA 01262
/18
$180,000 Sold Apr 25, 2025
- 2,700 Sq Ft
- $67/SF
- 14 Days On Market
- 6 Beds
- 2 Baths
- Built 1858
3 Apple St, Stockbridge, MA 01236

Property is being sold in AS IS condition. Charming 1850s Two-Family Home on a Quiet Dead-End Street - A Rare Berkshire Opportunity! Nestled in a peaceful Housatonic neighborhood, this historic fixer-upper offers incredible potential for homeowners and investors alike. Built in the 1850s, it's ideal for those seeking a homestead, rental income, or private retreat. Set on a quiet lot with room to

John Segalla HOUSATONIC REAL ESTATE

3 Apple St, Stockbridge, MA 01236

/16
Est $552,955 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,162 Sq Ft
72 Interlaken Rd Unit 1, West Stockbridge, MA 01266

72 Interlaken Rd Unit 1, West Stockbridge, MA 01266

/16
$1,800,000
- 40 Beds
- 20 Baths
- 30,000 Sq Ft
15 East St, Stockbridge, MA 01262

Located in a Sngle Family zoned area on a desirablle, private parcel consisting of nine total buildings with an in-ground pool amongst other amenities. Property is available for sale, lease or equity investment by new partners. This is an amazing property on the border of Stockbridge and Lenox with close proximity to Albany / Hartford / I-91. Many opportunities for possible hotel, B&B, family

Tim Damon Mercury Real Estate

15 East St, Stockbridge, MA 01262
/51
$1,300,000 Sold Apr 03, 2025
- 2,548 Sq Ft
- $510/SF
- 5 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1995
5 Wheatleigh Dr, Stockbridge, MA 01262

THE BERKSHIRE HOUSE YOU'VE BEEN LOOKING FOR IS NOW AVAILABLE!!! This Contemporary is minutes from Tanglewood and the Village of Lenox, private on 6+ acres overlooking Lily Pond and has deeded rights to a private beach on Stockbridge Bowl! An open Great Room of living/dining/kitchen with fireplace and a double volume wall of windows maximizes the view from every vantage and direct access to a

Cortney Dupont COHEN & WHITE ASSOCIATES

5 Wheatleigh Dr, Stockbridge, MA 01262

/30
Est $363,474 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,242 Sq Ft
1 Charles St, Dalton, MA 01226

1 Charles St, Dalton, MA 01226

/63
$1,100,000
- 4 Beds
- 3.5 Baths
- 2,861 Sq Ft
1 Train Hill Rd, Stockbridge, MA 01262

This Stockbridge Colonial has it all....location, separate guest suite and plenty of country chic design. This historic home boasts all the charm of yesteryear with fabulous wide pine floors, state of the art country kitchen that retains it's charm, formal dining room with fireplace, gracious banister to the second floor of guest bedrooms with renovated bath all while seamlessly blending with the

Cortney Dupont COHEN & WHITE ASSOCIATES

1 Train Hill Rd, Stockbridge, MA 01262
/5
$150,000 Sold Apr 03, 2025
- Land
- 21 Acres
- $7,096 per Acre
- 154 Days On Market
Unlisted Address

Beautiful lot located on a highly desirable street. Less than a mile from the town beach at Stockbridge Bowl ! Town sewer available on the street. Plenty of land to build your dream home and still have space for walking trails and ample acreage to enjoy all that nature has to offer.

Tanya Shepardson LAMACCHIA REALTY, INC

Unlisted Address

/41
Est $1,352,926 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 4,977 Sq Ft
47 Main St, Stockbridge, MA 01262

47 Main St, Stockbridge, MA 01262

/34
$1,295,000 Pending
- 4 Beds
- 2.5 Baths
- 2,511 Sq Ft
16 Glendale Middle Rd, Stockbridge, MA 01262

VINTAGE EYEBROW COLONIAL WITH VIEWS & A POST AND BEAM ADDITION. Updated and renovated open concept plan dripping with charm in pristine condition. 2013 addition by renowned builder David Lanoue. Systems updated at that time. Gorgeous wide pine flooring, a chef's kitchen with custom cabinets a Viking Range, a stone farmers sink with windows overlooking the beautiful view. 4 Bedrooms, 2.5 baths,

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

16 Glendale Middle Rd, Stockbridge, MA 01262
/17
$225,000 Sold Mar 24, 2025
- Land
- 10 Acres
- $21,635 per Acre
- 661 Days On Market
Unlisted Address

Prime Stockbridge land, prime Stockbridge location, and low Stockbridge taxes. A couple of short miles to Tanglewood in Lenox and a few minute drive to the Red Lion Inn in Stockbridge. Under a mile to Stockbridge public sandy beach on the Bowl. Includes drilled well already installed, septic design and roughed-in driveway. Excellent investment location for full or part-time

Gary Johnston STONE HOUSE PROPERTIES, LLC

Unlisted Address

/30
Est $529,013 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,409 Sq Ft
23 Church St, Stockbridge, MA 01262

23 Church St, Stockbridge, MA 01262

/64
$1,299,900 Pending
- 5 Beds
- 4 Baths
- 2,976 Sq Ft
44 Prospect Hill Rd, Stockbridge, MA 01263

Escape to incredible mountaintop views and woodland privacy on prestigious Prospect Hill Road, Stockbridge, in this contemporary treasure set on 7.43 secluded acres and minutes to Tanglewood, the Stockbridge Bowl, and all that is Berkshire. This exceptional five bedroom, four bath awe-inspiring home is a living art retreat, inviting you to own and experience nature's grandeur inside and out.

Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

44 Prospect Hill Rd, Stockbridge, MA 01263
/36
$1,550,000 Sold Mar 14, 2025
- 2,498 Sq Ft
- $620/SF
- 5 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2008
8 Bean Hill Rd, Stockbridge, MA 01262

Constructed in 2008, this contemporary New England classic offers a perfect balance of timeless charm and modern design. With high ceilings and abundant natural light, the home features an open, gracious floor plan that flows seamlessly, creating an inviting and airy ambiance throughout.The first-floor primary suite is a private retreat, thoughtfully designed for comfort and convenience. The

Selina Lamb BIRCH PROPERTIES

8 Bean Hill Rd, Stockbridge, MA 01262

/34
Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,610 Sq Ft
176 Old Stockbridge Rd Unit Smith 4, Stockbridge, MA 01262

176 Old Stockbridge Rd Unit Smith 4, Stockbridge, MA 01262

/70
$1,299,000 Pending
- 5 Beds
- 4 Baths
- 3,289 Sq Ft
49 Main St, Stockbridge, MA 01262

Improved stunning Stockbridge Village property that boasts an updated main house and includes a separate three apartment carriage house. The main property offers great natural light and ample common spaces that are gracious in size, updated lovely kitchen, five bedrooms, four baths, screened porch and inviting outdoor spaces. It has been thoughtfully updated while keeping the charm and character

Cortney Dupont COHEN & WHITE ASSOCIATES

49 Main St, Stockbridge, MA 01262
/12
$350,000 Sold Mar 03, 2025
- 872 Sq Ft
- $401/SF
- 25 Days On Market
- 2 Beds
- 1 Bath
- Built 1850
57 Main St Unit 4, Stockbridge, MA 01262

Wonderful SECOND-FLOOR unit at The Knoll! Located on Main Street, Stockbridge. The Knoll Condominiums have always been desired for the convenient walk to town location and lovely park-like setting. Light and bright with lots of windows. Comfortable living/dining area, charming galley kitchen and spacious bedrooms. Convenient laundry room and private storage area in the building. Tennis courts

Susan Calkins STONE HOUSE PROPERTIES, LLC

57 Main St Unit 4, Stockbridge, MA 01262

/34
Est $916,306 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,127 Sq Ft
25 Nielsen Ln, Lenox, MA 01240

25 Nielsen Ln, Lenox, MA 01240

Showing Results 1 - 40, Page 1 of 18

Massachusetts Berkshire County Stockbridge

Home Trends in Stockbridge, MA

On average, homes in Stockbridge, MA sell after 26 days on the market compared to the national average of 70 days. The median sale price for homes in Stockbridge, MA over the last 12 months is $1,900,000, up 274% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,900,000

Median Single Family Sale Price

$1,900,000

Median 2 Bedroom Sale Price

$425,000

Median 1 Bedroom Sale Price

$299,900

Average Price Per Sq Ft

$566

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

0.90

Median List Price

$1,795,000

Median Change From 1st List Price

-6%

Median Home Sale Price YoY Change

274%

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