Stockbridge Real Estate

Stockbridge is the quintessence of small-town New England charm, untainted by large-scale development. It is also the blueprint for small-town America as represented on the covers of the Saturday Evening Post by painter Norman Rockwell (the official state artist of Massachusetts). From 1953 until his death in 1978, Rockwell lived in Stockbridge and painted the simple charm of its buildings and residents. James Taylor sang about the town in his hit "Sweet Baby James," as did balladeer Arlo Guthrie in his famous Thanksgiving anthem "Alice's Restaurant," in which he tells what ensued when he tossed some garbage out the back of his Volkswagen bus down a Stockbridge hillside.

Search new real estate in the Berkshires town of Stockbridge, MA. Discover hundreds of current listings, including single-family homes, luxury estates, and residential land. Love what you see? Register with us to save your favorites, and receive notifications when similar properties are listed. Contact us to see any of the homes below!

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1 Lakeview Dr Stockbridge MA 01262

Price$1,255,000

Est. Mortgage: $/month

MLS Number 225962

  • Single Family
  • Village Berkshire - South
  • Year Built 2018
  • Bedrooms 4
  • Bathroom 3

This striking lakefront home offers privacy, contemporary design, and an open floor plan allowing for casual Berkshire living. An abundance of windows allows for natural light and picturesque views of the Stockbridge Bowl landscape. The cook's delight kitchen is perfect for easy entertaining and is equipped with soapstone countertops, a center island for hanging out, and a spacious pantry. The screened porch off the kitchen is the perfect respite to enjoy summer evenings while taking in the evening sunset. Kayakers will love the convenience of launching right off the back yard and paddling to the island and around the beautiful 372 acre Lake Mahkeenac. Beachwood is a wonderful community and allows access to the private Beachwood sandy beach. Be in for summer!

Listed by STONE HOUSE PROPERTIES, LLC

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Devon Rd Stockbridge MA 01262

MLS Number 225935

  • Commercial
  • Village Berkshire - South
  • Square Feet 4,952
  • Bedrooms 6
  • List Date 02/08/2019

House, 6 Bedrooms, 5.5 Baths, (Sleeps 12 in beds)The General Williams house is located 2 miles from Stockbridge Center and 5 miles from Lenox Center. Only 7 miles from the Mass Pike it is an easy commute from Boston or New York City. The house has 8 foot ceilings and provide a nice 'vacation' like feel with every bedroom but one having its own bath. The common areas are designed for fun and socializing with family and friends.The 6 fireplaces provide ambiance and a feeling of escape into a time long forgotten. Play a game of pool, chess or checkers with your family. Enjoy two kitchens in which to work from, sit together at the 12 person dining area while enjoy a fire in the large hearth as you drink your wine and soak in the feeling of the Berkshires. This home has it all and it is

Listed by PAULA MCLEAN REALTORS INC.

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Devon Rd Stockbridge MA 01262

Price$1,200,000

Est. Mortgage: $/month

MLS Number 223275

  • Single Family
  • Village Berkshire - South
  • Year Built 1795
  • Bedrooms 6
  • Bathroom 6

The Historic General Williams House circa 1795, has been lovingly restored and improved and now provides modern day comfort in quintessential Stockbridge MA. Featuring 6 inviting bedrooms, 5.5 modern baths, 6 elaborate wood burning fireplaces, two cook's kitchens, spacious dining and living areas, a sparkling new in-ground pool and separate ''Ice House'' that is ideal for group gatherings with it's own kitchen and full bath. Ideally situated on 4 acres this delightful residence is only 2 miles from Rockwell's famous Stockbridge Main Street and only 5 miles to Lenox township and Tanglewood Music Center. Bask in the Berkshire sunshine poolside, invite friends to chat on one of the stone terraces, or simply rock the afternoon away on a tree top porch.One can enjoy this grand property as a

Listed by Paula McLean of PAULA MCLEAN REALTORS INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Main St Stockbridge MA 01262

Price$995,000

Est. Mortgage: $/month

MLS Number 223362

  • Single Family
  • Village Berkshire - South
  • Year Built 1825
  • Parking Spaces 2
  • Bedrooms 4

One Main Street, Stockbridge features not only one of the most evocative addresses in America but also one of the finest golf course locations in Berkshire County. Ideally situated adjacent to the 2nd green of the Stockbridge Golf Course with no immediate neighbors this lovely historic colonial home is private yet convenient to everything. Stroll up Norman Rockwell's Main Street for coffee or a cocktail on the porch of the Red Lion Inn. Walk to the clubhouse or the tennis courts of the Stockbridge Golf Club. Minutes to Tanglewood. Four bedrooms, four and one half baths. Tastefully decorated throughout. Large private flat yard with plenty of room for a pool or gardening. Truly a unique opportunity.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28 Ice Glen Rd Stockbridge MA 01262

Price$949,000

Est. Mortgage: $/month

MLS Number 226968

  • Single Family
  • Village Berkshire - South
  • Year Built 1997
  • Bedrooms 3
  • Bathroom 4

Big Views, Privately Sited, and Dramatic Sunsets. It's easy to enjoy the beautiful approach on scenic Ice Glen Road to this nicely maintained home. The floor plan is open and comfortable and allows for one level living and most rooms enjoy the spectacular western views. Gourmet kitchen with high end appliances, including a Wolf cooktop and Bosch oven and dishwasher. Spacious living/dining with gas fireplace and sliding doors to the deck which overlooks the swimming pool and landscaped grounds and takes in the big views. A lovely, spacious solarium, which also opens to the deck is a wonderful room to enjoy all seasons. The lower level is finished with 2 bedrooms, yoga/exercise room/kitchenette and an easy walk out to the grounds. Great location, mid-way between Great Barrington and Lenox!

Listed by Lori Rose of STONE HOUSE PROPERTIES, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4 Cove Ln Stockbridge MA 01262

Price$899,000

Est. Mortgage: $/month

Pending

MLS Number 224797

  • Single Family
  • Village Berkshire - South
  • Year Built 1939
  • Bedrooms 3
  • Bathroom 1

Price reduced! A once in a lifetime opportunity to own a slice of paradise. Privately situated on a peninsula in the heart of Beachwood on the Stockbridge Bowl boasting a stunning 90 feet of lake frontage and dock. Unobstructed sunrise and sunset views over the water. The rustic cabin dates from 1939 and has a double volume living/dining room graced by a charming stone fireplace and views of the garden and the lake. Bonus enclosed sitting room/study off the living room. The cabin has been updated with modern amenities such as a custom Blue Star Prof. range, and split-system air-conditioning/heating. 3 bedrooms and 1 bathroom. Sensitively landscaped easy-to-maintain garden with River Birch and Black Walnut trees and 2 separate stone patio dining areas. Outdoor shower. Sold As is.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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29 Mahkeenac Rd Stockbridge MA 01262

Price$875,000

Est. Mortgage: $/month

MLS Number 220219

  • Single Family
  • Village Berkshire - South
  • Year Built 1969
  • Bedrooms 3
  • Bathroom 3

Stunning 3BR contemporary located in desirable Mahkeenac Terrace Stockbridge Bowl lake community. Deeded lake & boat access. Huge master suite, spacious great room with cathedral ceiling and loads of sunlight, 3 gas fireplaces. Large backyard w/ in-ground exercise pool, patio w/ built-in bbq. Less than 5 minutes to Tanglewood & close to the Berkshires' best cultural & recreational attractions. The ultimate year round country home. Don't miss this lake-living gem!

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Laurel Ln Stockbridge MA 01262

Price$799,000

Est. Mortgage: $/month

MLS Number 221790

  • Single Family
  • Village Berkshire - South
  • Year Built 1900
  • Bedrooms 5
  • Bathroom 6

One of a kind opportunity in Stockbridge!! This gracious colonial features 3800+ sq ft. Integrated living spaces work nicely for entertaining with formal living, dining, parlor and a large country kitchen. Fueled with natural gas. Accommodate family and guests with 5 BRs and 5.5 BAs; finished 3rd floor game room. Take in this .69 acre property from the large screened porch - rare to a village home. A private tranquil site with a easy stroll into town and abuts town trails leading to Ice Glen and Laura's Tower.

Listed by ROBERTS & ASSOC. REALTY, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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13 Park St Stockbridge MA 01262

Price$798,000

Est. Mortgage: $/month

MLS Number 226095

  • Multi-Family
  • Village Berkshire - South
  • Acreage 0.15
  • Bedrooms 9
  • Square Feet 4,863

Outstanding opportunity to own a fully rented 5-unit multifamily rental property in the heart of downtown Stockbridge. Electric is submetered. New boiler installed 4 years ago. Ideally located - walk to everything! Only 1 block from post office, library, restaurants, shopping & Red Lion Inn. Building is also across the street from Stockbridge Town Park & Housatonic River and great hiking trails are right down the block. For financials, please call listing agent.

Listed by Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28 Lake Dr Stockbridge MA 01262

Price$775,000

Est. Mortgage: $/month

MLS Number 224453

  • Single Family
  • Village Berkshire - South
  • Year Built 1971
  • Bedrooms 3
  • Bathroom 2

STOCKBRIDGE....Live in this unique modernized country style log house, located with a direct access dock on the Stockbridge Bowl outlet. Huge picture windows in most rooms frame woods and water views. This delightful year-round home with a 2 sided open fireplace, has a spacious country kitchen featuring a BBQ grill set in the fireplace and a large kitchen for family dining, plus 3 bedrooms and a 4th bedroom/office. Close to Tanglewood, ski areas, and Lenox, with bike and hike areas nearby.Come see the house of your dreams. Come see Shangri Log

Listed by COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5 Dugway Rd Stockbridge MA 01262

Price$698,000

Est. Mortgage: $/month

MLS Number 226405

  • Single Family
  • Village Berkshire - South
  • Year Built 2001
  • Parking Spaces 1
  • Bedrooms 4

Built in 2002, this beautiful contemporary home located on a quiet country lane in Stockbridge is ready for you to enjoy. Enter the foyer, hang up your coat and settle in. Relax by the fire in the beautiful great room with cathedral ceiling and beautiful two-story stone-clad chimney. When it's cold out, drive into your attached garage and enter through the kitchen with your groceries. Just behind the fireplace is the master bedroom suite with a lovely bathroom including double sinks, a large jet tub and tiled shower with dual shower heads. There's plenty of room for family and friends upstairs with three bedrooms, two full baths and ample closet and storage space. Utilities are located in the garage and easily accessible. Close to everything Berkshire... This is a must see property!

Listed by LANCE VERMEULEN RE, INC., LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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29 Rattlesnake Mountain Rd Stockbridge MA 01262

MLS Number 226727

  • Single Family
  • Village Berkshire - South
  • Year Built 1978
  • Bedrooms 4
  • Bathroom 3

Live in true Berkshires splendor with magnificent mountain views! This contemporary 3 bedroom has it all. Open floor plan with loads of sunlight, gourmet kitchen &large deck for entertaining. Level property with tranquil meadows. Ideally located within walking distance to Tanglewood & Stockbridge Bowl town beach. Very close to vibrant downtown Lenox & so many of the Berkshires' world class cultural attractions. Don't miss this gem!

Listed by Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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