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 Lahey Crossroad -- Stockbridge MA 01262

Price$1,589,000

Est. Mortgage: $/month

Pending

MLS Number 225660

  • Single Family
  • Village Berkshire - South
  • Year Built 1992
  • Parking Spaces 2
  • Bedrooms 5

Total privacy on 22 acres. Within a couple of miles you will find fresh baked bread, a pub, the Norman Rockwell Museum, the Berkshire Botanical Garden and Chesterwood. Within 6 or 7 miles you'll be at the boat ramp at Stockbridge Bowl, Kripalu Yoga Center, Tanglewood and downtown Great Barrington. A wonderful setting with mature trees, landscaped gardens, extensive stonework and in-ground pool. Southwest and southeast VIEW sheds to Mt. Everett and Beartown Mt. have been professionally laid out for clearing. The house is gorgeously designed and crafted with exceptional attention to detail and quality. Great flexibility with the 1,500 sq. ft. guesthouse/studio/office. Take a stroll through this FABULOUS place to live at https://berkshire3dsolutions.com/3d-model/1-lahey-crossroad/skinned/

Listed by STONE HOUSE PROPERTIES, LLC

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Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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60 Mahkeenac Rd Stockbridge MA 01262

Price$1,495,000

Est. Mortgage: $/month

MLS Number 225082

  • Single Family
  • Village Berkshire - South
  • Year Built 1955
  • Parking Spaces 3
  • Bedrooms 4

The Perfect Trio! Privacy, Stunning Views and Waterfront Access. This contemporary country home was originally designed and built in 1955 by renowned architect John Johansen. Named ''The McNiff House'', it is perched atop a rolling meadow overlooking Stockbridge bowl on nearly 10 acres including its very own 0.07 acre waterfront property just a mere 800 feet across the road. A perfect place to launch your kayak or relax along the shore. With nearly 3,000 square feet, this home features expansive windows looking out to a picturesque view, a first-floor master suite, 2 additional main floor bedrooms and bath, and a bright lower level bonus room.

Listed by LANCE VERMEULEN RE, INC., LENOX

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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 Stone Hill Rd Stockbridge MA 01262

Price$1,490,000

Est. Mortgage: $/month

MLS Number 224975

  • Single Family
  • Village Berkshire - South
  • Year Built 2001
  • Parking Spaces 2
  • Bedrooms 5

Stockbridge contemporary with a BIG western view from every room masterfully combining architecture with nature. The moment you enter this ''comfort house'' you are immediately drawn to the panoramic view of the Berkshire Hills. The main level living with an expansive open floor plan, dramatic cathedral ceiling w/exposed beams & fp in Great Room flow beautifully to the dining/kitchen; all w/direct access to the spacious screened porch & stone patio making this a perfect home for entertaining. Separate wing for the MB en suite offers complete privacy from the guest BR's en suite. Site specific architecture of this home has captured the skyline of the Berkshires & offers the owner the opportunity to live in the moment from every vantage point in this special home minutes from Tanglewood!!

Listed by COHEN & WHITE ASSOCIATES

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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$1,390,000

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 MCLEAN REALTORS

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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 of MCLEAN REALTORS

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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 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: 4.28% last updated on Mar 21, 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$1,100,000

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: 4.28% last updated on Mar 21, 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$995,000

Est. Mortgage: $/month

MLS Number 224797

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

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. Pontoon negotiable. Sold As Is.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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$898,000

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 WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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 Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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: 4.28% last updated on Mar 21, 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: 4.28% last updated on Mar 21, 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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