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!

82 Interlaken Stockbridge MA 01262

Stockbridge, MA82 Interlaken Rd

Price$3,500,000

Est. Mortgage: $/month

Pending

MLS Number 222056

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,000
  • Acreage 11.11

Rare waterfront opportunity on the stockbridge bowl: a paradise for your family. 11 acres on the beautiful bowl. Over 400 feet of pristine lake frontage looking across the ''belly'' of the bowl. Two beautiful site specific modern style plans have been drawn with walls of windows from every room facing the lake. Amazing mountain and water views in every season. Build one private home or a family compound. Three home sites with existing structure for rare opportunity to have your dream home within 71 feet of the lake. Minutes to tanglewood, kripalu, and canyon ranch.

Listed by Maureen White Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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82 Interlaken Stockbridge MA 01262

Stockbridge, MA82 Interlaken Rd

Price$3,500,000

Est. Mortgage: $/month

Pending

MLS Number 221640

  • Land
  • Acreage 11.11

Rare opportunity: 11 acres on the beautiful stockbridge bowl. Over 400 feet of pristine lake frontage across the ''belly'' of the bowl. Amazing mountain and water views in every season. Build one private home or a family compound. Three home sites with existing structure for possible rare opportunity to have your dream home within 71 feet of the lake. Minutes to tanglewood, kripalu, and canyon ranch.

Listed by Maureen White Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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82B Interlaken Stockbridge MA 01262

Stockbridge, MA82B Interlaken Rd

Price$2,400,000

Est. Mortgage: $/month

Pending

MLS Number 222057

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,500
  • Acreage 4.86

Rare waterfront opportunity: a summer paradise for your family. Build your dream home. There are beautiful renderings of possibilities on this nearly 5 acres on the beautiful stockbridge bowl. Over 300 feet of pristine lake frontage. Amazing mountain and water views in every season.Shared driveway in place. Rare opportunity to have your dream home within 71 feet of the lake. Minutes to tanglewood, kripalu, and canyon ranch.

Listed by Maureen White Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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36 Main Stockbridge MA 01262

Stockbridge, MA36 Main St

Price$2,200,000

Est. Mortgage: $/month

MLS Number 233139

  • Residential
  • Bathroom 6
  • Bedrooms 2
  • Square Feet 6,392
  • Acreage 0.25

Main street stockbridge historic property - home to williams & sons country store and the picturesque shops in ''the mews'', this building is an adored piece of stockbridge's historic downtown landscape, and one of the few featured in norman rockwell's world renowned 1967 painting - stockbridge main street at christmas. With a total of 10 units, including a well established restaurant, six retail spaces, two apartments, and one office, this property provides consistent and profitable income with a flexible layout. Two of the retail spaces have main street entrances, while the other four and the restaurant are accessed from the mews. With direct access from the mews to the courtyard of the red lion inn, these retail shops have plenty of foot traffic throughout each season.

Listed by Katie Williams of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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36 Main Stockbridge MA 01262

MLS Number 233140

  • Commercial
  • Acreage 0.25

Main street stockbridge historic property - home to williams & sons country store and the picturesque shops in ''the mews'', this building is an adored piece of stockbridge's historic downtown landscape, and one of the few featured in norman rockwell's world renowned 1967 painting - stockbridge main street at christmas. With a total of 10 units, including a well established restaurant, six retail spaces, two apartments, and one office, this property provides consistent and profitable income with a flexible layout. Two of the retail spaces have main street entrances, while the other four and the restaurant are accessed from the mews. With direct access from the mews to the courtyard of the red lion inn, these retail shops have plenty of foot traffic throughout each season.

Listed by Katie Williams of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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82C&D Interlaken Stockbridge MA 01262

Stockbridge, MA82C&D Interlaken Rd

Price$1,750,000

Est. Mortgage: $/month

Pending

MLS Number 221642

  • Land
  • Acreage 6.25

Rare building lot on the beautiful stockbridge bowl: beautiful open water frontage with views across the deep section of the bowl. Very special parcel. Building site perched above the lake to build your dream lake front home. There could be two homes on this site. Swimming, canoeing, boating, fishing from your waterfront. Very few parcels such as this will ever be available. Watch the josh billings from your own home. See concept schematics with the photos which are site specific for this lovely parcel. Over 100 feet of water frontage. More land available. Could be a lovely family compound.

Listed by Maureen White Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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44 Main Stockbridge MA 01262
Pending

MLS Number 228072

  • Commercial

Rare opportunity to own a berkshire landmark. Known as ''the antique shop'' in norman rockwell's main street painting, this iconic building is famous worldwide. Classic victorian style with acres of charm. 3 stories with on-site parking. 3 'main street' retail spaces, a large (and vacant) second floor residential/office space and an income producing third floor. Owned and well-maintained by the same family since the 1960's and steps away from the red lion inn and former ''alice's restaurant''. Minutes to tanglewood and all berkshire attractions. Ideal for investment, office, residential or retail use. A true 'once in a life-time opportunity' to be part of stockbridge history.

Listed by Maggie C Merelle and Steven J. Weisz of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

44 Main Stockbridge MA 01262

Stockbridge, MA44 Main St

Price$1,500,000

Est. Mortgage: $/month

Pending

MLS Number 228073

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 8,770

Rare opportunity to own a berkshire landmark. Known as ''the antique shop'' in norman rockwell's main street painting, this iconic building is famous worldwide. Classic victorian style with acres of charm. 3 stories with on-site parking. 3 'main street' retail spaces, a large (and vacant) second floor residential / office space and an income producing third floor. Owned and well-maintained by the same family since the 1960's and steps away from the red lion inn and former ''alice's restaurant''. Minutes to tanglewood and all berkshire attractions. Ideal for investment, office, residential or retail use. A true 'once in a life-time opportunity' to be part of stockbridge history.

Listed by Steven J. Weisz and Maggie C Merelle of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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47 Main Stockbridge MA 01262
Pending

MLS Number 228609

  • Commercial
  • Acreage 0.32

Rated #2 in the country in 2018 and #16 in the world, seasons on main is a nationally recognized top rated 1862 greek revival b&b in the center of stockbridge and has been lovingly restored to its original grandeur and maintained with the utmost care.This is your opportunity to own a turnkey business with a proven record of success, or to have as your own exquisite homestead.

Listed by Cortney K Dupont and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

47 Main Stockbridge MA 01262

Stockbridge, MA47 Main St

Price$998,500

Est. Mortgage: $/month

Pending

MLS Number 228608

  • Residential
  • Bathroom 7
  • Bedrooms 7
  • Square Feet 4,977
  • Acreage 0.33

What a beautiful home for today! Set in the heart of stockbridge -- that most gracious and iconic of berkshire towns -- ''seasons'' is a new england classic, a lovingly detailed, superbly renovated 1862 greek revival mansion, warm and welcoming. From the restful length of its shady porch to the elegantly appointed front parlor, from the serene formal dining room to its secluded bedroom retreats, ''seasons'' manages to both welcome the world, while offering friends and family a perfect refuge. This spectacular all-season ''getaway'' home, part 19th century, part 21st, generously arranged, with elegantly designed public rooms, and the pleasures of a spacious modern chef's kitchen with multi-zone air conditioning throughout. In perfect order, it's waiting for your fortunate family!

Listed by Cortney K Dupont and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

49 Main Stockbridge MA 01262

Stockbridge, MA49 Main St

Price$995,000

Est. Mortgage: $/month

MLS Number 233238

  • Residential
  • Bathroom 3
  • Bedrooms 6
  • Square Feet 3,289
  • Acreage 0.69

Gracious 1890 residence with carriage barn income property, graces the charming main street of stockbridge. The main house is comprised of 4 bedrooms, double parlors w/fireplace, formal dining room, country kitchen and the most delightful screened porch. An attached 2 bedroom apartment with separate entrance, is ideal for extended family and guests. Distanced from the main house by a circular drive, the converted carriage barn sets behind, housing three apartments. Mature landscaping, perennial gardens, stone patios, and a 3 bay garage complete this idyllic compound. Red lion inn, stockbridge golf club and theatre nearby.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

49 Main Stockbridge MA 01262

Stockbridge, MA49 Main St

Price$995,000

Est. Mortgage: $/month

MLS Number 233240

  • MultiFamily
  • Acreage 0.69
  • Year Built 1821

A gracious main street property with four rental apartments, a main house with four bedrooms, double parlors, country kitchen, two full baths, a wonderful screened porch and a three bay garage. The yard has wonderful out door spaces for the residents, and all a short walk to everything the town offers. Perfect for an investor owner occupier.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of February 27, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.