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!

14 Stone Hill Stockbridge MA 01262

Stockbridge, MA14 Stone Hill Rd

Price$3,995,000

Est. Mortgage: $/month

MLS Number 233847

  • Residential
  • Bathroom 7
  • Bedrooms 7
  • Square Feet 6,623
  • Acreage 18.25

A one-of-a-kind stockbridge luxury home. Mansion design. Every room features quality touches throughout. The living room/great room boasts two fireplaces and terrific exterior views from expansive decorative windows. The first floor master bedroom suite includes a very comfortable sitting room and a state-of-the art master bath. Conveniently placed off the master bedroom on the nearby deck is a wonderful gunite-lined hot-tub. The formal dining room boasts a fireplace along with impressive exterior views. The spacious eat-in kitchen features top-of-the-line appliances neatly positioned amongst attractive custom cabinetry. Leave the kitchen, go out and notice the delightful gunite heated pool with its attractive waterfall feature. While outside, also notice the perennial gardens

Listed by George Cain of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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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17 Mahkeenac Stockbridge MA 01262

Stockbridge, MA17 Mahkeenac Terr

Price$3,900,000

Est. Mortgage: $/month

MLS Number 233678

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,456
  • Acreage 0.59

Stockbridge bowl waterfront....Work from home and make this summer one long staycation in this meticulously maintained lakeside property. Three levels of living in move-in contemporary spaces, all with western exposure and panoramic view across the lake, make this the perfect berkshire location only minutes to tanglewood and the villlage of lenox. Enjoy the lake from the great outdoor spaces, have dinner on the patio, take an after dinner ride in your boat from your own private dock and end the evening down by the lake watching the sunset over the water......It doesn't get much better than that!!

Listed by Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES

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%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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 BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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 - GT BARRINGTON

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$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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 - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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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17 Wheatley Stockbridge MA 01262

Stockbridge, MA17 Wheatley Dr

Price$1,999,000

Est. Mortgage: $/month

MLS Number 233668

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 2,899
  • Acreage 5.09

Imagine a light filled contemporary home, located on an admired and private country road, with serene waterfrontage on the quintessential lily pond. Include deeded beach rights to stockbridge bowl, your own private tennis court and all of this within walking distance to tanglewood. Time to stop imagining and make this your forever place in the beautiful berkshires. Walls of glass invite the great outdoors within, custom kitchen with wolf & sub zero appliances, private baths for every bedroom, central a/c and 5 acres of peace and serenity to experience and create memories with friends and family for years to come. Hoa fee is annual at $1000 approx

Listed by Paula J. McLean of PAULA MCLEAN REALTORS INC.

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$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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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14 Pine Stockbridge MA 01262

MLS Number 234020

  • Commercial
  • Acreage 0.49

Completely renovated building steps to the center of stockbridge ! Lower level offers 3,000 available square feet for many potential uses! This space could be your own luxury living space walking distance to town, office space for your own use, or to generate additional income. So many possibilities. Incredible income history. All three apartments fully rented as well as main level space. Parking sufficient for up to 25 cars. All units have separate heat and electricity. Everything in this building has been renovated from top to bottom. All mechanicals also updated. Nothing to do but enjoy the building and the income that it provides !

Listed by Tanya Shepardson of RE/MAX COMPASS

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$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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 BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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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13 Wheatley Stockbridge MA 01262

Stockbridge, MA13 Wheatley Dr

Price$1,200,000

Est. Mortgage: $/month

MLS Number 233917

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,400
  • Acreage 4.2

Gorgeous water's edge views of lily pond from this privately set contemporary ranch with finished walk out lower level. Walk to tanglewood and enjoy deeded rights to a private stockbridge bowl beach. Inside find updated kitchen and baths, two wood burning fireplaces for cozy winter nights. This setting simply can't be beat on a private and admired country lane. Enjoy one level living with lower level guest quarters. Property can be sold fully furnished.

Listed by Paula J. McLean of PAULA MCLEAN REALTORS INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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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2 Brookside Stockbridge MA 01262

Stockbridge, MA2 Brookside Ln

Price$1,195,000

Est. Mortgage: $/month

MLS Number 232160

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,980
  • Acreage 3.33

Magnificent contemporary in spectacular setting. This move-in ready home has it all! Sun filled living room w/ double height, cathedral ceilings & floor to ceiling windows, great room that opens to a 4 season, enclosed, heated porch plus a large outdoor deck, perfect for entertaining friends. 1st floor also includes large first floor master suite w/ luxurious master bath & a state-of-the-art, open chef's kitchen. 2 spacious bedrooms upstairs plus an office. Fully finished, walk-out lower level w/ bedroom & full bath. Beautifully manicured grounds w/ mature plantings, lush lawns & waterfall. Deeded access to pvt. Dock on stockbridge bowl, just across the road - perfect for a kayak or paddleboard. Plus, additional deeded rights to private beachwood beach, just a short walk away.

Listed by Marc Bachman of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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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27 Church Stockbridge MA 01262

Stockbridge, MA27 Church St

Price$1,095,000

Est. Mortgage: $/month

MLS Number 233634

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,250
  • Acreage 0.58

Beautifully renovated, spacious antique home on over half an acre, with river and golf course views, and within easy walking distance of historic stockbridge. This home offers four bedrooms and three full baths and is the perfect home for a family or couple looking to escape the city. The location is minutes from tanglewood and allows for easy travel to all the berkshires has to offer.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.98% last updated on Apr 29, 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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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: 2.98% last updated on Apr 29, 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 May 6, 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.