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 Rd, Stockbridge, MA 01262

Price$3,500,000

Est. Mortgage: $/month

MLS Number 221640

  • Land
  • High School Monument Mountain
  • Village Berkshire - South
  • Square Feet 483,952
  • Waterfront 1

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 BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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 Rd, Stockbridge, MA 01262

Price$3,500,000

Est. Mortgage: $/month

MLS Number 222056

  • Single Family
  • Village Berkshire - South
  • Year Built 1959
  • Bedrooms 3
  • Bathroom 2

RARE WATERFRONT OPPORTUNITY ON THE STOCKBRIDGE BOWL: A PARADISE FOR YOUR FAMILY. Photo is a rendering. 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 Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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 Rd, Stockbridge, MA 01262

Price$2,400,000

Est. Mortgage: $/month

MLS Number 222057

  • Single Family
  • Village Berkshire - South
  • Year Built 1959
  • Bedrooms 4
  • Bathroom 4

RARE WATERFRONT OPPORTUNITY: A SUMMER PARADISE FOR YOUR FAMILY. Build your dream home. Photo is a rendering of a possibility on this nearly 5 acres on the beautiful Stockbridge Bowl. Over 300 feet of pristine lake frontage looking across the style plans have been drawn with walls of windows from every room facing the lake. Amazing mountain and water views in every season. Rare opportunity to have your dream home within 71 feet of the lake. Minutes to Tanglewood, Kripalu, and Canyon Ranch.

Listed by Maureen Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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21 Prospect Hill Rd, Stockbridge, MA 01262

Price$2,250,000

Est. Mortgage: $/month

MLS Number 222499

  • Single Family
  • Village Berkshire - South
  • Year Built 1775
  • Bedrooms 5
  • Bathroom 6

Exquisitely renovated late 1700 antique home w/ perfect proportions & amazing grounds. High ceilings, multiple fireplaces & historic details, flooded with light. Beautifully sited on over 9 acres on one of the most prestigious roads in the county. Barn, apple orchard, specimen trees, masterful stonework. Secluded and private heated Gunite pool w/ classic pool house & adventurous boardwalk.

Listed by BERKSHIRE PROPERTY AGENTS

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$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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8 Stone Hill Rd, Stockbridge, MA 01262

Price$2,240,000

Est. Mortgage: $/month

MLS Number 220955

  • Single Family
  • Village Berkshire - South
  • Year Built 1997
  • Bedrooms 5
  • Bathroom 7

Living is easy in this impressive Stockbridge contemporary located on a fantastic plot of land with western view, blazing sunsets and heated pool all minutes from Tanglewood. Three levels of thoughtful living spaces with soaring two level Great Room open to informal dining and gourmet kitchen make the perfect gathering space around the fireplace on cool fall days while taking in the view from the walls of glass. Wander out to the extensive decking on those warm fall days that overlook the heated pool and look forward to making memories of Berkshire summers. The master bedroom, with "His & Her" baths, are on the main level; guests have their own floor. Lower level family room with fireplace and galley kitchen with bar make this wonderful family space most convenient for exercising,

Listed by COHEN & WHITE ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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16 Maple Ln, Stockbridge, MA 01262

Price$1,975,000

Est. Mortgage: $/month

MLS Number 223548

  • Single Family
  • Village Berkshire - South
  • Year Built 2001
  • Bedrooms 4
  • Bathroom 3

Stockbridge Bowl waterfront home in private Beachwood with a sandy beach and wide views of the lake. When creating this gorgeous home, the owners and architect left no stone unturned. The timeless house lives large on its lot and there are views of the lake through Pella windows and French doors from every corner of the three floors. The bright living room has reclaimed wood floors and beams, and extensive bookshelves in the library area. It's open to the cook's kitchen just enough for gracious entertaining, and again to the dining room which overlooks the stone patio, level lawn, and the lake. The notable free-standing stairway leads up to the master suite and two guest rooms on the second floor, and fourth bedroom on the third - all with water views. Central A/C, generator, and spotless

Listed by BERKSHIRE PROPERTY AGENTS

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$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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 Lahey Cross Rd, Stockbridge, MA 01262

Price$1,895,000

Est. Mortgage: $/month

MLS Number 215909

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

Total privacy on 22 acres with back country roads for strolling. Within a couple of miles you will find fresh baked bread, a pub, the Norman Rockwell Museum, the Berkshire Botanical Garden and Chesterwood. And within 6 or 7 miles you'll be at the boat ramp at Stockbridge Bowl, Kripalu Yoga Center and Tanglewood. Wonderful setting with mature trees, landscaped gardens, extensive stonework and in-gorund pool. VIEW sheds to Mt. Everett and Beartown Mt. have been professionally mapped out and ready for clearing. The house is gorgeously designed and crafted with great attention to detail and quality. A FABULOUS place to live! See for yourself as you walk through the house at https://my.matterport.com/show/m=bPqkAKeDuNB&mls=1 And read more . . . A winding driveway through dappled sunlight and mature trees leads to the picturesque setting for this exceptional home. The house is surrounded by expansive landscaped gardens, with seasonally blooming perennials, rock garden plants, rare species, and ex

Listed by STONE HOUSE PROPERTIES, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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 Rd, Stockbridge, MA 01262

Price$1,750,000

Est. Mortgage: $/month

MLS Number 221642

  • Land
  • High School Monument Mountain
  • Village Berkshire - South
  • Square Feet 211,702
  • Waterfront 1

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 Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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 Rd, Stockbridge, MA 01262

Price$1,750,000

Est. Mortgage: $/month

MLS Number 221641

  • Land
  • High School Monument Mountain
  • Village Berkshire - South
  • Square Feet 211,702
  • Waterfront 1

RARE STOCKBRIDGE BOWL OPPORTUNITY: THE KIDS WILL COME WHEN YOU HAVE A SUMMER PARADISE: Boating, waterskiing, canoeing, paddle boarding etc. Over 300 feet of pristine lakefront. An existing structure offers a rare opportunity to build within 71 feet of the lake. This is pure lakefront delight. The views of the lake and mountains are absolutely beautiful. An additional waterfront parcel. This is sited overlooking the big part of the Bowl. Minutes to all the beautiful Berkshires has to offer.

Listed by Maureen Kirkby of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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Stockbridge, MA 01262

Price$1,750,000

Est. Mortgage: $/month

MLS Number 221926

  • Land
  • Co Listing Office Id 443
  • High School Monument Mountain
  • Village Berkshire - South
  • Square Feet 1,996,355

Longfellow's Oxbow consists of 45 acres within walking distance of the center of Stockbridge. This large undeveloped parcel offers Views, Privacy, Open Space and a mile of River Frontage. Ideal for a premiere home or homes with vast open maintained hayfields, and views to Naumkeag, the back meadows of Norman Rockwell Museum and overlooking the Stockbridge Golf Club. Once used as a polo field, there is a run-in shed for horses. Longfellow's Oxbow is named after the poet Henry Wadsworth Longfellow , who once owned the land.With high conservation potential, it is possible to both build and conserve in this highly desired Stockbridge location.

Listed by LANDVEST, INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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