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
  • Square Feet 483,952
  • Waterfront 1
  • Zoning Residential

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 Kirkby of BARNBROOK REALTY, INC.

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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
  • Year Built 1959
  • Bedrooms 3
  • Bathroom 2
  • Total Full Baths 2

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 Kirkby of BARNBROOK REALTY, INC.

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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86 Interlaken Rd, Stockbridge, MA 01262

Price$2,750,000

Est. Mortgage: $/month

Pending

MLS Number 221364

  • Land
  • Co Listing Office Id 7756
  • High School Monument Mountain
  • Square Feet 375,923
  • Waterfront 1

A once-in-a-lifetime opportunity to renovate or potentially to build on an existing 6,328sf footprint, in a prime 8.63-acre spot with significant lake frontage on the west side of the Stockbridge Bowl (Lake Mahkeenac). There is an existing six-bedroom home, which has been gutted. The site awaits a new owner with a new vision. Two architectural plans, one Arts & Crafts, one Modernist, both customized to the site, are available for review. This is a gorgeous building site on the lake and an ideal location, minutes from restaurants, galleries and shops in Lenox and Stockbridge; close to Kripalu, Tanglewood, and all the cultural, culinary and outdoor amenities for which the Berkshires are known; and just 2.5-hours drive from Boston and New York.

Listed by Maggie Barry and Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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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79 Hawthorne St, Stockbridge, MA 01262

Price$2,750,000

Est. Mortgage: $/month

MLS Number 219710

  • Single Family
  • Year Built 1988
  • Parking Spaces 3
  • Bedrooms 4
  • Bathroom 7

Spectacular 36-acre estate steps from Tanglewood's Hawthorne Gate. Enjoy the relaxed elegance of the impeccable New Traditional brick manor house, which combines 21st-century conveniences with exquisite top-quality custom details and graceful elements of another era. In a jewel-like setting with beautiful landscaping and views of emerald lawns and hills. Custom furnishings available separately.

Listed by Gladys Montgomery and Maggie Barry of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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
  • Year Built 1775
  • Bedrooms 5
  • Bathroom 6
  • Total Full Baths 5

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 Christian Deckert of BERKSHIRE PROPERTY AGENTS

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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
  • Year Built 1997
  • Bedrooms 5
  • Bathroom 7
  • Total Full Baths 5

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 Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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 Interlaken Rd, Stockbridge, MA 01262

Price$1,999,999

Est. Mortgage: $/month

MLS Number 217367

  • Land
  • High School Monument Mountain
  • Square Feet 3,087,097
  • Waterfront 1
  • Zoning Residential

Located across from the Stockbridge Bowl are 70 plus acres on picture perfect scenic land. Right on the Lenox/Stockbridge border, this property boasts absolute privacy all within walking distance to Tanglewood, Kripalu and many other cultural attractions. Walk across the street to the Stockbridge Bowl boat ramp. Build your dream house on a southern exposure hill surrounded by private hiking trails. Surrounded by land in conservation. A driveway and bridge has been installed for access to the back of the land.

Listed by Elle Villetto of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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$1,950,000

Est. Mortgage: $/month

MLS Number 221926

  • Land
  • Co Listing Office Id 443
  • High School Monument Mountain
  • Square Feet 1,996,355
  • Waterfront 1

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 Keith Ross and Cindy Welch of LANDVEST, INC.

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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 CROSSROAD --, Stockbridge, MA 01262

Price$1,895,000

Est. Mortgage: $/month

MLS Number 215909

  • Single Family
  • Year Built 1992
  • Parking Spaces 2
  • Bedrooms 5
  • Bathroom 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 will find the boat ramp at Stockbridge Bowl, Kripalu Yoga Center and Tanglewood. Wonderful setting with mature trees, landscaped gardens, extensive stonework and in-gorund pool. Beautifully designed home with dramatic two-story foyer, spacious living room, exceptional library, dining room and porch each with fireplace, country kitchen. Great wall space to display art. A covered colonnade joins the main house to the guest house with 2 bedrooms, bath and gathering room plus a large office/studio and a garden workshop. A FABULOUS place to live! 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 Martha Piper and Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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 A VisitAsk A QuestionMore Details

82C&D Interlaken Rd, Stockbridge, MA 01262

Price$1,750,000

Est. Mortgage: $/month

MLS Number 221642

  • Land
  • High School Monument Mountain
  • Square Feet 211,702
  • Waterfront 1
  • Zoning Residential

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 BARNBROOK REALTY, INC.

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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 A VisitAsk A QuestionMore Details

82B Interlaken Rd, Stockbridge, MA 01262

Price$1,750,000

Est. Mortgage: $/month

MLS Number 221641

  • Land
  • High School Monument Mountain
  • Square Feet 211,702
  • Waterfront 1
  • Zoning Residential

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 BARNBROOK REALTY, INC.

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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 A VisitAsk A QuestionMore Details

82B Interlaken Rd, Stockbridge, MA 01262

Price$1,750,000

Est. Mortgage: $/month

MLS Number 222057

  • Single Family
  • Year Built 1959
  • Bedrooms 4
  • Bathroom 4
  • Total Full Baths 4

RARE WATERFRONT OPPORTUNITY: A SUMMER PARADISE FOR YOUR FAMILY. Build your dream home. 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 BARNBROOK REALTY, INC.

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* 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 A VisitAsk A QuestionMore Details