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!

3 Ice Glen Rd Stockbridge MA 01262

Price$10,000,000

Est. Mortgage: $/month

MLS Number 225549

  • Single Family
  • Village Berkshire - South
  • Year Built 1915
  • Parking Spaces 2
  • Bedrooms 13

Built in 1915 believed to be the last of the Berkshire Cottages. This stunning home on 58.8 acres is just minutes to the village of Stockbridge MA. Restored to its original splendor with black and white marble floor entry, curved marble staircase, loggia with painted ceiling and fountain. The library includes book shelves flanking 3 walls and two fireplaces. The room is used as an office/family space with Tv and electronics hidden behind custom doors. Main salon with fireplace and views of the terrace and eastern light. Dining room with fireplace custom table seats 14 easily. Modern kitchen with Corian topped island and comfortable table spaces. A work area as well as tv space off of kitchen. Nine bedrooms. six baths on second and third floors. SEE ADDITIONAL INFO

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 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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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

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$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 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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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: 4.35% last updated on Feb 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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79 Hawthorne St Stockbridge MA 01262

Price$2,500,000

Est. Mortgage: $/month

MLS Number 225611

  • Single Family
  • Village Berkshire - South
  • Year Built 1988
  • Parking Spaces 3
  • Bedrooms 4

An exquisite traditional Georgian-style brick manor house is the centerpiece of this rare 36-acre Stockbridge estate, which offers both privacy and proximity to Lenox village, Wheatleigh, Tanglewood, and myriad Berkshire amenities. In a jewel-like setting with mature landscaping and views of lawns and hills, the residence combines 21st-century conveniences with impeccable architectural details, including elements from historic Georgian and Federal homes. Conveying quality and luxury, these details--a welcoming arms staircase, graceful columns and mantels, Palladian windows--epitomize the finest in traditional American design and create an ideal place for entertaining. The photos, virtual tour and floor plans are helpful, but, for the discerning buyer, this property is a must see.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 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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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: 4.35% last updated on Feb 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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106 Interlaken Rd Stockbridge MA 01262

Price$2,350,000

Est. Mortgage: $/month

MLS Number 225147

  • Land
  • Co Listing Office Id 1398
  • High School Monument Mountain
  • Village Berkshire - South
  • Square Feet 169,884

ONE OF A KIND WATER FRONT PROPERTY ON STOCKBRIDGE BOWL. This 3.9 acre property is cleared, open and level, with 400 feet of stunning water frontage, it's the perfect place for your dream home in the Berkshires. This property is open, yet private to neighbors with a mature tree line. Perfectly situated near the water is a stunning new boathouse with custom barn doors opening on both sides making storing yours sculls, kayaks and canoes a breeze. With Tanglewood less than a mile away, the best of the Berkshires is right in your backyard.

Listed by LANCE VERMEULEN RE, INC., LENOX

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$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 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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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. Please check out the virtual tour.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 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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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: 4.35% last updated on Feb 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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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: 4.35% last updated on Feb 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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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: 4.35% last updated on Feb 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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Glendale And Butler Rd 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: 4.35% last updated on Feb 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 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 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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