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Stockbridge MA Real Estate

It’s arguable that Stockbridge just may be the most famous small town in America. The iconic town looks just as it did when Norman Rockwell painted it in the 1950s. The Red Lion Inn holds court as the centerpiece of Main Street, surrounded by landmarks like Naumkeag Museum & Gardens, Berkshire Botanical Garden, Kripalu Center for Yoga and Health, Berkshire Theatre Festival, and of course, the Norman Rockwell Museum. And while you could easily spend all day in the village of Stockbridge purusing shops and visiting the restaurant that inspired “Alice’s Restaurant,”  Stockbridge Bowl, the largest lake in town, has a public boat ramp making the lake easily accessible.

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2 Glendale Middle, Stockbridge, MA 01262

Price$6,875,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 215244

  • Listings
  • Beds 8
  • Baths 10
  • Sq Ft 10971
  • Acres 33

SOUTHMAYD FARM Gilded Age at its finest in Stockbridge. This 1870 Berkshire estate has been fully restored & is privately sited on 33+ acres within walking distance of town. Adjacent to the Stockbridge Golf Club & the Norman Rockwell Museum, the view includes a mile of Housatonic River frontage. The 8500' main house w/ 8 bedrooms is complemented by a carriage house, greenhouse/studio, pool, , 3 bedroom guest house, barn complex and paddocks, a magnificent maze, and additional formal gardens. See documents file for detail of each building, room and floor plan.

Listing courtesy of Cindy Welch and Keith Ross of LANDVEST, INC.

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

82 Interlaken, Stockbridge, MA 01262

Price$4,600,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218152

  • Listings
  • Has Waterfront

Rare opportunity: 11 Acres on the beautiful Stockbridge Bowl. Nearly 400 ft of pristine lake frontage across the big part 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, Canyon Ranch.

Listing courtesy of Maureen White Kirkby of BARNBROOK REALTY, INC.

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

79 Hawthorne, Stockbridge, MA 01262

Price$2,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219710

  • Listings
  • Beds 4
  • Baths 7
  • Sq Ft 5952
  • Acres 36.4

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.

Listing courtesy of Gladys Montgomery and Maggie Barry of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

82B Interlaken, Stockbridge, MA 01262

Price$2,300,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218150

  • Listings
  • Has Waterfront

Over 300 feet of pristine lakefront. An existing structure offers a rare opportunity to possibly build within 71 feet of the lake. This is pure lakefront delight. The views of the lake and mountains are absolutely beautiful. This lot offers privacy and the driveway is already in via an easement. An additional waterfront parcel available abuts. This is sited overlooking the big part of the Bowl.

Listing courtesy of Maureen White Kirkby of BARNBROOK REALTY, INC.

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

82C&D Interlaken, Stockbridge, MA 01262

Price$2,300,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218151

  • Listings
  • Has Waterfront

Beautiful open frontage with views across the big section of the Stockbridge Bowl. Over looking Elm Court and mountains beyond. Gorgeous perch to site your dream lake 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.

Listing courtesy of Maureen White Kirkby of BARNBROOK REALTY, INC.

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

21 Prospect Hill, Stockbridge, MA 01262

Price$2,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217160

  • Listings
  • Beds 5
  • Baths 6
  • Sq Ft 4194
  • Acres 9.4

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.

Listing courtesy of Christian Deckert of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

8 Stone Hill, Stockbridge, MA 01262

Price$2,240,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220955

  • Listings
  • Beds 5
  • Baths 7
  • Sq Ft 4476
  • Acres 4.88

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,

Listing courtesy of Mary Jane White and Brandon White of COHEN & WHITE ASSOCIATES

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

49 & 51 Interlaken, Stockbridge, MA 01262

Price$1,999,999The price has recently decreased

Est. Mortgage: $/month

MLS Number 217367

  • Listings
  • Has Waterfront

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.

Listing courtesy of Elle Villetto of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1 LAHEY CROSSROAD, Stockbridge, MA 01262

Price$1,895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 215909

  • Listings
  • Beds 5
  • Baths 5
  • Sq Ft 4847
  • Acres 22.63

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 extensive stonework. Enter the gracious spacious two-story foyer. Step down into the sun filled living room with fireplace. The exceptional library is lined with bookshelves. Dining room has its own fireplace as does the adjacent dining porch. The large eat-in country kitchen has a wall of windows looking out to the gardens. The butler's pantry and the large back mudroom provide terrific work spaces for household activities and entertaining. Complete with wine cellar in the basement. The flow of spaces is excellent and there are multiple accesses to the outdoors. On the second floor is the master suite with a sunny southern exposure, his and her walk-in closets with custom cabinetry, and a grand European styled bath. Two other bedrooms, one with a fireplace, open onto an open balcony porch overlooking the gardens. The rooms are beautifully sized and have a dedicated bath. Two more bedrooms with a sitting area are easily available just steps away in the charming guesthouse reached by a covered stone colonnade. This building also contains a large open office space that could be used as a family game space or studio. On the lower of the three levels is a garden studio/workshop. Through the gardens and stone paths is the in-ground swimming pool for summer enjoyment. Take walks on the country back roads, stroll to Chesterwood. Terrific location near the Norman Rockwell Museum and the Berkshire Botanical Garden. 7 miles to Great Barrington and 6 miles to Tanglewood.

Listing courtesy of Martha Piper and Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1-A Bean Hill, Stockbridge, MA 01262

Price$1,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220949

  • Listings
  • Beds 4
  • Baths 4
  • Sq Ft 3719
  • Acres 5.05

Exquisite home with winter views. Walk to the town beach to your stored kayaks from this open, bright and beautiful contemporary home. Wide open plan with bamboo flooring, two fireplaces, a beautiful first floor master bedroom and glorious master bathroom. Top of the line materials, a gourmet kitchen with a center island, beautiful granite counters and stainless steel appliances. Sit on the peaceful screened porch and listen to the music from Tanglewood just minutes away. Minutes to the downtowns of Stockbridge, Lenox, Great Barrington, and West Stockbridge This is a perfect home in a perfect Stockbridge location. Please see supplement for specifications.

Listing courtesy of Maureen White Kirkby of BARNBROOK REALTY, INC.

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

11 Wheatley, Stockbridge, MA 01262

Price$1,690,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 212585

  • Listings
  • Beds 5
  • Baths 6
  • Sq Ft 4345
  • Acres 3.6

Quiet, serene and beautiful - a retreat or a place for magnificent entertaining - it's your choice. One of a kind home, built by the current owners in 1994 & lovingly maintained. Enter the foyer & take in a view across the great room through two stories of windows to the gunite pool, Lily Pond and views beyond. Living room, 1st floor master bedroom, atrium dining all take in the view. A custom paneled office is nestled away for privacy. The second floor offers three more bedrooms & 2 full baths. The lower lever has spacious media & game rooms & extra all purpose rooms with a full bath. Your dock on Lily Pond is great for canoes & kayaks. Less than 5 minutes to Lenox and Stockbridge. Deeded rights to private beach on Stockbridge Bowl.

Listing courtesy of Anthony C Blair and Suzanne Crerar of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

5 Stone Hill, Stockbridge, MA 01262

Price$1,595,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219969

  • Listings
  • Beds 5
  • Baths 5
  • Sq Ft 4247
  • Acres 4.2

Set on 4.2 acres in a prestigious neighborhood, this 5 bedroom contemporary has sensational pastoral views overlooking a farm and two mountain ridges. A spacious, open floor plan, large country kitchen, privately placed ensuite guest rooms and expansive patio and porch facing unending views, make this home perfect for entertaining. Within walking distance to Lenox for shopping and dining.

Listing courtesy of Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.85% last updated on 2017-10-05

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.