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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.

Browse current listings for sale in Stockbridge, MA. Don't hesitate to contact us with any of your questions.

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2 Glendale Middle, Stockbridge, MA 01262

Price$6,900,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 215244

  • Listings Residential
  • Address 2 Glendale Middle Rd
  • Bedrooms 8
  • Bathroom 10
  • Square Feet 10971

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,

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: 4.15% last updated on 2017-02-16

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 Lots/Land
  • Address 82 Interlaken Rd
  • 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: 4.15% last updated on 2017-02-16

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

44 & 46 Lake, Stockbridge, MA 01262

Price$3,495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216723

  • Listings Residential
  • Address 44 & 46 Lake Dr
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 3325

Spectacular lake front compound w/ 600+ feet of lake frontage & complete privacy. 2 homes on 2 separate tax lots w/ gorgeous gunite pool, pool house, 2 docks, level land, beautiful landscaping & large koi pond. Both homes are only steps to the lake w/ amazing lake & mountain views. A true swimming & boating paradise. Don't miss this rare opportunity to own your dream Stockbridge Bowl compound!

Listing courtesy of Marc Bachman 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: 4.15% last updated on 2017-02-16

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$2,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217367

  • Listings Lots/Land
  • 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

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: 4.15% last updated on 2017-02-16

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 Lots/Land
  • Address 82B Interlaken Rd
  • 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: 4.15% last updated on 2017-02-16

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 Lots/Land
  • Address 82C&D Interlaken Rd
  • 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: 4.15% last updated on 2017-02-16

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 Residential
  • Address 21 Prospect Hill Rd
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 4194

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: 4.15% last updated on 2017-02-16

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$2,150,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 215909

  • Listings Residential
  • Address 1 Lahey Crossroad --
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4847

Beautiful gardens, mature plantings & extensive stone work. Gracious sized rooms. Dramatic 2-story entry foyer, library, screened dining porch, butler's pantry, first & 2nd floor laundries, mudroom. 1, 500 sq ft guest house at the end of covered, colonnaded stone patio. Pool tucked behind the gardens. Perfect for active households & for entertaining. Stroll on the back country roads to Chesterwood

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: 4.15% last updated on 2017-02-16

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

46 Lake, Stockbridge, MA 01262

Price$1,998,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217609

  • Listings Residential
  • Address 46 Lake Dr
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1653

Spectacular lake front home w/ complete privacy, gunite pool, pool house, dock, level land & beautiful landscaping. A true swimming & boating paradise. Only minutes to Tanglewood, downtown Lenox, downtown Stockbridge, the Berkshires' best attractions, skiing, hiking, biking & acclaimed farm to table restaurants. Don't miss this rare opportunity to own your dream home on magical Stockbridge Bowl.

Listing courtesy of Marc Bachman 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: 4.15% last updated on 2017-02-16

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$1,895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 212585

  • Listings Residential
  • Address 11 Wheatley Dr
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 4345

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: 4.15% last updated on 2017-02-16

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

PRIVATE FIVE-BEDROOM HOME NEAR STOCKBRIDGE BOWL

1 Mahkeenac, Stockbridge, MA 01262

Price$1,700,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 215922

  • Listings Residential
  • Address 1 Mahkeenac Rd
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 4580

STOCKBRIDGE BOWL PRIVATE BEACHWOOD BEACH MEMBERSHIP with this extraordinary contemporary Shingle-Style residence on 20 acres. The design concept of four cabins connected by stone and glass passageways allows for private and public spaces for friends and family, with lofty gathering rooms, a master with 2 bathrooms, multiple en-suite guest bedrooms, a bunk room, and a huge screened porch.

Listing courtesy of Tim Lovett and Danielle Smith 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: 4.15% last updated on 2017-02-16

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

29 Prospect Hill, Stockbridge, MA 01262

Price$1,695,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217370

  • Listings Residential
  • Address 29 Prospect Hill Rd
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 9477

Magnificently restored 18th century colonial in spectacular setting w/ awesome mountain views. 1st floor is graced by double parlors, multiple fireplaces, loads of sunlight, spacious living room, game room, 3-season enclosed porch plus 3 bedroom in-law suite w/ separate kitchen. Spectacular, level grounds w/ gunite pool, fruit trees & beautiful landscaping & stone work.

Listing courtesy of Marc Bachman 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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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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