Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

Stockbridge MA Real Estate

Peacefully situated in the heart of a quiet and beautiful valley, Stockbridge, MA is a lovely town in the Berkshire Hills. Home to beautiful historic mansions, the Norman Rockwell Museum, and gorgeous natural beauty, it's no surprise that Stockbridge has been a summer destination for centuries. Browse through our real estate listings in Stockbridge, MA.

Browse Real Estate for Sale in Stockbridge MA

Below are all currently listed properties for sale in Stockbridge, Massachusetts.  Contact us if you have questions or would like to schedule a showing. Create an account to keep track of listing and get updates when new properties hit the market!

You may also be interested in viewing homes for sale in Alford, Lee, Lenox, Tyringham, or West Stockbridge!

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,

Listed by Cindy Welch and Keith Ross of LANDVEST, INC.

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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.

Listed by Maureen White Kirkby of BARNBROOK REALTY, INC.

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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 Residential
  • Address 79 Hawthorne St
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 5952

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

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

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

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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$2,360,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216723

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

Huge Price Reduction! 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!

Listed by Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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.

Listed by Maureen White Kirkby of BARNBROOK REALTY, INC.

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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.

Listed by Maureen White Kirkby of BARNBROOK REALTY, INC.

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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.

Listed by Christian G Deckert of BERKSHIRE PROPERTY AGENTS

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

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!

Listed by Martha Piper and Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

12 Prospect, Stockbridge, MA 01262

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

Est. Mortgage: $/month

MLS Number 219432

  • Listings Residential
  • Address 12 Prospect Rd
  • Bedrooms 7
  • Bathroom 5
  • Square Feet 4320

PROSPECT HILL RD. ONE OF THE MOST PRESTIGIOUS & PICTURESQUE ROADS IN THE BERKSHIRES. Walk to Town, Close to Stockbridge Bowl Beach. #12 is a recently renovated, well designed Sparkling Colonial Home. A Chefs Kitchen with Viking Stove, Subzero Fridge, Carerra Marble Counters. Sensational Screened Porch with Built in Grill. 3 Fireplaces. Exquisite Front Porch. 6/7 Bedrooms, Media Room & so much more

Listed by Marlene Goldstein of BERKSHIRE COUNTRY HOMES LLC

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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