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!

17 Prospect Hill Stockbridge MA 01262

Stockbridge, MA17 Prospect Hill Rd

Price$4,450,000

Est. Mortgage: $/month

MLS Number 236486

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,000
  • Acreage 15.6

Enjoy all the berkshire seasons. Winter brings sledding, cross country skiing, access to downhill runs or enjoy the fire pit or get cozy by one of thefour fireplaces. Magnificent unspoiled views to the south and west create interest at all hours of the day and at sunset in particular. Thought to be one the first of the large 'cottages' on prospect hill. A wraparound glass porch overlooks the walled sunken garden. Three floors of living spaces with almost every room open to the views. Beautiful detailing with marble fireplaces and antique woodwork. Four bedroom and four and a half baths. A large game room with full bath occupies the third floor. There is a gunite pool. Golf tee/driving area. Minutes from tanglewood . Additional building lot included.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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17 Prospect Hill Stockbridge MA 01262

Stockbridge, MA17 Prospect Hill Rd

Price$4,150,000

Est. Mortgage: $/month

MLS Number 234293

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6,000
  • Acreage 11

Enjoy all the berkshire seasons. Winter brings sledding, cross country skiing, access to downhill runs or enjoy the fire pit or get cozy by one of thefour fireplaces. Magnificent unspoiled views to the south and west create interest at all hours of the day and at sunset in particular. Thought to be one the first of the large 'cottages' on prospect hill. A wraparound glass porch overlooks the walled sunken garden. Three floors of living spaces with almost every room open to the views. Beautiful detailing with marble fireplaces and antique woodwork. Four bedroom and four and a half baths. A large game room with full bath occupies the third floor. There is a gunite pool. Golf tee/driving area. Minutes from tanglewood . Additional building lot available.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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 Cross Stockbridge MA 01262

Stockbridge, MA1 Lahey Cross Rd

Price$2,595,000

Est. Mortgage: $/month

Pending

MLS Number 237363

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,847
  • Acreage 22.63

Custom built estate on a 22+ acre picturesque lot. Thoughtfully designed with exceptional detail and quality. Enjoy a winding tree-lined driveway, seasonally blooming landscape, renowned goshen stonework, in-ground pool, & guest house w/ private deck. In the main house, a 2-story foyer leads you to a grand living room w/ superb views, & a library perfect for book lovers. Farmhouse kitchen, dining room w/ fireplace, & sweeping windows lead you to a screened porch. A 2nd-floor primary suite includes walk-in closets, european style bath & dual pedestal sinks. Perfect for entertaining w/ 5 total bedrooms, butlers pantry, wine cellar, & plenty of outdoor space overlooking the manicured landscape. Nearby attractions: norman rockwell museum, berkshire botanical garden, tanglewood, & chesterwood.

Listed by Joshua Stephens of NON-MEMBER: Reciprocal

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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108 Interlaken Stockbridge MA 01262

Stockbridge, MA108 Interlaken Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 236514

  • Residential
  • Square Feet 500
  • Acreage 1.34

279' of frontage on stockbridge bowl. A long groomed driveway leads to this large, gorgeous parcel of lakefront. Wide, stunning southeasterly views of the lake with mountains beyond. A boathouse at the waters edge, scarce for lakefront. A victorian cottage (no water or utilities) deemed historic. A rustic storage barn provides a footprint with potential. Septic fields in. Drilled well. Utilities easily accessible. Design plans for a 5,000+ square foot home with garage available. A rare opportunity to own a large parcel of land with frontage on deep lakefront on stockbridge bowl.

Listed by Tom Lynch of BERKSHIRE PROPERTY AGENTS,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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108 Interlaken Stockbridge MA 01262

Stockbridge, MA108 Interlaken Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 236377

  • Land
  • Acreage 1.34

279' of frontage on stockbridge bowl. A long groomed driveway leads to this large, gorgeous parcel of lakefront. Wide, stunning southeasterly views of the lake with mountains beyond. A boathouse at the waters edge, scarce for lakefront. A victorian cottage (no water or utilities) deemed historic. A rustic storage barn provides a footprint with potential. Septic fields in. Drilled well. Utilities easily accessible. Design plans for a 5,000+ square foot home with garage available. A rare opportunity to own a large parcel of land with frontage on deep lakefront on stockbridge bowl.

Listed by Tom Lynch of BERKSHIRE PROPERTY AGENTS,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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30 East Stockbridge MA 01262

Stockbridge, MA30 East St

Price$2,450,000

Est. Mortgage: $/month

MLS Number 237413

  • Residential
  • Bathroom 17
  • Bedrooms 16
  • Square Feet 9,337
  • Acreage 6.98

Move right in and take over this successful well established business in the heart of the berkshires. This beautiful property is complete with a heated in-ground pool, mature landscaping, and distant mountain views. The private location is perfectly situated between the picturesque towns of lenox, stockbridge and lee, close to tanglewood and many other berkshire attractions.This property would also be perfect for a large family compound.

Listed by Lauren Rosen and Lance Vermeulen of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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30 East Stockbridge MA 01262

MLS Number 237415

  • Commercial
  • Acreage 6.98

Move right in and take over this successful well established business in the heart of the berkshires. This beautiful property is complete with a heated in-ground pool, mature landscaping, and distant mountain views. The location is perfectly situated between the picturesque towns of lenox, stockbridge and lee, close to tanglewood and other berkshire attractions.This property would also be perfect for a large family compound.

Listed by Lance Vermeulen and Lauren Rosen of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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30 East Stockbridge MA 01262

MLS Number 237414

  • Commercial

Move right in and take over this successful well established business in the heart of the berkshires. This beautiful property is complete with a heated in-ground pool, mature landscaping, and distant mountain views. The location is perfectly situated between the picturesque towns of lenox, stockbridge and lee, close to tanglewood and other berkshire attractions.This property would also be perfect for a large family compound.

Listed by Lance Vermeulen and Lauren Rosen of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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2 South Hill Stockbridge MA 01262

Stockbridge, MA2 South Hill Rd

Price$865,000

Est. Mortgage: $/month

MLS Number 237430

  • Residential
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 2,111
  • Acreage 3.1

Fabulous location in stockbridge, close to all the best berkshire attractions. This pristine home sits back from a private road & is 1 of 2 homes on a dead end street. Manicured grass, landscaping & stone driveway, lead you to this contemporary home with attached barn structure. Light abounds in the large open living room with tall ceilings & many windows that bring in the beauty of the outdoors. Eat in kitchen attaches to formal dining room. First floor has a den that can be used as bedroom for extra guests. Full bathroom on first floor & laundry. Upstairs has a large open loft that is used as an office. 2 more spacious bedrooms & large bathroom with shower & free standing bathtub. The attached barn is a perfect place for summer parties. Charm & function, this property has it all!

Listed by Elle Villetto of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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9 Stone Hill Stockbridge MA 01262

Stockbridge, MA9 Stone Hill Rd

Price$750,000

Est. Mortgage: $/month

MLS Number 236944

  • Land
  • Acreage 5.33

And the best has been saved for last! Top of stone hill is the only remaining lot in this desirable luxury subdivision. Located on the cul- de- sac, top of stonehill is ready to build with electric, well and septic in place. A private site with quick acess to tanglewood , shopping and town. Views can be maximized with selective clearing.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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9 South Stockbridge MA 01262
Pending

MLS Number 237423

  • Commercial
  • Acreage 0.19
  • Parking Spaces 10

Beautiful classic stockbridge building just off main street with seven apartments. Excellent investment opportunity. Off street parking, quick walk to town. Well maintained building with recent upgrades to electrical systems and heating. Currently fully occupied with longer term tenants.

Listed by Richard G. Aldrich and Anthony C Blair of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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44 Main Stockbridge MA 01262

Stockbridge, MA44 Main St

Price$700,000

Est. Mortgage: $/month

Pending

MLS Number 236915

  • Condo
  • Bedrooms 6
  • Bathroom 3
  • Year Built 1870
  • Square Feet 1,000

$700,000 development opportunity. Portfolio of 3 condos located in historic downtown stockbridge. Being sold as is; units to be built-out by new owner. Condo #2 - 1,448 sf, condo #3 - 1,023 sf, condo #4 - 1,844 sf. Current floor plans attached. On site private parking. Minutes to mass pike, steps away from the red lion inn and berkshire theater. Minutes to shopping, tanglewood, jacob's pillow, norman rockwell museum.

Listed by Richard G. Aldrich of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 2022
* 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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Based on information submitted to BCMLS  as of May 21, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.