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!

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Parcel A&b Glendale Road Stockbridge MA 01262

MLS Number 241540

  • Land
  • Acreage 25.22

A perfectly situated wooded building parcel with multiple building sites in desirable stockbridge. This property offers frontage for multiple dwellings, privacy, and an installed driveway leading to the building site. Come make this your berkshire estate!

Listed by Antonio M Segalla of LANCE VERMEULEN RE,INC ((413) 528-6011)

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$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 Road Stockbridge MA 01262

Stockbridge, MA9 Stone Hill Road

Price$425,000

Est. Mortgage: $/month

MLS Number 241279

  • Land
  • Acreage 5.33

Is it time to build your dream home on the perfect hill? Look no further than to this ultimate location in stockbridge, massachusetts. Surrounded by outstanding homes and lovely views, this coveted cul-de-sac is awaiting your new home. This is the last lot available at stone hill road. 5.3 acres of light woods with potential big views. Minutes from downtown lenox and tanglewood. The building area has been roughly determined and there is electric and water in place. Bring your design and get ready to build your dream home, this land will not disappoint.

Listed by Elle Villetto of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

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$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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3 Mahkeenac Heights Stockbridge MA 01262

Stockbridge, MA3 Mahkeenac Heights

Price$419,000

Est. Mortgage: $/month

MLS Number 241593

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,116
  • Acreage 0.32

A perfect berkshire's 3-season nest. This immaculately maintained cottage consists of a large living/dining area featuring vaulted ceilings, hardwood floors & a country stone wood-burning fp. The lr w/ windows looking out onto the garden & trees beyond leads onto a big raised entertainment deck. Bright eat-in fully applianced kitchen. Generous 1st floor main br w/ good storage & laundry has an en-suite ba. There is a 2nd br & ba on the 1st floor. Upstairs are 2 large sleeping loft areas. The property has a delightful rebuilt studio building w/ electricity which might be used as an artist's studio, yoga studio or for extra guest accommodation. Quiet, comfortable and so conveniently positioned betw/ stockbridge & lenox, close to tanglewood, minutes from the stockbridge town beach. A gem!

Listed by Levin + Lazarus Team of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

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%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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46 Prospect Hill Road Stockbridge MA 01262

MLS Number 240154

  • Land
  • Acreage 10.4

Prime stockbridge land, prime stockbridge location, and low stockbridge taxes. A couple of short miles to tanglewood in lenox and a few minute drive to the red lion inn in stockbridge. Under a mile to stockbridge public sandy beach on the bowl. Includes drilled well already installed, septic design and roughed-in driveway. Excellent investment location for full or part-time residents.Included: *lot 21 with 6.52 acres and 315 ft. Of frontage, plus an additional lot 29 directly across the street that has 3.8 acres with 465 ft. Of frontage and private pond. Total acreage of the 2 lots combined is about 10.4 acres as noted in ''acres apr'' on the listing sheet.

Listed by Susan Calkins and Gary Johnston of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

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$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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Parcel B Glendale Road Stockbridge MA 01262

MLS Number 241542

  • Land
  • Acreage 12.66

A perfectly situated wooded building lot in desirable stockbridge. With the building site set off the road and over 12 acres this property is a perfect spot to construct a berkshire getaway. The property has a constructed driveway leading to the desired building site.

Listed by Antonio M Segalla of LANCE VERMEULEN RE,INC ((413) 528-6011)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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24 Lake Drive Stockbridge MA 01262

Stockbridge, MA24 Lake Drive

Price$249,000

Est. Mortgage: $/month

MLS Number 239605

  • Land
  • Acreage 1.7

One of the few remaining opportunities to build on the stockbridge bowl in the quiet lake drive area. Permitting in place, including con com, planning board, and board of health - all that remains for the new owner is to obtain a building permit. Permitting allows for a 1200 sq.Ft. Footprint home (additional second floor is an option for those seeking a larger house). Board walk and dock permit in place for access to the lake. Great stockbridge location.

Listed by Lori J Rose of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

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$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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Parcel A Glendale Road Stockbridge MA 01262

MLS Number 241541

  • Land
  • Acreage 12.56

A perfectly situated wooded building lot in desirable stockbridge. With the building site set off the road and over 12 acres this property is a perfect spot to construct a berkshire getaway. The property has a constructed driveway leading into the property.

Listed by Antonio M Segalla of LANCE VERMEULEN RE,INC ((413) 528-6011)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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5a North Church Street Stockbridge MA 01262

MLS Number 239953

  • Land
  • Acreage 26.98

Close to 27 acres a mile outside of downtown stockbridge. Located on a quiet side street, a potential building site has been cleared with a possibility for nice views to the south and west. Frontage on both north church street and route 102.

Listed by C. Randolph Thunfors and Katie Williams of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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15 Lake Drive Stockbridge MA 01262

Stockbridge, MA15 Lake Drive

Price$139,000

Est. Mortgage: $/month

Pending

MLS Number 236936

  • Land
  • Acreage 2.12

A lightly wooded sloping two acre parcel with frontage on a gravel road off route 183. Potential water views. A short walk to deeded access to stockbridge bowl.

Listed by Brandon White of COHEN & WHITE ASSOCIATES ((413) 637-1086)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 Housatonnuck Road Stockbridge MA 01262

Stockbridge, MA1 Housatonnuck Road

Price$129,000

Est. Mortgage: $/month

MLS Number 240242

  • Land
  • Acreage 0.65

Great location near the stockbridge bowl town beach, tangelwood and the village of lenox! Wooded lot in mahkeenac heights on the upper part. Privacy, well drilled, sewer access and previous house plans available.

Listed by Cortney K Dupont of COHEN & WHITE ASSOCIATES ((413) 637-1086)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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Cherry Hill Road Stockbridge MA 01262

Stockbridge, MACherry Hill Road

Price$39,000

Est. Mortgage: $/month

MLS Number 236898

  • Land
  • Acreage 0.53

Over half acre lot on quiet residential street, so close to stockbridge! Convenient to both stockbridge and great barrington.

Listed by Sonya Butler and Sherry Street of REALTY STREET,LLC ((413) 684-4000)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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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4 Old Colonial Road Stockbridge MA 01230
For Rent

Listing Number X93758868

  • Exclusive Vacation Rentals

The epitome of single level living. There are no steps to get in to this gorgeous brand new home.  Open floor plan with hardwood floors and beautiful fixtures. Beautiful kitchen to cook in while you feel like you are living in the woods. Centrally located and easy to get to the Masspike or the New York State Thruway. Tanglewood is a five minute drive away!

Listed by Michael Harrigan of Berkshire Hathaway HomeServices Barnbrook Realty ((413) 528-4423)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of September 30, 2023 . 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.