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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3 Yale Court Stockbridge MA 01262

Stockbridge, MA3 Yale Court

Price$667,000

Est. Mortgage: $/month

MLS Number 243067

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,922
  • Acreage 0.13

Introducing a meticulously well-maintained and charming colonial home. Situated on a highly sought-after dead-end street just a short walk to downtown stockbridge. The first floor features a cook's kitchen with ample storage, cozy breakfast nook, half bath w/ laundry, a dining room with gleaming wood floors which opens to a comfortable living room with a gas fireplace. Additionally, there is a three season sunroom that provides a peaceful retreat. Upstairs you'll find two inviting guest rooms and a full bathroom - accessed by the hallway and primary bedroom. The primary bedroom boasts of abundant natural light, cathedral ceilings, exposed beams with plenty of closet space. Fenced in yard, heated garage, walk-up attic and a heated basement. This home is not to be missed!

Listed by Molly E Thomas of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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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38a Glendale Road Stockbridge MA 01262

Stockbridge, MA38a Glendale Road

Price$599,900

Est. Mortgage: $/month

MLS Number 243431

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,502
  • Acreage 2.09

Fantastic location! This property boasts proximity to the norman rockwell museum and golf courses. The residence features 3/4 bedrooms and 3 full bathrooms. On the second floor, you'll find a delightful master suite, while a guest bathroom is nestled between two additional bedrooms. The first floor offers a full bathroom and one bedroom, with a relatively open floor plan that seamlessly combines the kitchen, dining area, and living room. The only other room on the first floor is the laundry mudroom at the rear. Architecturally, this house was thoughtfully designed and exudes charm.

Listed by Clifford Ponte of KELLER WILIAMS SOUTH WATTUPA ((508) 675-0995)

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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 Christian Hill Road Stockbridge MA 01262
Pending

MLS Number 242836

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,360
  • Acreage 0.74

Introducing an exquisite colonial masterpiece in the heart of historic stockbridge. Nestled amidst the picturesque berkshire mountains, this charming residence is situated on 0.74 acres with a bonus cottage. Close to many local attractions including tanglewood, norman rockwell museum, and chesterwood. Inside, you'll discover a harmonious fusion of old-world charm and contemporary convenience. The spacious living areas exude warmth and sophistication, with gleaming wide-plank hardwood floors, and a cozy fireplace off the remolded kitchen and dining area. The main home has been completely renovated with a new roof, windows, siding, heating and electrical. Including one full bathroom, three bedrooms, one on the first floor and two on the second. Additional cottage included on the lot

Listed by Cory Evangelisto of NOCHER REALTY ((413) 441-9761)

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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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Mohawk Lake Road Stockbridge MA 01262

Stockbridge, MAMohawk Lake Road

Price$550,000

Est. Mortgage: $/month

Pending

MLS Number 239012

  • Land
  • Acreage 19

Incredible land in stockbridge available for the first time in over 120 years. Build your dream home here in a private setting yet very close to the norman rockwell museum, berkshire botanical gardens and under 3 miles to the historical downtown stockbridge! Trails, the original chimney and fireplace from the 1800's homestead along with the old trees and gently sloping topography make this unique property a must see. Currently in chapter 61 for tax benefits. Call today for your appointment!

Listed by Jeff Gagnon and Gary L. Fuls Jr. of RE/MAX TRANSITIONS ((413) 884-5511)

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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 Wallace Road Stockbridge MA 01262

Stockbridge, MA2 Wallace Road

Price$510,000

Est. Mortgage: $/month

MLS Number 242810

  • Condo
  • Bedrooms 2
  • Bathroom 2
  • Year Built 1900
  • Square Feet 1,768

Looking for a peaceful and picturesque place to call home? Look no further than heron pond! This beautiful second floor end unit is situated on the serene grounds of heron pond and offers water views and a large screened-in porch, so you can feel like you're living in your own private oasis.The open floor plan and vaulted ceilings create a light-filled great room, perfect for entertaining guests or relaxing after a long day. Cozy up by the fireplace on chilly evenings and enjoy the tranquil atmosphere of your new home.This unit features not one, but two primary bedrooms, making it perfect for couples or small families. And with its convenient location just three minutes from main st., you'll have easy access to all the best berkshire attractions.

Listed by Matt Carlino of MACCARO REAL ESTATE ((413) 243-4647)

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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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23 Church Street Stockbridge MA 01262

Stockbridge, MA23 Church Street

Price$495,000

Est. Mortgage: $/month

MLS Number 243236

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,409
  • Acreage 0.53

Adorable town center cottageready for its next chapter, this adorable cottage in stockbridge with river frontage and less than 2-minutes to the red lion inn or naumkeag offers a classic, enclosed porch, sweet living and dining room and a first floor bathroom and bright kitchen and pantry. And a 2-car garage.The setting could not be more serene. On a roughly 1/2-acre lot with views across the river which meanders through town. A rare blank canvas to re-imagine village life in the berkshires.Note: roof 1997, furnace 2011

Listed by Selina Lamb of BIRCH PROPERTIES ((415) 515-3750)

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$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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&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: 6.95% last updated on Jun 13, 2024
* 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 Wheatley Drive Stockbridge MA 01262

Stockbridge, MA9 Wheatley Drive

Price$425,000

Est. Mortgage: $/month

MLS Number 242957

  • Land
  • Acreage 3.3

Rare opportunity to build your new berkshires home moments from tanglewood's back gate and share deeded rights to a private beach on the stockbridge bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on lily pond. Wheatley drive is a private rd. There is a voluntary hoa. Contribution of $1,000. Annually for road maintenance and plowing is voluntary.

Listed by Selina Lamb of BIRCH PROPERTIES ((415) 515-3750)

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$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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 242410

  • 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: 6.95% last updated on Jun 13, 2024
* 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: 6.95% last updated on Jun 13, 2024
* 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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13 Rattlesnake Mountain Road Stockbridge MA 01262

MLS Number 242230

  • Land
  • Acreage 7.83

prime berkshire land, where you will feel 'away from it all' without being soset on a serene & forested country road, this location makes the perfect retreat - yet you are in the heart of the berkshires just minutes to stockbridge and lenox, tanglewood, the bowl, the mount, kripalu, great barrington, the pike, shopping & more. the home site & septic area are already cleared, wetlands approvals are in place, and rough-in driveway cut in.this 7.8 acre parcel offers peace & quiet, beauty, ample road frontage, and low stockbridge taxes. With an assessed value of $351,400, this land offers a tremendous value proposition for those looking to build soon on prime berkshire land. This is so close to 'ready to go' - plan your design, drill a well, and finish permits

Listed by Jared Kelly and Chapin Fish of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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: 6.95% last updated on Jun 13, 2024
* 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 June 19, 2024 . 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.