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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2 Meadow Road Stockbridge MA 01262

Stockbridge, MA2 Meadow Road

Price$749,000

Est. Mortgage: $/month

MLS Number 240644

  • Residential
  • Bedrooms 3
  • Square Feet 2,012
  • Acreage 2.1

Stockbridge contemporary, sited on 2 private acres includes an artist's studio! First time offered, renown sculptor, jay moss designed his 1974-built home. Distinctive features: two-story living room w fireplace bathed in natural light from skylight and six custom windows. First floor open plan includes updated kitchen with quartz counters, dining area, an office/bedroom option, 1/2 bath and laundry. Primary bedroom and 2 guest bedrooms complete the balconied upper level. Attached 1 room efficiency apt with private entrance.! Total privacy from rear deck enveloped in nature. Canopy of mature trees offers a tranquil setting to start or end your day. Artist's studio incorporates natural light - creative space to work, work-out, or relax. Stockbridge bowl is across the street!

Listed by Pamela Roberts of ROBERTS & ASSOC. REALTY,INC ((413) 637-4200)

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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 Yale Hill Road Stockbridge MA 01262

Stockbridge, MA3 Yale Hill Road

Price$725,000

Est. Mortgage: $/month

MLS Number 241640

  • Residential
  • Bedrooms 3
  • Square Feet 2,395
  • Acreage 0.39

Mid-century flair on much-coveted yale hill road.Form, function, and flair combine in this 2395 sq ft home located in stockbridge's coveted yale hill rd neighborhood. The home's 1970s lines and layout offer great potential for a mid-century aesthetic with contemporary touches. Located on a quiet road, and set on a beautifully landscaped yard with gazebo, this home offers the rare combination of privacy, space, and convenience. The home consists of three bedrooms, an office, an open living-dining area with fireplace, a separate family room (or music/art studio), a centrally located kitchen, a first floor laundry room, and two full baths. The office is notable for its beautiful custom wood built-ins, and the open living-dining area is perfectly suited for mid-century design.

Listed by Jared Kelly and Chapin Fish 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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5 Cherry Hill Road Stockbridge MA 01262

Stockbridge, MA5 Cherry Hill Road

Price$595,000

Est. Mortgage: $/month

MLS Number 241371

  • Residential
  • Bedrooms 3
  • Square Feet 2,031
  • Acreage 2

Spacious 1-level ranch in stockbridge, 1.2 miles to the red lion inn & downtown, 2 beautiful private acres w/mountain view & 303.5' of frontage, 3 bedrooms, 1 1/2 baths, many updates & renovations & electrical upgrades, completely renovated living room, large dining room w/brick fireplace, kitchen has lots of cabinets, granite countertops, garage was converted to living space, could be in-law quarters/family room, fenced in patio area, 2 stall shed/barn, horseshoe driveway, close to tanglewood, gt. Barrington, mass. Pike & all the berkshires has to offer!

Listed by Kim Gordnier of RE/MAX COMPASS ((413) 394-4543)

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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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12 Stone Ridge Road Stockbridge MA 01262

Stockbridge, MA12 Stone Ridge Road

Price$595,000

Est. Mortgage: $/month

MLS Number 241182

  • Land
  • Acreage 12.69

This is your chance to acquire almost 13 private beautiful acres with a view. Campion farms is a private community with 9 home sites. This is one of if not the best site in the community. There is underground power going to the entrance of the site, a well in place and a 4 bedroom septic system designed and ready to go. Just drop off your plans with your builder and in a few months start to enjoy your life in the berkshires. Conveniently located to all of the many local attractions that make the berkshires so special.

Listed by William Morrow 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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1 Campion Farms Road Stockbridge MA 01262

Stockbridge, MA1 Campion Farms Road

Price$570,000

Est. Mortgage: $/month

MLS Number 221846

  • Land
  • Acreage 14.9

Boulder terrace parcel at campion farms is nestled on a natural terrace that lies within a moss covered rock outcropping to the west. It benefits from the privacy and seclusion provided by the geography as well as the exceptionally unique landscape of boulders, rocks and a gentle rock ridge springing from the eastern side. Campion farms is located within the historic township of stockbridge, massachusetts. The rural setting offers a stunning natural landscape with over 30 conservation acres. Within minutes of the berkshires premier cultural and outdoor attractions.

Listed by Claudia Crane 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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36 Glendale Road Stockbridge MA 01262

Stockbridge, MA36 Glendale Road

Price$558,000

Est. Mortgage: $/month

Pending

MLS Number 241572

  • Residential
  • Bathroom 3
  • Bedrooms 2
  • Square Feet 1,829
  • Acreage 4.02

Single level home on 4 lightly wooded acres.Living room with wood burning fireplace,den, two bedrooms, two full baths, dining room, eat in kitchen, screen porch, deck, partiallly finished lower level with private bath. Two car attached garage, vynal siding, town water, private septic,( title 5 completed.)......This charming home with great light and easy floor plan is awaiting your decorating ideas.

Listed by Patrice C. Melluzzo 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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34-a Main Street Stockbridge MA 01262

Stockbridge, MA34-a Main Street

Price$550,000

Est. Mortgage: $/month

MLS Number 239804

  • Residential
  • Bathroom 1
  • Bedrooms 1
  • Square Feet 900
  • Acreage 0.22

The most iconic building on main st in stockbridge is now offering the front condo for sale or rent! Have your business downstairs and live above.Original stockbridge town hall building.Incredible foot traffic all year round. This three floor condo is ready to transform into whatever it is you desire. Soaring 12 foot ceiling height, exposed brick throughout. Giant windows facing main st. Upstairs has full bath and was once used as a studio apartment! Basement has dry storage. Available for sale or rent.This is the front condo only.

Listed by Lawrence Reilly of BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY ((413) 528-4423)

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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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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 G. FULS JR. REAL ESTATE CO. ((413) 884-5511)

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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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Stockbridge MA 01262

Stockbridge, MA

Price$550,000

MLS Number 240067

  • Commercial
  • Acreage 0.25

The most iconic building on main st in stockbridge is now offering the front condo for sale or rent!Original stockbridge town hall building.Incredible foot traffic all year round. This three floor condo is ready to transform into whatever it is you desire. Soaring 12 foot ceiling height, exposed brick throughout. Giant windows facing main st. Upstairs has full bath and was once used as a studio apartment! Basement has dry storage. Available for sale or rent.This is the front condo only. $2500/month

Listed by Lawrence Reilly 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.

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17 Christian Hill Road Stockbridge MA 01262
Open House

MLS Number 241486

  • Residential
  • Next Open House: Sat 09/30 10:30 am. to 12:00 pm.
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,360

Open house saturday 9/30 from 10:30-12:00. 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 or in-law apartment. 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. 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.

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

$
$
%
$/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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200 Old Stockbridge Road Stockbridge MA 01262
Pending

MLS Number 239758

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,772

Live in an historic stockbridge mansion at lovely winden hill condominiums, nearby lenox village. The grand living room miraculously retains its wood-paneled walls and working fireplace and has enough room to hold a dining room table for formal dinners. The kitchen is large enough to have a breakfast table. There's a full bath nearby the small bedroom, which is also perfect for a home office, and the two large bedrooms on the second floor have ensuite baths. The washer and dryer are in unit and there's plenty of storage via a close elevator to the basement. The main great hall leads out to a lawn with a view, where one may leave summer outdoor furniture. The pool, pool house and tennis court are available for gatherings. Live life graciously without any house maintenance.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/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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200 Old Stockbridge Road Stockbridge MA 01262
Pending

MLS Number 239756

  • Condo
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1930
  • Square Feet 1,772

Live in an historic stockbridge mansion at lovely winden hill condominiums, nearby lenox village. The grand living room miraculously retains its wood-paneled walls and working fireplace and has enough room to hold a dining room table for formal dinners. The kitchen is large enough to have a breakfast table. There's a full bath nearby the small bedroom, which is also perfect for a home office, and the two large bedrooms on the second floor have ensuite baths. The washer and dryer are in unit and there's plenty of storage via a close elevator to the basement. The main great hall leads out to a lawn with a view, where one may leave summer outdoor furniture. The pool, pool house and tennis court are available for gatherings. Live life graciously without any house maintenance.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/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.

Virtual TourSave 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.