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!

7 Prospect Hill Road Stockbridge MA 01262

Stockbridge, MA7 Prospect Hill Road

Price$12,500,000

Est. Mortgage: $/month

MLS Number 239285

  • Residential
  • Bathroom 9
  • Bedrooms 5
  • Square Feet 9,339
  • Acreage 6.2

One of the berkshires' finest residences, basking in the idyllic mountain scenery. Designed and crafted to meticulous standards, this distinguished 6.2 acre compound is surrounded by captivating, protected vistas far and wide. In the enduring tradition of the regions iconic estates, this extraordinary residence is a place for life to the fullest, providing an endless source of enjoyment in exquisite indoor /outdoor spaces. Fine millwork and 9 fireplaces underscore the comfortably elegant environment. Lower-level entertainment (media)room, wine cellar, fitness studio. Elevator, computerized systems. 9,339 sf with 5 bedrooms,6 full/3half baths. Wraparound tiered terraces feature pool with pool house. Glorious terraced gardens and formal gardens with fountain. Separate 3 bedroom guest house

Listed by Patrice C. Melluzzo of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 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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23 Prospect Hill Road Stockbridge MA 01262

Stockbridge, MA23 Prospect Hill Road

Price$4,899,000

Est. Mortgage: $/month

Open House

MLS Number 240500

  • Residential
  • Next Open House: Sun 06/11 3:00 pm. to 4:30 pm.
  • Bathroom 7
  • Bedrooms 7
  • Square Feet 8,200

Legacy property of culturally influential family retained under their stewardship since 1968 is a rare offering. This truly generational, mid-century modern masterpiece prominently sited on 57+ acres on prestigious prospect hill rd, is close to the stockbridge bowl and quaint downtown stockbridge. The masterful design of the home w/ its 8200 sq ft of versatile living space strikes a perfect balance w/ its surrounding natural landscape. The interiors are drenched in sunlight with the most dramatic and oversize windows imaginable! Chef's kitchen and stunning living rm open to the manicured lawns through floor to ceiling sliding glass doors offers sublime views of the resort-like grounds complete with tennis court, in-ground swimming pool, cultivated gardens and distant mountain views!

Listed by Nancy Cole of COMPASS MASSACHUSETTS,LLC.

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 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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Fenn Farm And Rear Cherry Road Stockbridge MA 01262

MLS Number 239122

  • Land
  • Acreage 351

Come and see this rare kaleidoscope of beauty. Canopies of oaks, pines, and towering birch trees. An inexpressible allure to this mountain with ever-changing views. See nature's landscape through your lens. Profound possibilities with long-range views, level building sites, and road frontage. Hidden retreat close to all things berkshire in the heart of stockbridge.

Listed by George Cain and Maggie C Merelle of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 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 Lahey Cross Road Stockbridge MA 01262

Stockbridge, MA1 Lahey Cross Road

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

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 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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44 Main Street Stockbridge MA 01262

MLS Number 239601

  • Commercial
  • Acreage 0.18
  • Parking Spaces 5

Rare and unique opportunity. Iconic stockbridge main street building, shown in rockwell's famous main street painting. Beautiful and classic victorian architecture. Property consists of two storefronts (1,387 sf & 640 sf) and a 409 sf shop in the rear. Two apartments on the second floor (1,448 sf & 1,023 sf) and the entire third floor is an additional unit of 1, 844 sf). Located in the center of downtown stockbridge, steps away from the red lion inn and next to the library.

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

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 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 Castle Hill Road Stockbridge MA 01262

Stockbridge, MA12 Castle Hill Road

Price$1,499,000

Est. Mortgage: $/month

Pending

MLS Number 239842

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,224
  • Acreage 8.81

Privately sited atop a hill on almost 9 acres with views spanning to butternut and beyond, you will find serenity while only being minutes to downtown stockbridge and all other south county attractions. Open plan with excellent natural light, chef's kitchen, great room, study w/fireplace, powder room, back deck, screened in porch, and large primary bedroom with ensuite round out the first floor. Upstairs are 3 more gracious sized bedrooms and 2 more full baths, one being ensuite.Radiant heated lower-level w/ billiards & home gym. Oversized & heated 2 car garage with separate heated pottery studio, barn, & outbuilding with unlimited potential. What are you waiting for? Come see this beautiful stockbridge country home today!Vid tour available at https://www.Youtube.Com/watch?V=twltjwolbr

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 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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20 Ice Glen Road Stockbridge MA 01262

Stockbridge, MA20 Ice Glen Road

Price$1,450,000

Est. Mortgage: $/month

MLS Number 239912

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 4,300
  • Acreage 3.63

Equal parts elegance, vintage, and fun, the ''barn in the glen'' is intimate enough for a single family, yet large enough to host guests. This nearly 4500 square foot sun-soaked 1900s converted barn, fully modernized while maintaining its charm, sits on more than 3.5 acres at the private end of ice glen rd, just over a mile's walk to the town of stockbridge. The main home has 20' cathedral ceilings, a massive loft with a wood-burning fireplace, and endless nooks to read and nap. The loft has an 8' x 12' window which offers an unobstructed view of monument mountain. The barn offers complete tranquility yet is only a minute's drive to the resident-only stockbridge bowl and tanglewood. The original barn has been restored with the original 15' sliding barn doors in the front of the

Listed by Cindy Welch of LANDVEST,INC.

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 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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7 Hawthorne Road Stockbridge MA 01262

Stockbridge, MA7 Hawthorne Road

Price$1,450,000

Est. Mortgage: $/month

MLS Number 239831

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 2,829
  • Acreage 0.62

Great stockbridge location with pool and a wonderful backyard!Calling all tanglewood and stockbridge bowl fans! Stroll to the music shed at tanglewood in just 8 minu, or 10 minutes to stockbridge bowl for picnics or kayaking! Drinks or dinner at wheatleigh is just a 5 minute amble away - and the back yard is your own summer resort. This 2,829 sq ft home has been substantially renovated and improved since it was purchased in 2018. It now features all the coveted features one seeks in a berkshires getaway: in-ground pool (with new liner and systems); beautifully landscaped backyard with patio, fire pit, hot tub & space for outdoor games; screened porch; 1st floor primary suite; renovated kitchen & new great room with fireplace; 4 bedrooms and 5 bathrooms; and a bonus basement rec room.

Listed by Chapin Fish and Jared Kelly of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 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 Madison's Way Stockbridge MA 01262

Stockbridge, MA1 Madison's Way

Price$1,100,000

Est. Mortgage: $/month

Pending

MLS Number 240161

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 2,410
  • Acreage 14.33

Beautiful modern colonial conveniently located a short drive to great barrington and stockbridge. Open common spaces with several windows to take in the natural light. First floor primary en suite with cathedral ceilings, three additional guest bedrooms each with en suite bathrooms; family room with built ins and access to back patio. Under house garage and gracious screened porch to take in the private setting.

Listed by Cortney K Dupont of COHEN & WHITE ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 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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19 Church Street Stockbridge MA 01262

Stockbridge, MA19 Church Street

Price$985,000

Est. Mortgage: $/month

MLS Number 240316

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,432
  • Acreage 0.89

The ideal marriage of antique and modern. Reported to be the oldest inhabited house in stockbridge, this 1739 cape features a chef's kitchen with exceptional views of the perennial gardens leading to the private housatonic riverfront. With three (plus) bedrooms and two baths, the home has numerous rooms for entertaining or just cozying up by the fireplace, but you'll spend much of your time living inside all four seasons through the kitchen window walls. The primary bedroom is on the first floor, as is an office/den that could be a fourth bedroom. The dining room is currently used as a library. The separate artist's studio is heated and outfitted with cabinetry. All systems have been renovated or replaced. Purchase soon and harvest the vegetables in the front raised beds this summer!

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 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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16 Yale Hill Road Stockbridge MA 01262

Stockbridge, MA16 Yale Hill Road

Price$975,000

Est. Mortgage: $/month

MLS Number 240423

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,112
  • Acreage 0.36

The combination of a gracious and meticulous federal style home, antique barn, frontage on the kampoosa brook and privacy is rare in this coveted neighborhood in stockbridge. Light and airy, the generous foyer is flanked by a living room with wood burning fireplace, and a library. A large eat in kitchen with french doors which open to a sun porch, a modest dining room, screened in porch and half bath complete the first floor, providing ample space for entertaining.The second level has a primary bedroom with large walk in closet, a smaller adjoining bedroom, and two others with nice views, a full bath and laundry. The attic has a walk up access and potential for more than simply storage. The antique barn, loaded with potential. Is situated along the edge of the brook, and has a private

Listed by Susan Laidlaw of BERKSHIRE PROPERTY AGENTS,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 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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6 Maple Lane Stockbridge MA 01262

Stockbridge, MA6 Maple Lane

Price$899,000

Est. Mortgage: $/month

Pending

MLS Number 240261

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,000
  • Acreage 0.46

First time in 40 years! 4 br four-season home circa 2000 sq.Ft. On almost 1/2 acre with lake views boasts a coveted, quiet, private position in the highly sought-after beachwood community, open plan large kitchen, dr & lr featuring windows w/ lake views, wood burning fp & doors opening onto a 24' deck & garden. Also downstairs is 1 br/office & 1 ba. Upstairs is a huge primary br running the length of the house w/ lovely lake & berkshire hills views, 2 additional brs & 1 ba. Washer & dryer. Detached garage/barn currently used for storage needs renovation. Very close to the beachwood community beach w/ swimming area & kayak launch. Conveniently located just a short drive to tanglewood, stockbridge center, lenox & many wonderful cultural & other amenities for which the berkshires are famous.

Listed by Levin + Lazarus Team of BERKSHIRE PROPERTY AGENTS,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 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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Based on information submitted to BCMLS  as of June 8, 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.