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$9,950,000

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 ((413) 528-4192)

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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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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 ((413) 442-8049)

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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 Cherry Street Stockbridge MA 01262

Stockbridge, MA2 Cherry Street

Price$1,790,000

Est. Mortgage: $/month

MLS Number 242048

  • Residential
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 4,057
  • Acreage 0.91

A magnificent 6 bedroom stucco residence less than a mile to the center of stockbridge. Enjoy views of the golf course and mountains in the distance. Five fireplaces, a beautiful eat in kitchen, stunning butlers pantry with a cozy nook to sit in, and a sun filled spacious dining room. Read a good book in the beautiful library next to one of the five fire places throughout the house. Step out beautiful french doors to your screened in patio which leads to a well lit and heated pool. A 20 ft hallway wall of built in cabinets and closets leading to the primary bedroom. Three en suite bedroom areas for guests and family. Electric car charger in the heated garage. Majestic stonewalls. Not far to all attractions tanglewood, norman rockwell, ski areas etc. A must see!

Listed by Patricia Andrew of STONE HOUSE PROPERTIES,LLC ((413) 232-4253)

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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 Main Street Stockbridge MA 01262

Stockbridge, MA17 Main Street

Price$1,535,000

Est. Mortgage: $/month

MLS Number 242400

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,300
  • Acreage 4.3

A classic main st stockbridge residence on a remarkable 4.3 acres. Walk to shops, restaurants, town tennis courts, the library, the stockbridge golf club, the berkshire theatre festival and more. The david dudley field house c.1824 is steeped in history remaining in the field family until 1984. The current owners have lovingly maintained and cherished this exceptional property for 40 yrs. The gracious interior is bathed in natural light and full of beautiful period details. Front and back staircases, pocket doors, built-in shelving, exceptional fireplace mantels, beautiful floors, etc. The carriage barn is a delight. An exceptional property perfectly located in the center of berkshire activities. Lenox and great barrington are only a quick 10 minutes away.

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

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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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7 Hawthorne Road Stockbridge MA 01262

Stockbridge, MA7 Hawthorne Road

Price$1,295,000

Est. Mortgage: $/month

MLS Number 242586

  • Residential
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 2,829
  • Acreage 0.62

Great stockbridge-lenox home with poolfor tanglewood + stockbridge bowl (lake) fans - stroll to the music shed at tanglewood in just over 5 minutes, or 10 minutes to your deeded access at the bowl for picnics or kayaking! The back yard is your own summer resort! This 2,829 sq ft home has been substantially renovated & improved since it was purchased in 2018. It now features all the coveted features one seeks in a berkshire getaway or full-time home: pool (w/ new liner & systems); beautifully landscaped, very private backyard, patio, fire pit, hot tub & space for outdoor games; screened porch; 1st floor primary suite with fireplace; new kitchen & new great room with gas fireplace since 2018 + 3 ensuite bedrooms & 5 baths, office/den/add'l sleeping space + a bonus basement area.

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

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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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25 Nielsen Lane Stockbridge MA 01262

Stockbridge, MA25 Nielsen Lane

Price$849,000

Est. Mortgage: $/month

Pending

MLS Number 242464

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,127
  • Acreage 0.59

The best of both worlds....A stockbridge address, yet walk to lenox! This charming 1950's cape has recently received an update with the addition of a first floor primary suite with adjoining office and atrium doors to the deck, 2.5 new bathrooms, expanded and updated kitchen, breakfast nook and den with built ins and access to the large deck, surrounded by stone walls. The original living room with fireplace and wood floors evokes all the charm of the original cape while the 3 bedrooms and full bath on the second floor offers great guest or family space. Windows, roof, buderus gas boiler, hot water, and septic have all been replaced within the last 10+- years. Walk to town, shakespeare & co or ozawa hall, or sit on your back deck and enjoy the privacy!

Listed by Mary Jo Piretti Miller of PIRETTI REAL ESTATE ((413) 637-1696x1)

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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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176 Old Stockbridge Road Stockbridge MA 01262
Coming Soon

MLS Number 242593

  • Condo
  • Bedrooms 2
  • Bathroom 3
  • Year Built 1988
  • Square Feet 1,853

Showings begin on wednesday march 6th! Some of the best views the berkshires have to offer. Winden hill condos are in stockbridge, but within 1.5 miles of downtown lenox and a short drive to tanglewood. Two bedrooms each with private bath; great room with vaulted ceiling and french door to the spacious deck. Den serves as bonus third sleeping space. Natural gas heat, central a/c, charging station for your electric vehicle. Community pool, tennis/pickleball.

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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$670,000

Est. Mortgage: $/month

MLS Number 242273

  • 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: 6.94% last updated on Feb 29, 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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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: 6.94% last updated on Feb 29, 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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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: 6.94% last updated on Feb 29, 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 G. FULS JR. REAL ESTATE CO. ((413) 884-5511)

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 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: 6.94% last updated on Feb 29, 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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Based on information submitted to BCMLS  as of March 4, 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.