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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Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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 steet painting. Beautiful and classic victorian architecture. Property consists of two storefronts and a 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: 6.09% last updated on Feb 2, 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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21 Interlaken Cross Road Stockbridge MA 01262
Pending

MLS Number 235817

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,216
  • Acreage 2.6

This wonderful one-level home features beautiful grounds, and a wonderful, private location walking distance to stockbridge bowl. The house consists of a well maintained mid-century ranch, plus a dramatic primary suite addition with sleeping and living areas, adobe fireplace, cathedral ceilings, built-in cherry cabinetry, and a nicely appointed bathroom. There is a wood-paneled living room with propane fireplace and built-ins, open kitchen/dining area, screened porch, expansive trex decking, two-car garage, and lovely gardens with pond. Minutes to stockbridge, lenox, and all the berkshires has to offer, this unique oasis would make a wonderful getaway or full-time home.

Listed by Claire Naylor Pollart and Lance Vermeulen of LANCE VERMEULEN RE,INC

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$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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

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$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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

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.

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$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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 Main St.

Stockbridge MA 01262

Stockbridge, MA

Price$550,000

MLS Number 239584

  • 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. $2600/month

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

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$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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$545,000

Est. Mortgage: $/month

MLS Number 236944

  • Land
  • Acreage 5.33

And the best has been saved for last! Top of stone hill is the only remaining lot in this desirable luxury subdivision. Located on the cul- de- sac, top of stonehill is ready to build with electric, well and septic in place.The optimum building site has been identified and marked with brush cleared . A private site with quick access to tanglewood , shopping and town. Views can be maximized with more selective clearing..

Listed by Keith Ross and Cindy Welch of LANDVEST,INC.

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$
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$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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Prospecthill + Rattlesnake Mountain Road Stockbridge MA 01262

MLS Number 237462

  • Land
  • Acreage 22.29

**new price for 2023** over 22 acres of prime stockbridge land on 2 adjoining parcels. Build your dream estate with possible frontage on both prospect hill rd and rattlesnake mountain rd. Wonderful views and close to stockbridge, tanglewood and most berkshire attractions. Great property for solar power. **now available at $288,000 under assessed value!** the 2 parcels are available separately. See mls#237463 and mls#237464 .

Listed by Steven J. Weisz of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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 Mahkeenac Heights Road Stockbridge MA 01262

MLS Number 239162

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,592
  • Acreage 0.41

Three season bungalow with three bedrooms, two full bathrooms along with loft for additional sleeping space. Living room boast a floor to ceiling field stone fireplace creating that perfect cool night atmosphere. The primary bedroom and bath is in the silo section of the house with the other two bedrooms in the main section of the house that has access to their own full bathroom. There is an ample sized kitchen that can accommodate a small table for eating. The rear of the house has two separate decks for morning sun along with a nice back yard. There also is a front deck for the afternoon sun. House is currently on the association water source that is shut off around the end of october for the winter season. Other houses in the area have drilled their own wells to enable year-round use.

Listed by Michael A Sorrentino of BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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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21A Interlaken Road Stockbridge MA 01262

Stockbridge, MA21A Interlaken Road

Price$289,000

Est. Mortgage: $/month

MLS Number 239548

  • Land
  • Acreage 5.04

Five lovely acres in stockbridge with seasonal views. Two minutes to stockbridge bowl boat ramp and four minutes to tanglewood. Recent survey, cleared and ready to go. Town sewer available.

Listed by Kristin P. Piasecki of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 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 February 4, 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.