Communities – Stockbridge

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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13 Park St, Stockbridge, Massachusetts 01262

Multifamily For Sale

9Bedroom(s)
7Bathroom(s)
8Picture(s)
4,863Sqft
PRICE REDUCTION! Outstanding opportunity to own a fully rented 5-unit multifamily rental property in the heart of downtown Stockbridge. Electric is submetered. New boiler installed 4 years ago. Pre-painted siding means no need to paint exterior. Ideally located - walk to everything! Only 1 block from post office, library, restaurants, shopping & Red Lion Inn.
$695,000

27 Lenox Rd, West Stockbridge, Massachusetts 01266

Residential For Sale

4Bedroom(s)
3Bathroom(s)
43Picture(s)
1,501Sqft
Extensive renovation by a noted design/builder, this charming farmhouse is within walking distance to the village of West Stockbridge. Nice layout with good flow. Pleasing selection of finish details and quality craftsmanship throughout. Cook's kitchen with center island. LR with gas fireplace.
$535,000

11 Prospect Hill Rd, Rd, Stockbridge, Massachusetts 01262

Condominium For Sale

4Bedroom(s)
3Bathroom(s)
27Picture(s)
2,144Sqft
Rare opportunity to own a beautiful modern condo on the property of the historic Oronoque Estate. With quick access to Stockbridge, Tanglewood, and local attractions, the location is ideal for enjoying the Berkshires. With 4 bedrooms and 2.5 bathrooms, this spacious floor plan offers a main floor primary suite and living space.
$595,000

108 Interlaken Rd, Stockbridge, Massachusetts 01262

Residential For Sale

2Room(s)
22Picture(s)
500Sqft
279' OF FRONTAGE ON STOCKBRIDGE BOWL. A long groomed driveway leads to this large, gorgeous parcel of lakefront. Wide, stunning southeasterly views of the lake with mountains beyond. A boathouse at the waters edge, scarce for lakefront. A Victorian cottage (no water or utilities) deemed historic. A rustic storage barn provides a footprint with potential. Septic fields in. Drilled well.
$2,500,000

17 Prospect Hill Rd, Stockbridge, Massachusetts 01262

Residential For Sale

4Bedroom(s)
5Bathroom(s)
53Picture(s)
6,000Sqft
The property, anchored by a 200 year old copper beech, runs along the crest of Prospect Hill. Magnificent unspoiled views to the south and west create interest at all hours of the day and at sunset in particular.Rumored to have been the first of the large 'cottages' on Prospect Hill. A cornerstone dated 1823 still exists although the house has undergone numerous renovations.
$4,450,000

Lot 3 Silver Mine Ln, West Stockbridge, Massachusetts 01266

Land For Sale

6Picture(s)
1.42Acre
Luxury Homesite on 1.42 acres with rolling topography and distant views. Apple trees and wildflowers abound on this bright and open lot. A thoughtful cul de sac of fine homes just minutes to West Stockbridge, Lenox and all the Berkshires has to offer. This lot is peaceful and tranquil and well protected from neighboring properties.
$149,000

17 Smith Rd, West Stockbridge, Massachusetts 01266

Residential For Sale

3Bedroom(s)
2Bathroom(s)
55Picture(s)
1,856Sqft
Country living at its best! This immaculate and move in ready ranch sits on 3 sprawling acres. Located minutes from local attractions like Tanglewood, lakes and shopping. Home boasts a formal living room with fireplace, a spacious family room with vaulted ceilings, fireplace and skylights. Kitchen has newer appliances and laundry.
$575,000

389 Stockbridge Rd, Great Barrington, Massachusetts 01230

Commercial For Sale

5Picture(s)
1,600Sqft
Prime retail space or professional offices, salon.
$2,500

108 Interlaken Rd, Stockbridge, Massachusetts 01262

Land For Sale

22Picture(s)
1.34Acre
279' OF FRONTAGE ON STOCKBRIDGE BOWL. A long groomed driveway leads to this large, gorgeous parcel of lakefront. Wide, stunning southeasterly views of the lake with mountains beyond. A boathouse at the waters edge, scarce for lakefront. A Victorian cottage (no water or utilities) deemed historic. A rustic storage barn provides a footprint with potential. Septic fields in. Drilled well.
$2,500,000

42 Stockbridge Rd, Great Barrington, Massachusetts 01230

Commercial For Sale

37Picture(s)
2,173Sqft
Great potential in B2 Zone for commercial, residential or live/work. High visibility for destination RETAIL! Perfect move-in condition, freshly painted inside & out. Town water, sewer, natural gas heat, high speed internet and excellent cell phone service. Ample off-street parking, plus a large fenced yard to relax and enjoy.
$467,797

42 Stockbridge Rd, Great Barrington, Massachusetts 01230

Residential For Sale

5Bedroom(s)
3Bathroom(s)
59Picture(s)
2,173Sqft
Endless potential for commercial, residential or live/work. Great visibility for destination RETAIL! Perfect move-in condition, freshly painted inside & out. Town water, sewer, natural gas heat, high speed internet and excellent cell phone service. Ample off -street parking, plus a large fenced yard to relax and enjoy.
$467,797

24 Glendale Rd, Stockbridge, Massachusetts 01262

Residential For Sale

3Bedroom(s)
1Bathroom(s)
9Picture(s)
2,140Sqft
A classic 'fixer-upper'. Rustic charm in a bucolic location. An opportunity to make a new home. Restore, renew, rejuvenate. The house is not currently habitable. and would be for sale ''as is'' only.Did I mention the fabulous Barn ?? It will entertain your every need.
$319,000
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