Communities – Sheffield

The oldest town in Berkshire County, Sheffield was purchased from Chief Konkapot and other Stockbridge Indians in 1724. Noted for its natural beauty and deep agricultural soils, much of Sheffield remains open and in agricultural production. A combination of wide open river valley, mountain vistas and active farmland makes Sheffield one of the most scenic towns in the Commonwealth. Located on US Route 7, Sheffield is approximately one hour from Hartford, Springfield and Albany, and two and one-half hours from Boston and New York City.

Search new real estate in the Berkshire town of Sheffield, MA. Discover hundreds of current listings, including beautiful antique properties and single-family homes. Like what you see? Register with us to save your favorites, and receive notifications with similar properties are listed. Contact us today to see any of the homes below!

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358 Main St, Sheffield, Massachusetts 01257

Residential For Sale

2Bedroom(s)
1Bathroom(s)
49Picture(s)
960Sqft
The Perfect Pied a Terre. Just completely renovated and stylishly finished. Convenient location with lovely private backyard to enjoy the firepit or yard games. Open plan living with sparkling new counters and all Jennair appliances. Large windows let in tons of natural light. Two spacious bedrooms.
$399,000

84 Main St, Sheffield, Massachusetts 01222

Residential For Sale

1Bedroom(s)
1Bathroom(s)
31Picture(s)
642Sqft
Tiny home was just ahead of its time! Sweet and petite home on a scenic level 1 acre lot in the Southern Berkshire. Open living room/dining area, kitchen, one bedroom, one full bath all on one level. Separate barn/garage. Replacement windows. Make no mistake, this property needs updating, but will be well worth the effort. BEING SOLD AS IS.
$125,000

508 Polikoff Rd, Sheffield, Massachusetts 01222

Residential For Sale

3Bedroom(s)
4Bathroom(s)
4Parking(s)
33Picture(s)
2,156Sqft
Perfect home with plenty of space to play outside in your fenced-in backyard. Live and work from this Colonial home built in 2000. Wood floors throughout and large windows for natural light. Generous back deck, perennials, and a fire pit for entertaining family and friends. Beautiful mature trees and newly refreshed landscaping. 3 beds, 3 baths.
$525,000

622 West Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
21Picture(s)
1,300Sqft
Such a delightful sunny 3 bedroom Farm Colonial with 1.5 baths, sitting pretty on a 1/2 acre lot with beautiful mountain views! The main floor boasts brand new wood floors, a wood burning fireplace, dining room and bright eat-in kitchen with direct access to a sun deck with lovely views. Two garage stalls offer great storage as well as a workshop.
$339,000

429 Berkshire School (Lot 1B) Rd, Sheffield, Massachusetts 01257

Land For Sale

5Picture(s)
4.77Acre
Set Back off Berkshire School Road near Undermountain School this surveyed 4+ acre lot has been cleared with public water access & successful existing perc test. All the work has been done ....Ready to Build!The abutting 5acres lot is also cleared and available but not included in this pricing. See Maps.
$67,000

535 Sheffield-Egremont Rd, Sheffield, Massachusetts 01257

Residential For Sale

5Bedroom(s)
7Bathroom(s)
60Picture(s)
6,746Sqft
SUNSET MOUNTAIN VIEWS, PRIVACY & WONDERFUL AMENITIES IN YOUR OWN PRIVATE HOME RESORT.......
$3,995,000

749 Hewins St, Sheffield, Massachusetts 01257

Residential For Sale

2Bedroom(s)
2Bathroom(s)
22Picture(s)
1,248Sqft
With the same owner for the last 40 years, this home has been thoughtfully maintained and taken care of with updates as needed. Located on an acre with quick access to downtown Great Barrington, this country bungalow is perfectly situated to enjoy the beauty of the Berkshires and the amenities of the city.
$289,000

277 County Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
30Picture(s)
1,512Sqft
Lovely updated Ranch on over 2.5 sunny acres. Large entry room with half bath and direct access to the two car oversized garage. Beautiful bright eat-in kitchen with soapstone counters, new appliances and large skylight with a slider to the screened in porch. Living room with fireplace and hall to the three bedrooms and updated hall bath.
$495,000

599 Cooper Hill Rd, Sheffield, Massachusetts 01257

Residential For Sale

5Bedroom(s)
3Bathroom(s)
22Picture(s)
3,364Sqft
Location and views are what this listing is all about. Perched on top of Cooper Hill these 20 acres offer unobstructed views in all directions. It is possible to see both magnificent sunrises and sunsets. The listing is comprised of 5 lots that must be sold together. There are two existing houses either of which could become part of an estate.
$2,500,000

35 School St, Sheffield, Massachusetts 01222

Residential For Sale

5Bedroom(s)
2Bathroom(s)
32Picture(s)
3,060Sqft
BUILT IN 1880 THIS DELIGHTFUL HOME ON THE OUTSKIRTS OF THE QUAINT VILLAGE OF ASHLEY FALLS, OFFERS COMFORTABLE COUNTRY LIVING. HIGH CEILINGS, BEAUTIFUL WOOD FLOORS, AND DECORATIVE MOLDINGS THROUGHOUT.5 BEDROOMS, 2 FULL BATHS,A LARGE COUNTRY KITCHEN WITH PANTRY, FORMAL DINING ROOM AND A SPACIOUS FRONT PARLOR. THE SCREENED PORCH IS THE PERFECT PLACE TO ENTERTAIN, DINE & JUST PLAIN RELAX. On 1.
$699,000

23 Elm Ct, Sheffield, Massachusetts 01257

Residential For Sale

2Bedroom(s)
2Bathroom(s)
35Picture(s)
2,400Sqft
STUNNING TURNKEY CONTEMPORARY - CENTRALLY LOCATED, YET TUCKED AWAY!Steps from some of South County's favorite eating spots, yet off the main road and privately situated, this 2 bed, 2.5 bath home is the perfect getaway for those seeking modern, well-appointed living in a convenient location.
$695,000

145 Hewins St, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
20Picture(s)
1,320Sqft
Perched on a quiet road of gentle rolling hills, this meticulously maintained ranch is country living at its best. The 3-bedroom, 1.5 bath single-level home boasts a spacious living room with working fireplace and a vast picture window offering distant mountain views. Formal dining room steps down to a 3-season screened-in porch that's perfect for quiet reading or entertaining.
$399,000

356 Miller Ave, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
34Picture(s)
1,432Sqft
Near the intersection of Cook Road and Miller Ave you will find this beautiful home on a quiet country road, that is only 10 minutes from downtown Great Barrington! This light filled offering features 3 bedrooms, 2 full baths, and plenty of storage space. Above the garage you will find what could be a lovely in-law suite which hosts the third bedroom, and second full bath.
$449,000

0 County Rd, Sheffield, Massachusetts 01257

Land For Sale

4Picture(s)
35.77Acre
If you've been looking in the Berkshires for a build site with high ground, this wooded lot is for you! Over 100 feet of driveway already constructed from County Road. You could choose to continue up the hill, and establish a home site with views of Mount Everett, or build lower down and enjoy the sounds of the Ironworks Brook, a year-round stream running along the edge of the property.
$179,000

305 Undermountain Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
64Picture(s)
1,700Sqft
Post and Beam contemporary home on 2.03 acres with a path to a parcel on Berkshire Lake. for swimming and canoeing. This move in condition home has an open plan dining, living and kitchen, an office/bedroom and a full bath on the first floor and 3 bedrooms and a full bath on the second level. Full basement.
$575,000
$95,000

42 Oak St, Sheffield, Massachusetts 01257

Residential For Sale

2Bedroom(s)
1Bathroom(s)
28Picture(s)
1,044Sqft
Immaculate 2 bedroom 1 bath contemporary bungalow in the heart of Berkshire Lake Estates. This 2006 home was meticulously built, complete with cathedral-ceiling living room dominated by native fieldstone fireplace and wrought-iron chandelier. Loft-like bedroom upstairs, while first floor houses galley-type kitchen, bathroom with shower and second bedroom, which could also be a den or dining room.
$395,000

39 Farmview Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
31Picture(s)
1,132Sqft
Adorable 3 bedroom, 2 bathroom ranch surrounded by evergreens. This home has been tastefully updated throughout. It has a large breezeway with new flooring, kitchen with gas stove, dining area and built-in bookcases, primary bathroom with marble tiles. Relax in the huge 20'x20' screen porch or walk to the small stream on the back of the property. Flat shaded yard with a shed with electric.
$525,000

347 Undermountain Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
31Picture(s)
1,680Sqft
Immaculate 3 bedroom, 2 bath contemporary New England craftsman cape. This sweet home was thoughtfully built, maintained, and recently updated by the original family of owners. Situated on 1.82 acres, the property offers a large private yard with mature landscaping, a detached two car garage with available water, electric and its own septic system, and a handy garden shed.
$495,000

0 Shunpike Rd, Sheffield, Massachusetts 01257

Land For Sale

1Picture(s)
9.33Acre
Spacious Building Lot. Quiet country road with potential for views. Easy to get to, town maintained road. Build your Berkshire dream home on a lovely lot, with easy access from NY or CT.
$145,000

94 Pike W Rd, Sheffield, Massachusetts 01257

Residential For Sale

4Bedroom(s)
3Bathroom(s)
8.00Parking(s)
26Picture(s)
2,422Sqft
This well-maintained cape sits on over 5 acres facing the south, offering a sunny yard for outdoor fun and entertaining. Front entryway opens to a center stairwell with the living room to your right, dining room to left, kitchen, full bath, bedroom, laundry room, & separate half bath complete the 1st floor.
$475,000

1076 County Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
3Bathroom(s)
38Picture(s)
2,642Sqft
Set in a tranquil, park-like setting this home set atop a hill offers gorgeous zen like views from every room & deck. 1st floor has a large open living plan w/ living room, dining area & kitchen. It's accentuated by a wainscoted cathedral ceiling, skylights, central fireplace with granite surround.
$750,000

246 County Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
72Picture(s)
1,236Sqft
Delightful country home with a 960 sq ft guest house. The main house has 3 bedrooms, 2 full baths, sauna and lovely stone terrace The guest house next to the tennis court has cathedral ceilings, tile floor, full kitchen, full bath, a large open floor plan and deck. All perfect for entertaining with great potential for rental income.
$695,000

181 Hulett Hill Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
3Bathroom(s)
25Picture(s)
1,944Sqft
Custom cape on over an acre in a sun filled setting. Open plan living with kitchen, dining and living room all flowing together with a wood stove in the dining area. Two sets of french doors take you to the deck overlooking the backyard or the patio off the front. Primary suite on main level with powder room and laundry closet at the entry.
$595,000
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