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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561 West Rd, Sheffield, Massachusetts 01230

Residential For Sale

3Bedroom(s)
2Bathroom(s)
66Picture(s)
1,668Sqft
Set back on 1 acre, this stylish move-in ready c.1910 farmhouse boasts sweeping pastoral views and has been refreshed with modern touches while keeping true vintage charm throughout, with 3 well-sized bedrooms, 1.
$525,000

397 Clayton Rd, Sheffield, Massachusetts 01222

Residential For Sale

4Bedroom(s)
2Bathroom(s)
21Picture(s)
1,245Sqft
Four bedroom, 1.5 bath Cape. First time on market. Enjoy this lovely setting on one acre near Great Barrington, Sheffield, Egremont, Northwest Corner and New York State. Hardwood floors throughout the home. On a cold night, enjoy sitting in the living room next to the fireplace. The Four Season Room is a bonus room with heated floors. Top of the line furnace, approx. 6 years old.
$297,500

371 Berkshire School Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
3Bathroom(s)
21Picture(s)
2,585Sqft
This property is located in a treasured part of Berkshire County. It is walking distance to the center of town, to the State Park, the Library, and within a 20 min. drive 2 major Ski Areas, 4 major Golf Courses, Riding Stables, Tanglewood, and Car Racing, Sheffield is on the boarder of NY State &Ct. less than 2 hours to Mid Town.
$729,000

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

Land For Sale

2Picture(s)
5.14Acre
Setback off Berkshire School Road near Undermountain School the surveyed 5+ acre parcelhas been cleared with public water access & a successful perc test. Ready to build. The abutting 4+ acre parcel also available see MLS# 235776.See Maps.
$67,000

446 Boardman St, Sheffield, Massachusetts 01257

Residential For Sale

5Bedroom(s)
1Bathroom(s)
1Picture(s)
1,512Sqft
Investors take note. 5.25 acres with Structures. Property is being sold as is.
$199,000

935 Ashley Falls Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
33Picture(s)
1,800Sqft
A quirky, craftsman cottage on a divisible lot. Large, newer insulated barn with almost 1600 square feet could be an amazing workshop or artist's studio. Lots of local history and no shortage of potential. First floor primary suite could be an Accessory Dwelling Unit (ADU) by permit from the Planning Board. Freestanding studio/office insulated and currently without heat.
$425,000

210 Ashley Falls Rd, Sheffield, Massachusetts 01257

Residential For Sale

5Bedroom(s)
1Bathroom(s)
10.00Parking(s)
31Picture(s)
1,740Sqft
This home has been lived in by the same family for over 50 years. It could use some updating. The lot is just over three acres! Could be a great starter home for a young family or a nice second home as well! This home is being sold as-is.
$249,000

319 Berkshire School Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
3Bathroom(s)
27Picture(s)
1,940Sqft
Beautifully renovated colonial on the Schenob Brook. Light filled living room takes in east, south and west light, open dining and kitchen with walk in pantry also filled with light. Entry room with fireplace and newly added powder room complete the first floor. Upstairs there are two guest bedrooms and a hall bath with a landing and laundry closet.
$835,000

151 W Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
1Bathroom(s)
28Picture(s)
1,100Sqft
Lovely setting with a beautiful vista set back off a country road close to Great Barrington, Sheffield and Egremont. Large mudroom, oversized garage, galley kitchen open to dining area, large living room with fireplace and view! Three bedrooms and one full bath all on one level. Many improvements have been made.
$329,000

139 Main St, Sheffield, Massachusetts 01257

Multifamily For Sale

4Bedroom(s)
4Bathroom(s)
33Picture(s)
5,005Sqft
Prime commercial /mixed-use / multi-family property on the high-traffic Route 7 Berkshire corridor. Situated just south of the scenic Sheffield green, this unique property offers endless possibilities for re-use & reinvention.
$729,000

139 Main St, Sheffield, Massachusetts 01257

Commercial For Sale

33Picture(s)
5,005Sqft
Prime commercial /mixed-use / multi-family property on the high-traffic Route 7 Berkshire corridor. Situated just south of the scenic Sheffield green, this unique property offers endless possibilities for re-use & reinvention.
$729,000

200 Water Farm Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
42Picture(s)
2,300Sqft
Picture a winding dirt driveway lined with apple trees on a fantastic estate set on over 17 acres. Welcome home to 200 Water Farm Rd with views of Mt. Everett. Light filled kitchen-dining room with large wood burning brick fireplace. First floor has spacious living room with french doors. Two first floor bedrooms share bath with soaking tub. Fabulous newly refinished wood floors.
$949,000

59 Main St, Sheffield, Massachusetts 01257

Commercial For Sale

47Picture(s)
5,358Sqft
STAVELEIGH HOUSE B&B. A lovely 7 bedroom, 7 bath turnkey B&B fully furnished in the historic village center of Sheffield. 1600 sq ft owner's quarters with open floor plan, 2 bedrooms and 1.5 baths. Originally built by Reverend Bradford around 1818, this handsome gracious home has been operated as a successful B&B for thirty years.
$839,000

59 Main St, Sheffield, Massachusetts 01257

Residential For Sale

9Bedroom(s)
9Bathroom(s)
47Picture(s)
5,358Sqft
GRACIOUS 1818 COLONIAL IN THE VILLAGE OF SHEFFIELD on a beautifully landscaped acre. Walk to restaurants, library, post office and historical society. Currently a turnkey fully furnished 7 bedroom, 7 bath B&B with a 1600 sq ft open plan owner's quarters with 2 bedrooms and 1.5 baths. Many permitted uses in the Village Center District.
$839,000

147 Main St, Sheffield, Massachusetts 01257

Residential For Sale

4Bedroom(s)
3Bathroom(s)
48Picture(s)
2,803Sqft
DRIPPING WITH CHARM. Village setting with rocking chair front porch. Gracious rooms and an easy flow. Beautiful gleaming wood floors, fireplaces, screened porch, large windows overlooking the sunny level lawn. A first floor primary bedroom with fireplace and on suite bath with tub.
$650,000

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. New roof; new triple pain windows, new gutter and downspouts, new decks; new plumbing,new heat and ac, new doors and hardware throughout, new bathroom. Convenient location with lovely private backyard to enjoy the firepit or yard games. Open plan living with sparkling new counters and all Jennair appliances.
$399,000

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

3Picture(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!Under Contract.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

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
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