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!
Sheffield MA
704 Main St, Sheffield, Massachusetts 01257
2Bedroom(s)
1Bathroom(s)
11Picture(s)
875Sqft
Ranch style fixer-upper with possibilities! A simple home with detached garage, and partially fenced yard. The price reflects the need for repairs and upgrades. Being sold ''as-is''.
$167,000
MLS Number 242002
Sheffield MA
647 Silver St, Sheffield, Massachusetts 01257
3Bedroom(s)
3Bathroom(s)
40Picture(s)
1,792Sqft
Welcome to your dream retreat on one of the prettiest roads in south Berkshire. This charming log cabin exudes warmth and character, featuring two inviting porches with breathtaking views of the surrounding landscape. The large kitchen boasts lovely views, handmade cabinetry, granite tops and ample built in storage. The Updated baths seamlessly blend modern convenience with rustic charm.
$725,000
MLS Number 242005
Sheffield MA
216 Undermountain Rd, Sheffield, Massachusetts 01257
3Bedroom(s)
2Bathroom(s)
23Picture(s)
1,506Sqft
Mid Century Modern Mountain & Lakeside Retreat-open floor plan and indoor/outdoor layout perfect for entertaining. Enjoy single level living-three bedrooms & two full baths. Original details include- mid-century modern lighting and cabinetry. Spacious great room features stone fireplace and open living/dining area with built-ins. Seasonal screened porch off the kitchen.
$549,000
MLS Number 241830
Sheffield MA
524 Hewins St, Sheffield, Massachusetts 01257
4Bedroom(s)
3Bathroom(s)
32Picture(s)
2,480Sqft
Enjoy the tranquil charm of country living in this attractive Berkshire home. Abutting over 35 acres of untouched farm land and situated on 1.5 acres, it boasts a front porch and a spacious back deck with sweeping pastoral views - offering the perfect backdrop for morning coffee or entertaining guests.
$695,000
MLS Number 241831
Sheffield MA
616 Sheffield Plain Rd, Sheffield, Massachusetts 01257
6Parking(s)
40Picture(s)
6,105Sqft
Great Mixed Use business opportunity with just under 300 feet of frontage on route 7. Grand old estate with tons of potential. Would make a great retreat. 8 bedrooms, 5.5 baths, 8 firepaces. on the river! A winery, distillary, brewery, dispencery and 2 restaurants and a convenient store all within a few minutes walk. A campground with rooms to rent, boats on the river.
$649,000
MLS Number 241789
Sheffield MA
24 Cactus St, Sheffield, Massachusetts 01257
3Bedroom(s)
2Bathroom(s)
29Picture(s)
1,494Sqft
Absolute gem, conveniently located on a country Berkshire road. Open floor plan, move in ready. First floor full bath and bedroom. Upstairs two bedrooms, office/den and full bath. Access to Berkshire Trout Pond. Hot tub for year round use. Furnishings available.
$499,000
MLS Number 241777
Sheffield MA
169 Ashley Falls Rd, Sheffield, Massachusetts 01257
3Bedroom(s)
3Bathroom(s)
22Picture(s)
2,016Sqft
Beautiful home on picturesque Ashley Falls Rd. Long list of recent renovations includes kitchen, bathrooms, electrical, plumbing, heat and air conditioning, and roof. Living room features propane fireplace and bay window. The kitchen and dining room share a dramatic space with cathedral ceiling. First floor primary suite plus a half bath/laundry. Upstairs, two bedrooms share a hall bath.
$575,000
MLS Number 241479
Sheffield MA
139 Silver St, Sheffield, Massachusetts 01257
18Picture(s)
1,656Sqft
SHEFFIELD.....If you are looking for a rehab project, this is the property for you! A good amount of the demolition work has begun taking the interior down to bare bones leaving the layout pallet for your imagination.
$189,000
MLS Number 241455
Sheffield MA
1373 Boardman St, Sheffield, Massachusetts 01257
76Picture(s)
14,114Sqft
Over 10,000sf of studio or manufacturing space available along with two extraordinary living spaces available under the same roof in the General Business District of Sheffield, MA.
$3,500,000
MLS Number 241420
Sheffield MA
1373 Boardman St, Sheffield, Massachusetts 01257
4Bedroom(s)
5Bathroom(s)
76Picture(s)
14,114Sqft
Welcome to The Factory - a gorgeous three bedroom, three bath loft that comes with a rather large 10,000 foot manufacturing or studio space, along with an executive office with its own bedroom, another full bath and a service kitchen. Essentially two separate living spaces within the commercial space.
$3,500,000
MLS Number 241419
Sheffield MA
117 Main St, Sheffield, Massachusetts 01257
9Picture(s)
1,000Sqft
Boutique Bakery in the heart of Sheffield is for Sale. Space was renovated for bakery use in late 2020 and opened in February 2021. Space is 1,000 SF and all equipment and inventory are included in the sale. Lease will need to be assumed, business only for sale, no real estate. Current owners have built a nice solid business with loyal clientele.
$145,000
MLS Number 241594
Sheffield MA
Lot #3 County Rd, Sheffield, Massachusetts 01257
9Picture(s)
9.49Acre
Embrace the allure of nature with this private 9-acre building lot. Nestled in Sheffield, this wooded paradise offers a shared driveway, approved 4-bedroom septic tank (just the tank), and the potential to create your dream retreat. Seize this opportunity to craft a harmonious haven amidst the trees.
$179,000
MLS Number 241294
Sheffield MA
45 Root Ln, Sheffield, Massachusetts 01257
5Bedroom(s)
6Parking(s)
33Picture(s)
2,415Sqft
Escape to Sheffield, MA's enchanting town with this captivating 5-bed, 2-bath home. Step into a spacious living room, perfect for guests and cozy nights by the fireplace. Discover a generous kitchen, ideal for culinary enthusiasts with room for an eat-in island or table. Adjacent, a versatile dining room awaits. Nestled on a private street, enjoy tranquility just moments from downtown.
$581,000
MLS Number 241252
Sheffield MA
590 Main St, Sheffield, Massachusetts 01257
2Bedroom(s)
1Bathroom(s)
19Picture(s)
1,160Sqft
This sweet little house is ready to move in, with lots of potential for first-time buyers or anyone looking to down-size. Conveniently located just south of the center of Sheffield and 5 minutes north of CT border, this home has had many updates since 2021 including a new boiler and siding.
$329,000
MLS Number 241222
Sheffield MA
11-25 Maple Ave, Sheffield, Massachusetts 01257
21Picture(s)
3,008Sqft
Multi use building conveniently located in the heart of downtown Sheffield. Currently comprising of 2 business-use spaces and 3 one bedroom residential units. This property offers ample parking, high exposure and comfortable sized living units. Great opportunity to own an income producing property in a great location.
$395,000
MLS Number 241225
Sheffield MA
11-25 Maple Ave, Sheffield, Massachusetts 01257
3Bedroom(s)
4Bathroom(s)
21Picture(s)
3,008Sqft
Multi use building conveniently located in the heart of downtown Sheffield. Currently comprising of 2 business-use spaces and 3 one bedroom residential units. This property offers ample parking, high exposure and comfortable sized living units. Great opportunity to own an income producing property in a great location.
$395,000
MLS Number 241224
Sheffield MA
960 South Undermountain Rd, Sheffield, Massachusetts 01257
3Bedroom(s)
3Bathroom(s)
6Parking(s)
43Picture(s)
2,289Sqft
21st Century Homestead! Refurbished antique house, new barn, timber frame studio, salt water pool, and heated 4-car garage at the foot of Taconic Mountain range in Sheffield. On a manageable 12-acres, the current stewards have prioritized character and quality of materials without sacrificing energy efficiency.
$1,595,000
MLS Number 241212
Sheffield MA
616 Sheffield Plain Rd, Sheffield, Massachusetts 01257
8Bedroom(s)
5Bathroom(s)
6Parking(s)
88Picture(s)
6,105Sqft
This Pre Revolutionary War home is one of the oldest estates in Sheffield (1774) It has been expanded over the years to 6000 sqft. There is also a very charming carriage house on the property as well. This magical property has tons of potential. Zoned mixed use, this home consists of 6 bedrooms, 8 fireplaces with 20 rooms.
$649,000
MLS Number 241605
Sheffield MA
259 Salisbury Rd, Sheffield, Massachusetts 01257
3Bedroom(s)
3Bathroom(s)
4Parking(s)
51Picture(s)
2,866Sqft
A Berkshire Dairy Barn conversion in Sheffield awaits you!3 Beds and 2 baths and just under 3000 sq ft. Soaring ceiling height, oversize windows and an open concept floor plan to entertain. Hang by the fire downstairs or go up the stairs to the loft for whatever you make it. Living room opens up to a beautiful lawn for gardens.
$449,000
MLS Number 241110
Sheffield MA
690 Main St, Sheffield, Massachusetts 01257
25Picture(s)
3,280Sqft
ASTONISHING AND UNIQUE BERKSHIRE COMMERCIAL SPACEImagine a 21st CENTURY BUILDING WITHIN AN 18th CENTURY POST & BEAM BARN, embodying the very best of what's old and what's new...
$625,000
MLS Number 241025
Sheffield MA
1014 Salisbury Rd, Sheffield, Massachusetts 01257
2Bedroom(s)
4Parking(s)
36Picture(s)
1,379Sqft
If you are looking for the charm of an 1800 two bedroom house this could be what you are looking for. There is a good sized period kitchen with two Dutch doors, one leading to the screened porch and the other to the back yard. The living room has wide board flooring a beamed ceiling and a wood burning fireplace.
$350,000
MLS Number 240819
Sheffield MA
296 South Main St, Sheffield, Massachusetts 01257
1Bedroom(s)
2Bathroom(s)
20.00Parking(s)
15Picture(s)
5,045Sqft
This building is a craftsman work of art with a rustic post and beam design, the vaulted ceilings and gracious windows offer an elegant, light filled atmosphere for the business of your dreams.Private suite offers a kitchen, full bath and lofted office/bedroom for a unique live/work opportunity.
$1,129,000
MLS Number 240838
Sheffield MA
296 South Main St, Sheffield, Massachusetts 01257
2Bathroom(s)
20.00Parking(s)
19Picture(s)
5,045Sqft
This building is a craftsman work of art with a rustic post and beam design, the vaulted ceilings and gracious windows offer an elegant, light filled atmosphere for the business of your dreams. Presently home to a successful winery, you will find a tasting room and retail store in the left wing with a second level loft.
$1,129,000
MLS Number 240811
Sheffield MA
296 South Main St, Sheffield, Massachusetts 01257
2Bathroom(s)
20.00Parking(s)
18Picture(s)
5,045Sqft
This building is a craftsman work of art with a rustic post and beam design, the vaulted ceilings and gracious windows offer an elegant, light filled atmosphere for the business of your dreams. Presently home to a successful winery, you will find a tasting room and retail store in the left wing with a second level loft.
$1,129,000
MLS Number 240810
