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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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! You'll be only minutes from nearby Berkshire attractions in Great Barrington, Main Street in Stockbridge, Tanglewood, or Mass MoCA. From your convenient Southern Berkshire County location, you could shop in NYC in a few hours, or lunch in Boston if you wish.
$199,000

305 Undermountain Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
32Picture(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.
$635,000
$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)
36Picture(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.
$795,000

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

991 Home Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
2Bathroom(s)
26Picture(s)
2,010Sqft
Sweet Antique Farmhouse with far reaching expansive views and over 70 acres of recreational land. Property is in the 61A and has low taxes! Only 5 miles to downtown Great Barrington. Separate studio space for office or home gym. Pool is open and ready for your summer enjoyment.
$695,000

793 Salisbury Rd, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
3Bathroom(s)
10.00Parking(s)
32Picture(s)
2,280Sqft
Move-in ready and nestled amidst trees off Sheffield's highly-desirable Salisbury Road sits this striking single floor home, custom-crafted to highest contemporary standards. Enter through the expansive front door to an open floor plan, kitchen/dining/living area with vaulted ceilings - perfect for entertaining.
$715,000

1095 Ashley Falls Rd, Sheffield, Massachusetts 01222

Residential For Sale

2Bedroom(s)
2Bathroom(s)
18Picture(s)
1,425Sqft
ANTIQUE COLONIAL in the charming historic village of Ashley Falls. First floor has a living room with wood-stove insert, dining room, kitchen, half bath, and guest bedroom. Upstairs is the primary bedroom suite with a full bath and walk-in closet. Wide-plank hard pine floors, exposed beams, and other original details. Nice front porch overlooking a large side yard. Attached one car garage.
$349,000

59 Main St, Sheffield, Massachusetts 01257

Residential For Sale

9Bedroom(s)
9Bathroom(s)
46Picture(s)
4,928Sqft
This handsome Colonial two-story inn resides in historic Sheffield. Originally built for Rev. Bradford, this house has watched over generations of families. A successful B & B for the last 30+ years -Trip Advisor Award of Excellence/#1 B & B. 7BR/7BA in the Inn, gracious dining, country kitchen & contemporary innkeepers quarters 2BR/1.5 BA. Barn/garage 24x40. Lush gardens and grounds.
$925,000

59 Main St, Sheffield, Massachusetts 01257

Commercial For Sale

47Picture(s)
4,928Sqft
This handsome Colonial two-story inn resides in historic Sheffield. Originally built for Reverend Bradford, this house has watched over generations of families. A successful B & B for the last 30+ years -Trip Advisor Award of Excellence/#1 B & B. 7BR/7BA in the Inn, gracious dining, country kitchen & contemporary innkeepers quarters 2BR/1.5 BA. Barn/garage 24x40.
$925,000

2080 Undermountain Rd, Sheffield, Massachusetts 01257

Commercial For Sale

39Picture(s)
5,850Sqft
Breathtaking Educational Facility, Residential Complex or Corporate Retreat This spectacular 85+/- acre property is a destination Educational Center.
$11,890,000

2080 Undermountain Rd, Sheffield, Massachusetts 01257

Residential For Sale

11Bedroom(s)
6Bathroom(s)
38Picture(s)
5,850Sqft
This spectacular 85+/- acre property is a destination Educational Center. It offers a magnificent 1880 Manor House, with spectacular distant Views, a Pond, and 11 additional buildings which house an Auditorium, Group Meeting Areas, Breakout Private Offices, a Fitness Center, Pondside Cottage, huge Dining Hall with Commercial Kitchen, and accommodations in over 56 Guest Rooms.
$11,890,000

481 Shunpike Rd, Sheffield, Massachusetts 01257

Residential For Sale

1Bedroom(s)
2Bathroom(s)
34Picture(s)
1,296Sqft
Passive solar home with views to South and West. Separate summer cottage or office space with screened porch and deck w/views facing west. Includes a 2 story Barn/Studio space 36'x28' 3 over head doors, concrete floors used as sculpture studio. 2nd floor with two finished rooms with hardwood floors to private deck to capture views. Buildings finished with Red Cedar vertical siding.
$995,000

21 Sheffield Business Park, Sheffield, Massachusetts 01222

Commercial For Sale

12Picture(s)
5,000Sqft
5,000 SF Commercial Space located in the Sheffield Business Park on 4.04 acres. This 60x80 building includes an office, two bathrooms, large open warehouse space with three overhead doors - two are 14'. Loading dock and a loft for additional storage. Expansion possibilities. 3 Phase Power. Propane heat.
$675,000

1151 Ashley Falls Rd, Sheffield, Massachusetts 01222

Residential For Sale

2Bedroom(s)
1Bathroom(s)
21Picture(s)
1,255Sqft
This petite antique Federal-era home offers easy country living & rustic elegance in a quaint New England village setting. The interior features beautiful wide plank floors, a front living room w/ fireplace, dining room w/ built-in corner cabinet, and small vintage kitchen.
$369,000

Sheffield, Massachusetts 01257

Commercial For Sale

7Picture(s)
1,800Sqft
This property holds the field where J.W. Western Steakhouse's black Angus cattle once roamed, before they were served across the street at their restaurant, before farm-to-table was en vogue. This property has an endless amount of possibilities. A 40' x 30' commercial building is in place with power. This property could be made into multiple building lots as well.
$349,000

24 Maple Ave, Sheffield, Massachusetts 01257

Residential For Sale

3Bedroom(s)
3Bathroom(s)
30Picture(s)
1,858Sqft
This immaculate property has been tastefully renovated yet retains the character and craftsmanship of a classic New England home. Situated on a jewel-box .25 acres, the house is surrounded by world-class landscaping and the backdrop of a sanctuary-like marsh and bird-watchers paradise.
$499,000

1144 Ashley Falls Rd, Sheffield, Massachusetts 01222

Land For Sale

8Picture(s)
3.32Acre
Partly wooded and partly in pasture, these three lots enjoy Southwesterly vistas towards Rannapo Rd. Great opportunity for a family compound in a quiet setting yet still in a central location. Enjoy the Sheffield Land Trust, and Bartholomew's Cobble close by. 4 miles south of Main St, Sheffield.
$649,000
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