Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

Sheffield MA Real Estate

Sheffield abuts the Connecticut line and has many natural resources, most notably Bartholomew's Cobble, a 329-acre National Natural Landmark agricultural preserve. There are moderate hiking trails at the Cobble, as well as open space for picnicking and fun and informative classes and workshops offered by The Trustees of Reservations. Sheffield also has great historic significance, home to the Colonel John Ashley House, a historic house museum operated by The Trustees of Reservations and listed on the National Register of Historic Places.

Browse current listings for sale in Sheffield, MA. Don't hesitate to contact us with any of your questions.

Search SimplerRegister now to save your favorite listings and custom searches. Best of all, we'll email you when new properties that match your criteria hit the market.

Click here to view homes for sale in Sheffield.

927 Boardman, Sheffield, MA 01230

Price$1,999,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218975

  • Listings
  • Beds 5
  • Baths 4
  • Sq Ft 3679
  • Acres 13

This magical property is an ideal blend of country comfort with hip chic style. The ease and elegance were designed for those desiring a casual Berkshire lifestyle. The floor plan is perfect for gathering friends & the attention to detail is evident the minute you walk in the door ~ prepare to be wowed! The kitchen is awe inspiring as the focal point of the house and will entice even the most novice of cooks! Cathedral ceiling, exposed preserved beams, pizza oven, & LaCanche range are just a few of the highlights. The wall of glass from the living room takes in the VIEW and has a fireplace for cool Berkshire evenings. The property and VIEWS are breathtaking and the wide open skies showcase the surrounding fields, mountains, pond, and DRAMATIC NIGHTLY SUNSETS.STUNNING!

Listing courtesy of Lori J Rose and Martha Piper of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

242 Hickey Hill, Sheffield, MA 01257

Price$1,225,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220243

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 3571
  • Acres 6.97

This Energy Star rated home was thoughtfully designed and sited in the middle of a pasture with views over church steeples of the village below, to the Taconic Hills and sunset to the west. As spotless as the day the owners took residency in 2008 and flooded with light from every direction, this Bensonwood Timber frame home is a joy to live in full time or to escape to from the city. Just eight miles from Great Barrington and convenient to a variety of restaurants and cultural activities in both Berkshire and Litchfield counties, the neighborhood is a mix of fine new and antique country homes and farms. The spotless house features a first floor master suite, central A/C, finished lower level with view and storage space, and an attached two-car garage. A perfect Berkshire country house.

Listing courtesy of Tim Lovett of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

73-89 Main, Sheffield, MA 01257

Price$1,100,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 221702

  • Listings
  • Beds 5
  • Sq Ft 16020
  • Acres 1.9
  • Exterior Features Bus-Public

9 Commercial and 5 Residential Rentals. Village Center location with high traffic count.

Listing courtesy of Robert Killiard and Eric Steuernagle of Isgood Realty

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

121 Hickey Hill, Sheffield, MA 01257

Price$1,100,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220757

  • Listings
  • Beds 4
  • Baths 4
  • Sq Ft 3543
  • Acres 2.41

Country Road take me home to this Luxurious 4 bedroom, 3.5 bath Contemporary Cape on 2.4 acres with panoramic views, perennial gardens, stone walls and total privacy, just two miles from the village. First floor master bedroom suite, sun-room, fireplace, fabulous chefs kitchen and a view from every window. Quality ever where, from the Tiger Maple staircase to the divided light windows to raised panels in the dining room to custom moldings.

Listing courtesy of Barnbrook Realty and Mary R White of BARNBROOK REALTY, INC.

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

102 Rannapo, Sheffield, MA 01222

Price$998,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217293

  • Listings
  • Beds 3
  • Baths 2
  • Sq Ft 3456
  • Acres 4.26

Breathtaking Timber Frame home offers a modern lifestyle while embracing a centuries old Berkshire tradition. The home features three bedrooms and two bathrooms, and a private one-bedroom, one-bathroom guest suite above the oversized, heated garage. The home is loaded with custom finishes and has an open floor plan, yellow pine timbers, reclaimed chestnut floors in the great room, dramatic fireplace, radiant heat on the main floor and iron works railings which lead to beautiful second floor loft area. The warm and inviting kitchen features cherry cabinets topped with soap stone and honed limestone countertops, dramatic lighting and top-of-the-line stainless appliances. Flowing from the kitchen is the light-filled great room hosting vaulted ceilings and French doors spilling onto the blue stone patio creating additional summertime entertaining space. Barn and additional outbuilding on property.

Listing courtesy of Lance Vermeulen of LANCE VERMEULEN RE, INC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1350 Berkshire School, Sheffield, MA 01257

Price$995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219503

  • Listings
  • Beds 2
  • Baths 5
  • Sq Ft 15000
  • Acres 2.44

Charming post & beam in Sheffield comprised of multiple barns from around New England. This 15, 000(+) square foot building has been used as an antique shop for over 30 years. Car collectors, retail, or multi-family conversion are only some of the possibilities. Expansive open rooms on the first floor open to a lofted second floor. A two bedroom apartment on the far wing lends itself perfectly for a live/work space. Newly constructed four car garage, enormous wood shop, two full kitchens, fully insulated walls and roof, the future of this special property is limited only by your imagination.

Listing courtesy of Evan Collins of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

130 Root, Sheffield, MA 01257

Price$975,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218916

  • Listings
  • Beds 5
  • Baths 5
  • Sq Ft 5000
  • Acres 13.19

This graceful and comfortable home has been carefully updated. The same family has lovingly maintained it for 46 years. 6 fireplaces, leaded glass windows. Formal living room, dining room and library. Eat-in kitchen with Viking range. Game room, TV room and office. Front and back staircases. 3+ bay garage with attached income producing 1-bedroom apartment. Room for everyone! An exceptionally beautiful expanse of level land. Great for gardening, crops, horses and outdoor activities. Plenty of room for a pool and tennis court. Blueberries, raspberries, day lilies. Birds in abundance. Great local roads for cycling. The property has sufficient frontage and acreage for by-right subdivision into several lots.

Listing courtesy of Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

130 Root, Sheffield, MA 01257

Price$975,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219889

  • Listings
  • Beds 5
  • Sq Ft 5000
  • Acres 13.19
  • Exterior Features Gardens

Subdivision possibilities with 13 acres and 540 feet of frontage. The Village Center District requires a minimum of 50 feet of frontage and a half-acre for a building lot. Permitted uses include professional offices, retail store, restaurant, green house, B&B, market, bank, home occupation. Handsome shingle style building with 5, 000 sq. ft. and 3+ bay garage with apartment. Perfect for horses! A beautiful spread of 13 level acres located just off Route 7 and within walking distance of the village. Beautifully maintained and in excellent condition. Possibilities abound.

Listing courtesy of Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

394 Berkshire School, Sheffield, MA 01257

Price$895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 221434

  • Listings
  • Beds 4
  • Baths 2
  • Sq Ft 2466
  • Acres 25

Amazing and Magical getaway! Set on 25+/- very private acres this 4 bedroom home with it's private pond, 2 guest cottages is one of Nature's best preserved and unspoiled properties in Southern Berkshire country. Boarding the Schnenob Brook, this property offers the best in country living. Minutes from town, ski areas.and all of the cultural amenities that area has to offer

Listing courtesy of Carol Staats of ELYSE HARNEY REAL ESTATE - FALLS VILLAGE

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

650 Main, Sheffield, MA 01257

Price$680,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220315

  • Listings
  • Beds 1
  • Baths 4
  • Sq Ft 6007
  • Acres 0.8

THE BRIDGE - TURNKEY OPPORTUNITY. Well known and long time successful restaurant along Route 7 in Sheffield. Steady income, steady and regular repeat customers. Bar & tavern, dining room, banquet space. The Bridge is an institution and an opportunity. Property includes all equipment and furnishings, and includes owner's apartment upstairs. Financials available after signing an NDA. Prime real estate and prime business (and prime rib) - great combination!

Listing courtesy of Anthony C Blair and Richard G. Aldrich of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

954 Boardman, Sheffield, MA 01257

Price$649,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220078

  • Listings
  • Beds 4
  • Baths 2
  • Sq Ft 2924
  • Acres 2

This 4BR antique farmhouse sits on 2 beautifully landscaped acres surrounded by mountain and pastoral views. Just five minutes from Great Barrington, this meticulously renovated 1907 home is tucked away on a quiet country road in an area of farms and fine homes. Open kitchen/dining, enormous sunporch, large living room with woodburning fireplace, family room, and multiple decks and patios to enjoy the magical views!

Listing courtesy of Vashti Poor of LANCE VERMEULEN RE, INC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

21 Sheffield Business, Sheffield, MA 01222

Price$599,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 218912

  • Listings
  • Baths 2
  • Sq Ft 5000
  • Acres 4.04

Approximately 5, 000 SF steel building. Warehouse with three overhead doors and office space. Two half bathrooms, and one is plumbed to expand to a full bathroom if needed. Spacious four-acre lot allows for expansion. Real estate only.

Listing courtesy of Lance Vermeulen of LANCE VERMEULEN RE, INC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.