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Sheffield MA Homes for Sale

Situated on the Massachusetts-Connecticut border, Sheffield, Massachusett is a rural, historic community with beautiful landscapes. Sheffield is home to Bartholomew’s Cobble, a 329-acre National Natural Landmark agricultural preserve which offers hiking as well as informative classes. It’s a great place to have a picnic!

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

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927 Boardman, Sheffield, MA 01230

Price$1,860,000The 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 of STONE HOUSE PROPERTIES, LLC

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

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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

50 East, Sheffield, MA 01257

Price$1,825,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222174

  • Listings
  • Beds 4
  • Baths 4
  • Sq Ft 3950
  • Acres 12.4

Inherent Beauty unites this 1790 Colonial Estate with the ultimate in contemporary design and luxury. Its own mini village, private compound with a 4 bedroom 3950 sq ft all season retreat, or should we say playground. New new additions by master architect and builder alike. Located on 12.40 mature landscaped acres, with a brook, oversized heated in-ground pool, new heated Guesthouse which has one bedroom and two baths. A hot and cold water outdoor shower, beautiful arbor, huge two story antique barn with a 2 car garage, open space, office and a gym (but let your imagination go wild), Close to Salisbury CT, Great Barrington, everything Berkshires. 2.5 hours from NYC

Listing courtesy of Barbara Schulman and Deborah Levinson of Berkshire Property Agents

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

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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

54 Rannapo, Sheffield, MA 01257

Price$1,695,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 223565

  • Listings
  • Beds 4
  • Baths 4
  • Sq Ft 3481
  • Acres 7.7

A rare blend of timeless New England design, craftsmanship and world-class finishes, this stunning home combines post & beam construction and the highest level of reproduction detail from every angle. The house was originally built in 1984 and in 2003 was given a stunning makeover and added level of refinement that is rare to find. The 7.7 acres are privately situated on of the prettiest 'best-kept-secret' roads of the southern Berkshires and offer elegant yet manageable cottage-style gardens, heated pool, two-car over-sized garage with bonus space and classic barn.

Listing courtesy of Dan Alden of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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

1474 Undermountain, Sheffield, MA 01257

Price$1,195,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 223019

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 2840
  • Acres 12.66

Panoramic views from this utterly magical 1806 colonial that was moved up the hill in the early 1980s creating a combination that is rare to find--the charm of an old house set back from the road with extraordinary views. In addition to a new concrete foundation, a wing was added in 1983 consisting of the front porch, library with fireplace and a bedroom above. Then comes a wonderful surprise when you enter the kitchen with its vaulted ceiling, Palladian window, beams and stone fireplace. A lovely living room with fireplace and original chestnut floor is perfect for entertaining and the sunny front room with bay window can be used as a dining room. The 12+ acres feature a mature apple orchard and the parcel is protected on all sides. A truly special property!

Listing courtesy of Laurie Dunham of BEST & CAVALLARO

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

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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$995,000The 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 every 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 BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK 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:

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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

93 Hillside, Sheffield, MA 01257

Price$974,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 223617

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 2632
  • Acres 13.93

Enjoy expansive western views from this stylish log home perched on 14 acres. Horse lovers will delight in the four stall barn, plenty of pasture area and loads of privacy. Open living area with cathedral ceilings, a true cook's kitchen with a six burner Viking stove and farmhouse sink. A large stone fireplace is flanked by floor to ceiling windows so you never miss the views. Off the kitchen/ dining area is an open deck. the master also has its own balcony.Upstairs, two large bedrooms give family or guests their own privacy. The lower level is finished for TV, pool, games or other activities.

Listing courtesy of Martha Piper of WILLIAM PITT SOTHEBY'S INTERNATIONAL 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: 4.52% last updated on 2018-07-19

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

296 S Main, Sheffield, MA 01257

Price$925,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 224015

  • Listings
  • Beds 1
  • Baths 2
  • Sq Ft 5000
  • Acres 1.94

EXTRA-ORDINARY OPPORTUNITY IN BEAUTIFULLY CRAFTED TIMBER FRAME 5,000 SQ. FT. LIGHT FILLED BUILDING. Designed and built with live/work options in mind this building has three components. All three components are accessed by an inviting (20'L x 10'W) entry. On either side are open, large (average 42'L x 30'W) spaces with lofted second floor access and one adjoined but separate living space, full-kitchen, full bathroom and lofted sleeping area. All three areas have double-door rear access to private outdoor seating areas. Business or pleasure this is a unique opportunity.(Currently home to a successful antique business it is the building only that is for sale.) (Roof in process of being replaced.)

Listing courtesy of Deborah Levinson and Christian Deckert of Berkshire Property Agents

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

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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$895,000The 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

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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

132 Bull Hill, Sheffield, MA 01257

Price$895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 223012

  • Listings
  • Beds 5
  • Baths 3
  • Sq Ft 3365
  • Acres 26.57

Designed by a leading American architect Hugh Hardy for his family, this eclectic, very private Modernist retreat has landscapes in every direction to delight the eye. The main house comprises a two-level living/dining room, great room & three bedrooms, while the poolside guest house offers a living room, two bedrooms & a snug office for your creative fancies. A magical contemporary Berkshire estate!

Listing courtesy of Leslie G Chesloff and Gladys Montgomery of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.52% last updated on 2018-07-19

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