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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$1,999,000The 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

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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.

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 with the ultimate in contemporary design, heritage and luxury. Located on 12.40 mature landscaped acres, gardens, oversized heated in-ground pool, new heated pool-house with bedroom and two baths, 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), and the 4 bedroom 3950 sq ft house. This four season compound, or should we say playground, has new additions by master architect and builder alike. Close to everything Berkshires.

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: 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

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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

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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

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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: 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

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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: 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.

82 Stahl, Sheffield, MA 01222

Price$849,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222151

  • Listings
  • Beds 4
  • Baths 4
  • Sq Ft 2760
  • Acres 6

Early 1808 Georgia Colonial with 5 fireplaces, pine floors, original hardware, 4 Bedrooms, post & beam construction. Stone foundation .Must be seen! Well maintained. In-ground pool with Cabana.Child's cottage. Buttonwood tree claimed to be the oldest in the area (300 years).Close to all Berkshire amenities.

Listing courtesy of Sandra Preston of SANDRA M. PRESTON REAL ESTATE

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: 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.

199 Hickey Hill, Sheffield, MA 01257

Price$832,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 222155

  • Listings
  • Beds 4
  • Baths 5
  • Sq Ft 3500
  • Acres 4.97

Stunning four-bedroom Dutch Gambrel home only minutes to Great Barrington. Set on almost 5 acres, of which a 1.57-acre parcel abuts the property & is a legal building lot. This home has it all -- great entertaining space, cook's kitchen, privacy, incredibly peaceful gardens & great outdoor living areas including beautiful screened porch & adjoining deck. Meticulously maintained & in move-in condition. Home built in 1989 with renovation in 2004. Furniture included.

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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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.

674 Foley, Sheffield, MA 01257

Price$695,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222128

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 2337
  • Acres 4.53

Private, well-maintained Colonial with a contemporary twist. Lots of natural light, hardwood floors, and incredible gardens outside. Living room with fireplace, informal dining and living area, kitchen, and first-floor bedroom and bathroom comprise the first floor. Huge master suite on the second floor and additional guest suite. A newer second-story deck, front porch, and three-season room enjoy the lightly-wooded, landscaped property. A cool, separate studio offers a wood stove and is ideal for artists or as a work space.

Listing courtesy of Jen Harvey of Berkshire Property Agents

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

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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$629,000The 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

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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: 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.

685 Undermountain, Sheffield, MA 01257

Price$598,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 217145

  • Listings
  • Beds 7
  • Baths 5
  • Sq Ft 6342
  • Acres 2

First time offered! Built in 1768 by the first Dutch settlers of Sheffield, & in the same family for FIVE generations. Well-maintained Colonial with over 6,000 SF, 7 bedrooms, 4.5 bathrooms, 6 fireplaces, hand-blown glass windows, & porte cochere which brings you back to a different time! Mostly wood floors throughout. Situated on 2 acres with spectacular views over protected land.

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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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 Park, Sheffield, MA 01257

Price$548,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 220956

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 3050
  • Acres 1.31

Gracious single story living with addition of large guest apartment. The house and property newly renovated. Country living in-town surrounded by lawn, trees and stone terrace for relaxing. 3 bright spacious bedrooms, 1 converted to cozy library, open living room w/ wood burning fireplace, dining room overlooking lawn, mature shade trees, kitchens with granite counters. Gather in a sun room that leads to stone terrace topped with retractable awning.Enter guest apartment thru separate sun filled atrium. Unit has large custom kitchen, granite counters, ss appliances, all open to living and dining room. Bedroom connected to bath that includes luxurious walking in shower and 4 person swedish sauna. Genarac generator, two car garage.

Listing courtesy of Anita Schilling and Leslie G Chesloff 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: 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.