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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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135 Fiddlehead, Sheffield, MA 01257

Price$2,100,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 225467

  • Listings
  • Beds 5
  • Baths 5
  • Sq Ft 5800
  • Acres 2.3

NEWLY CONSTRUCTED POST & BEAM WATERFRONT PARADISE ON 168-ACRE LAKE WITHIN A 1,000 ACRE PROTECTED WILDLIFE AREA. Striking views & fabulous amenities includinga soaring great room, 5+ bedrooms, heated swimming pool, outdoor hot tub, movie theater, bar, game room & gym, radiant heat, central a/c, solar panels and much, much more - all on a true treasure of a lake that is virtually unknown. Astonishing privacy and wildlife - you will most often be the only one fishing or kayaking on the lake, watching the Great Blue Heron, or relaxing with no jet skis or power boats to disturb you - yet you're just 12 minutes to Guido's in Great Barrington. Control all systems remotely. Painstakingly built for optimal casual comfort, low maintenance, and as your own private waterfront Berkshire resort.

Listing courtesy of L. Chapin Fish and Kevin Fish of BROCKMAN REAL ESTATE, 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: 4.63% last updated on 2018-12-13

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$1,495,000The 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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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.63% last updated on 2018-12-13

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: 4.63% last updated on 2018-12-13

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$949,000The 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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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.63% last updated on 2018-12-13

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.) (New Roof 10/2018)

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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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.63% last updated on 2018-12-13

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$925,000The 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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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.63% last updated on 2018-12-13

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$919,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 224817

  • Listings
  • Beds 4
  • Baths 4
  • Sq Ft 3753
  • Acres 2.41

Enjoy the panoramic views and beautiful perennial gardens from this luxuriously built and lovingly maintained, four bedroom home. Conveniently located about 10 minutes south of Guido's and 2 minutes from the Marketplace in Sheffield. Filled with custom detailing from tiger maple trim to custom cabinets and library shelves. First floor master bedroom suite with office. Sun-filled four season sun room opens to the well appointed cook's kitchen. Two bedrooms and 2 baths upstairs plus a large finished bonus room for exercise, office, extra bedroom or media. Stone walls surround the bursting flowerbeds. A large and comfortable deck overlooks the long views over fields to the mountains beyond.

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

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.63% last updated on 2018-12-13

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

93 Hillside, Sheffield, MA 01230

Price$895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 223617

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 3632
  • Acres 13.93

Enjoy expansive western views with gorgeous sunsets from this stylish log home perched on 14 acres. Open living area with cathedral ceilings, a true cook's kitchen, granite counters, cherry cabinets, six burner Viking stove and a 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.Animal lovers will delight in the four stall barn, plenty of pasture area and loads of privacy. Near Berkshire culture and recreation.

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

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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: 4.63% last updated on 2018-12-13

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

264 Brush Hill, Sheffield, MA 01257

Price$895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 224536

  • Listings
  • Beds 3
  • Baths 4
  • Sq Ft 4085
  • Acres 7.35

Tucked away on a quiet dirt road sits this beautifully maintained 90's contemporary home. Enjoy total privacy and frontage on Three Mile Pond while being a short 10-minute drive to Guido's and downtown Great Barrington. The privacy of this home can be enjoyed from the abundance of outdoor space as well as the large three-season screened porch. Inside you'll find Cathedral ceilings, a stunning stone fireplace, Cook's kitchen with an abundance of maple cabinetry, formal dining, a cozy den with an additional fireplace and a large master suite. The Master Suite features cathedral ceilings, his and hers walk-in closets and an oversized bathroom featuring his and hers sinks, tiled shower and a large soak/jet tub.

Listing courtesy of Antonio M Segalla and 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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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.63% last updated on 2018-12-13

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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Price Down Payment Interest Rate Years
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Est. Mortgage: $/month

Federal 30-year interest rate: 4.63% last updated on 2018-12-13

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

1070 Ashley Falls, Sheffield, MA 01257

Price$695,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 224595

  • Listings
  • Beds 4
  • Baths 3
  • Sq Ft 3500
  • Acres 1.1

This warm and inviting home dating from 1887 has been lovingly updated, added onto, and meticulously maintained for modern living. On 1+ acre and abutting 35 acres of protected Land Trust, the garden filled compound includes a main house with 3 bedrooms, and 2 baths, as well as a guest house with large living area, kitchenette, full bath, office, and large bedroom. There's a beautifully landscaped pool with an outdoor shower, a barn with a 2 car garage, and an apple orchard. Years of thoughtful planting and landscape design, now mature, has created a magical compound of outdoor garden rooms. This property offers a true escape from urban life in the comfort of the historic, friendly village of Ashley Falls.

Listing courtesy of Robin Ban 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: 4.63% last updated on 2018-12-13

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$635,000The 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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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.63% last updated on 2018-12-13

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