Sheffield Real Estate

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!

927 Boardman St, Sheffield, MA 01230

Price$1,999,000

Est. Mortgage: $/month

MLS Number 218975

  • Single Family
  • Year Built 1960
  • Bedrooms 5
  • Bathroom 4
  • Total Full Baths 3

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!

Listed by Lori Rose and Martha Piper of STONE HOUSE PROPERTIES, LLC

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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50 East Rd, Sheffield, MA 01257

Price$1,825,000

Est. Mortgage: $/month

MLS Number 222174

  • Single Family
  • Year Built 1790
  • Bedrooms 4
  • Bathroom 4
  • Total Full Baths 3

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.

Listed by Barbara Schulman and Deborah Levinson of BERKSHIRE PROPERTY AGENTS

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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242 Hickey Hill Rd, Sheffield, MA 01257

Price$1,225,000

Est. Mortgage: $/month

MLS Number 220243

  • Single Family
  • Year Built 2007
  • Parking Spaces 2
  • Bedrooms 3
  • Bathroom 3

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.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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121 Hickey Hill Rd, Sheffield, MA 01257

Price$1,100,000

Est. Mortgage: $/month

MLS Number 220757

  • Single Family
  • Year Built 2000
  • Bedrooms 4
  • Bathroom 4
  • Total Full Baths 3

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.

Listed by Barnbrook Realty and Mary White of BARNBROOK REALTY, INC.

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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73-89 Main St, Sheffield, MA 01257

MLS Number 221702

  • Commercial
  • Year Built 1900
  • Square Feet 16,020
  • Bedrooms 5
  • List Date 01/09/2018

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

Listed by Eric Steuernagle and Robert Killiard of ISGOOD REALTY

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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102 Rannapo Rd, Sheffield, MA 01222

Price$998,000

Est. Mortgage: $/month

MLS Number 217293

  • Single Family
  • Year Built 2002
  • Parking Spaces 2
  • Bedrooms 3
  • Bathroom 2

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-t

Listed by Lance Vermeulen of LANCE VERMEULEN RE, INC

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1350 Berkshire School Rd, Sheffield, MA 01257

MLS Number 219503

  • Multi-Family
  • Acreage 2.44
  • Bedrooms 2
  • Square Feet 15,000
  • Bathroom 5

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.

Listed by Evan Collins of STONE HOUSE PROPERTIES, LLC

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Sheffield, MA 01257

Price$995,000

Est. Mortgage: $/month

MLS Number 222109

  • Land
  • High School Mount Everett
  • Square Feet 4,399,560
  • Zoning Residential

SPECTACULAR 101 ACRE PARCEL WITH OPEN FIELD FOR YOUR DREAM HOME PLUS GROOMED TRAILS through the woods - perfect for cross country skiing, horses and hiking. A rare parcel on a quiet dirt road just over the Salisbury , CT border and a short distance to Twin Lakes. This very private lot abuts conservation land. Easy access off Barnum Road. Beautiful views.

Listed by Patricia Best of Best & Cavallaro

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

130 Root Ln, Sheffield, MA 01257

MLS Number 219889

  • Commercial
  • Year Built 1938
  • Parking Spaces 3
  • Square Feet 5,000
  • Bedrooms 5

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.

Listed by Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

130 Root Ln, Sheffield, MA 01257

Price$975,000

Est. Mortgage: $/month

MLS Number 218916

  • Single Family
  • Year Built 1938
  • Parking Spaces 3
  • Bedrooms 5
  • Bathroom 5

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.

Listed by Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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82 Stahl Rd, Sheffield, MA 01222

Price$849,000

Est. Mortgage: $/month

MLS Number 222151

  • Single Family
  • Year Built 1808
  • Parking Spaces 2
  • Bedrooms 4
  • Bathroom 4

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.

Listed by Sandra Preston of SANDRA M. PRESTON REAL ESTATE

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Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

199 Hickey Hill Rd, Sheffield, MA 01257

Price$832,500

Est. Mortgage: $/month

MLS Number 222155

  • Single Family
  • Year Built 1989
  • Bedrooms 4
  • Bathroom 5
  • Total Full Baths 3

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.

Listed by Lance Vermeulen of LANCE VERMEULEN RE, INC

{$agent->Name}

Barnbrook Realty
271 Main Street
Great Barrington MA, 01230
Office: (413) 528-4423

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.44% last updated on Dec 21, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details