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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$1,860,000

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 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: 4.59% last updated on Aug 9, 2018
* 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 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

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: 4.59% last updated on Aug 9, 2018
* 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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54 Rannapo Rd, Sheffield, MA 01257

Price$1,695,000

Est. Mortgage: $/month

MLS Number 223565

  • Single Family
  • Year Built 1984
  • Bedrooms 4
  • Bathroom 4
  • Total Full Baths 3

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.

Listed by Dan Alden of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK 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: 4.59% last updated on Aug 9, 2018
* 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: 4.59% last updated on Aug 9, 2018
* 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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1474 Undermountain Rd, Sheffield, MA 01257

Price$1,195,000

Est. Mortgage: $/month

MLS Number 223019

  • Single Family
  • Year Built 1806
  • Parking Spaces 2
  • Bedrooms 3
  • Bathroom 3

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!

Listed by Laurie Dunham 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: 4.59% last updated on Aug 9, 2018
* 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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1 Water Farm Rd, Sheffield, MA 01257

Price$1,150,000

Est. Mortgage: $/month

MLS Number 223162

  • Land
  • Co Listing Office Id 443
  • High School Mount Everett
  • Square Feet 16,117,200
  • Waterfront 1

370 acres of forest & wetlands with 8,828 feet of road frontage on Water Farm Road and 606' of road frontage on Soda Spring Creek Road. There are extensive wetlands with significant uplands associated that might support 6 to 8 large house lots. Spring water infrastructures include two 30,000 gal covered concrete storage tanks and associated infrastructure. Historic records show water volume range from 9 to 17 mil gal/yr. The Soda Spring Creek flows into the Ironworks brook just south of the property boundary which then joins the Housatonic River. The property has been professionally managed by licensed foresters for more than 15 years.

Listed by Cindy Welch and Keith Ross of LANDVEST, 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: 4.59% last updated on Aug 9, 2018
* 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

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: 4.59% last updated on Aug 9, 2018
* 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

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

{$office->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: 4.59% last updated on Aug 9, 2018
* 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

121 Hickey Hill Rd, Sheffield, MA 01257

Price$995,000

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 every 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 BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

{$office->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: 4.59% last updated on Aug 9, 2018
* 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

Price$975,000

MLS Number 221702

  • Commercial
  • Co Listing Office Id 277
  • Year Built 1900
  • Square Feet 16,020
  • Bedrooms 5

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: 4.59% last updated on Aug 9, 2018
* 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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296 S Main St, Sheffield, MA 01257

Price$925,000

Est. Mortgage: $/month

MLS Number 224015

  • Single Family
  • Year Built 1990
  • Bedrooms 1
  • Bathroom 2
  • Total Full Baths 1

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.)

Listed by Deborah Levinson and Christian Deckert of BERKSHIRE PROPERTY AGENTS

{$office->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: 4.59% last updated on Aug 9, 2018
* 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

296 Main St, Sheffield, MA 01257

Price$925,000

MLS Number 224014

  • Commercial
  • Co Listing Office Id 486
  • Year Built 1989
  • Square Feet 5,000
  • List Date 07/18/2018

EXTRA-ORDINARY MIXED USE 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.)

Listed by Christian Deckert and Deborah Levinson of BERKSHIRE PROPERTY AGENTS

{$office->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: 4.59% last updated on Aug 9, 2018
* 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