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!

135 Fiddlehead Trail, Sheffield, MA 01257

Price$2,100,000

Est. Mortgage: $/month

MLS Number 225467

  • Single Family
  • Village Berkshire - South
  • Year Built 2015
  • Parking Spaces 2
  • Bedrooms 5

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.

Listed by BROCKMAN REAL ESTATE, LLC

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Federal 30-year interest rate: 4.63% last updated on Dec 13, 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$1,495,000

Est. Mortgage: $/month

MLS Number 223565

  • Single Family
  • Village Berkshire - South
  • Year Built 1984
  • Bedrooms 4
  • Bathroom 4

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 BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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
  • Village Berkshire - South
  • Year Built 2007
  • Parking Spaces 2
  • Bedrooms 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 BERKSHIRE PROPERTY AGENTS

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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
  • Village Berkshire - South
  • Square Feet 16,117,200

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 LANDVEST, INC.

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$
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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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

MLS Number 221702

  • Commercial
  • Co Listing Office Id 277
  • Village Berkshire - South
  • Year Built 1900
  • Square Feet 16,020

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

Listed by ISGOOD REALTY

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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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102 Rannapo Rd, Sheffield, MA 01222

Price$949,000

Est. Mortgage: $/month

MLS Number 217293

  • Single Family
  • Village Berkshire - South
  • Year Built 2002
  • Parking Spaces 2
  • Bedrooms 3

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 RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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$925,000

Est. Mortgage: $/month

MLS Number 223019

  • Single Family
  • Village Berkshire - South
  • Year Built 1806
  • Parking Spaces 2
  • Bedrooms 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 Best & Cavallaro

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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
  • Village Berkshire - South
  • Year Built 1990
  • Bedrooms 1
  • Bathroom 2

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)

Listed by BERKSHIRE PROPERTY AGENTS

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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 Main St, Sheffield, MA 01257

MLS Number 224014

  • Commercial
  • Co Listing Office Id 486
  • Village Berkshire - South
  • Year Built 1989
  • Square Feet 5,000

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. Great event space, condos, restaurant...you name it!(Currently home to a successful antique business it is the building only that is for sale.) (New Roof 10/2018)

Listed by Christian Deckert and Deborah Levinson of BERKSHIRE PROPERTY AGENTS

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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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121 Hickey Hill Rd, Sheffield, MA 01257

Price$919,000

Est. Mortgage: $/month

MLS Number 224817

  • Single Family
  • Village Berkshire - South
  • Year Built 2000
  • Parking Spaces 2
  • Bedrooms 4

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.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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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93 Hillside Ln, Sheffield, MA 01230

Price$895,000

Est. Mortgage: $/month

MLS Number 223617

  • Single Family
  • Village Berkshire - South
  • Year Built 2000
  • Bedrooms 3
  • Bathroom 3

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.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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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264 Brush Hill Rd, Sheffield, MA 01257

Price$895,000

Est. Mortgage: $/month

MLS Number 224536

  • Single Family
  • Village Berkshire - South
  • Year Built 1992
  • Parking Spaces 2
  • Bedrooms 3

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.

Listed by LANCE VERMEULEN RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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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