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$2,150,000

Est. Mortgage: $/month

MLS Number 225467

  • Single Family
  • Address 135 Fiddlehead Trail
  • Village Berkshire - South
  • Year Built 2015
  • Parking Spaces 2

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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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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927 Boardman St Sheffield MA 01230

Price$1,760,000

Est. Mortgage: $/month

MLS Number 226393

  • Single Family
  • Address 927 Boardman St
  • Village Berkshire - South
  • Year Built 1960
  • Bedrooms 4

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 STONE HOUSE PROPERTIES, LLC

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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$1,395,000

Est. Mortgage: $/month

Pending

MLS Number 227701

  • Single Family
  • Address 54 Rannapo Rd
  • Village Berkshire - South
  • Year Built 1984
  • Bedrooms 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 ALDEN COUNTRY REAL ESTATE SERVICES

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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398 Weatogue Rd Sheffield MA 01222

Price$1,345,000

Est. Mortgage: $/month

MLS Number 226441

  • Single Family
  • Address 398 Weatogue Rd
  • Village Berkshire - South
  • Year Built 1988
  • Parking Spaces 3

Monarch Hill - A dramatic hilltop setting, a unique contemporary with quality and style throughout, beautiful decks, patios and landscaping, an in ground pool, views forever, and so much more, all combine to make Monarch Hill the ultimate retreat. High above the Housatonic River and bordered by hundreds of acres at Bartholomew's Cobble, this home is designed for peace and comfort.

Listed by Elyse Harney Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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$935,000

Est. Mortgage: $/month

MLS Number 227549

  • Single Family
  • Address 242 Hickey Hill Rd
  • Village Berkshire - South
  • Year Built 2007
  • Parking Spaces 2

This custom-built Bensonwood Timber Frame home was designed w/ a classic open living floor plan & built to Energy Star standards. The craftsmanship, materials & design details are extraordinary. The main living area w/ vaulted ceiling has an abundance of windows & natural light. The gorgeous Berkshire vistas & views can be enjoyed throughout the house. The well-equipped cook's kitchen opens to the dining/living area and the raised hearth fireplace. The screened porch & patio were designed to take in the evening sunsets. There is first floor master suite with walk-in closet. Central AC. This beautiful property has been impeccably maintained. A great location convenient to the southern Berkshire & northern Litchfield county recreational & cultural venues. Only 8 miles to Great Barrington.

Listed by STONE HOUSE PROPERTIES, LLC

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$
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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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
  • Address 121 Hickey Hill Rd
  • Village Berkshire - South
  • Year Built 2000
  • Parking Spaces 2

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: 3.6% last updated on Aug 15, 2019
* 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$895,000

Est. Mortgage: $/month

MLS Number 223162

  • Land
  • Co Listing Office Name LANDVEST, INC.
  • Co Listing Office Id 443
  • High School Mount Everett
  • Village Berkshire - South

301 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: 3.6% last updated on Aug 15, 2019
* 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 West Stahl Rd Sheffield MA 01222

Price$799,000

Est. Mortgage: $/month

MLS Number 227218

  • Single Family
  • Address 82 West Stahl Rd
  • Village Berkshire - South
  • Year Built 1808
  • Bedrooms 4

An Antique Gem that has been lovingly restored to a warm and inviting place to gather with friends and family. Spacious living room with original fireplace, fabulous wood floors through out. With 4 bedrooms and 4 full baths plus a bunk cottage and a pool house cabana, you can entertain a crowd. Or relax by yourself on 6 peaceful acres, gardens and inground pool. A large barn rounds out the perfect country home.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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$795,000

Est. Mortgage: $/month

MLS Number 224536

  • Single Family
  • Address 264 Brush Hill Rd
  • Village Berkshire - South
  • Year Built 1992
  • Parking Spaces 2

Tucked away on a quiet dirt road sits this spacious, beautifully maintained 1990s contemporary. Enjoy total privacy and pond frontage only 10 minutes from downtown Great Barrington, 20 from two major ski areas and 25 from Tanglewood. The privacy of this home can be enjoyed from the abundance of outdoor space as well as the inviting three-season screened porch surrounded by amid lush wooded conservation land. 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: 3.6% last updated on Aug 15, 2019
* 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 South Main St Sheffield MA 01257

Price$775,000

Est. Mortgage: $/month

MLS Number 227683

  • Single Family
  • Address 296 South Main St
  • Village Berkshire - South
  • Year Built 1990
  • Bedrooms 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.) (New Roof 10/2018)

Listed by BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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 227682

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

OPPORTUNITY ON MAIN ROAD SHEFFIELD a portal in to coveted South County Berkshires is 5,046 sq.ft. of solidly crafted Timber-Frame space with three distinct areas. Abutting the popular Berkshire Mountain Distillery the uses includes but are not limited to a Restaurant, Offices, Service Establishment, Retail Store, Bank, School, Yoga/Dance Studio & or any combination of the above. Professionals & Artists in all mediums who want to Live & Work in the Berkshires should take a look at this offering.

Listed by Deborah Levinson and Christian Deckert of BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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132 Bull Hill Rd Sheffield MA 01257

Price$770,000

Est. Mortgage: $/month

MLS Number 227812

  • Single Family
  • Address 132 Bull Hill Rd
  • Village Berkshire - South
  • Year Built 1975
  • Bedrooms 5

Magical Contemporary designed by Hugh Hardy nestled in the privacy of Ashley Falls. This property is a must see for any lover of modern homes. This home features an abundance of outdoor living space surrounded by outstanding gardens and mature landscaping. Inside you will find spacious light-filled living quarters with multiple levels to explore, 3 bedrooms and a quaint kitchen. Just a few steps away from the main house is a calming oasis with an in-ground pool and a large guest cottage/pool house. This home was designed to be a three season cottage, the house would need some renovations done to be converted to a year round residence.

Listed by Lance Vermeulen and Antonio Segalla of LANCE VERMEULEN RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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