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Sheffield MA Real Estate

Sheffield, MA -- comprised of 2 villages, Sheffield and Ashley Falls, is a picturesque New England town in the Housatonic River Valley of Berkshire County.The oldest town in the Berkshires, Sheffield offers a plethora of historic homes, strong agricultural roots, and a strong sense of community. Scroll down to browse through our real estate listings in Sheffield, MA. Contact us if you have questions or would like to schedule a showing.

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You may also be interested in homes for sale in Egremont, Monterey, Mt. Washington, or New Marlborough!

795 Rannapo, Sheffield, MA 01257

Price$2,800,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217224

  • Listings Residential
  • Address 795 Rannapo Rd
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 6315

A true American treasure, beautifully expanded yet perfectly preserved, might grace our market once in a lifetime: Such a treasure is the Gen. John Ashley House(c.1762, renov. 1857, 1984, 1992). Upon a bucolic bend of the gentle Housatonic, this historic estate hosts elegant luxuries-- 6 BR, 6 bath, pool & pool house, sauna, summer porch, dining arbor, guest wing, +/- 8.5 sheltered acres & much more!

Listed by Mary Jane White and Nancy Kalodner of COHEN & WHITE ASSOCIATES

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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

927 Boardman, Sheffield, MA 01230

Price$2,400,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218975

  • Listings Residential
  • Address 927 Boardman St
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3679

This magical property is an ideal blend of county 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 J Rose and Martha Piper of STONE HOUSE PROPERTIES, LLC

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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

514 Rannapo, Sheffield, MA 01257

Price$1,995,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 214887

  • Listings Residential
  • Address 514 Rannapo Rd
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4892

Built in 1785, Bull Hill Farm is a masterpiece restoration and re-imagination of a classic New England barn & farmhouse that is a true sum of its parts. The 3 BR 2 1/2 BA, 3, 552 sq. ft. farmhouse features Colonial & Federal details throughout including original hardware, antique glass, wide-board floors & 2 working fireplaces. Living spaces include 2 formal parlors, family room with

Listed by Dan Alden and Nick Geranios of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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

304 HICKEY HILL, Sheffield, MA 01257

Price$1,395,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217829

  • Listings Residential
  • Address 304 Hickey Hill Rd
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 4000

Historic farmhouse originally part of Merryfield Farm in Sheffield. Built in the 1790's, it was meticulously renovated in 2012 with the help of a talented architect, renowned builder and exacting owner. Structural improvements include a new foundation, septic tank, well, roof, 5 zone heating and central air conditioning, new hot water tank, plumbing and electrical systems.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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

50 Undermountain, Sheffield, MA 01257

Price$1,175,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217276

  • Listings Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 6684
  • Year Built 1818

Minutes to the Connecticut border this handsome brick Federal home is situated on 8+ acres of gardens, lawn, in ground pool and woods. Original home dates to 1818 with a 1917 addition. Stately rooms; 5 working fireplaces, gleaming wood floors, plaster walls, dental molding, dining room with raised paneling, and a spacious eat in kitchen. Large sun room with fireplace, gallery with private entrance

Listed by Dawn Z. Farley and Patrice C. Melluzzo of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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$1,050,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217293

  • Listings Residential
  • Address 102 Rannapo Rd
  • Village Ashley Falls
  • 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

Listed by Lance Vermeulen of LANCE VERMEULEN RE, INC

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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

1884 N. Main, Sheffield, MA 01257

Price$989,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217730

  • Listings Commercial
  • Address 1884 N. Main St
  • Square Feet 7872
  • Year Built 1987

Immaculate and well-equipped, air-conditioned manufacturing facility plus 3 defined office spaces, storage and more. 3 Phase power facilitating 400amp and 800 amp service; in floor water and air service. Convenient location to the tri-state region of CT, MA & NY.

Listed by Thomas Doyle of GATEWAY BERKSHIRE REAL ESTATE & SERVICES, LLC.

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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

130 Root, Sheffield, MA 01257

Price$975,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218916

  • Listings Residential
  • Address 130 Root Ln
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5000

This graceful and comfortable home has been lovingly restored and maintained by the same family for 46 years. Many of the original details are still intact - 6 fireplaces, leaded glass windows, original bathroom tile. 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 1-bedroom apartment. An exceptionally beautiful expanse of level land. Great for gardening, crops, horses and outdoor activities. 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. Property is within the Village Center District allowing for some commercial uses. VERY SPECIAL!

Listed by Sheila Thunfors of STONE HOUSE PROPERTIES, LLC

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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

394 Berkshire School, Sheffield, MA 01257

Price$895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 214166

  • Listings Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3800
  • Year Built 1975

THE PERFECT COUNTRY RETREAT FOR LOADS OF FAMILY AND FRIENDS. Surrounded by 25 acres, this private compound offers a 3-4 bedroom contemporary farmhouse; a rustic cottage with a kitchenette and full bath; and a large studio with a kitchenette and full bath above the detached garage. Plenty to do... large lawn, pond, brook for fishing/swimming, hiking trails. All just 5 minutes to Sheffield center.

Listed by Tom Lynch of BERKSHIRE PROPERTY AGENTS

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.03% last updated on 2017-04-27

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

199 Hickey Hill, Sheffield, MA 01257

Price$799,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217968

  • Listings Residential
  • Address 199 Hickey Hill Rd
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3500

Stunning four-bedroom Dutch Gambrel home on almost 5 acres, 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. Taxes shown are house parcel only.

Listed by Lance Vermeulen of LANCE VERMEULEN RE, INC

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

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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: 4.03% last updated on 2017-04-27

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