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!

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394 Berkshire School Rd Sheffield MA 01257

MLS Number 225871

  • Single Family
  • Village Berkshire - South
  • Year Built 1975
  • Parking Spaces 2
  • Bedrooms 6

Terrific Berkshire Compound, ready to sell, with main house, 2nd floor garage apartment (full bath & kitchenette) guest cabin (full bath + kitchenette) In a 25 acre park-like setting! The acreage includes a spring-fed pond, direct access to Schnenob Brook, beautiful established perennial beds, & walking trails! The original 1975 home was completely rebuilt around the original brick fireplace which is so cozy... and really brings in those great Berkshire vibes! Main house has 4 BRs & 2 full baths + the cabin & apt. makes for a total of 6 bedroom/4 baths. Oak flooring throughout, screened porch PLUS long south-facing porch overlooks the pond & brook with pretty views. Walkout basement and super private, this long driveway is well maintained, inclds additional building lot - see supplement.

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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246 County Rd Sheffield MA 01257

Price$680,000

Est. Mortgage: $/month

MLS Number 223653

  • Single Family
  • Address 246 County Rd
  • Village Berkshire - South
  • Year Built 1915
  • Parking Spaces 1

If you are looking for a wonderful getaway for your active family to enjoy their vacation home with your own private Tennis court and modern Guest Cabana in a desirable location near skiing, too! Quiet, open outdoor space with thoughtful landscaping including mature shade trees and multiple perennial gardens. The slate patio perfect for dining outdoors, or join the guests in the 'South of the Border' designed cabana with its own patio for seating or watching the tennis matches on the all season/all weather fenced court. Includes spacious family area, full kitchen & 'Ice cream pastel' tile bath. The main house has an abundance of natural light in the large family/living room complete with seated bow windows and a wood burning fireplace. With 3 bedrooms and 2 full baths, 23+ acres,

Listed by COHEN & WHITE ASSOCIATES

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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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39 Silver St Sheffield MA 01257

MLS Number 227051

  • Commercial
  • Village Berkshire - South
  • Year Built 2004
  • Square Feet 4,404
  • List Date 05/13/2019

Commercial building and land for sale. Current home of established, successful masonry business. Owner plans to retire. Business, equipment and stone inventory available separately. See MLS# 227052. 40'x60' metal building with attached 25'x25' office and 35'x25' patio with specimen trees on 3.32 acres. Radiant heat in all floors, oil furnace, wood burning fireplace, propane gas stove heater, AC, 18' ceilings, (3) 14'x14' overhead doors. Tool room, storage room. 3 phase 150A (2) electric. Zoned to allow marijuana cultivation or manufacturing.

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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703 North Main St Sheffield MA 01257

MLS Number 222988

  • Commercial
  • Village Berkshire - South
  • Year Built 1970
  • Square Feet 8,336
  • Bedrooms 4

Great investment opportunity. This property consists of three commercial spaces, a one-bedroom apartment, and a three-bedroom house. Only one commercial space is vacant.

Listed by LANCE VERMEULEN RE, INC

$
$
%
$/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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249 Boardman St Sheffield MA 01257

Price$599,000

Est. Mortgage: $/month

MLS Number 228015

  • Single Family
  • Address 249 Boardman St
  • Village Berkshire - South
  • Year Built 1987
  • Parking Spaces 2

Sited on the bucolic Housatonic River and comprised of 4 acres, this charming center hall colonial offers a quintessential Berkshire experience. This home provides an open floor plan with beautifully appointed kitchen, living room with fireplace and dining area and half bath. 3 bedrooms, a master bedroom with fieldstone fireplace, en suite bath and hall bath complete the second floor. The lower level has a finished play room and laundry room. The generous two car garage has a large breezeway/mud room adjacent the main house. Enjoy the sound of the river as you sit on the rear deck. The occasional bald eagle perches in the trees overlooking the river. Find your bliss in this inviting setting!

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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290 Bow Wow Rd Sheffield MA 01257

Price$595,000

Est. Mortgage: $/month

MLS Number 226176

  • Single Family
  • Address 290 Bow Wow Rd
  • Village Berkshire - South
  • Year Built 1975
  • Bedrooms 2

An utterly charming contemporary lake place. Sited on a peninsula at the end of a private drive through mature two acre woods. About 900 feet of waterfront on three sides, a private dock, ''away from it all'', tranquility without isolation. The interior is bright and airy, with cathedral ceilings, open living plan, hardwood floors and lots of windows looking onto lake and deck.

Listed by FRIDAY & CO. REAL ESTATE

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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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1135 Ashley Falls Rd Sheffield MA 01222

Price$555,000

Est. Mortgage: $/month

MLS Number 227459

  • Single Family
  • Address 1135 Ashley Falls Rd
  • Village Berkshire - South
  • Year Built 1850
  • Bedrooms 3

Completely Renovated Greek Revival home in the charming village of Ashley Falls. Amazing sunlight throughout every room. Double sized living room, large enough to entertain a crowd. Modern kitchen that is open to the dining. First floor master suite with incredible bath. Office, mud room with laundry and full bath on the main level.Upstairs to 2 charming bedrooms and a 3rd full bath. Gardens, and porches and patios throughout the open and level yard. Walk to the post office, the annual Christmas Tree lighting, summer yoga on the green, numerous hiking trails and boat launches and many of the other fun activities that Ashley Falls has to offer.

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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18 Bow Wow Rd Sheffield MA 01257

Price$529,000

Est. Mortgage: $/month

Pending

MLS Number 226214

  • Single Family
  • Address 18 Bow Wow Rd
  • Village Berkshire - South
  • Year Built 1935
  • Bedrooms 3

WATERFRONT - Charming Cape with Master Suite on first floor. WHAT VIEWS!! Beautifully designed Kitchen w/access to a grand screen Porch. (radiant heat in K & MBR )Living Room w/wood burning fireplace. flows into an enclosed Porch. 2BR & Bath on second floor. Attached Garage. Garden that is all organic and lovingly maintained with many perennials & specimen trees. Swim, fish, kayak, canoe on this beautiful Mill Pond.

Listed by SANDRA M. PRESTON REAL ESTATE

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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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27 Main St Sheffield MA 01257

MLS Number 227756

  • Commercial
  • Village Berkshire - South
  • Year Built 1830
  • Parking Spaces 3
  • Square Feet 3,955

Great opportunity in the heart of historic Sheffield village. This exceptional Greek Revival is in the Village Center District allowing for a LIVE-WORK mixed use and a variety of by-right commercial uses such as offices, restaurant, market, inn (please refer to the Town of Sheffield Zoning By-Laws). It is currently configured as a gracious private home with a two-room boutique antique shop with private entrance. To learn more about the residential features of this property refer to MLS #227053. One of the 3-bays in the garage is set up as a workshop. The out building is perfect for storage or further workshop space. The large finished attic provides additional space options. There is ample off-street parking. Excellent condition throughout.

Listed by STONE HOUSE PROPERTIES, LLC

$
$
%
$/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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27 Main St Sheffield MA 01257

Price$500,000

Est. Mortgage: $/month

MLS Number 227053

  • Single Family
  • Address 27 Main St
  • Village Berkshire - South
  • Year Built 1830
  • Parking Spaces 3

Zoned residential and/or commercial in the heart of historic Sheffield Village, this 4 bedroom generously proportioned Greek Revival artfully blends charming details of the of the past with modern conveniences of today and is perfect for LIVE-WORK. The grand entry hall, dominated by a handsome stairway, flows graciously to the front parlor, formal dining room, and large country kitchen. Period elements include meticulously restored classic moldings, high beamed ceilings, 6 over 6 windows, 3 fireplaces, elegant wood floors, and a cavernous easily accessed attic, which offers multiple use possibilities. The expanded, vaulted ceiling kitchen features a center island, granite counters, updated appliances, and walls of windows surrounding an inviting and comfortable eating area.

Listed by Sheila Thunfors and Brian Farrell of STONE HOUSE PROPERTIES, LLC

$
$
%
$/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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481-A Shunpike Rd Sheffield MA 01257

Price$499,000

Est. Mortgage: $/month

MLS Number 221917

  • Land
  • High School Mount Everett
  • Village Berkshire - South
  • Square Feet 870,329

Looking for that perfect hilltop setting to build your dream house? Situated on 26.38 private acres with a plateau at 1,100'. Distant views above the Sheffield Valley as the sunset unfolds over the Taconic Range. A beautiful unspoiled lot surrounded by mature hardwoods, stonewalls, a small pond and you. One building site is permitted on this land. You may judiciously clear trees for views of your choice. A gravel driveway is in place to reach the plateau where you would build. Land is surrounded by 3 large estate parcels and 150 acres of conservation.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/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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650 Main St Sheffield MA 01257

MLS Number 227649

  • Commercial
  • Village Berkshire - South
  • Year Built 1947
  • Square Feet 6,007
  • Bedrooms 1

**NEW PRICE ** Owner retiring. His dream Restaurant in the Berkshires can be yours. Purchase this local institution in the morning, and open for dinner the very same day! Business & Property sold together. Everything included. 100% turn-key with dedicated patrons and staff. THE BRIDGE RESTAURANT (named for the famed Covered Bridge of Sheffield, MA) is minutes from the CT & NY State Border and close to all Summer & Winter Berkshire attractions. Seating for 98, large Bar, Banquet Room and spacious Kitchen. Property includes a 1 Bedroom Apartment for Owner or staff. Profitable, with significant untapped potential.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/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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