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!

2080 South Undermountain Road Sheffield MA 01257

MLS Number 234183

  • Residential
  • Bathroom 6
  • Bedrooms 11
  • Square Feet 5,850
  • Acreage 85

This spectacular 85+/- acre property is a destination educational center. It offers a magnificent 1880 manor house, with spectacular distant views, a pond, and 11 additional buildings which house an auditorium, group meeting areas, breakout private offices, a fitness center, pondside cottage, huge dining hall with commercial kitchen, and accommodations in over 56 guest rooms. The land is made up of 70+/- acres in the southern berkshires and 15+/- abutting acres in salisbury, ct - the entire ct side runs along sage's ravine. There are walking trails throughout the land and access to the appalachian trail. You will be smitten by this property and totally taken with the possibilities... Building and property tax details are for the main house only. Please contact agent for more details.

Listed by Juliet Moore and Elyse Harney Morris of ELYSE HARNEY REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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2080 South Undermountain Road Sheffield MA 01257

MLS Number 234204

  • Commercial
  • Acreage 85

Breathtaking educational facility, residential complex or corporate retreat this spectacular 85+/- acre property is a destination educational center. It offers a magnificent 1880 manor house, with spectacular distant views, a pond, and 11 additional buildings which house an auditorium, group meeting areas, breakout private offices, a fitness center, pondside cottage, huge dining hall with commercial kitchen, and accommodations in over 56 guest rooms. The land is made up of 70+/- acres in the southern berkshires and 15+/- abutting acres in salisbury, ct - the entire ct side runs along sage's ravine. There are walking trails throughout the land and access to the appalachian trail. Details and taxes are only for the main house, please ask for details for all 12 buildings and total property.

Listed by Elyse Harney Morris and Juliet Moore of ELYSE HARNEY REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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554 Sheffield Egremont Road Sheffield MA 01257
Pending

MLS Number 238763

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 5,000
  • Acreage 4.33

Need a 1,100 sq. Ft. Workshop-studio? This custom built country home is for you. Magnificent living in glass, wood, stone and metal. Open plan living-room and dining-room with fireplace. Primary suite on main floor. Gourmet kitchen, 4 additional bedrooms. Billiard room, media room and glorious mountain views. Passed title v. This unique property is minutes from shopping, skiing, dining and all berkshire, litchfield county and ny state attractions. A true one-of-a-kind home (watch the video!)***bonus: huge 1,100 sq. Ft. Workshop - studio with full bath. Use it as is, or convert it to an ada accessible apartment, professional office, gym or even an indoor pool .

Listed by Steven J. Weisz of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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1350 Berkshire School Road Sheffield MA 01257
Pending

MLS Number 238561

  • Residential
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 15,000
  • Acreage 2.44

Unique opportunity to own a 15,000 +/- sq ft post & beam barn with two apartments for owner-occupied business venture. Formerly twin fire antiques for many successful years, opportunity is knocking for the next entrepreneur. Two oversized doors will accommodate a car collection, art gallery, antiques center, or retail, to name ja few options. Two workshops and 4-bay garage on 2.44 acres complete the package. Heated and partially air conditioned. Video survielance cameras on and alarm system.

Listed by Rosemary Ann Baumann of WHEELER & TAYLOR REALTY CO.,INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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1350 Berkshire School Road Sheffield MA 01257
Pending

MLS Number 238566

  • MultiFamily
  • Acreage 2.44
  • Year Built 1975
  • Parking Spaces 4

Unique opportunity to own a 15,000 +/- sq ft post & beam barn with two apartments for owner-occupied business venture. Formerly twin fire antiques for many successful years, opportunity is knocking for the next entrepreneur. Two oversized doors will accommodate a car collection, art gallery, antiques center, or retail, to name just a few options. Two workshops and 4-bay garage on 2.44 acres complete the package. Heated and air conditioned and waiting for its next entrepreneur.

Listed by Rosemary Ann Baumann of WHEELER & TAYLOR REALTY CO.,INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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48 South Main Street Sheffield MA 01257

Sheffield, MA48 South Main Street

Price$895,000

Est. Mortgage: $/month

MLS Number 238829

  • Residential
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 3,983
  • Acreage 2

This striking home, formerly a popular bed & breakfast, recently underwent a thorough upscale renovation. Highlights include an extraordinary gourmet kitchen, new ensuite bathrooms & mini-split a/c units in 6 bedrooms, new electric, plumbing, central heat/air, ev charger & septic. In addition, a primary suite consists of a sitting room, bedroom and another ensuite bath. Much of the original detailing was lovingly preserved, including a classic spindled staircase railing and the distinctive floor to ceiling windows. The yard has lovely plantings, gazebo, and large barn, ripe for repurposing. What a perfect home for holiday gatherings in a quintessential new england village, and the best part is all the work has been done!

Listed by Brian Farrell of STONE HOUSE PROPERTIES,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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48 South Main Street Sheffield MA 01257

MLS Number 238834

  • Commercial
  • Acreage 2

This is an outstanding bed & breakfast, recently renovated top to bottom and in immaculate condition. There are 6 guest rooms, each with private bath, mini-split a/c, and flat screen tv. In addition, there is an owner/host suite with sitting room, bedroom, and private bath. The renovations include a large gourmet kitchen with 2 ovens, new electric, new plumbing, new central heat & air, ev charger and new septic. Much of the original detailing was lovingly preserved, including a classic spindled staircase railing and the distinctive floor to ceiling windows. The large yard has beautiful plantings, and there is ample off-street parking space. Excellent high visibility location, close to ski areas, hiking trails, berkshire cultural venues, and multiple famous prep schools.

Listed by Brian Farrell of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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1180 Ashley Falls Road Sheffield MA 01222

Sheffield, MA1180 Ashley Falls Road

Price$699,000

Est. Mortgage: $/month

MLS Number 239414

  • MultiFamily
  • Acreage 0.25
  • Year Built 1860

Historic new england merchant's building in the village of ashley falls - an investment opportunity to own the commercial center in the ne village of ashley falls, ma. Currently home to - a 2 bedroom apartment, a studio apartment, the post office, a salon & a therapist's office. This building has a variety of configurations and uses for a new owner. Currently fully occupied. Financials available. Nearly the entire building has been renovated since 2019.

Listed by Elle Villetto and Karen Climo of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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1180 Ashley Falls Road Sheffield MA 01222

MLS Number 239415

  • Commercial
  • Acreage 0.25

Historic new england merchant's building in the village of ashley falls - an investment opportunity to own the commercial center in the ne village of ashley falls, ma. Currently home to - the post office, a salon, a therapist's office, a 2 bedroom apartment & a studio apartment. This building has a variety of configurations and uses for a new owner. Currently fully occupied. Financials available. Nearly the entire building has been renovated since 2019.

Listed by Elle Villetto and Karen Climo of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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 TourAsk A QuestionMore Details

371 Berkshire School Road Sheffield MA 01257

MLS Number 239543

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,585
  • Acreage 2.96

Behind this traditional facade lies a flexible floor plan offering loads of space for family, guests, work and entertaining. Sited on 2.96 acres, there is plenty of yard & sun for gardens, play & pets. Eat-in kitchen with vaulted ceiling opens to decks accessing backyard. Lovely 1st floor primary suite with huge closet and deluxe full bath. Formal lr and dining room, both with fireplaces. A cozy office/den and 1/2 bath complete the first floor. Two large bedrooms & a full bath upstairs.There is an attached garage. A move-in ready gem, near hiking, biking, skiing, berkshire school, and minutes to village center, connecticut, and great barrington.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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 TourAsk A QuestionMore Details

703 North Main Street Sheffield MA 01257

MLS Number 222988

  • Commercial
  • Acreage 1.41

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 of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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Hickey Hill Road Sheffield MA 01257

Sheffield, MAHickey Hill Road

Price$540,000

Est. Mortgage: $/month

MLS Number 238343

  • Land
  • Acreage 27

Located in a private setting on a peaceful, country road among beautiful, fine, berkshire county homes. A combined 27 acres with approximately 520 total feet of road frontage along hickey hill rd. Lot 4 offers 13.79 acres with a trail in place branching off of a, private drive, leading to an approximate five acre clearing awaiting your dream home. Perc test available for lot 4. Lot 5 offers 7.55 acres in sheffield and flows into new marlborough, adding an additional 5.66 acres. Potential second build site on lot 5. Continue to use lot 5 for privacy or build a second home/guest house. The lots will only be sold together. Deed requires a minimum 2,000 sq. Ft. Residential home to be built.

Listed by Molly DiGiovanni of HOUSATONIC REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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 TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of February 4, 2023 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.