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 Undermountain Sheffield MA 01257

Sheffield, MA2080 Undermountain Rd

Price$11,890,000

Est. Mortgage: $/month

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

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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 Undermountain 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: 3.45% last updated on Jan 13, 2022
* 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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599 Cooper Hill Sheffield MA 01257

Sheffield, MA599 Cooper Hill Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 235590

  • Residential
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 3,364
  • Acreage 20.04

Location and views are what this listing is all about. Perched on top of cooper hill these 20 acres offer unobstructed views in all directions. It is possible to see both magnificent sunrises and sunsets. The listing is comprised of 5 lots that must be sold together. There are two existing houses either of which could become part of an estate. The is ample room for a large main residence facing east overlooking protected land.

Listed by John Harney of WILLIAM PITT SOTHEBY'S - SALISBURY

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$
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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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 Shunpike Sheffield MA 01257

Sheffield, MA481 Shunpike Rd

Price$995,000

Est. Mortgage: $/month

MLS Number 234104

  • Residential
  • Bathroom 2
  • Bedrooms 1
  • Square Feet 1,296
  • Acreage 15

Passive solar home with views to south and west. Separate summer cottage or office space with screened porch and deck w/views facing west. Includes a 2 story barn/studio space 36'x28' 3 over head doors, concrete floors used as sculpture studio. 2nd floor with two finished rooms with hardwood floors to private deck to capture views. Buildings finished with red cedar vertical siding. Adjoining additional 26 acre building lot available surrounded by conservation land and large private parcels.

Listed by Suzann Laverack Ward of HOUSATONIC REAL ESTATE

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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59 Main Sheffield MA 01257

Sheffield, MA59 Main St

Price$839,000

Est. Mortgage: $/month

MLS Number 236099

  • Residential
  • Bathroom 9
  • Bedrooms 9
  • Square Feet 5,358
  • Acreage 1

Gracious 1818 colonial in the village of sheffield on a beautifully landscaped acre. Walk to restaurants, library, post office and historical society. Currently a turnkey fully furnished 7 bedroom, 7 bath b&b with a 1600 sq ft open plan owner's quarters with 2 bedrooms and 1.5 baths. Many permitted uses in the village center district. The property is perfect to continue as a b&b or consider other live/work home businesses. Perhaps a family compound. The 40x24 barn with concrete floor and second floor is ideal for workshop, studio, car storage. So many possibilities!

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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59 Main Sheffield MA 01257

MLS Number 236100

  • Commercial
  • Acreage 1

Staveleigh house b&b. A lovely 7 bedroom, 7 bath turnkey b&b fully furnished in the historic village center of sheffield. 1600 sq ft owner's quarters with open floor plan, 2 bedrooms and 1.5 baths. Originally built by reverend bradford around 1818, this handsome gracious home has been operated as a successful b&b for thirty years. Many other permitted uses in the village center district. 6 exterior doors and two interior staircases, two heating systems, two laundries, two kitchens. 40x24 barn with concrete floor and second floor perfect for work shop, studio, car storage, etc. All in great condition a beautifully landscaped acre..

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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371 Berkshire School Sheffield MA 01257

MLS Number 236463

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

This property is located in a treasured part of berkshire county. It is walking distance to the center of town, to the state park, the library, and within a 20 min. Drive 2 major ski areas, 4 major golf courses, riding stables, tanglewood, and car racing, sheffield is on the boarder of ny state &ct. Less than 2 hours to mid town. The house has a wonder floor plan with master bdr on first floor. The character of this new england has not changed in 4 generations. It has civic pride!

Listed by Donna Peck of COPAKE REALTY

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$
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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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139 Main Sheffield MA 01257

Sheffield, MA139 Main St

Price$729,000

Est. Mortgage: $/month

MLS Number 236228

  • MultiFamily
  • Acreage 1.3
  • Year Built 1727

Prime commercial /mixed-use / multi-family property on the high-traffic route 7 berkshire corridor. Situated just south of the scenic sheffield green, this unique property offers endless possibilities for re-use & reinvention. The property consists of 2,120 square feet of retail commercial space across the entire first floor (formerly a deli & convenience store), two spacious 2nd floor apartments, each with 2 bedrooms & separate utilities, and a free-standing 33'x22' sq ft studio building w/ loft, full bath & kitchen for potential residential or commercial wet use. The level & sunny 1.3 acre parcel offers extensive paved parking with circular driveway, landscaped backyard, and an in-ground pool. Great spot for food service, retail, art gallery, professional or medical office space.

Listed by Dan Alden of ALDEN COUNTRY REAL ESTATE SERVICES

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$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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139 Main Sheffield MA 01257

MLS Number 236227

  • Commercial
  • Acreage 1.3

Prime commercial /mixed-use / multi-family property on the high-traffic route 7 berkshire corridor. Situated just south of the scenic sheffield green, this unique property offers endless possibilities for re-use & reinvention. The property consists of 2,120 square feet of retail commercial space across the entire first floor (formerly a deli & convenience store), two spacious 2nd floor apartments, each with 2 bedrooms & separate utilities, and a free-standing 33'x22' sq ft studio building w/ loft, full bath & kitchen for potential residential or commercial wet use. The level & sunny 1.3 acre parcel offers extensive paved parking with circular driveway, landscaped backyard, and an in-ground pool. Great spot for food service, retail, art gallery, professional or medical office space.

Listed by Dan Alden of ALDEN COUNTRY REAL ESTATE SERVICES

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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35 School Sheffield MA 01222

Sheffield, MA35 School St

Price$699,000

Est. Mortgage: $/month

MLS Number 235367

  • Residential
  • Bathroom 2
  • Bedrooms 5
  • Square Feet 3,060
  • Acreage 1.5

Built in 1880 this delightful home on the outskirts of the quaint village of ashley falls, offers comfortable country living. High ceilings, beautiful wood floors, and decorative moldings throughout.5 bedrooms, 2 full baths,a large country kitchen with pantry, formal dining room and a spacious front parlor. The screened porch is the perfect place to entertain, dine & just plain relax. On 1.5 acres of open level lawn perfect for play, pets & gardens. Close proximity to egremont, great barrington, waldorf school & many area attractions.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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 Sheffield MA 01257

Sheffield, MA246 County Rd

Price$695,000

Est. Mortgage: $/month

MLS Number 234596

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,236
  • Acreage 23

Delightful country home with a 960 sq ft guest house. The main house has 3 bedrooms, 2 full baths, sauna and lovely stone terrace the guest house next to the tennis court has cathedral ceilings, tile floor, full kitchen, full bath, a large open floor plan and deck. All perfect for entertaining with great potential for rental income. Beautifully landscaped with mature trees, shrubbery and perennial gardens . Soda spring joins the magical ironwork brook as it meanders through the 23 acres. A nature lover's paradise. The sellers have cherished this country get-away since 1966. Masks required.

Listed by Sheila Thunfors and Allison Rada of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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147 Main Sheffield MA 01257

Sheffield, MA147 Main St

Price$650,000

Est. Mortgage: $/month

Pending

MLS Number 236088

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,803
  • Acreage 2.6

Dripping with charm. Village setting with rocking chair front porch. Gracious rooms and an easy flow. Beautiful gleaming wood floors, fireplaces, screened porch, large windows overlooking the sunny level lawn. A first floor primary bedroom with fireplace and on suite bath with tub. This home was recently updated, and work was done on the fabulous old barn to last another 100 years!

Listed by BERKSHIRE HATHAWAY HOMESERVICESBARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* 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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Based on information submitted to BCMLS  as of January 19, 2022 . 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.