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: 2.78% last updated on Jul 22, 2021
* 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: 2.78% last updated on Jul 22, 2021
* 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: 2.78% last updated on Jul 22, 2021
* 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$925,000

Est. Mortgage: $/month

MLS Number 234236

  • Residential
  • Bathroom 9
  • Bedrooms 9
  • Square Feet 4,928
  • Acreage 1

This handsome colonial two-story inn resides in historic sheffield. Originally built for rev. Bradford, this house has watched over generations of families. A successful b & b for the last 30+ years -trip advisor award of excellence/#1 b & b. 7br/7ba in the inn, gracious dining, country kitchen & contemporary innkeepers quarters 2br/1.5 ba. Barn/garage 24x40. Lush gardens and grounds. Solar panels. 2 kitchens & 2 laundry areas. Turn key. Would make a gracious private home - must see!

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 234235

  • Commercial
  • Acreage 1

This handsome colonial two-story inn resides in historic sheffield. Originally built for reverend bradford, this house has watched over generations of families. A successful b & b for the last 30+ years -trip advisor award of excellence/#1 b & b. 7br/7ba in the inn, gracious dining, country kitchen & contemporary innkeepers quarters 2br/1.5 ba. Barn/garage 24x40. Lush gardens and grounds. Turn key property. Separate kitchens and laundry areas. Solar panels. Must see!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 Sheffield MA 01257

Sheffield, MA1 Water Farm Rd

Price$895,000

Est. Mortgage: $/month

Pending

MLS Number 223162

  • Land
  • Acreage 301.58

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 Cindy Welch and Keith Ross of LANDVEST, INC.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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$795,000

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. Closing after november 1, 2021.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 S. Main Sheffield MA 01257

MLS Number 233150

  • Commercial
  • Acreage 1.33

Currently a well-established business operates in the first floor commercial space with diverse offerings in food and beverage, including a retail beer and wine license. Two large 2-bedroom apartments on the second floor of this mixed-use building provides additional income. A separate accessory residential building adjacent to the large in-ground pool enhances the 1.3 acres. Several additional outbuildings completes the versatility of this unique property. The existing commercial tenant is willing to remain or vacate. Part of the main structure (circa 1727) was moved from ct to this location. The oldest building in sheffield with four fireplaces and original wide board kings planking

Listed by Thomas K. Doyle, Sr. of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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$785,000

Est. Mortgage: $/month

MLS Number 233151

  • MultiFamily
  • Acreage 1.33
  • Year Built 1972

Currently a well-established business operates in the first floor commercial space with diverse offerings in food and beverage, including a retail beer and wine license. Two large 2-bedroom apartments on the second floor of this mixed-use building provides additional income. A separate accessory residential building adjacent to the large in-ground pool enhances the 1.3 acres. Several additional outbuildings completes the versatility of this unique property. The existing commercial tenant is willing to remain or vacate. Part of the main structure (circa 1727) was moved from ct to this location. The oldest building in sheffield with four fireplaces and original wide board kings planking.

Listed by Thomas K. Doyle, Sr. of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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

139 Main Sheffield MA 01257

Sheffield, MA139 Main St

Price$785,000

Est. Mortgage: $/month

MLS Number 233351

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 6,094
  • Acreage 1.33

This complex could be returned to a single-family residence or a family compound. Currently a well-established business (with wet use facilities) operates in the first floor commercial space with diverse offerings in food and beverage, including a retail beer and wine license (requires separate application). Two large 2-bedroom apartments on the second floor of this mixed-use building provides additional income. A separate accessory residential building adjacent to the large in-ground pool enhances the 1.3 acres. Several additional outbuildings completes the versatility of this unique property. The existing commercial tenant is willing to remain or vacate. Part of the main structure (circa 1727) was moved from ct to this location

Listed by Thomas K. Doyle, Sr. of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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

1076 County Sheffield MA 01257

Sheffield, MA1076 County Rd

Price$750,000

Est. Mortgage: $/month

Pending

MLS Number 234635

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,642
  • Acreage 3.28

Set in a tranquil, park-like setting this home set atop a hill offers gorgeous zen like views from every room & deck. 1st floor has a large open living plan w/ living room, dining area & kitchen. It's accentuated by a wainscoted cathedral ceiling, skylights, central fireplace with granite surround. Sliding doors let natural light in & lead out to the deck to enjoy the peace this property has to offer. Also on the 1st floor: two bedrooms, full bath with jacuzzi tub & laundry room. Upstairs the primary bedroom offers ensuite bath, walk-in closet, fireplace and private porch. The lower level hosts a generously sized tiled family room w/sliders to the brick patio. A full bath, clean mechanical room w/workshop & cedar closet round it out. Stream on the premises. Must be seen to be appreciated!

Listed by Elisabeth Wheeler of LANCE VERMEULEN RE, INC., LENOX

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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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793 Salisbury Sheffield MA 01257

Sheffield, MA793 Salisbury Rd

Price$715,000

Est. Mortgage: $/month

MLS Number 234354

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,280
  • Acreage 1.11

Move-in ready and nestled amidst trees off sheffield's highly-desirable salisbury road sits this striking single floor home, custom-crafted to highest contemporary standards. Enter through the expansive front door to an open floor plan, kitchen/dining/living area with vaulted ceilings - perfect for entertaining.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 2021
* 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 July 27, 2021 . 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.