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 ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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 ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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700 Cooper Hill Road Sheffield MA 01257

Sheffield, MA700 Cooper Hill Road

Price$4,499,000

Est. Mortgage: $/month

Pending

MLS Number 240775

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 2,452
  • Acreage 233

Discover an exceptional estate with a recently renovated farmhouse, two expansive barns, and 233 acres of magnificent land. The farmhouse features four spacious bedrooms, four and a half bathrooms, and breathtaking western views. Immerse yourself in the tranquility of this tastefully updated residence. The versatile barns, spanning 16,000 square feet, offer endless possibilities for parties, equestrian pursuits, artistry, or storage. The surrounding acreage showcases lush fields for farming and multiple world-class building sites, allowing you to create your dream home with stunning vistas. Enjoy the convenience of nearby attractions in salisbury, ct, and great barrington, ma, while relishing the serenity of bartholomew's cobble.

Listed by William Melnick and Elyse Harney of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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1373 Boardman Street Sheffield MA 01257

Sheffield, MA1373 Boardman Street

Price$3,500,000

Est. Mortgage: $/month

MLS Number 241419

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 14,114
  • Acreage 5.13

Welcome to the factory - a gorgeous three bedroom, three bath loft that comes with a rather large 10,000 foot manufacturing or studio space, along with an executive office with its own bedroom, another full bath and a service kitchen. Essentially two separate living spaces within the commercial space. The loft space is extraordinary, featuring a huge common area with a glass garage door to a large screened porch and deck, and a malm 360 fireplace. All bedrooms and baths are generous. The commercial space includes two offices and other ancillary rooms with lots of storage on the second level. Enjoy the one year old in-ground lounge pool, newer barn with a corral and the neighboring appalachian trail. Located in the housatonic valley with views of neighboring protected cornfields.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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1373 Boardman Street Sheffield MA 01257

MLS Number 241420

  • Commercial
  • Acreage 5.13

Over 10,000sf of studio or manufacturing space available along with two extraordinary living spaces available under the same roof in the general business district of sheffield, ma. The large work space is conjoined with an large and exciting three bedroom, three bath loft with a glass garage door to a huge screened porch and deck overlooking a new in-ground lounge pool and another executive office with more sleeping space. Views over the appalachian trail land and protected cornfields to the south and berkshire hills to the east all in proximity of great barrington, ma and salisbury, ct. It's a beautiful and convenient location in the middle of the housatonic valley for a true live/work situation.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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960 South Undermountain Road Sheffield MA 01257

MLS Number 241212

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,289
  • Acreage 11.95

21st century homestead! Refurbished antique house, new barn, timber frame studio, salt water pool, and heated 4-car garage at the foot of taconic mountain range in sheffield. On a manageable 12-acres, the current stewards have prioritized character and quality of materials without sacrificing energy efficiency. Highlights of the house include marble floored screen porch, three fireplaces, a wheelchair accessible 1st floor bath, spray foam insulation, new siding, new windows, and a standing seam metal roof. New heating system, whole house generator. Gardens and meadow abound. 2 floors of studio space across the street include a full bath, pellet stove, fireplace, high ceilings and windows overlooking a spring fed pond. Utterly pristine, this is a dynamic and rare offering in the berkshires

Listed by Kenzie Fields of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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 Sheffield Business Park Sheffield MA 01257

MLS Number 240784

  • Commercial
  • Acreage 4.21

This large industrial building located in the sheffield business park on 4.212 acres offers many opportunities, a potential division of the building for tenants and room for possible expansion. Large warehouse space with 35' ceiling at peak and two 12' overhead doors. There is a separate production area with another 12' overhead door. Two separate finished office units with their own exterior entrances. Shared break room and two restrooms. Large parking area. Efficient metal building with propane hot air heat, central ac - overhead fans in warehouse.

Listed by Wendy Eichman of RAYNARD AND PEIRCE REALTY LLC (((86) 453-4148)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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296 South Main Street Sheffield MA 01257

MLS Number 240811

  • Commercial
  • Parking Spaces 20

This building is a craftsman work of art with a rustic post and beam design, the vaulted ceilings and gracious windows offer an elegant, light filled atmosphere for the business of your dreams. Presently home to a successful winery, you will find a tasting room and retail store in the left wing with a second level loft. A private suite offers a kitchen, full bath and lofted office/bedroom for a unique live/work opportunity. To the right of the center foyer is an additional private tasting room suitable for small events or group gathering. Outside you will find ample parking for your patrons, mature gardens surrounding the building, and a stone patio with mountain views. Whether you dream of being a vintner or have a vision of your own, this property will not disappoint.

Listed by Molly DiGiovanni and Suzann Laverack Ward of HOUSATONIC REAL ESTATE ((413) 274-5065)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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

296 South Main Street Sheffield MA 01257

MLS Number 240810

  • Commercial
  • Parking Spaces 20

This building is a craftsman work of art with a rustic post and beam design, the vaulted ceilings and gracious windows offer an elegant, light filled atmosphere for the business of your dreams. Presently home to a successful winery, you will find a tasting room and retail store in the left wing with a second level loft. A private suite offers a kitchen, full bath and lofted office/bedroom for a unique live/work opportunity. To the right of the center foyer is an additional private tasting room suitable for small events or group gathering. Outside you will find ample parking for your patrons, mature gardens surrounding the building, and a stone patio with mountain views. Whether you dream of being a vintner or have a vision of your own, this property will not disappoint.

Listed by Molly DiGiovanni and Suzann Laverack Ward of HOUSATONIC REAL ESTATE ((413) 274-5065)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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

296 South Main Street Sheffield MA 01257

Sheffield, MA296 South Main Street

Price$1,129,000

Est. Mortgage: $/month

MLS Number 240838

  • Residential
  • Bathroom 2
  • Bedrooms 1
  • Square Feet 5,045
  • Acreage 1.94

This building is a craftsman work of art with a rustic post and beam design, the vaulted ceilings and gracious windows offer an elegant, light filled atmosphere for the business of your dreams.Private suite offers a kitchen, full bath and lofted office/bedroom for a unique live/work opportunity. Outside you will find ample parking, mature gardens surrounding the building, and a stone patio with mountain views. This property will not disappoint.

Listed by Suzann Laverack Ward and Molly DiGiovanni of HOUSATONIC REAL ESTATE ((413) 274-5065)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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

15 Guilder Hollow Road Sheffield MA 01257

Sheffield, MA15 Guilder Hollow Road

Price$996,700

Est. Mortgage: $/month

MLS Number 240709

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 4,134
  • Acreage 10.65

Private, quiet, architect designed 1910 carriage house, originally built for both carriages and new autos, off of route 41. There are vast loft-like spaces ready for conversion or use as studios along with two apartments. One apartment on the second floor has three bedrooms, a full bath, living/dining and kitchen, with laundry, along with a huge great room. The second apartment is a great airbnb or room for more guests. It, too, has a full kitchen and bath, living/dining room and an area for a bedroom. The roof was replaced in 2019, along with a new septic system (2013), water well (2016), a boiler within the last 10 years and a new hot water heater. Currently two parcels with a writer/artist studio outbuilding. A possible building site in an old apple orchard with views to mount everett.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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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86 Main Street Sheffield MA 01257

Sheffield, MA86 Main Street

Price$798,900

Est. Mortgage: $/month

MLS Number 240768

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 3,082
  • Acreage 0.5

If you are looking for in town convenience along with gracious country living, this may be the property for you! A classic 1875 new england greek revival with 3 bedrooms & 2.5 baths situated on .5 acres, the home has been lovingly maintained and tastefully updated over the past 22 years by its current owners, with classic period features including gleaming wood floors, high ceilings, period moldings & trim, large modern country-style kitchen, heated attached 2-car garage w/ finished 2nd floor, a large detached outbuilding with extra storage and room for other uses. Steps from the yard you will find all the charm & conveniences of the sheffield green including the sheffield library, dewey hall, marketplace cafe, robbie's pizza & much more to discover & explore!

Listed by Dan Alden of ALDEN COUNTRY REAL ESTATE SERVICES ((413) 335-9300)

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of September 30, 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.