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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

481 Shunpike Sheffield MA 01257

Sheffield, MA481 Shunpike Rd

Price$1,495,000

Est. Mortgage: $/month

MLS Number 237928

  • Residential
  • Bathroom 2
  • Bedrooms 1
  • Square Feet 1,296
  • Acreage 41

The seller has a life estate in the main home. Terms can be negotiable. There is also a summer cottage with screened porch and deck. Includes a 36x28 workshop. Included is an additional 26 acre building lot. Some land does go into new marlborough. Surrounded by conservation land. Passive solar views facing south and west

Listed by Suzann Laverack Ward of HOUSATONIC REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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: 5.7% last updated on Jun 30, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

1180 Ashley Falls Sheffield MA 01222

MLS Number 237817

  • 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 Karen Climo of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

246 County Sheffield MA 01257

Sheffield, MA246 County Rd

Price$695,000

Est. Mortgage: $/month

Pending

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. Possession end of september 2022. Masks required.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

35 School Sheffield MA 01222

Sheffield, MA35 School St

Price$675,000

Est. Mortgage: $/month

MLS Number 238120

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

Comfort, space, and style in this beautiful 1880s home on 1.5 sunny acres. Located on a quiet street in the historic village of ashley falls, this 3060 sq ft home combines comfortable living with stylish detail. An understated, yet handsome, exterior belies the elegant details within, including nearly 10 ft ceilings, wide plank floors, curved plaster walls, decorative moldings, and a beautiful bending banister and newell post. But the sense of space and sunlight is perhaps the most arresting feature of this home. A bright and airy screened porch allows for outdoor living and dining. Inside, the high-ceilinged first floor features separate living and dining rooms, a bedroom, full bath, kitchen with walk-in pantry, and a large laundry room or office.

Listed by Jared Kelly and L. Chapin Fish of BROCKMAN REAL ESTATE,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

203 Berkshire school Sheffield MA 01257
Pending

MLS Number 237498

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,875
  • Acreage 4.3

Cape style home on 4.30 acres of land. Beautiful back yard with lots of open space. Nicely maintained home that sits up away from the road. Primary bedroom is on the 1st floor. Spacious open living room with a fireplaced dining room. Library/office and laundry w/1/2 bath complete the first floor. Two additional large bedrooms on 2nd floor. Lots of windows with great light throughout. New heating system.

Listed by Suzann Laverack Ward of HOUSATONIC REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

184 Silver Sheffield MA 01257

Sheffield, MA184 Silver St

Price$599,000

Est. Mortgage: $/month

MLS Number 237465

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,400
  • Acreage 1.15

This home offers three bedrooms and two and a half baths. The first floor consists of a beautiful primary suite, half bath, living room, kitchen and dining room. The primary suite has an oversized shower with two shower heads and side spraying units. The second floor offers two huge bedrooms with a shared bathroom. The basement is unfinished but easily could be finished. There is a shed that the owners renovated beautifully that could be used for many different things including a she shed. The home is surrounded by conservation land on three sides so it is very private. Thirty minutes to wassaic and tanglewood. Close to all sheffield amenities. Don't miss this gem of a home!

Listed by BERKSHIRE HATHAWAY HOMESERVICESBARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

703 North Main 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: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

20 Hillside Sheffield MA 01222

Sheffield, MA20 Hillside Ln

Price$573,000

Est. Mortgage: $/month

Pending

MLS Number 237484

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,057
  • Acreage 4.14

Set on over four acres on a private drive you will find this sun filled, open concepts, chalet style home. Enter through a side mudroom to the living room/dining room with vaulted ceilings, double sliding doors and chalet windows overlooking the front deck. Kitchen, two bedrooms and a full bath on the main floor. Second floor offers a loft overlooking the open space below, and a primary bedroom with en-suite bathroom. Log siding and log style interior banisters offer a slight rustic touch. An oversized two plus car garage is connected by a stairway leading to the basement which could easily become finished space. Additional outbuildings offer ample storage for all of your lawn and garden needs.

Listed by Molly DiGiovanni of HOUSATONIC REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to BCMLS  as of July 2, 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.