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!

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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

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$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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23 Elm Sheffield MA 01257

Sheffield, MA23 Elm Ct

Price$695,000

Est. Mortgage: $/month

MLS Number 235360

  • Residential
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 2,400
  • Acreage 0.51

Stunning turnkey contemporary - centrally located, yet tucked away!Steps from some of south county's favorite eating spots, yet off the main road and privately situated, this 2 bed, 2.5 bath home is the perfect getaway for those seeking modern, well-appointed living in a convenient location. What began as a 1923 cottage has been meticulously rebuilt, expanded, and reimagined by its design-build owners. Amenities and little luxuries abound - large outdoor patio + fire pit, screened-in porch + gas fireplace, gourmet kitchen with oversized island, primary en suite with private screened porch, radiant heat in living areas and bathrooms. Premium finishes include heated shower floors, quartz and granite counters, high-end appliances, and a viessmann boiler. Well built and beautifully designed.

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

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$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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147 Main Sheffield MA 01257

Sheffield, MA147 Main St

Price$650,000

Est. Mortgage: $/month

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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305 Undermountain Sheffield MA 01257

Sheffield, MA305 Undermountain Rd

Price$575,000

Est. Mortgage: $/month

Pending

MLS Number 234745

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,700
  • Acreage 2.03

Post and beam contemporary home on 2.03 acres with a path to a parcel on berkshire lake. For swimming and canoeing. This move in condition home has an open plan dining, living and kitchen, an office/bedroom and a full bath on the first floor and 3 bedrooms and a full bath on the second level. Full basement. Set back from the road

Listed by BERKSHIRE HATHAWAY HOMESERVICESBARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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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

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$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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839 Bow Wow Sheffield MA 01257

Sheffield, MA839 Bow Wow Rd

Price$549,500

Est. Mortgage: $/month

MLS Number 232003

  • Land
  • Acreage 57

Fabulous opportunity to own 57 acres of land with a four acre building envelope. Build your dream house and be surrounded by 53 acres of total privacy but not isolated. On beautiful bow wow rd. Just minutes to all of our berkshire amenities

Listed by BERKSHIRE HATHAWAY HOMESERVICESBARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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594 Shunpike Sheffield MA 01257

Sheffield, MA594 Shunpike Rd

Price$545,000

Est. Mortgage: $/month

MLS Number 233608

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2,600
  • Acreage 2.32

In a beautiful clearing in the woods, off a quiet country road, this house offers comfort and privacy. Step in to bright inviting foyer. Living and dining rooms have sliding glass doors to large outdoor deck spaces, both covered and open. Kitchen features butternut cabinets and adjacent powder room. Upstairs, there are two completely separate bedroom suites--one with dressing room and shiplap ceilings, one with cathedral ceilings. A third bedroom suite and sitting area/office is in the walk-out lower level. You'll enjoy plenty of peace and quiet at this lovely hideaway.

Listed by Claire Naylor Pollart of LANCE VERMEULEN RE,INC

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$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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508 Polikoff Sheffield MA 01222

Sheffield, MA508 Polikoff Rd

Price$525,000

Est. Mortgage: $/month

MLS Number 235939

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2,156
  • Acreage 1.21

Perfect home with plenty of space to play outside in your fenced-in backyard. Live and work from this colonial home built in 2000. Wood floors throughout and large windows for natural light. Generous back deck, perennials, and a fire pit for entertaining family and friends. Beautiful mature trees and newly refreshed landscaping. 3 beds, 3 baths. There is a studio above the garage with a separate entrance and full bathroom. This is a must see at $525,000.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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119 Main Sheffield MA 01257

Sheffield, MA119 Main St

Price$525,000

Est. Mortgage: $/month

MLS Number 233718

  • Residential
  • Bathroom 3
  • Bedrooms 6
  • Square Feet 4,184
  • Acreage 0.87

Oh the possibilities! A grand greek revival with 6 bedrooms and a large kitchen, sunny dining room and warm and inviting double parlor. Beautiful antique details. The second building is currently a 2 bedroom guest apartment. But in this location, you can use it for a shop, an office or a studio. A great live/work situation or multigenerational living.

Listed by BERKSHIRE HATHAWAY HOMESERVICESBARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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 A Shunpike Sheffield MA 01257

Sheffield, MA481 A Shunpike Rd

Price$445,000

Est. Mortgage: $/month

MLS Number 233805

  • Land
  • Acreage 26.38

Looking for that perfect hilltop setting to build your dream house? Situated on 26.38 private acres with a plateau at 1,100'. Distant views above the sheffield valley as the sunset unfolds over the taconic range. A beautiful unspoiled lot surrounded by mature hardwoods, stonewalls, and a small pond. One building site is permitted on this land. You may judiciously clear trees for views of your choice. A gravel driveway is in place to reach the plateau where you would build. Land is surrounded by 3 large estate parcels and 150 acres of conservation.

Listed by Suzann Laverack Ward of HOUSATONIC REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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650 Main Sheffield MA 01257

MLS Number 233548

  • Commercial
  • Acreage 0.8

Currently a well-established restaurant with consistent track record, this high traffic location offers an ideal spot for casual dining / gastro-pub / brew-pub / farm-to-table / takeout / catering food service operations or other commercial uses. Sale includes real estate, 98 seat restaurant, all fixtures & equipment for a turn-key business, 500 sq. Ft. Owner's quarters and room to grow.

Listed by Dan Alden of ALDEN COUNTRY REAL ESTATE SERVICES

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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935 Ashley Falls Sheffield MA 01257

Sheffield, MA935 Ashley Falls Rd

Price$425,000

Est. Mortgage: $/month

MLS Number 236388

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,800
  • Acreage 2.4

A quirky, craftsman cottage on a divisible lot. Large, newer insulated barn with almost 1600 square feet could be an amazing workshop or artist's studio. Lots of local history and no shortage of potential. First floor primary suite could be an accessory dwelling unit (adu) by permit from the planning board. Freestanding studio/office insulated and currently without heat. Expansive deck, fire pit, and potential koi pond. Convenient to great barrington and connecticut.

Listed by Jonathan Hankin of BERKSHIRE PROPERTY AGENTS,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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 December 3, 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.