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!

1373 Boardman Street Sheffield MA 01257

Sheffield, MA1373 Boardman Street

Price$2,500,000

Est. Mortgage: $/month

MLS Number 245292

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 3,100
  • Acreage 5.13

The ultimate live-work-play retreatstep onto a property as striking as the berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''the factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked by 3,000-sq ft of stunning living spaces that seamlessly blend design, sophistication, comfort. From the glass walls that open to sweeping views, to its bespoke kitchen or design forward guest suite, every inch has been crafted to inspire. Host gatherings on the spacious screened deck, unwind by the 360 glass fireplace, find solitude in the ''tower'' - and redefine living, creating, & thriving.

Listed by Chapin Fish of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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1669 Silver Street Sheffield MA 01257

Sheffield, MA1669 Silver Street

Price$1,495,000

Est. Mortgage: $/month

MLS Number 245474

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 3,528
  • Acreage 10.23

Experience breathtaking panoramic vistas over protected land from every angle in this renovated classic american farmhouse. Nestled on two parcels, this residence boasts a pool, a detached garage, and gracious proportions throughout. Relax in the majestic long-range mountain vistas. The house is perfectly positioned to experience both sunrise and sunset views.Step inside to discover an extra-large chef's kitchen seamlessly connected to a delightful breakfast room, sunroom, and screened porch, each offering tranquil views of the pool and raised garden beds. The inviting living room, complete with a cozy fireplace, flows effortlessly into the dining area, creating an ideal space for entertaining. Adjacent, find a sunlit den and office area, bathed in natural light.

Listed by William Melnick and Elyse Harney Morris of ELYSE HARNEY REAL ESTATE

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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 Road Sheffield MA 01257

Sheffield, MA481 Shunpike Road

Price$1,475,000

Est. Mortgage: $/month

MLS Number 244075

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

A total 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own home with mountain views. A 36x52 work shop. One full time residence and a separate summer studio. Some land does go into new marlborough. Surrounded by conservation land. Passive solar views facing south and west. Property has been a sculpture park for many years. Trails throughout. Views to connecticut.

Listed by Suzann Laverack Ward of HOUSATONIC REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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1955 North Main Street Sheffield MA 01257

MLS Number 244475

  • Commercial
  • Acreage 8.3
  • Parking Spaces 100

Large 5 bay auto / truck sales and service center on route 7 (garage over 5000 sq ft - room for @ 100 cars). Over 1000 feet of frontage on route 7 at sheffield-great barrington border. Huge parking lot, high visibility, heavy power. Additional storage building on over 8 acres of land. Ideal for a multitude of uses.(former gmc dealership location.)

Listed by Richard G. Aldrich and Steven J. Weisz of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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567 South Main Street Sheffield MA 01257

Sheffield, MA567 South Main Street

Price$995,000

Est. Mortgage: $/month

MLS Number 243414

  • MultiFamily
  • Acreage 11.07
  • Year Built 1900
  • Parking Spaces 10

Investment opportunity in sheffield. Set way back from the main road, this multi family dwelling awaits its new stewards after almost 40 years in the same family. The property consists of 3 separate buildings, the main house with four 1 br apts.In the rear of the main house is a semi attached 2 br apt with its own separate entrance. You then have an additional 3 bedroom 2 bath home with 3 season room and rear garden. There is also a separate 2 bay garage with maintenance room. The grounds are beautifully manicured with flowering bushes and trees with lovely mountain views. Its really a little bit of paradise just off the beaten path yet close to everything. 15 minutes in great barrington, 10 minutes to n canaan ct. This lovely homestead is set on almost 13 secluded acres.

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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64 Hewins Street Sheffield MA 01257

Sheffield, MA64 Hewins Street

Price$849,000

Est. Mortgage: $/month

MLS Number 244746

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,455
  • Acreage 1.56

A rare & authentic 1842 post & beam farmhouse w/ many original details. This one-of-a-kind antique home awaits the reinvention & stewardship of it's next owners. In the same family for the last 125 years, and with just two prior owners since being built, the structure features post & beam construction, two original fireplaces, antique hardware, woodwork and doors that exemplify early american craftsmanship. The home offers a spacious first floor with two kitchens (once used as a two-family), dining room & parlor, and 2nd floor offers 4 bedrooms and two baths. The 1.5 acre parcel offers extraordinary western sunset views towards mt. Everett overlooking the housatonic river valley. A once-in-a-lifetime opportunity to own and restore an iconic home.

Listed by Dan Alden of ALDEN COUNTRY REAL ESTATE SERVICES

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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Bull Hill Road Sheffield MA 01257

Sheffield, MABull Hill Road

Price$795,000

Est. Mortgage: $/month

MLS Number 244891

  • Land
  • Acreage 18

Eighteen acres on the quitest dirt road with its own exceptional landscape feature: a boulder-strewn, mossy-rocked cobble. The cobble bisects a flat, three acre cleared field to the east, and a wooded forest with old stone wall remnants to the west. Live amongst the ancient spirits in whatever beautiful house you build. Fifteen wooded acres in chapter 61a.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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355 Clayton Road Sheffield MA 01222

Sheffield, MA355 Clayton Road

Price$610,000

Est. Mortgage: $/month

MLS Number 245162

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 6,420
  • Acreage 6.05

Opportunities and potential abound. Set back on 6+- acres in rural ashley falls. Presently greenwoods church, can now be yours to live and work from. The large bright and open main room is 42' x 70' with a concrete floor and forced air heat. Create the space you've envisioned for yourself and your business, the ideas are endless from continuing a place of worship, a grand home, a car collectors dream space. The original house is a 3 bedroom, 3 baths and 6000+- square feet to expand into.Continue to be a part of the positive energy that this property has shared over the years and many more years to come.

Listed by Mark Rosengren of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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690 North Main Street Sheffield MA 01257

MLS Number 243971

  • Commercial
  • Acreage 0.83

This stunning property boasts a perfect blend of modern features and preserved post and beam architecture to maintain its timeless historic charm. Meticulously renovated and used by a master craftsman, it boasts a host of eco-friendly features ranging from solar panels, to offset electricity usage to radiant heating in the ground floor concrete. In addition, the floors have been insulated with hi-r insulation, the 2x6 walls are insulated with r-35, roof with r-49 and the basement exterior walls insulated with open cell spray foam. All insulation was installed on the exterior of the shell to preserve the interior sheathing and look of the original barn.

Listed by Timothy Gallagher of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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690 Main Street Sheffield MA 01257

Sheffield, MA690 Main Street

Price$575,000

Est. Mortgage: $/month

MLS Number 245046

  • Residential
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 3,280
  • Acreage 0.83

Upgrade this property for residential use. This stunning building boasts a perfect blend of modern features and preserved post and beam architecture to maintain its timeless historic charm. Meticulously renovated and used by a master craftsman, it boasts a host of eco-friendly features ranging from owned solar panels, to offset electricity usage to radiant heating in the ground floor concrete. In addition, the floors have been insulated with hi-r insulation, the 2x6 walls are insulated with r-35, roof with r-49 and the basement exterior walls insulated with open cell spray foam. All insulation was installed on the exterior of the shell to preserve the interior sheathing and look of the original barn. Zoning allows residential/live/work by right-zoning should be confirmed by buyer.

Listed by Timothy Gallagher of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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163 Main Street Sheffield MA 01257

Sheffield, MA163 Main Street

Price$529,000

Est. Mortgage: $/month

MLS Number 243856

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,152
  • Acreage 0.25

Built in 1802, this delightful 3-bedroom home is full of original details and charm. The 1st floor features two parlors with a double-sided fireplace, built-in bookcases, and a bay window with window seat perfect for curling up with a good book by the fire. French doors lead to a large open dining room and kitchen with granite countertops and cherry cabinets. Just off the kitchen is a cozy den with more built-ins, a full bath with shower, a rear entry mudroom leading to a paved patio, and a cheerful sunroom overlooking a charming backyard and garage outbuilding. Upstairs is the primary bedroom with its own fireplace, an office alcove with a quaint dutch door to a lovely balcony, two smaller bedrooms, and a full bath with vaulted ceiling. Open house sat 7/13/24 11am-2pm

Listed by Vashti Poor and Lance Vermeulen of LANCE VERMEULEN RE,INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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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127 Old Joe Road Sheffield MA 01257

Sheffield, MA127 Old Joe Road

Price$499,000

Est. Mortgage: $/month

MLS Number 243648

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,152
  • Acreage 2.63

Perfect one level living! Great location, 4 bedrooms & two full baths! This well maintained ranch is a compact and efficient layout. A large sunny living room with corner gas fireplace, and an open kitchen/ dining area that expands out to a private deck for your summer entertaining and relaxing. Ample closets throughout, a mud room entry, attached garage, convenient 1st floor laundry. The basement, currently used as a recreation/tv area, has plenty of room for a home gym, play room, and lots of storage. Beautiful 2.63 acres of sunny level lawn, ideal for gardening, pets and play. Minutes to both sheffield & great barrington town centers for shopping, activities and restaurants. Great country get-away! Well kept and ready to occupy!

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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 February 8, 2025 . 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.