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: 6.94% last updated on Feb 29, 2024
* 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: 6.94% last updated on Feb 29, 2024
* 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 of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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: 6.94% last updated on Feb 29, 2024
* 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: 6.94% last updated on Feb 29, 2024
* 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

Sheffield, MA296 South Main Street

Price$1,375,000

Est. Mortgage: $/month

MLS Number 242390

  • Residential
  • Bathroom 2
  • Bedrooms 1
  • Square Feet 5,045
  • Acreage 8.18

Welcome to this winery and tasting room located in the beautiful southern berkshires! This business/farm is located right on rt 7 which is considered the ultimate new england road trip. Capture tourists year round with nearby tanglewood, the botanical gardens, butternut ski resort and so much more! This spacious post and beam building consists mainly of two large rooms both with lofts. One, currently a tasting room with a wrap around loft, floor to ceiling windows for abundant light, a dramatic center staircase and french doors leading to the patio and outdoor space. The second room is currently an event center with loft. The tiled lobby has access to storage and a handicapped bathroom. The opportunity exists to live on site with the attached apartment; kitchen, full bath, small

Listed by Grace Golden of EQUINE HOMES REAL ESTATE,LLC ((800) 859-2745)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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 242394

  • Commercial
  • Acreage 8.18

Welcome to this winery and tasting room located in the beautiful southern berkshires! This business/farm is located right on rt 7 which is considered the ultimate new england road trip. Capture tourists year round with nearby tanglewood, the botanical gardens, butternut ski resort and so much more! This spacious post and beam building consists mainly of two large rooms both with lofts. One, currently a tasting room with a wrap around loft, floor to ceiling windows for abundant light, a dramatic center staircase and french doors leading to the patio and outdoor space. The second room is currently an event center with loft. The tiled lobby has access to storage and a handicapped bathroom. The opportunity exists to live on site with the attached apartment; kitchen, full bath, small

Listed by Grace Golden of EQUINE HOMES REAL ESTATE,LLC ((800) 859-2745)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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

194 East Main Street Sheffield MA 01222

Sheffield, MA194 East Main Street

Price$945,000

Est. Mortgage: $/month

MLS Number 241957

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,200
  • Acreage 1.5

Set on a large 1.5 acre corner lot in the village of ashley falls, this c. 1900 quintessential new england farmhouse has it all - antique charm, modern comfort, and energy efficiency. This 4-bedroom, 3-bath home enjoys all the classic details you'd expect of the vernacular along with so many upgrades, including a whitewashed front porch, exposed beams, bay window, wood burning fireplace, open kitchen/ dining with vaulted ceiling, and engineered oak flooring. This house has been completely rebuilt with new roof, new framing, wiring, and plumbing, new poured concrete basement, new windows, engineered wood siding, new solid closed cell spray foam insulation, new bathrooms and kitchen, high-efficiency heating and cooling and all new mechanicals. See ''more''.

Listed by Vashti Poor of LANCE VERMEULEN RE,INC ((413) 528-6011)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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616 Sheffield Plain Road Sheffield MA 01257

MLS Number 242549

  • Residential
  • Bathroom 5
  • Bedrooms 8
  • Square Feet 6,105
  • Acreage 4.4

This pre revolutionary war home is one of the oldest estates in sheffield (1774) it has been expanded over the years to 6000 sqft. There is also a very charming carriage house on the property as well. This magical property has tons of potential. Zoned mixed use, this home consists of 6 bedrooms, 8 fireplaces with 20 rooms. The lower level was recently opened up to expose the brickwork and post & beam framing. Whether it continues as a single-family home or a business will be the decision of the next owners. The house sits far back from the road on 4.4 acres. It is perched above the housatonic river with gorgeous stone walls, terraced gardens and frontage on the river. A charming, covered bridge sits practically in the corner of the property. A boat launch is just behind the house as well.

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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616 Sheffield Plain Road Sheffield MA 01257

MLS Number 242550

  • Commercial
  • Acreage 4.4
  • Parking Spaces 6

Great mixed use business opportunity with just under 300 feet of frontage on route 7. Grand old estate with tons of potential. Possibilities are endless. Restaurant, event space, nursery, antique center. Currently 8 bedrooms, 5.5 baths, 8 firepaces. On the river!You will find a winery, distillary, brewery, dispencery, 2 restaurants and a convenient store all within a few minutes walk. Imagine a campground with rooms to rent, boats on the river!! Beautiful gardnes and stonwalls throughout. Its a stunning property with a coverd bridge and the ufo park (the first off-world ufo case in us history) right in your backyard!

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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 241025

  • Commercial
  • Acreage 0.83

Astonishing and unique berkshire commercial spaceimagine a 21st century building within an 18th century post & beam barn, embodying the very best of what's old and what's new... Built by a master craftsman to his exacting standards for his own workshop, this extraordinary building could host a myriad of potential uses, such as:retail - market - business or professional offices - gallery - restaurant - cafe - service establishment - light manufacturingimprovements include (not limited to) new in the last 10 yrs: interior framing, insulation, plumbing, electrical, boiler, radiant heat, flooring, sheetrock, trim, windows, siding, roof, solar, tile, millwork, masonry, cabinetry & more. This amazing building is in a prime sheffield rt 7 location, and at an affordable price

Listed by Jared Kelly and Chapin Fish of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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1609 County Road Sheffield MA 01257

Sheffield, MA1609 County Road

Price$605,000

Est. Mortgage: $/month

Pending

MLS Number 242228

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,792
  • Acreage 5.07

Set on 5-acres on a quiet road in sheffield, you'll find a great opportunity in the clean lines of this split-level ranch with pool. The open and cleared yard with gorgeous views is adjacent to 170-acres of preserved land encompassing 3-mile pond. All less than 15 minutes from great barrington. On the main floor there is a light and open kitchen offering access to the deck and pool area. The living room with windows facing both south and north as well as 3 bedrooms and a shared full bath comprise the 2nd floor. The primary bedroom featuring locally hewn wide-plank floors offers privacy, an en-suite bathroom and walk-in-closet.Offered as-is. Fantastic view and location, updates needed.

Listed by Selina Lamb of BIRCH PROPERTIES ((415) 515-3750)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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 March 4, 2024 . 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.