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

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

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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.

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2080 Undermountain Sheffield MA 01257

Sheffield, MA2080 Undermountain Rd

Price$9,600,000

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: 6.29% last updated on Sep 22, 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.

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554 Sheffield Egremont Sheffield MA 01257

Sheffield, MA554 Sheffield Egremont Rd

Price$1,850,000

Est. Mortgage: $/month

MLS Number 238763

  • Residential
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 5,000
  • Acreage 4.33

Artist? Craftsperson? Race car builder? This custom built country home is for you. Magnificent open plan living in glass, wood, stone and metal. Open plan living-room and dining-room with fireplace. Primary suite on main floor. Gourmet kitchen, 4 additional bedrooms. Billiard room, media room and glorious mountain views. ***bonus: huge workshop studio with full bath. Use it as is, or convert it to an ada accessible 'in-law' apartment or professional office.This unique property is minutes from all berkshire and litchfield county shopping & attractions. A one-of-a-kind home (watch the video!)

Listed by Steven J. Weisz of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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.

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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

Life estate for seller. 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own home with use of 36x52 work shop and out building while present owner in her 80's retains use of existing house during her life time. Some adjustment in price would be offered to reflect the life estate. 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

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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.

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48 Main Sheffield MA 01257

MLS Number 238834

  • Commercial
  • Acreage 2

This is an outstanding bed & breakfast, recently renovated top to bottom and in immaculate condition. There are 6 guest rooms, each with private bath, mini-split a/c, and flat screen tv. In addition, there is an owner/host suite with sitting room, bedroom, and private bath. The renovations include a large gourmet kitchen with 2 ovens, new electric, new plumbing, new central heat & air, ev charger and new septic. Much of the original detailing was lovingly preserved, including a classic spindled staircase railing and the distinctive floor to ceiling windows. The large yard has beautiful plantings, and there is ample off-street parking space. Excellent high visibility location, close to ski areas, hiking trails, berkshire cultural venues, and multiple famous secondary boarding schools.

Listed by Brian Farrell of STONE HOUSE PROPERTIES,LLC

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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.

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48 Main Sheffield MA 01257

Sheffield, MA48 Main St

Price$895,000

Est. Mortgage: $/month

MLS Number 238829

  • Residential
  • Bathroom 8
  • Bedrooms 7
  • Square Feet 3,983
  • Acreage 2

This striking home, currently a bed & breakfast convertible into a private residence, recently underwent a thorough upscale renovation. Highlights include an extraordinary gourmet kitchen, new ensuite bathrooms & mini-split a/c units in 6 bedrooms, new electric, plumbing, central heat/air, ev charger & septic. In addition, a primary suite consists of a sitting room, bedroom and another ensuite bath. Much of the original detailing was lovingly preserved, including a classic spindled staircase railing and the distinctive floor to ceiling windows. The expansive yard has lovely plantings, gazebo, and large barn, ripe for repurposing. What a perfect home for large holiday gatherings of family & friends in a quintessential new england village, and the best part is all the work has been done!

Listed by Brian Farrell of STONE HOUSE PROPERTIES,LLC

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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.

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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

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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.

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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: 6.29% last updated on Sep 22, 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.

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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: 6.29% last updated on Sep 22, 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.

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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

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$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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.

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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

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$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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.

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371 Berkshire School Sheffield MA 01257

MLS Number 238256

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,585
  • Acreage 2.96

Behind this traditional facade lies a flexible floor plan offering loads of space for family, guests, work and entertaining. Sited on 2.96 acres, there is plenty of yard & sun for gardens, play & pets. Eat-in kitchen with vaulted ceiling opens to decks accessing backyard. Lovely 1st floor primary suite with huge closet and deluxe full bath. Formal lr and dining room, both with fireplaces. A cozy office/den and 1/2 bath complete the first floor. Two large bedrooms & a full bath upstairs.There is an attached garage. A move-in ready gem, near hiking, biking, skiing, berkshire school, and minutes to village center, connecticut, and great barrington.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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.

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Based on information submitted to BCMLS  as of September 25, 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.