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
Pending

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: 6.95% last updated on Jun 13, 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
Pending

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: 6.95% last updated on Jun 13, 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: 6.95% last updated on Jun 13, 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: 6.95% last updated on Jun 13, 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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403 South Undermountain Road Sheffield MA 01257

MLS Number 243261

  • Residential
  • Bathroom 5
  • Bedrooms 3
  • Square Feet 3,000
  • Acreage 12.29

Undermountain house. Nestled beneath majestic views of mt. Everett, this stunning modern barn-style home floats above the landscape. A boulder strewn rain garden creates a covered bridge effect. Clad in ebony stained cypress and stone with a standing seam metal roof, this award winning house has wonderful privacy with views of a wildlife pond and a fruit orchard. The house has an open living/dining area with a wood-burning fireplace adjacent to a three season porch with its own wood-burning fireplace. The architects designed a pierced wood screen to separate the dining area from an intimate banquette in the kitchen, and to create the most marvelous lighting effect at night. An office, powder room, and a primary suite complete the first floor.

Listed by Tom Lynch of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 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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1669 Silver Street Sheffield MA 01257

Sheffield, MA1669 Silver Street

Price$1,825,000

Est. Mortgage: $/month

MLS Number 242950

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

Classic american farmhouse with epic views - 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.

Listed by William Melnick and Elyse Harney Morris of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 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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199 Hickey Hill Road Sheffield MA 01257

Sheffield, MA199 Hickey Hill Road

Price$1,650,000

Est. Mortgage: $/month

Pending

MLS Number 242708

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 3,500
  • Acreage 4.97

At the end of a long tree lined driveway, you'll find a fabulous 4 bedroom, 5 bath dutch gambrel with detached garage only minutes to great barrington. This spacious home is set on almost 5 sunny acres, which include a possible abutting building lot. This place has it all - great entertaining spaces, perfect cook's kitchen, fireplaces and private and peaceful outdoor gardens, along with a lovely screened-in porch to take in the gorgeous landscaping. Home built in 1989 with 2004 and 2019 renovations. A luscious hi-beamed master suite is on the first floor. Meticulously maintained so you can move right in!

Listed by Claire Naylor Pollart and Lance Vermeulen of LANCE VERMEULEN RE,INC ((413) 528-6011)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 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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452 Shunpike Road Sheffield MA 01257

Sheffield, MA452 Shunpike Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 243453

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2,800
  • Acreage 15

This timeless and well-loved residence offers 3 spacious bedrooms and 3.5 luxurious bathrooms, all set against the backdrop of breathtaking views and spectacular sunsets. The beautifully landscaped property features a large variety of flora and charming stone walls and details, creating an inviting and serene atmosphere. Step inside the main living area, where you'll find a convenient mudroom with a half bath. The open-concept kitchen, dining, and living room boast a big glass wall that floods the space with natural light, complemented by the warmth of a wood stove. The den, with its elegant french doors, opens onto a large deck and a screened porch, perfect for entertaining or enjoying quiet moments outdoors.Upstairs, the main bedroom is a true retreat with big views, featuring..

Listed by Christian G Deckert of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 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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42 Valley View Road Sheffield MA 01222

Sheffield, MA42 Valley View Road

Price$1,300,000

Est. Mortgage: $/month

MLS Number 243218

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,644
  • Acreage 8.34

An idyllic setting on 8.34 acres w/panoramic views of lush meadows and protected land. With frontage on the konkapot river, this is a serene retreat just 15 min from great barrington and the rolling hills of litchfield county. The one level home has a thoughtful layout with a dedicated primary wing and 2 guest bedrooms conveniently located on the opposite side of the house. The heart of the home is the impressive great room, complete with radiant-heated floors, vaulted ceilings and a jaw-dropping stone fireplace. Large windows and doors, newly installed, frame the heavenly surroundings from every room including the open, bright kitchen w/soapstone countertops. Practicality meets style in the contemporary 2-car garage. Improvements include a newer septic system, roof and propane generator.

Listed by Kate Lascar of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 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

49 Bow Wow Road Sheffield MA 01257

Sheffield, MA49 Bow Wow Road

Price$1,200,000

Est. Mortgage: $/month

MLS Number 243190

  • Residential
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,929
  • Acreage 31

49 bow wow - a gilligan brothers masterpiece on 30+ acres!Set on over 30 acres of stunning meadows, mountain, pond access, and forest, the gilligan family home at 49 bow wow rd comes to the market for the first time.In the second half of the 20th century, the gilligan brothers name was synonymous in southern berkshire county with a quality built home. Founded by three brothers - matthew, william, and earl - in the 1940s, gilligan brothers homes were often a showcase for the ingenuity and craftsmanship of their founders. And perhaps no home better illustrates their innovative streak than matthew's family home at 49 bow wow road. Built in 1941 for his family - and retained by them to this day - 49 bow wow was stylistically and functionally ahead of its time.

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: 6.95% last updated on Jun 13, 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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567 South Main Street Sheffield MA 01257

Sheffield, MA567 South Main Street

Price$1,195,000

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: 6.95% last updated on Jun 13, 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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594 Shunpike Road Sheffield MA 01257

Sheffield, MA594 Shunpike Road

Price$1,175,000

Est. Mortgage: $/month

MLS Number 243597

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

Experience the serenity of 594 shunpike rd. This cozy 2600 sq. Ft. Gambrel-style home, set on 2.32 acres, has been meticulously & extensively renovated for modern living. Enter through a bright, open foyer & enjoy central air/heat, a full house generator, & new wood flooring. The home features all new kitchen, bathrooms, gas fire place, plumbing, electric, windows & more. The newly finished lower level w/ walkout offers additional living space. Relax on the spacious deck, surrounded by a beautiful clearing in the woods. The primary suite w/ a spa-like bathroom & walk-in closet. This property is ideal for year-round living, vacation home, or potential rental income. Located on a quiet country road, minutes from town, enjoy location for recreation & cultural attractions.

Listed by Claire Naylor Pollart of LANCE VERMEULEN RE,INC ((413) 528-6011)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 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 June 19, 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.