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

Sheffield, MA2080 Undermountain Rd

Price$12,500,000

Est. Mortgage: $/month

MLS Number 229173

  • Residential
  • Bathroom 7
  • Bedrooms 11
  • Square Feet 7,946
  • Acreage 85

The jewel of new england... Offered for the first time in four decades, this 85 acre berkshire mountainside campus awaits your imagination. This property offers an atmosphere for breakout creative expression with great potential for an enterprise for retreats, wellness center, writers/ artists workshops, educational endeavors or your family's private estate. The property consists of 12 buildings; conference halls, dining/ meeting facilities, lodging accommodations, offices and an historic queen anne manor house sitting on a knoll with breathtaking views. 40 years of stewarding this campus where thousands of participants made life long memories, the owners are ready to pass it on. Let their growth be your opportunity. For details & digital brochure please see jewelinnewengland.Com

Listed by Mary Jane White and Nancy K. Kalodner of COHEN & WHITE ASSOCIATES

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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50 East Sheffield MA 01257

Sheffield, MA50 East Rd

Price$1,975,000

Est. Mortgage: $/month

MLS Number 232290

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 4,250
  • Acreage 12.4

Historic expansion - a 12.4 acre estate you can move right in to. Take the new england concept of original house, new house, back house, guest house, pool and barn- this 1780 colonial has grown to reflect the needs of the owner's generational family. New additions include a first floor open flowing gourmet kitchen, living-dining room, master suite, library, bathrooms, screened porch, laundry, new wood floors and windows, new roof, heating system and so much more. Original section has a dining room, front parlor, 3 upstairs bedrooms, 3 fireplaces, 2 bathrooms. The guesthouse has 1 bedroom, 2 baths with its own open living, porch and laundry. A huge 2 story barn with a garage and gym. The heated gunite pool is central to all the structures; pergola, patios and an outdoor shower.

Listed by Deborah Levinson and Barbara Schulman of BERKSHIRE PROPERTY AGENTS, LLC

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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670 Boardman Sheffield MA 01257

Sheffield, MA670 Boardman St

Price$1,650,000

Est. Mortgage: $/month

MLS Number 231987

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 3,576
  • Acreage 5.5

Exquisite country retreat on 5.5 private, manicured acres available for the first time since 1958! Expansive and bright rooms throughout, including 3,576 square feet of living space, 4 bedrooms, and 4 full baths. Oak flooring, maple flooring, wide pine plank flooring, ceramic tile, cedar closet, walk-in closet, central a/c, and a backup generator are just a few of the amenities included in this property. Custom, inground heated pool, pool house, and patio. Gorgeous, 1 br apt with new stainless steel appliances over the oversized, 3-car garage. Beautiful landscaping & incredible perennial flower gardens throughout the property. A 2-story barn with endless possibilities also included in the property. This once-in-a-lifetime property won't come around again soon! 4 minutes south of guido's.

Listed by William Morrow of WHEELER & TAYLOR REALTY CO., INC.

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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927 Boardman Sheffield MA 01230

Sheffield, MA927 Boardman St

Price$1,470,000

Est. Mortgage: $/month

Pending

MLS Number 229501

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,679
  • Acreage 13

This magical property is an ideal blend of country comfort with hip chic style. The ease and elegance were designed for those desiring a casual berkshire lifestyle. The floor plan is perfect for gathering friends & the attention to detail is evident the minute you walk in the door ~ prepare to be wowed! The kitchen is awe inspiring as the focal point of the house and will entice even the most novice of cooks! Cathedral ceiling, exposed preserved beams, pizza oven, & lacanche range are just a few of the highlights. The wall of glass from the living room takes in the view and has a fireplace for cool berkshire evenings. The property and views are breathtaking and the wide open skies showcase the surrounding fields, mountains, pond, and dramatic nightly sunsets.Stunning!

Listed by Lori J Rose of STONE HOUSE PROPERTIES, LLC

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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11 School Sheffield MA 01257

Sheffield, MA11 School St

Price$1,125,000

Est. Mortgage: $/month

Pending

MLS Number 231782

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,184
  • Acreage 22

This very unique property features a home and 5 acre private pond, on 22 acres. Once an active marble quarry, fed by artesian springs, now your own desirable swimming pond, 65 feet deep. The original brick section was once the old quarry engine room. An addition added to accommodate the family is all on one level. Two fireplaces, wood and stone floors, large windows for views of lake from every room. Adjacent to the stone terrace is a small beach and dock.Once you enter through stone pillars you are in a magical tree lined park setting. Paths meander throughout the entire property. This ''mini-estate'' is the perfect place to relax and enjoy your time at home.There is an additional cabin on it own one acre, for the perfect guest house or studio/office included.Look for video

Listed by Anita Schilling of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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1144 Ashley Falls Sheffield MA 01222

Sheffield, MA1144 Ashley Falls Rd

Price$995,000

Est. Mortgage: $/month

MLS Number 232109

  • Residential
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 3,800
  • Acreage 1.56

New construction... 5 bedroom, 4 full bath, 2 half bath, shingle style cape cod home, with attention to detail in the heart of ashley falls village. This sprawling cape, with seasonal mountain views, will feature high efficiency heating & cooling system, french doors, hardwood floors through out, first floor master, second floor master option, 2-car detached garage with option for in-law suite, and much more! Still time to add your personal details and enjoy all that ashley falls has to offer! *to be built similar to images*

Listed by Reciprocal Listing: See Realtor Remarks of NON-MEMBER

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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73 Main St, 89 Sheffield MA 01257
Pending

MLS Number 229088

  • Commercial
  • Acreage 1.9

Great opportunity to own on the village green. Prime sheffield center location. 9 commercial and 5 residential rentals. Attractive brick building with high traffic count.

Listed by Eric Steuernagle of FAIRGROUND REAL ESTATE, INC>

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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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282 Main Sheffield MA 01222

Sheffield, MA282 Main St

Price$900,000

Est. Mortgage: $/month

MLS Number 228925

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 4,472
  • Acreage 1.5

The former maplewood inn, set in the quiet hamlet of ashley falls is an elegant historic house which dates back originally to the 1770s. Spacious, bright open living areas, high ceilings, beautiful floors, staircases, windows, fireplaces and expansive screened porches on the first and second floors are just some of the characteristics that set this property apart from others. The back garden and heated gunite in-ground pool and spa are protected by mature trees and unique outbuildings including two barns, one with a two-car garage, a former barbershop, smoke house, and two-story ice house. The compound offers mature plantings a fruit orchard.. The chef's kitchen has a wolf range and open to the family room. A/c on the second floor, alarm system, and beautiful light throughout the house.

Listed by Timothy Lovett of BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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522 Rote Hill Sheffield MA 01257

Sheffield, MA522 Rote Hill Rd

Price$875,000

Est. Mortgage: $/month

MLS Number 232100

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,534
  • Acreage 1.8

Beautiful ranch-style home minutes from great barrington. Almost two acres at the top of a country road affording complete privacy to enjoy the gorgeous backyard from the large wood deck and screened porch. Relax and entertain around the heated gunite pool, with generous seating areas (perimeter of backyard completely enclosed by wildlife fencing). Enjoy the open floor plan, dining room and kitchen flow into a cozy family room, with large windows and wood burning fireplace. Hallway to three bedrooms, including hall full bath and en-suite master bath. Downstairs, a spacious finished family room with many windows, walk-out sliding door, custom bar, full bath/laundry room, bonus room and storage space.

Listed by Leslie G Chesloff of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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1 Water Farm Sheffield MA 01257

Sheffield, MA1 Water Farm Rd

Price$845,000

Est. Mortgage: $/month

MLS Number 230311

  • Land
  • Acreage 301

The water farm road land consists of 301+/- acres of forest and wetlands with 8,828 feet of road frontage on water farm road and 606 feet of road frontage on soda spring creek road. The property has been the source of public drinking water for the town of sheffield since 1895. The off site drilled deep wells and infrastructure were sold several years ago and the land that remains has two springs, generating 9 to 17 mil gallons a year. There are extensive wetlands on the property with significant uplands associated. These uplands could support 6 to 8 large house lots. The property has been professionally managed by licensed foresters for more than 15 years.

Listed by Keith Ross and Cindy Welch of LANDVEST, INC.

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$
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$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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1210 Sheffield - Egremont Sheffield MA 01257
Pending

MLS Number 231131

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,418
  • Acreage 2.5

Walk in and unpack your bags in this custom built cape in a convenient location just minutes to great barrington. Nestled amongst the trees, this home's landscaping will make you feel like you're living in a private oasis. Inside you will find a thoughtful open floor plan with stunning great room perfect for curling up near the fire. The cook's kitchen features granite countertops and top-of-the-line stainless appliances --perfect for entertaining! Large first-floor master features hickory floors, large bathroom with jacuzzi tub and a ''california'' style walk-in closet. Upstairs are two more spacious bedrooms and a guest bath. Above the oversized garage is a studio apartment that consists of 588 feet of the home's total square footage--perfect for short-term rental or the in-laws!

Listed by Antonio M Segalla and Cara Carroll of LANCE VERMEULEN RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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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264 Brush Hill Sheffield MA 01257

Sheffield, MA264 Brush Hill Rd

Price$749,000

Est. Mortgage: $/month

Pending

MLS Number 224536

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 4,085
  • Acreage 7.35

Tucked away on a quiet dirt road sits this spacious, beautifully maintained 1990s contemporary. Enjoy total privacy and pond frontage only 10 minutes from downtown great barrington, 20 from two major ski areas and 25 from tanglewood. The privacy of this home can be enjoyed from the abundance of outdoor space as well as the inviting three-season screened porch surrounded by amid lush wooded conservation land. Inside you'll find cathedral ceilings, a stunning stone fireplace, cook's kitchen with an abundance of maple cabinetry, formal dining, a cozy den with an additional fireplace and a large master suite. The master suite features cathedral ceilings, his and hers walk-in closets and an oversized bathroom featuring his and hers sinks, tiled shower and a large soak/jet tub.

Listed by Antonio M Segalla and Lance Vermeulen of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.9% last updated on Sep 24, 2020
* 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 28, 2020 . 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.