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: 3.04% last updated on Apr 15, 2021
* 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 233820

  • 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 & bright rooms throughout, including 3,576 sq ft of living space, 4 bedrooms, and 5 full baths. Oak flooring, maple flooring, wide pine plank flooring, ceramic tile, cedar closet, walk-in closet, central a/c, and backup generator are just a few of the amenities included in this property. Custom, in-ground heated pool, pool house, and patio. Gorgeous 1-br guest quarters w/ new stainless steel appliances above oversized, 3-car garage. Beautiful landscaping & incredible perennial flower gardens throughout the property. A 2-story post & beam barn with endless possibilities also included. This once-in-a-lifetime country retreat won't come around again soon! 4 minutes south of guidos.

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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121 Hickey Hill Sheffield MA 01257

Sheffield, MA121 Hickey Hill Rd

Price$1,050,000

Est. Mortgage: $/month

MLS Number 233819

  • Residential
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,753
  • Acreage 2.41

Looking for that little piece of berkshire sky? A quiet place to watch the sunset? Just gaze at the stars as you relax on your back deck. This counrty home is just the place. Situated on a hilltop in sheffield drenched in sunlight. If your looking for quiet, mountain views, privacy, land, move in ready and under a 3 hour drive from the city, you must come and see this house!Four bedrooms and baths. A beautiful stone fireplace that anchors the living room for those chilly winter nights.Formal dining room for the holidays. A wonderful eat in kitchen that opens up to a great four season sun room. Slip outside onto the large deck for entertaining, or just stroll around the lovely perenial gardens. Plenty of room for a pool. 10 miles to great barrington and 20 to tanglewood.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 Sheffield MA 01222

Sheffield, MA42 Valley View Rd

Price$975,000

Est. Mortgage: $/month

Pending

MLS Number 233748

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

Valley view - views to the distant hills and river frontage in a classic new england setting. Simple, tasteful, and just right, this single level country retreat on the outskirts of ashley falls offers comfort and serenity in every season. The home is filled with light and there is nature out every window. You can stroll through your meadows to the banks of the konkapot river, or just relax on the patio and enjoy the sunset. Freshly painted, modern amenities, top of the line appliances and mechanicals. Minutes to the litchfield hills, a short ride north to great barrington and the berkshires. Come see for yourself!

Listed by David W Taylor and Elyse Harney Morris of ELYSE HARNEY REAL ESTATE

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 233713

  • 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 - GT BARRINGTON

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 S. Main Sheffield MA 01257

MLS Number 233150

  • Commercial
  • Acreage 1.33

Currently a well-established business operates in the first floor commercial space with diverse offerings in food and beverage, including a retail beer and wine license. Two large 2 bedroom apartments on the second floor of this mixed-use building provides additional income. A separate accessory residential building adjacent to the large in-ground pool enhances the 1.3 acres. Several additional outbuildings completes the versatility of this unique property. Sale is for the real estate only. The existing commercial business can be made available for sale or lease. Certain capital equipment will be a separate sale. Part of the main structure (circa 1727) was moved from ct to this location. The oldest building in sheffield with four fireplaces and original wide board kings planking

Listed by Thomas K. Doyle, Sr. of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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$785,000

Est. Mortgage: $/month

MLS Number 233351

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 6,094
  • Acreage 1.33

This complex could be returned to single-family residence or multi-generational dwelling complex currently a well-established business operates in the first floor commercial space with diverse offerings in food and beverage, including a retail beer and wine license. Two large 2 bedroom apartments on the second floor of this mixed-use building provides additional income. A separate accessory residential building adjacent to the large in-ground pool enhances the 1.3 acres. Several additional outbuildings completes the versatility of this unique property. Sale is for the real estate only. The existing commercial business can be made available for sale or lease. Certain capital equipment will be a separate sale. Part of the main structure (circa 1727) was moved from ct to this location.

Listed by Thomas K. Doyle, Sr. of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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$785,000

Est. Mortgage: $/month

MLS Number 233151

  • MultiFamily
  • Acreage 1.33
  • Year Built 1972

Currently a well-established business operates in the first floor commercial space with diverse offerings in food and beverage, including a retail beer and wine license. Two large 2 bedroom apartments on the second floor of this mixed-use building provides additional income. A separate accessory residential building adjacent to the large in-ground pool enhances the 1.3 acres. Several additional outbuildings completes the versatility of this unique property. Sale is for the real estate only. The existing commercial business can be made available for sale or lease. Certain capital equipment will be a separate sale. Part of the main structure (circa 1727) was moved from ct to this location. The oldest building in sheffield with four fireplaces and original wide board kings planking.

Listed by Thomas K. Doyle, Sr. of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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704 Hewins Sheffield MA 01257

Sheffield, MA704 Hewins St

Price$775,000

Est. Mortgage: $/month

MLS Number 233565

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,152
  • Acreage 2.73

Beautiful contemporary farmhouse with gorgeous pasture and river views, nestled on hewins street, known for its amazing distant, scenic mountain vistas. Open first floor plan complete with farmer's porch and new deck. Large master suite, 2 car garage, newly finished walkout lower level and back up generator are just a few of the amenities.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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$695,000

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 Sheffield MA 01257

Sheffield, MA594 Shunpike Rd

Price$675,000

Est. Mortgage: $/month

MLS Number 233608

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,980
  • Acreage 2.32

In a beautiful clearing in the woods, off a quiet country road, this house offers comfort and privacy. Step in to bright inviting foyer. Living and dining rooms have sliding glass doors to large outdoor deck spaces, both covered and open. Kitchen features butternut cabinets and adjacent office/pantry. Upstairs, there are two completely separate bedroom suites--one with dressing room and shiplap ceilings, one with cathedral ceilings. A third bedroom suite is in the walk-out lower level. You'll enjoy plenty of peace and quiet at this lovely hideaway.

Listed by Claire Naylor Pollart of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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$649,000

Est. Mortgage: $/month

MLS Number 233926

  • Land
  • Acreage 3.32

Partly wooded and partly in pasture, these three lots enjoy southwesterly vistas towards rannapo rd. Great opportunity for a family compound in a quiet setting yet still in a central location. Enjoy the sheffield land trust, and bartholomew's cobble close by. 4 miles south of main st, sheffield.

Listed by Vashti Poor of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 April 22, 2021 . 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.