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$11,890,000

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: 3.05% last updated on Oct 14, 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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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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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535 Sheffield-Egremont Sheffield MA 01257

Sheffield, MA535 Sheffield-Egremont Rd

Price$3,995,000

Est. Mortgage: $/month

MLS Number 235743

  • Residential
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 6,746
  • Acreage 55.3

Sunset mountain views, privacy & wonderful amenities in your own private home resort.......Architect designed 5 br, 6 bath contemporary with spacious open common living, stunning main level primary bedroom en suite, office w/built-ins, guest rooms & baths for all, media room w/separate game room, classic adirondack guest/pool house, in-ground heated pool, turf sports tennis/basketball/lacrosse complex, incredible gardens with mature landscaping and extensive stone work, hiking trails on 55+ acres with river frontage for kayaking and fishing.....And should you ever want to leave this magical property, it is located within minutes of fine and casual dining, skiing, zip lining, boutique shopping and a short driveto the movie theatre and berkshire cultural venues .....Perfect in every way!!!

Listed by Mary Jane White and Cortney K Dupont of COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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599 Cooper Hill Sheffield MA 01257

Sheffield, MA599 Cooper Hill Rd

Price$2,500,000

Est. Mortgage: $/month

MLS Number 235590

  • Residential
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 3,364
  • Acreage 20.04

Location and views are what this listing is all about. Perched on top of cooper hill these 20 acres offer unobstructed views in all directions. It is possible to see both magnificent sunrises and sunsets. The listing is comprised of 5 lots that must be sold together. There are two existing houses either of which could become part of an estate. The is ample room for a large main residence facing east overlooking protected land.

Listed by John Harney of WILLIAM PITT SOTHEBY'S - SALISBURY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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481 Shunpike Sheffield MA 01257

Sheffield, MA481 Shunpike Rd

Price$995,000

Est. Mortgage: $/month

MLS Number 234104

  • Residential
  • Bathroom 2
  • Bedrooms 1
  • Square Feet 1,296
  • Acreage 15

Passive solar home with views to south and west. Separate summer cottage or office space with screened porch and deck w/views facing west. Includes a 2 story barn/studio space 36'x28' 3 over head doors, concrete floors used as sculpture studio. 2nd floor with two finished rooms with hardwood floors to private deck to capture views. Buildings finished with red cedar vertical siding. Adjoining additional 26 acre building lot available surrounded by conservation land and large private parcels.

Listed by Suzann Laverack Ward of HOUSATONIC REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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 a single-family residence or a family compound. Currently a well-established business (with wet use facilities) operates in the first floor commercial space with diverse offerings in food and beverage, including a retail beer and wine license (requires separate application). 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. The existing commercial tenant is willing to remain or vacate. 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: 3.05% last updated on Oct 14, 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. The existing commercial tenant is willing to remain or vacate. 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: 3.05% last updated on Oct 14, 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. The existing commercial tenant is willing to remain or vacate. 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: 3.05% last updated on Oct 14, 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

35 School Sheffield MA 01222

Sheffield, MA35 School St

Price$699,000

Est. Mortgage: $/month

MLS Number 235367

  • Residential
  • Bathroom 2
  • Bedrooms 5
  • Square Feet 3,060
  • Acreage 1.5

Built in 1880 this delightful home on the outskirts of the quaint village of ashley falls, offers comfortable country living. High ceilings, beautiful wood floors, and decorative moldings throughout.5 bedrooms, 2 full baths,a large country kitchen with pantry, formal dining room and a spacious front parlor. The screened porch is the perfect place to entertain, dine & just plain relax. On 1.5 acres of open level lawn perfect for play, pets & gardens. Close proximity to egremont, great barrington, waldorf school & many area attractions.

Listed by Helen Mullany of HELEN MULLANY REAL ESTATE,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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991 Home Sheffield MA 01257

Sheffield, MA991 Home Rd

Price$695,000

Est. Mortgage: $/month

Pending

MLS Number 234367

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,010
  • Acreage 74.55

Sweet antique farmhouse with far reaching expansive views and over 70 acres of recreational land. Property is in the 61a and has low taxes! Only 5 miles to downtown great barrington. Separate studio space for office or home gym. Pool is open and ready for your summer enjoyment.

Listed by Nikki Carchedi and Allison Rada of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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23 Elm Sheffield MA 01257

Sheffield, MA23 Elm Ct

Price$695,000

Est. Mortgage: $/month

MLS Number 235360

  • Residential
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 2,400
  • Acreage 0.51

Stunning turnkey contemporary - centrally located, yet tucked away!Steps from some of south county's favorite eating spots, yet off the main road and privately situated, this 2 bed, 2.5 bath home is the perfect getaway for those seeking modern, well-appointed living in a convenient location. What began as a 1923 cottage has been meticulously rebuilt, expanded, and reimagined by its design-build owners. Amenities and little luxuries abound - large outdoor patio + fire pit, screened-in porch + gas fireplace, gourmet kitchen with oversized island, primary en suite with private screened porch, radiant heat in living areas and bathrooms. Premium finishes include heated shower floors, quartz and granite counters, high-end appliances, and a viessmann boiler. Well built and beautifully designed.

Listed by Jared Kelly and L. Chapin Fish of BROCKMAN REAL ESTATE,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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246 County Sheffield MA 01257

Sheffield, MA246 County Rd

Price$695,000

Est. Mortgage: $/month

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. Closing after november 1, 2021. Masks required.

Listed by Sheila Thunfors and Allison Rada of STONE HOUSE PROPERTIES,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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 October 17, 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.