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!

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264 Brush Hill Rd Sheffield MA 01257

Price$795,000

Est. Mortgage: $/month

MLS Number 224536

  • Single Family
  • Village Berkshire - South
  • Year Built 1992
  • Parking Spaces 2
  • Bedrooms 3

Tucked away on a quiet dirt road sits this beautifully maintained 90's contemporary home. Enjoy total privacy and frontage on Three Mile Pond while being a short 10-minute drive to Guido's and downtown Great Barrington. The privacy of this home can be enjoyed from the abundance of outdoor space as well as the large three-season screened porch. 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 LANCE VERMEULEN RE, INC

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$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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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394 Berkshire School Rd Sheffield MA 01257

MLS Number 225871

  • Single Family
  • Village Berkshire - South
  • Year Built 1975
  • Parking Spaces 2
  • Bedrooms 6

Terrific Berkshire Compound, ready to sell, with main house, 2nd floor garage apartment (full bath & kitchenette) guest cabin (full bath + kitchenette) In a 25 acre park-like setting! The acreage includes a spring-fed pond, direct access to Schnenob Brook, beautiful established perennial beds, & walking trails! The original 1975 home was completely rebuilt around the original brick fireplace which is so cozy... and really brings in those great Berkshire vibes! Main house has 4 BRs & 2 full baths + the cabin & apt. makes for a total of 6 bedroom/4 baths. Oak flooring throughout, screened porch PLUS long south-facing porch overlooks the pond & brook with pretty views. Walkout basement and super private, this long driveway is well maintained, inclds additional building lot - see supplement.

Listed by LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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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703 North Main St Sheffield MA 01257

MLS Number 222988

  • Commercial
  • Village Berkshire - South
  • Year Built 1970
  • Square Feet 8,336
  • Bedrooms 4

Great investment opportunity. This property consists of three commercial spaces, a one-bedroom apartment, and a three-bedroom house. Only one commercial space is vacant.

Listed by Lance Vermeulen of LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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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18 Bow Wow Rd Sheffield MA 01257

Price$564,000

Est. Mortgage: $/month

MLS Number 225091

  • Single Family
  • Village Berkshire - South
  • Year Built 1935
  • Parking Spaces 1
  • Bedrooms 3

WATERFRONT - what a wonderful life!Enjoy the magnificent views from this home right on the edge of Mill Pond . Ideal for kayaking, fishing, swimming, wildlife galore!Organic gardens meticulously maintained by current owner. Master Bedroom and Bath on first floor, large eat-in kitchen with lovely cabinets, access to large Porch overlooking the water. Really SPECIAL! MUST BE SEEN!

Listed by SANDRA M. PRESTON REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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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954 Boardman St Sheffield MA 01257

Price$550,000

Est. Mortgage: $/month

MLS Number 220078

  • Single Family
  • Village Berkshire - South
  • Year Built 1907
  • Bedrooms 4
  • Bathroom 2

This 4BR antique farmhouse sits on 2 beautifully landscaped acres surrounded by mountain and pastoral views. Just five minutes from Great Barrington, this meticulously renovated 1907 home is tucked away on a quiet country road in an area of farms and fine homes. Open kitchen/dining, enormous sunporch, large living room with woodburning fireplace, family room, and multiple decks and patios to enjoy the magical views!

Listed by LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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-A Shunpike Rd Sheffield MA 01257

Price$499,000

Est. Mortgage: $/month

MLS Number 221917

  • Land
  • High School Mount Everett
  • Village Berkshire - South
  • Square Feet 870,329

Looking for that perfect hilltop setting to build your dream house? Situated on 26.38 private acres with a plateau at 1,100'. Distant views above the Sheffield Valley as the sunset unfolds over the Taconic Range. A beautiful unspoiled lot surrounded by mature hardwoods, stonewalls, a small pond and you. One building site is permitted on this land. You may judiciously clear trees for views of your choice. A gravel driveway is in place to reach the plateau where you would build. Land is surrounded by 3 large estate parcels and 150 acres of conservation.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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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130 Park Ln Sheffield MA 01257

Price$499,000

Est. Mortgage: $/month

MLS Number 224962

  • Single Family
  • Village Berkshire - South
  • Year Built 1972
  • Parking Spaces 2
  • Bedrooms 4

PERFECT SKI HOUSE FOR FRIENDS AND FAMLY. INCLUDES A SEPARATE ONE BEDROOM APARTMENT.Owners relocating. This home is ready for you to enjoy. Comfortable single level living with guest apartment. Country living in town surrounded by lawn and trees. Stone terrace with retractable awning. 3 bright spacious bedrooms, 2 full baths, cozy library, open living room with wood burning fireplace, dining room overlooking park like lawn, mature trees. Kitchen with granite counters. Delightful sun filled 4 season room. Enter guest apartment thru separate glass atrium. Unit has large living room, kitchen, dining area, bedroom, private bath with walk in shower and separate sauna, Genarac generator. Two car garage.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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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7 Plymouth Ln Sheffield MA 01257

Price$499,000

Est. Mortgage: $/month

MLS Number 225425

  • Single Family
  • Village Berkshire - South
  • Year Built 1941
  • Parking Spaces 1
  • Bedrooms 3

Curb appeal is just the beginning! A classic picket fence and country vibe are the first clues that this bright and beautiful, renovated Gilligan-built Colonial, within walking distance to Sheffield village, will not disappoint. This wonderful home features three bedrooms and two full baths, a living room with fireplace and wood-paneled overmantel, dining room, three season porch and cook's kitchen. Outside, a separate studio building with heat and air conditioning, and a terrific glass ''barn'' enclosing a hot tub and cocoon fireplace, increase the wow factor. Don't miss out on this one.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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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1434 Main St Sheffield MA 01257

Price$475,000

Est. Mortgage: $/month

MLS Number 225651

  • Multi-Family
  • Village Berkshire - South
  • Acreage 8.6
  • Bedrooms 4
  • Square Feet 3,252

GREAT OPPORTUNITY IN A CONVENIENT LOCATION! Two separate buildings each with 3 potential rental income apartments; Main building can stay as is or be converted back into a single family; live in one, rent the others; solid rental history.

Listed by COHEN & WHITE ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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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1592 Salisbury Rd Sheffield MA 01257

Price$425,000

Est. Mortgage: $/month

MLS Number 225097

  • Single Family
  • Village Berkshire - South
  • Year Built 1998
  • Parking Spaces 3
  • Bedrooms 4

New listing with lots of living space. First floor has a great flow with a 1st floor master bedroom bath. Open kitchen den dining room and living room to enjoy. Screened porch with decks to enjoy the outdoors. There are 3 exceptionally large bedrooms and full bath on second floor. Across the street from some of the best hiking on the Appalachian Trail. Oversize 3 car garage. Come enjoy the piece and quiet. Great completely dry basement

Listed by Suzann Ward of BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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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29 Richard Dr Sheffield MA 01257

Price$425,000

Est. Mortgage: $/month

MLS Number 225738

  • Single Family
  • Village Berkshire - South
  • Year Built 1989
  • Parking Spaces 3
  • Bedrooms 4

Looking for a piece of paradise? Tranquil, private 2.27 acres with a well maintained country contemporary! Separate in-law suite with fireplace and separate entrance! Oversized 3-car garage can convert to an artist studio or wood shop. Electric installed. The expansive rear deck is accessed from the dining room or kitchen. Great for entertaining or your private oasis in nature! Master bedroom has jet tub, walk-in closet and maple flooring. Living room with new carpet, fireplace, vaulted ceiling with skylights! Cook's kitchen with wood cabinets and counter seating. Delight inside and out. Meticulously maintained, parklike setting with no through traffic! What more can you ask for? Serenity is yours. Come and see!!

Listed by MCFARLAND REALTY CO.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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 A VisitAsk A QuestionMore Details

1161 Home Rd Sheffield MA 01257

Price$425,000

Est. Mortgage: $/month

MLS Number 225115

  • Single Family
  • Village Berkshire - South
  • Year Built 2002
  • Bedrooms 4
  • Bathroom 3

Great family house. Close to all Gt. Barrington amenities, theatre, reataurants, Guido's, etc. Nice spot for gardening, horses (horse barn fencing installed)Easy to Show

Listed by Sandra Preston of SANDRA M. PRESTON REAL ESTATE

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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 A VisitAsk A QuestionMore Details