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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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

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Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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1070 Ashley Falls Rd Sheffield MA 01257

Price$695,000

Est. Mortgage: $/month

Pending

MLS Number 226420

  • Single Family
  • Village Berkshire - South
  • Year Built 1887
  • Parking Spaces 2
  • Bedrooms 4

Listed by BERKSHIRE PROPERTY AGENTS, LLC

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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Sheffield MA 01257

Price$679,000

Est. Mortgage: $/month

MLS Number 226176

  • Single Family
  • Year Built 1975
  • Bedrooms 2
  • Bathroom 2
  • Total Full Baths 2

An utterly charming small contemporary lake place. Sited on a peninsula at the end of a private drive through mature two acre woods. About 900 feet of waterfront on three sides, a private little dock, ''away from it all'', tranquility without isolation. The interior is bright and airy, with cathedral ceilings, open living plan, hardwood floors and lots of windows looking onto lake and deck.

Listed by FRIDAY & CO. REAL ESTATE

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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 RE, INC

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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674 Foley Rd Sheffield MA 01257

Price$595,000

Est. Mortgage: $/month

MLS Number 226593

  • Single Family
  • Village Berkshire - South
  • Year Built 1992
  • Bedrooms 3
  • Bathroom 3

This is a ''feel good'' property. The great light, the layout, the beautiful grounds, the detached studio--it just works. Bright, airy living room with stone fireplace and French doors to stone patio. Sunny kitchen, informal dining/family room, lovely bedroom, full bath, and three-season porch complete the first floor. Upstairs is a splendid master suite with cathedral ceilings and the perfect spa bathroom with soaking tub, plus a guest suite, laundry, and a wonderful deck overlooking your very private paradise. One-car garage under. Stunning gardens and landscaping, and terrific detached studio w/ propane fireplace. This is a gem--and you can be in by summer!

Listed by LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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 226214

  • Single Family
  • Village Berkshire - South
  • Year Built 1935
  • Bedrooms 3
  • Bathroom 3

Listed by SANDRA M. PRESTON REAL ESTATE

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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$529,000

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. Now listed 100k below its bank appraised value!

Listed by LANCE VERMEULEN RE, INC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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 3

GET READY TO ENJOY THE SUMMER. LARGE STONE TERRACE AND LAWN.Owners relocating. This home is ready for you to move in . 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. Guest unit has large living room, kitchen, dining area, bedroom, private bath with walk in shower and Swedish sauna, Generac generator. Two car garage.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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: 4.17% last updated on Apr 18, 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: 4.17% last updated on Apr 18, 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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1189 Ashley Falls Rd Sheffield MA 01257

Price$489,000

Est. Mortgage: $/month

MLS Number 226237

  • Single Family
  • Village Berkshire - South
  • Year Built 1740
  • Bedrooms 3
  • Bathroom 3

The Mary Ballantyne Ashley House is one of the oldest residences in the Berkshires. Built in 1740 by Colonel John Ashley for his family, this saltbox has been lovingly restored over the last 50 years. A cozy colonial with 1st Floor Master + 2 additional Bedrooms. It has a slate roof, up-graded heating, A/C, and electrical in addition to many other amenities. The house is over 2400 square feet. A restored barn serves as a private guesthouse with bath and kitchen, approximately 1000 square feet. The house features a private Patio garden with Hot Tub. Situated across from the Post Office and Village green, minutes from Sheffield, Great Barrington and the CT & NY State Border. The property is zoned C-commercial. A must see for Antique House lovers !!**Includes Leased Apt at $ 10,500/yr

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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 8
  • 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: 4.17% last updated on Apr 18, 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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