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!

135 Fiddlehead Trail Sheffield MA 01257

Price$2,150,000

Est. Mortgage: $/month

MLS Number 225467

  • Single Family
  • Address 135 Fiddlehead Trail
  • Village Berkshire - South
  • Year Built 2015
  • Parking Spaces 2

NEWLY CONSTRUCTED POST & BEAM WATERFRONT PARADISE ON 168-ACRE LAKE WITHIN A 1,000 ACRE PROTECTED WILDLIFE AREA. Striking views & fabulous amenities includinga soaring great room, 5+ bedrooms, heated swimming pool, outdoor hot tub, movie theater, bar, game room & gym, radiant heat, central a/c, solar panels and much, much more - all on a true treasure of a lake that is virtually unknown. Astonishing privacy and wildlife - you will most often be the only one fishing or kayaking on the lake, watching the Great Blue Heron, or relaxing with no jet skis or power boats to disturb you - yet you're just 12 minutes to Guido's in Great Barrington. Control all systems remotely. Painstakingly built for optimal casual comfort, low maintenance, and as your own private waterfront Berkshire resort.

Listed by BROCKMAN REAL ESTATE, LLC

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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927 Boardman St Sheffield MA 01230

Price$1,760,000

Est. Mortgage: $/month

MLS Number 226393

  • Single Family
  • Address 927 Boardman St
  • Village Berkshire - South
  • Year Built 1960
  • Bedrooms 4

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 STONE HOUSE PROPERTIES, LLC

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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398 Weatogue Rd Sheffield MA 01222

Price$1,345,000

Est. Mortgage: $/month

MLS Number 226441

  • Single Family
  • Address 398 Weatogue Rd
  • Village Berkshire - South
  • Year Built 1988
  • Parking Spaces 3

Monarch Hill - A dramatic hilltop setting, a unique contemporary with quality and style throughout, beautiful decks, patios and landscaping, an in ground pool, views forever, and so much more, all combine to make Monarch Hill the ultimate retreat. High above the Housatonic River and bordered by hundreds of acres at Bartholomew's Cobble, this home is designed for peace and comfort.

Listed by Elyse Harney Real Estate

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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73-89 Main St Sheffield MA 01257

MLS Number 221702

  • Commercial
  • Village Berkshire - South
  • Year Built 1900
  • Square Feet 16,020
  • Bedrooms 5

9 Commercial and 5 Residential Rentals. Village Center location with high traffic count.

Listed by ISGOOD REALTY

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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242 Hickey Hill Rd Sheffield MA 01257

Price$935,000

Est. Mortgage: $/month

MLS Number 227549

  • Single Family
  • Address 242 Hickey Hill Rd
  • Village Berkshire - South
  • Year Built 2007
  • Parking Spaces 2

This custom-built Bensonwood Timber Frame home was designed w/ a classic open living floor plan & built to Energy Star standards. The craftsmanship, materials & design details are extraordinary. The main living area w/ vaulted ceiling has an abundance of windows & natural light. The gorgeous Berkshire vistas & views can be enjoyed throughout the house. The well-equipped cook's kitchen opens to the dining/living area and the raised hearth fireplace. The screened porch & patio were designed to take in the evening sunsets. There is first floor master suite with walk-in closet. Central AC. This beautiful property has been impeccably maintained. A great location convenient to the southern Berkshire & northern Litchfield county recreational & cultural venues. Only 8 miles to Great Barrington.

Listed by STONE HOUSE PROPERTIES, LLC

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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121 Hickey Hill Rd Sheffield MA 01257

Price$919,000

Est. Mortgage: $/month

MLS Number 224817

  • Single Family
  • Address 121 Hickey Hill Rd
  • Village Berkshire - South
  • Year Built 2000
  • Parking Spaces 2

Enjoy the panoramic views and beautiful perennial gardens from this luxuriously built and lovingly maintained, four bedroom home. Conveniently located about 10 minutes south of Guido's and 2 minutes from the Marketplace in Sheffield. Filled with custom detailing from tiger maple trim to custom cabinets and library shelves. First floor master bedroom suite with office. Sun-filled four season sun room opens to the well appointed cook's kitchen. Two bedrooms and 2 baths upstairs plus a large finished bonus room for exercise, office, extra bedroom or media. Stone walls surround the bursting flowerbeds. A large and comfortable deck overlooks the long views over fields to the mountains beyond.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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1 Water Farm Rd Sheffield MA 01257

Price$895,000

Est. Mortgage: $/month

MLS Number 223162

  • Land
  • Co Listing Office Name LANDVEST, INC.
  • High School Mount Everett
  • Village Berkshire - South
  • Square Feet 16,117,200

301 acres of forest & wetlands with 8,828 feet of road frontage on Water Farm Road and 606' of road frontage on Soda Spring Creek Road. There are extensive wetlands with significant uplands associated that might support 6 to 8 large house lots. Spring water infrastructures include two 30,000 gal covered concrete storage tanks and associated infrastructure. Historic records show water volume range from 9 to 17 mil gal/yr. The Soda Spring Creek flows into the Ironworks brook just south of the property boundary which then joins the Housatonic River. The property has been professionally managed by licensed foresters for more than 15 years.

Listed by LANDVEST, INC.

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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82 West Stahl Rd Sheffield MA 01222

Price$799,000

Est. Mortgage: $/month

MLS Number 227218

  • Single Family
  • Address 82 West Stahl Rd
  • Village Berkshire - South
  • Year Built 1808
  • Bedrooms 4

An Antique Gem that has been lovingly restored to a warm and inviting place to gather with friends and family. Spacious living room with original fireplace, fabulous wood floors through out. With 4 bedrooms and 4 full baths plus a bunk cottage and a pool house cabana, you can entertain a crowd. Or relax by yourself on 6 peaceful acres, gardens and inground pool. A large barn rounds out the perfect country home.

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$
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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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264 Brush Hill Rd Sheffield MA 01257

Price$795,000

Est. Mortgage: $/month

MLS Number 224536

  • Single Family
  • Address 264 Brush Hill Rd
  • Village Berkshire - South
  • Year Built 1992
  • Parking Spaces 2

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: 3.82% last updated on Jun 13, 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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246 County Rd Sheffield MA 01257

Price$680,000

Est. Mortgage: $/month

MLS Number 223653

  • Single Family
  • Address 246 County Rd
  • Village Berkshire - South
  • Year Built 1915
  • Parking Spaces 1

If you are looking for a wonderful getaway for your active family to enjoy their vacation home with your own private Tennis court and modern Guest Cabana in a desirable location near skiing, too! Quiet, open outdoor space with thoughtful landscaping including mature shade trees and multiple perennial gardens. The slate patio perfect for dining outdoors, or join the guests in the 'South of the Border' designed cabana with its own patio for seating or watching the tennis matches on the all season/all weather fenced court. Includes spacious family area, full kitchen & 'Ice cream pastel' tile bath. The main house has an abundance of natural light in the large family/living room complete with seated bow windows and a wood burning fireplace. With 3 bedrooms and 2 full baths, 23+ acres,

Listed by COHEN & WHITE ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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290 Bow Wow Rd Sheffield MA 01257

Price$679,000

Est. Mortgage: $/month

MLS Number 226176

  • Single Family
  • Address 290 Bow Wow Rd
  • Village Berkshire - South
  • Year Built 1975
  • Bedrooms 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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