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$1,995,000

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 10 MINUTES TO GUIDOS IN GREAT BARRINGTON!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. 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.. 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: 3.69% last updated on Oct 17, 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: 3.69% last updated on Oct 17, 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: 3.69% last updated on Oct 17, 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: 3.69% last updated on Oct 17, 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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282 East Main St Sheffield MA 01222

Price$900,000

Est. Mortgage: $/month

MLS Number 228925

  • Single Family
  • Address 282 East Main St
  • Village Berkshire - South
  • Year Built 1770
  • Bedrooms 4

The former Maplewood Inn, set in the quiet hamlet of Ashley Falls is an elegant historic house which dates back originally to the 1770s. Spacious, bright open living areas, high ceilings, beautiful floors, staircases, windows, fireplaces and expansive screened porches on the first and second floors are just some of the characteristics that set this property apart from others. The back garden and heated Gunite in-ground pool and spa are protected by mature trees and unique outbuildings including two barns, one with a two-car garage, a former barbershop, smoke house, and two-story ice house. The compound offers mature plantings a fruit orchard.. The chef's kitchen has a Wolf range and open to the family room. A/C on the second floor, alarm system, and beautiful light throughout the house.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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 Main St, 89 St Sheffield MA 01257

MLS Number 229088

  • Commercial
  • Village Berkshire - South
  • Year Built 1900
  • Square Feet 6,000
  • Bedrooms 7

Great opportunity to own on the Village Green. Prime Sheffield Center location. 9 Commercial and 5 Residential Rentals. Attractive brick building with high traffic count.

Listed by FAIRGROUND REAL ESTATE

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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$899,000

Est. Mortgage: $/month

MLS Number 228764

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

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. 10 miles to Great Barrington and 20 to Tanglewood. Come see what others have missed!

Listed by BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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
  • Acreage 301.58

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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93 Hillside Ln Sheffield MA 01230

Price$860,000

Est. Mortgage: $/month

MLS Number 229052

  • Single Family
  • Address 93 Hillside Ln
  • Village Berkshire - South
  • Year Built 2000
  • Bedrooms 3

Enjoy expansive western views with gorgeous sunsets from this stylish log home perched on 14 acres. Open living area with cathedral ceilings, a true cook's kitchen, granite counters, cherry cabinets, six burner Viking stove and a farmhouse sink. A large stone fireplace is flanked by floor to ceiling windows so you never miss the views. Off the kitchen/ dining area is an open deck. the master also has its own balcony. Upstairs, two large bedrooms give family or guests their own privacy. The lower level is finished for TV, pool, games or other activities.Totally renovated in 2019.Animal lovers will delight in the four stall barn, plenty of pasture area and loads of privacy. Near Berkshire culture and recreation.

Listed by WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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 spacious, beautifully maintained 1990s contemporary. Enjoy total privacy and pond frontage only 10 minutes from downtown Great Barrington, 20 from two major ski areas and 25 from Tanglewood. The privacy of this home can be enjoyed from the abundance of outdoor space as well as the inviting three-season screened porch surrounded by amid lush wooded conservation land. 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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716 Rannapo Rd Sheffield MA 01257

Price$790,000

Est. Mortgage: $/month

MLS Number 229083

  • Single Family
  • Address 716 Rannapo Rd
  • Village Berkshire - South
  • Year Built 1870
  • Parking Spaces 2

A venerable Folk Victorian on 20.4 acres on both sides of Rannapo Road with over 600 ft of Housatonic river frontage. Long southwesterly views to nearby Hurlburt Hill and Bear Mountain in CT are protected by the Trustees of the Reservations. The main house was built in 1871, updated in 1987, and again in 1994, with six bedrooms, three baths, high ceilings, hardwood floors, and extraordinary molding throughout. Separate but nearby, the 1998 air-conditioned two-floor studio building has a large bright studio with a mezzanine, a full bath, a workshop, a storage attic, and a two-car garage. The solar-heated in-ground pool overlooks the wide pastoral and mountain views. An attached barn shed acts as the pool house and great room for holiday gatherings. A rare offering in a beautiful setting.

Listed by BERKSHIRE PROPERTY AGENTS, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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