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!

1669 Silver Street Sheffield MA 01257

Sheffield, MA1669 Silver Street

Price$1,650,000

Est. Mortgage: $/month

MLS Number 242950

  • Residential
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 3,528
  • Acreage 10.23

Classic american farmhouse with epic views - experience breathtaking panoramic vistas over protected land from every angle in this renovated classic american farmhouse. Nestled on two parcels, this residence boasts a pool, a detached garage, and gracious proportions throughout. Relax in the majestic long-range mountain vistas. The house is perfectly positioned to experience both sunrise and sunset views. Step inside to discover an extra-large chef's kitchen seamlessly connected to a delightful breakfast room, sunroom, and screened porch, each offering tranquil views of the pool and raised garden beds. The inviting living room, complete with a cozy fireplace, flows effortlessly into the dining area, creating an ideal space for entertaining.

Listed by William Melnick and Elyse Harney Morris of ELYSE HARNEY REAL ESTATE ((860) 435-0120)

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$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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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1955 North Main Street Sheffield MA 01257

MLS Number 244475

  • Commercial
  • Acreage 8.3

Large 5 bay auto / truck sales and service center on route 7 (garage over 5000 sq ft - room for @ 100 cars). On sheffield-great barrington border. Huge parking lot, high visibility, heavy power. Additional storage building on over 8 acres of land. Ideal for a multitude of uses.(former gmc dealership location.)

Listed by Richard G. Aldrich and Steven J. Weisz of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

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$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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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1166 Rannapo Road Sheffield MA 01222

Sheffield, MA1166 Rannapo Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 243884

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,510
  • Acreage 17.29

Welcome to rannapo road, and your forever home! Sitting at the crest of the hill, this home peers across the valley overlooking cornfields, 2 rivers and mt everett. With 17 workable acres and a horse barn, this equestrian property is a perfect opportunity to own your own gentleman's farm. Inside you will appreciate the open floor plan and fireplace while enjoying the views as they paint pictures in every window. The large primary en-suite bedroom boasts a juliette balcony overlooking the valley - the perfect spot for morning meditation. Two additional bedrooms, an office and a den can be found throughout the home - including a first floor bedroom. Additionally, the home features a large bonus room above the garage with a separate staircase - plumbed for heat and ready to finish.

Listed by Antonio M Segalla and Lance Vermeulen of LANCE VERMEULEN RE,INC ((413) 528-6011)

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$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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 Road Sheffield MA 01257

Sheffield, MA481 Shunpike Road

Price$1,475,000

Est. Mortgage: $/month

MLS Number 244075

  • Residential
  • Bathroom 2
  • Bedrooms 1
  • Square Feet 1,296
  • Acreage 41

A total 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own home with mountain views. A 36x52 work shop. One full time residence and a separate summer studio. Some land does go into new marlborough. Surrounded by conservation land. Passive solar views facing south and west. Property has been a sculpture park for many years. Trails throughout. Views to connecticut.

Listed by Suzann Laverack Ward of HOUSATONIC REAL ESTATE ((413) 274-5065)

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$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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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105 Bears Den Road Sheffield MA 01257

Sheffield, MA105 Bears Den Road

Price$1,375,000

Est. Mortgage: $/month

Pending

MLS Number 243850

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,550
  • Acreage 3.39

Berkshire contemporary masterpiece - offering privacy, a gunite pool and stunning mature landscaping with a meadow creating an estate-like feel. Inside you will find yourself drenched in sunlight streaming in from the wall of windows and looking over the westerly view. With glass doors leading to the large cedar deck from every room, you will always feel a connection to nature. Recently updated, the kitchen and baths are a continuation of the modern vibe. Featuring 4 bedrooms - including a first-floor primary suite with cathedral ceilings and a walk-in closet - you will find plenty of space to spread out. The highlight is the luxurious gunite swimming pool with a built-in spa, perfect for relaxation and entertainment. In addition, the home features central a/c and a back-up generator.

Listed by Antonio M Segalla of LANCE VERMEULEN RE,INC ((413) 528-6011)

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$
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$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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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594 Shunpike Road Sheffield MA 01257

Sheffield, MA594 Shunpike Road

Price$1,175,000

Est. Mortgage: $/month

MLS Number 243597

  • Residential
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2,600
  • Acreage 2.32

Experience the serenity of 594 shunpike rd. This cozy 2600 sq. Ft. Gambrel-style home, set on 2.32 acres, has been meticulously & extensively renovated for modern living. Enter through a bright, open foyer & enjoy central air/heat, a full house generator, & new wood flooring. The home features all new kitchen, bathrooms, gas fire place, plumbing, electric, windows & more. The newly finished lower level w/ walkout offers additional living space. Relax on the spacious deck, surrounded by a beautiful clearing in the woods. The primary suite w/ a spa-like bathroom & walk-in closet. This property is ideal for year-round living, vacation home, or potential rental income. Located on a quiet country road, minutes from town, enjoy location for recreation & cultural attractions.

Listed by Claire Naylor Pollart of LANCE VERMEULEN RE,INC ((413) 528-6011)

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$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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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567 South Main Street Sheffield MA 01257

Sheffield, MA567 South Main Street

Price$1,159,000

Est. Mortgage: $/month

MLS Number 243414

  • MultiFamily
  • Acreage 11.07
  • Year Built 1900
  • Parking Spaces 10

Investment opportunity in sheffield. Set way back from the main road, this multi family dwelling awaits its new stewards after almost 40 years in the same family. The property consists of 3 separate buildings, the main house with four 1 br apts.In the rear of the main house is a semi attached 2 br apt with its own separate entrance. You then have an additional 3 bedroom 2 bath home with 3 season room and rear garden. There is also a separate 2 bay garage with maintenance room. The grounds are beautifully manicured with flowering bushes and trees with lovely mountain views. Its really a little bit of paradise just off the beaten path yet close to everything. 15 minutes in great barrington, 10 minutes to n canaan ct. This lovely homestead is set on almost 13 secluded acres.

Listed by BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

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%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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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856 Barnum Street Sheffield MA 01257

Sheffield, MA856 Barnum Street

Price$1,100,000

Est. Mortgage: $/month

MLS Number 244059

  • Residential
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,800
  • Acreage 2.01

Welcome to 856 barnum. This home is a collaboration between a skilled photographer & debora k. Reiser, a renowned new york architect. Once a humble cape cod, it's now a modernist delight.The front exterior features clean lines, dark paint, & copper accents. The side profile shows multi-dimensional lines & a dramatic turret. Inside, the grand room has a vaulted ceiling & expansive windows, blending the countryside into the living space. Multiple closets along the front wall offer ample storage. This area is perfect for dining & entertaining.The back wall centers around a fireplace flanked by built-in bookshelves. Large glass doors flood the living area with natural light. Skylights & vaulted ceilings add modern dimension & shape, making this space ideal for both lounging & dining.

Listed by Elle Villetto and Jared Kelly of WILLIAM PITT SOTHEBY'S - GT BARRINGTON ((413) 528-4192)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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 South Main Street Sheffield MA 01257

MLS Number 244605

  • Commercial
  • Acreage 1.33

Sugar & rye: a vibrant market and deli located on main street in sheffield, this turnkey business is beloved for its freshly prepared foods, including custom sandwiches, grab-and-go meals, and baked goods. Key features include a liquor license, ice cream bar, and a coffee bar, attracting a wide range of customers. The store offers both casual seating and takeout, ensuring steady traffic from locals and visitors alike. With an established customer base, supplier relationships, and popular items such as rotisserie chickens and baked goods, sugar & rye is perfectly positioned for continued success. Real estate details: in addition to the business, this listing includes two 2-bedroom apartments and a carriage house apartment, offering additional income potential or a residence for the owner.

Listed by Antonio M Segalla of LANCE VERMEULEN RE,INC ((413) 528-6011)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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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194 East Main Street Sheffield MA 01222

Sheffield, MA194 East Main Street

Price$799,000

Est. Mortgage: $/month

MLS Number 241957

  • Residential
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,200
  • Acreage 0.75

Nestled on a corner lot in the quaint village of ashley falls, this c. 1900 new england farmhouse blends timeless charm with modern comfort and energy efficiency. This completely renovated 4-bedroom 3-bath home preserves its classic allure with numerous modern upgrades and all new mechanicals. Step onto the white-washed front porch and into the front parlor, where a wood-burning fireplace and engineered oak floors greet you with warmth and character. The bright open kitchen/dining area with exposed original beams and vaulted ceiling invites gatherings of family and friends. Sliding doors offer sunshine from the south-facing patio. Rounding out the first floor is a spacious 1st-floor bedroom and full bath, plus a side entry mudroom. Open house sunday 9/15 10-1pm.

Listed by Vashti Poor of LANCE VERMEULEN RE,INC ((413) 528-6011)

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$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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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550 Sheffield Plain Road Sheffield MA 01257

MLS Number 244248

  • Residential
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,479
  • Acreage 0.71

Splendid historic greek revival with lovely protected views of hills and farmland. Built in 1740 by the first congregational minister, reverend jonathan hubbard. Added onto in 1810, this home is on the national register of historic places. The front door leads to large foyer, with a den off the entry. The dining room has gorgeous original details, including wideboard chestnut floors, paneling, and mantel above the wood-burning fireplace. The formal living room also has a wood-burning fireplace. The first floor also has a kitchen, full bath, laundry room, and two bonus rooms with many potential uses. Upstairs, are three bedrooms and an office which share a full bath. The property is beautifully landscaped and comprises two lots. Two car garage.

Listed by Tom Lynch of BERKSHIRE PROPERTY AGENTS,LLC ((413) 528-6800)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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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424 Cooper Hill Road Sheffield MA 01257

Sheffield, MA424 Cooper Hill Road

Price$650,000

Est. Mortgage: $/month

Pending

MLS Number 243893

  • Residential
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 1,728
  • Acreage 3.3

A true berkshire gem ! This home has been impeccably maintained and loved for over 50 years by the same owners. Beautiful country roads will lead you home. Conservation land surrounds. Perfect flow as you enter the front door, cozy living room with wood burning fireplace, a screen porch for your summer nights, and so many other highlights to see. This home also has a room on the first floor that could be a wonderful main floor bedroom , guest room, or living space. Passing title 5, full pre-listing inspection completed , high speed internet access, with all mechanicals in great working order.

Listed by Tanya Shepardson of RE/MAX COMPASS ((413) 394-4543)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.12% last updated on Oct 3, 2024
* 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 5, 2024 . 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.