Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

Sheffield MA Real Estate

Sheffield, MA -- comprised of 2 villages, Sheffield and Ashley Falls, is a picturesque New England town in the Housatonic River Valley of Berkshire County.The oldest town in the Berkshires, Sheffield offers a plethora of historic homes, strong agricultural roots, and a strong sense of community.

Search Real Estate for Sale in Sheffield, MA

Scroll down to browse through our real estate listings in Sheffield, MA. Contact us if you have questions or would like to schedule a showing.

Upgrade Your SearchCreate an account to keep track of listing and get updates when new properties hit the market!

You may also be interested in homes for sale in Egremont, Monterey, Mt. Washington, or New Marlborough!

r=1-10
1161 Home, Sheffield, MA 01257

Price$425,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 221059

  • Listings Residential
  • Address 1161 Home Rd
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2464

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

{$agent->Name}

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-11-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

25 Cross, Sheffield, MA 01257

Price$425,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219365

  • Listings Residential
  • Address 25 Cross Rd
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2568

This 4 BR/ 3 BA 2, 568 sq.ft. home features an open floor plan, a renovated kitchen with tile back splash with laminate flooring, and glass sliders that lead to a large private deck that looks out on mature fruit trees, and 3 beautiful acres of land that abuts preserved state land on one side.Built in 1998, the lower level was finished by the sellers seven years ago adding about 800 sq. ft. of living space. The lower level features a large space that could be use as for TV, exercise or play.Equipped with a full bath, closets with organizers and a room that could be utilized as a study.The possibilities are endless.Loved and cared for in a meticulous manner, this is an excellent opportunity to live in a coveted Berkshire location.

Listed by Kristin P. Piasecki of BARNBROOK REALTY, INC.

{$agent->Name}

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-11-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

604 Polikoff, Sheffield, MA 01222

Price$425,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 221400

  • Listings Residential
  • Address 604 Polikoff Rd
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1600

Your perfect vision of country living in this 1830's farmhouse completely renovated from top to bottom. Stunning cathedral ceilings in living, chic kitchen with grey cabinets and wood countertops, first floor bedroom with bath. Stunning wood floors throughout. This charming house is located on 2.49 cleared, flat acres, perfect for your little farm. Parcel has two outbuildings.

Listed by Elle Villetto of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

{$agent->Name}

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-11-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

28 Main, Sheffield, MA 01257

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219903

  • Listings Commercial
  • Address 28 South Main St
  • Bedrooms 4
  • Square Feet 3200
  • Year Built 1900

Located in the heart of downtown Sheffield, this elegant home has a 1600 sq ft detached studio perfect for live/work. The house has a tried and true vacation rental history and is designated as an Air BnB SuperHost Property. Close to skiing and all Southern Berkshire attractions, this large home with ample off street parking could be the perfect solution for you!

Listed by Annie M. Alquist of BARNBROOK REALTY, INC.

{$agent->Name}

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-11-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

28 Main, Sheffield, MA 01257

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219335

  • Listings Residential
  • Address 28 South Main St
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 4406

AIR BnB SUPERHOST PROPERTY! Beautiful home with detached office/studio space, attached garage and plenty of parking. Strong vacation rental history in this charming home. Perfect for work/live or a beautiful vacation home that pays for itself with rental income. Featured on HGTV, this home is a must see

Listed by Annie M. Alquist of BARNBROOK REALTY, INC.

{$agent->Name}

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-11-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

81/85 County, Sheffield, MA 01257

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219957

  • Listings Residential
  • Address 81/85 County Rd
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2626

Charming New England Farmhouse in idyllic setting complete with babbling brook. Walking through the classic front porch there is a large mudroom off foyer. Large open kitchen area with dining room, huge walk in pantry, sun room. Fieldstone Fireplace graces the living room which flows into family room. Off of the sunroom is a cozy office. Guest house on property. Great location off a country road.

Listed by Russ Stein of BERKSHIRE PROPERTY AGENTS

{$agent->Name}

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-11-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

974 Berkshire School, Sheffield, MA 01257

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220746

  • Listings Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1620
  • Year Built 1925

METICULOUSLY RENOVATED HOME WITH FABULOUS STYLE! Great corner lot with screened porch and outdoor fire pit on over 3 acres. The new kitchen with soapstone countertops flows to the dining area and into the living room with large stone fireplace. Must see this three bedroom and two bath home.

Listed by Susan Laidlaw of BERKSHIRE PROPERTY AGENTS

{$agent->Name}

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-11-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

30 Glennana, Sheffield, MA 01257

Price$389,900The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 220930

  • Listings Residential
  • Address 30 Glennana Way
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1918

Charming Sheffield New England Expanded Cape with today's construction and features. High ceilings and big windows flood the open space with light and make the wood floors gleam. Warm yourself by the hearth in autumn's chill, or take in the cool breezes on the screened porch in the summer. Spacious first floor master suite, with two generously sized bedrooms on the second floor. Oversized two car detached garage. Privately set on a low traffic side street tucked behind a stone wall and mature trees, with easy access to main routes to Great Barrington. Beautifully maintained and move-in ready!

Listed by Anne B. Meczywor of ROBERTS & ASSOC. REALTY, INC

{$agent->Name}

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-11-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

647 MAIN, Sheffield, MA 01257

Price$379,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 191033

  • Listings Commercial
  • Address 647 North Main St
  • Bathroom 2
  • Square Feet 1800
  • Year Built 1997

Located on busy Rte. 7 in Sheffield. Currently an open floor plan on the first floor, full one bedroom apartment on the second floor. Many possibilities.

Listed by Lance Vermeulen of LANCE VERMEULEN RE, INC

{$agent->Name}

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-11-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

96 Main, Sheffield, MA 01257

Price$375,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 212599

  • Listings Commercial
  • Address 96 Main St
  • Bedrooms 2
  • Square Feet 2920
  • Year Built 1872

Nearly 3, 000 sq. ft. and .33 acres in the center of downtown Sheffield this turn of the century building has old world craftsmanship and charm. Great visibility and easily accessible this property includes a two bedroom apartment located on the second floor.

Listed by Douglas M Goudey of WHEELER & TAYLOR REALTY CO., INC.

{$agent->Name}

Benchmark Real Estate
Corner of Routes 8 & 23, Otis Village Center
Otis MA, 01253
Office: (413) 269-4089

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-11-02

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.