Sheffield, MA Homes

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  /62

  $715,000

  • 3 Beds
  • 3 Baths
  • 2,395 Sq Ft

  649 Hewins St, Sheffield, MA 01257

  This special property has been thoughtfully renovated to preserve its antique farmhouse charm. Set on an open 1-acre lot along a pastural country road and shaded by a stately maple tree, this home exudes that timeless vintage character that is so rare to find. Step through the rustic pine door onto the brick floor of the white washed pine-paneled mudroom. Upon entering the bright kitchen, you may

  Vashti Poor LANCE VERMEULEN RE, INC

  649 Hewins St, Sheffield, MA 01257
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  /28

  $530,000 Sold May 01, 2025

  • 3,280 Sq Ft
  • $162/SF
  • 231 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1790

  690 N Main St, Sheffield, MA 01257

  Upgrade this property for residential use. This stunning building boasts a perfect blend of modern features and preserved post and beam architecture to maintain its timeless historic charm. Meticulously renovated and used by a master craftsman, it boasts a host of eco-friendly features ranging from owned solar panels, to offset electricity usage to radiant heating in the ground floor concrete. In

  Tim Gallagher STONE HOUSE PROPERTIES, LLC

  690 N Main St, Sheffield, MA 01257
• 

  

  

  /31

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,160 Sq Ft

  206 E Main St, Ashley Falls, MA 01222

  206 E Main St, Ashley Falls, MA 01222
• 

  

  

  /59

  $1,190,000

  • 4 Beds
  • 2.5 Baths
  • 3,155 Sq Ft

  405 S Undermountain Rd, Sheffield, MA 01257

  Idyllic Contemporary Cape on Sprawling 13 Acres in Sheffield - Welcome to 405 South Undermountain Road, where the charm of a classic cape meets the allure of modern living on 13 private acres in Sheffield. Built in 1955 and beautifully updated, this home strikes a harmonious balance between comfort and elegance. Offering an open floor plan with 2 full baths, one 1/2 bath and a functional tiled

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  405 S Undermountain Rd, Sheffield, MA 01257
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  /41

  $250,000 Sold Apr 30, 2025

  • 1,765 Sq Ft
  • $142/SF
  • 169 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1793

  107 S Main St, Sheffield, MA 01257

  Step into a piece of history with this iconic property known as ''The Hatfield's,'' a beloved antique landmark in Sheffield. Built in 1793, the original home exudes historic charm with timeless architecture, in the late 1990s a separate wing was added, creating a flexible two-family configuration. Alternatively, it can easily be used as a spacious single-family residence. The home's basement has

  Mary Naylor LANCE VERMEULEN RE, INC

  107 S Main St, Sheffield, MA 01257
• 

  

  /25

  Est $543,222 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,230 Sq Ft

  658 S Main St, Sheffield, MA 01257

  658 S Main St, Sheffield, MA 01257
• 

  

  /42

  $995,000

  • 3 Beds
  • 3.5 Baths
  • 2,600 Sq Ft

  594 Shunpike Rd, Sheffield, MA 01257

  Beautifully renovated 2600 sq. ft. Gambrel-style home offering the perfect balance of privacy, comfort, and modern convenience. Step into a welcoming, open foyer that leads to an expansive living space with all-new features, including wood flooring, central air/heat, a full house generator, & updated plumbing/electrical systems. The heart of the home is a brand-new kitchen, complete with sleek

  Claire Pollart LANCE VERMEULEN RE, INC

  594 Shunpike Rd, Sheffield, MA 01257
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  /14

  $210,000 Sold Mar 18, 2025

  • 2,258 Sq Ft
  • $93/SF
  • 92 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1957

  689 N Main St, Sheffield, MA 01257

  4-bedroom, 2-family house on a main road, offering great potential with some TLC. This duplex includes a very spacious backyard as well as a detached garage. Just north of Sheffield Center. Fantastic opportunity for a buyer who is looking to offset the mortgage with rental income or a potential investment. This property is commercially zoned making it a a fantastic location for Sheffields

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  689 N Main St, Sheffield, MA 01257
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  /43

  Est $428,319 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,202 Sq Ft

  728 Hewins St, Sheffield, MA 01257

  728 Hewins St, Sheffield, MA 01257
• 

  

  /33

  $798,000

  • 3 Beds
  • 2.5 Baths
  • 3,082 Sq Ft

  86 Main St, Sheffield, MA 01257

  This gracious vintage home has been thoughtfully renovated and lovingly maintained by the current owners for over 20 years. High ceilings, wonderful light, spacious rooms, a ''walk to everything'' in town location, and residential/commercial zoning provide comfort and unlimited possibilities. A 1,000 sq. ft. outbuilding with water & electric service adds more potential. Beautiful period

  David Taylor ELYSE HARNEY REAL ESTATE

  86 Main St, Sheffield, MA 01257
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  /27

  $419,000 Sold Feb 28, 2025

  • 1,603 Sq Ft
  • $261/SF
  • 19 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1987

  487 Polikoff Rd, Ashley Falls, MA 01222

  Move in ready, younger cape home. New kitchen, hickory flooring and interior paint. Nicely updated bathrooms. Composite deck overlooking a private yard with woods behind. The smaller of the 4 bedrooms does not have a closet.

  Tim Hart HART REALTY

  487 Polikoff Rd, Ashley Falls, MA 01222
• 

  

  /22

  Est $617,064 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  169 Ashley Falls Rd, Sheffield, MA 01257

  169 Ashley Falls Rd, Sheffield, MA 01257
• 

  

  /40

  $1,275,000

  • 3 Beds
  • 3 Baths
  • 2,878 Sq Ft

  1166 Rannapo Rd, Sheffield, MA 01257

  It's no wonder this property is the home of Berkshire county's oldest elm tree! The abundant sunshine & quietude would make anybody want to set down roots. This light filled home has wood floors throughout the main level. Kitchen has granite counters, pantry & large island. As part of the open floor plan there is a dining room and living room that opens to an expansive deck. The great room

  Grace Golden Equine Homes Real Estate, LLC

  1166 Rannapo Rd, Sheffield, MA 01257
• 

  

  /19

  $385,000 Sold Feb 28, 2025

  • 1,600 Sq Ft
  • $241/SF
  • 122 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  350 S Undermountain Rd, Sheffield, MA 01257

  This 3 bedroom 2 bath home tucked away in the peaceful woods of Berkshire County is perfect for someone who is looking to be close to town, but also looking for privacy. A screened in porch alongside the spacious deck allows for maximum opportunity to engage with nature. Located minutes to both the Appalachian Trail and Great Barrington.

  Adam Dingman BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  350 S Undermountain Rd, Sheffield, MA 01257
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  /29

  Est $529,119 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  24 Cactus St, Sheffield, MA 01257

  24 Cactus St, Sheffield, MA 01257
• 

  

  /53

  $725,000

  • 4 Beds
  • 4 Baths
  • 3,455 Sq Ft

  64 Hewins St, Sheffield, MA 01257

  A rare & authentic 1842 post & beam farmhouse w/ many original details. This one-of-a-kind antique home awaits the reinvention & stewardship of it's next owners. In the same family for the last 125 years, and with just two prior owners since being built, the structure features post & beam construction, two original fireplaces, antique hardware, woodwork and doors that exemplify early American

  Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  64 Hewins St, Sheffield, MA 01257
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  /25

  $565,000 Sold Jan 24, 2025

  • 1,850 Sq Ft
  • $305/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1928

  210 Ashley Falls Rd, Sheffield, MA 01222

  Renovated country home with distant mountain views.

  Comparable Listing COMPARABLE LISTING ONLY

  210 Ashley Falls Rd, Sheffield, MA 01222
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  /4

  Est $605,688 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  1609 County Rd, Great Barrington, MA 01230

  1609 County Rd, Great Barrington, MA 01230
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  /37

  $1,475,000

  • 1 Bed
  • 2 Baths
  • 1,296 Sq Ft

  481 Shunpike Rd, Sheffield, MA 01257

  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.

  Suzann Ward HOUSATONIC REAL ESTATE

  481 Shunpike Rd, Sheffield, MA 01257
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  /3

  $121,000 Sold Jan 17, 2025

  • Land
  • 20 Acres
  • $6,148 per Acre

  • 1620 Days On Market

  Unlisted Address

  COUNTRY LIVING. Nearly 20 wooded acres with 600' frontage on rural Water Farm Road. Also has frontage on East Road. Town water likely accessible. Electricity accessible on road. Property perced by White Engineering.

  Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  Unlisted Address
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  /7

  Est $780,102 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,784 Sq Ft

  215 Cross Rd, Great Barrington, MA 01230

  215 Cross Rd, Great Barrington, MA 01230
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  /52

  $998,000

  • 2 Beds
  • 3 Baths
  • 1,800 Sq Ft

  856 Barnum St, Sheffield, MA 01257

  Welcome to 856 Barnum, a stunning residence born from the creative vision of a talented photographer and acclaimed New York architect, Debora K. Reiser. What was once a modest Cape Cod has been transformed into a sophisticated modern masterpiece.The exterior showcases sleek lines and elegant copper details, with a striking turret adding depth to its profile. Upon entering, you are greeted by a

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  856 Barnum St, Sheffield, MA 01257
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  /72

  $330,650 Sold Jan 17, 2025

  • 1,770 Sq Ft
  • $187/SF
  • 122 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1955

  136 Clayton Rd, Ashley Falls, MA 01222

  Enjoy life in the Southern Berkshires with everything it has to offer, only minutes to the CT/NY Borders. Located in the Village of Ashley Falls, this lovely Cape features four Bedrooms, two full Baths, fireplaced living room, a large four season sunroom that opens to an oversized patio style deck.In addition an attached garage with tiled breezeway and a large private yard.Only a short drive to

  Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  136 Clayton Rd, Ashley Falls, MA 01222
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  /36

  Est $395,971 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,379 Sq Ft

  1014 Salisbury Rd, Sheffield, MA 01257

  1014 Salisbury Rd, Sheffield, MA 01257
• 

  

  /34

  $795,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,633 Sq Ft

  371 Berkshire School Rd, Sheffield, MA 01257

  Step into a world of elegance and comfort with this gracious home, bathed in natural light and designed for sophisticated living. Set on a sprawling three-acre lot, this property features well-designed rooms that create an inviting atmosphere for both relaxation and entertainment. At the heart of the home, the updated kitchen serves as a culinary haven. The first-floor primary en-suite bedroom

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  371 Berkshire School Rd, Sheffield, MA 01257
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  /36

  $559,000 Sold Jan 16, 2025

  • 1,400 Sq Ft
  • $399/SF
  • 144 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  78 Ashley Falls Rd, Sheffield, MA 01257

  Move right into this perfectly kept ranch-style home in picturesque Ashley Falls village. This inviting property sits on 2.5 flat acres and is conveniently located near most local amenities. Inside you will find an open floor plan flooded with natural sunlight featuring an en-suite primary with 2 additional bedrooms and laundry on the main floor - perfect for easy living. The large finished

  Tony Segalla LANCE VERMEULEN RE, INC

  78 Ashley Falls Rd, Sheffield, MA 01257
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  /40

  Est $375,339 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft

  1507 Home Rd, Great Barrington, MA 01230

  1507 Home Rd, Great Barrington, MA 01230
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  /9

  $379,500

  • Land
  • 6 Acres
  • $60,720 per Acre

  0 S Main St, Sheffield, MA 01257

  Mountain views with Rt 7 access. Whether you are interested in a private residence to farm, raise horses, or escape the city life or if you are looking for a business opportunity with amazing Rt 7 exposure this land is the perfect opportunity. Totaling 6.25 acres of completely usable, flat, dry land. Currently the fields are hayed and have an approximate 1 acre vineyard. The 6.25 acres is

  Grace Golden EQUINE HOMES REAL ESTATE, LLC

  0 S Main St, Sheffield, MA 01257
• 

  

  /43

  $569,500 Sold Dec 20, 2024

  • 2,081 Sq Ft
  • $274/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1942

  345 Miller Ave, Sheffield, MA 01257

  Charming and Cozy home in a picture perfect setting. There are, three bedrooms, two full baths, a first floor en-suite primary. fire-placed living room with cathedral ceilings and beautiful beams, formal dining room with second fireplace, efficient kitchen with walk in pantry, beautiful screened in porch and family room on first level. Second floor offers two large bedrooms and a second full

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  345 Miller Ave, Sheffield, MA 01257
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  /42

  Est $454,892 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  505 Sheffield Plain, Sheffield, MA 01257

  505 Sheffield Plain, Sheffield, MA 01257
• 

  

  /31

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 2,008 Sq Ft

  95 Main St, Sheffield, MA 01257

  Beautiful Colonial right in the Village Center with acircular driveway and ample parking. Enter to an open kitchen and dining area with exposed beams, gracious living room with walls of windows and a family room with bar, custom stone flooring and fireplace. Convenient access from the family room to the back patio for grilling and entertaining with an exterior fireplace! The 2nd level features

  Cortney Dupont COHEN & WHITE ASSOCIATES

  95 Main St, Sheffield, MA 01257
• 

  

  /43

  $650,000 Sold Dec 13, 2024

  • 2,479 Sq Ft
  • $262/SF
  • 93 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1740

  550 Sheffield Plain, Sheffield, MA 01257

  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,

  Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  550 Sheffield Plain, Sheffield, MA 01257
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  /36

  Est $802,447 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,991 Sq Ft

  483 Home Rd, Great Barrington, MA 01230

  483 Home Rd, Great Barrington, MA 01230
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  /53

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 4,853 Sq Ft

  360 Brush Hill Rd, Sheffield, MA 01257

  Tucked away in the woods with access to Three Mile Pond, this contemporary home will leave you longing to return. With views from most rooms, the thoughtfully designed floor plan leaves little to be desired. The main living spaces include an inviting living room with a stone fireplace that opens to a screened porch, a cozy den/library, and a spacious great room with soaring ceilings, a grand

  Tony Segalla LANCE VERMEULEN RE, INC

  360 Brush Hill Rd, Sheffield, MA 01257
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  /20

  $400,000 Sold Dec 06, 2024

  • 1,461 Sq Ft
  • $274/SF
  • 3 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1985

  773 Clayton Rd, Ashley Falls, MA 01222

  A sweet & simple country cape on 1.45 acres awaiting it new owner's updates & personal touches. Privately situated on a level lot, this home offers a lot of potential to a wide range of buyers, from starter home to downsizing and anything in between. First floor offers open kitchen & dining area, half bath, and spacious living room, and the 2nd floor features 3 cozy bedrooms and shared full bath.

  Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  773 Clayton Rd, Ashley Falls, MA 01222
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  /11

  Est $201,649 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 875 Sq Ft

  704 S Main St, Sheffield, MA 01257

  704 S Main St, Sheffield, MA 01257
• 

  

  /40

  $400,000

  • 5 Beds
  • 2 Baths
  • 2,485 Sq Ft

  254 Main St, Sheffield, MA 01257

  Welcome the historic Foxdale and the opportunity to own a piece of history that begins before the declaration of independence. This property originally was built in the 1750s. If a house with character is what you're looking for, look no further! In the heart of the village of Sheffield, you will find this property unlike any other. After its complete restoration by its visionary new owner this

  Cortney Dupont COHEN & WHITE ASSOCIATES

  254 Main St, Sheffield, MA 01257
• 

  

  /30

  $849,000 Sold Dec 02, 2024

  • 1,552 Sq Ft
  • $547/SF
  • 11 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1971

  815 S Undermountain Rd, Sheffield, MA 01257

  This property offers a blend of comfort, style, and spaciousness, set within the picturesque landscape of Sheffield. The 16-acre property provides an idyllic country setting, ensuring privacy and a connection with nature. The residence, a charming 3-bedroom, 2-bath home, has been thoughtfully updated to combine modern amenities with rustic charm, new hardwood floors and bathrooms complement the

  Tracy Macgowan ELYSE HARNEY REAL ESTATE

  815 S Undermountain Rd, Sheffield, MA 01257
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  /33

  Est $521,083 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,415 Sq Ft

  45 Root Ln, Sheffield, MA 01257

  45 Root Ln, Sheffield, MA 01257
• 

  

  /10

  $119,000

  • Land
  • 1.45 Acres
  • $82,069 per Acre

  0 Bunce Rd Unit 245787, Sheffield, MA 01257

  Situated in a peaceful well-established neighborhood, and surrounded by a natural buffer of mature trees, this beautiful 1.45 acre lot is cleared and ready for construction. Underground phone, cable, and electric utilities are conveniently located right at the end of the roughed-in driveway. Percolation test was completed in 2023. This charming parcel is the last available building lot on this

  Vashti Poor LANCE VERMEULEN RE, INC

  0 Bunce Rd Unit 245787, Sheffield, MA 01257

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