Berkshire, MA Homes

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  /32

  $425,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,700 Sq Ft

  1291 Ashley Falls Rd, Sheffield, MA 01222

  Nestled in the charming village of Ashley Falls, this cozy single-level home offers a perfect blend of comfort and scenic beauty. The open floor plan includes 2 bedrooms, 1 bath, an eat-in kitchen, and a spacious living room with a wood-burning fireplace, large picture windows, and direct access to a screened porch overlooking acres of picturesque farmland. Additional features include a slab

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 728-1649

  1291 Ashley Falls Rd, Sheffield, MA 01222
• 

  

  

  /31

  $390,000 Sold Jul 15, 2025

  • 2,008 Sq Ft
  • $194/SF
  • 19 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1804

  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
• 

  

  

  /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
• 

  

  

  /40

  $499,000

  • 6 Beds
  • 2.5 Baths
  • 3,184 Sq Ft

  119 S Main St, Sheffield, MA 01257

  A unique opportunity to make this terrific property your own, with a separate bungalow apartment for income or other home business uses. Property features a 6 bedroom, 2 bath 1880's Victorian with a classic yet casual style. First floor features a sunny living room, large country kitchen, formal dining room w/ built-ins, and front parlor/bedroom. Second floor offers 5 bedrooms, 2 full baths, and

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 481-1637

  119 S Main St, Sheffield, MA 01257
• 

  

  

  /40

  $1,250,000 Sold Jul 11, 2025

  • 2,100 Sq Ft
  • $595/SF
  • 12 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1984

  40 Veeley Rd, Sheffield, MA 01257

  A unique example of repurposing executed to perfection. This wonderful Gambrel style home sits on three private acres and used a lot natures offerings to help bring this home to its present glory. The home was built using the beams from a 200 year old barn that once sat on the property. The floors were milled from cherry trees that grew on the parcel, the fireplace stone is from the foundation

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  40 Veeley Rd, Sheffield, MA 01257
• 

  

  /31

  Est $448,337 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft

  166 Berkshire School Rd, Sheffield, MA 01257

  166 Berkshire School Rd, Sheffield, MA 01257
• 

  

  /53

  $695,000

  • 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

  (413) 296-3500

  64 Hewins St, Sheffield, MA 01257
• 

  

  /59

  $2,295,000 Sold Jun 27, 2025

  • 3,150 Sq Ft
  • $729/SF
  • 1 Day On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1915

  246 County Rd, Sheffield, MA 01257

  Welcome to Brookland, an enchanting property of 23 acres surrounded by the Ironwork Brook. A truly move in ready home, this modern family compound has been gut renovated to the highest standards using custom Danby marble, handmade brass Italian lighting and custom cabinetry. The main house with three bedrooms and two and a half baths has oak flooring throughout, patio access from the main living

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  246 County Rd, Sheffield, MA 01257
• 

  

  /43

  Est $490,508 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,202 Sq Ft

  728 Hewins St, Sheffield, MA 01257

  728 Hewins St, Sheffield, MA 01257
• 

  

  /22

  $285,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  339 Alum Hill Rd, Sheffield, MA 01257

  Opportunity awaits the next owners of this privately situated 3 bedroom, 1.5 bath raised ranch. The first floor offers an easy layout of kitchen, laundry room, living room and three bedrooms, one with a private half bath and shared hall full bath. The lower level offers additional unfinished space for expansion and/or storage. The house is ready for updating and will make a great first, second,

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 600-0094

  339 Alum Hill Rd, Sheffield, MA 01257
• 

  

  /34

  $795,000 Sold Jun 09, 2025

  • 2,633 Sq Ft
  • $302/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1949

  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
• 

  

  /22

  Est $606,137 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
• 

  

  /44

  $999,000 Pending

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

  1166 Rannapo Rd, Sheffield, MA 01257

  It's no wonder why this property is the home of Berkshire county's oldest elm tree! The abundant sunshine, quietude and peace would make anybody want to set down roots and stay a while. This light filled home has refinished wood floors throughout the main level. Kitchen has granite counters, ample cabinet space, pantry and large island. As part of the open floor plan there is a bright dining

  Grace Golden EQUINE HOMES REAL ESTATE, LLC

  1166 Rannapo Rd, Sheffield, MA 01257
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  /33

  $675,000 Sold May 16, 2025

  • 2,576 Sq Ft
  • $262/SF
  • 34 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2002

  1105 Boardman St, Sheffield, MA 01257

  This contemporary Saltbox home offers 2,576 sq ft of living space and sits on a flat, dry, level acre with views of open fields and mountains, just five minutes from Great Barrington. A perfect country escape, the home is move-in ready, featuring a vaulted ceiling in the living room with a gas fireplace, and glass doors that open to a spacious deck facing west, perfect for enjoying stunning

  William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1105 Boardman St, Sheffield, MA 01257
• 

  

  /29

  Est $531,082 Not Listed For Sale

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

  24 Cactus St, Sheffield, MA 01257

  24 Cactus St, Sheffield, MA 01257
• 

  

  /9

  $379,500 Pending

  • 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
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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
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  /4

  Est $628,426 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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  /34

  $775,000

  • 4 Beds
  • 2 Baths
  • 2,310 Sq Ft

  662 Foley Rd, Sheffield, MA 01257

  Nature-Lover's Retreat Enjoy the best of country living on 4.55 acres in Sheffield. Tucked away, this sunlit Cape offers privacy, and timeless charm. A wooded drive leads to a 4-bed, 2-bath home with 2,300 sq ft of living space and a warm, open-concept layout featuring wood-beamed ceilings and a spacious great room addition. The second-floor primary suite offers a peaceful escape, while the

  Claire Pollart LANCE VERMEULEN RE, INC

  662 Foley 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
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  /7

  Est $780,286 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
• 

  

  /40

  $1,240,000

  • 5 Beds
  • 4.5 Baths
  • 3,100 Sq Ft

  60 Parsley Ln, Sheffield, MA 01257

  Nestled at the end of a quiet country cul-de-sac, this newly built 5-bedroom, 4.5-bath home embodies refined country living. A dramatic primary suite offers dual walk-in closets and a spa-inspired bath with soaking tub, while a first-floor ensuite bedroom enhances comfort and flexibility. The gas fireplace living room and chef's kitchen create a seamless flow for entertaining, extending to a

  Vashti Poor LANCE VERMEULEN RE, INC

  60 Parsley Ln, Sheffield, MA 01257
• 

  

  /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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  /48

  Est $1,592,004 Not Listed For Sale

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

  452 Shunpike Rd, Sheffield, MA 01257

  452 Shunpike Rd, Sheffield, MA 01257
• 

  

  /75

  $895,000

  • 9 Beds
  • 7 Baths
  • 5,267 Sq Ft

  567 S Main St, Sheffield, MA 01257

  Charming Multi-Home Property in Sheffield. Welcome to a rare homestead tucked away on 11 acres of peace and privacy in Sheffield. This inviting property offers an ideal setup for multi-generational living or families seeking extra space and privacy. Main House with (4) 1BR and (1) 2BR apartments, a second 3 BR home, and a three-bay garage. A short drive to Great Barrington (15 mins) and North

  Claire Pollart LANCE VERMEULEN RE, INC

  567 S Main St, Sheffield, MA 01257
• 

  

  /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
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  /36

  Est $377,940 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,379 Sq Ft

  1014 Salisbury Rd, Sheffield, MA 01257

  1014 Salisbury Rd, Sheffield, MA 01257
• 

  

  /17

  $845,000

  • 3 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  1786 S Undermountain Rd, Sheffield, MA 01257

  Classic 3-Bedroom Cape with Pool Perfectly positioned between NW Connecticut and Sheffield, MA in the Berkshires. Sheffield is the oldest Town in Berkshire County - the township was purchased in 1724 from Chief Konkapot and other Stockbridge Native Americans. This bright, lovely 3-Bedroom Cape features a beautiful, heated pool, a Bedroom and Full Bath on the Main Floor, 2 Bedrooms and another

  Juliet Moore Elyse Harney Real Estate

  1786 S Undermountain 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
• 

  

  /40

  Est $405,568 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
• 

  

  /54

  $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
• 

  

  /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
• 

  

  /42

  Est $437,893 Not Listed For Sale

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

  505 Sheffield Plain, Sheffield, MA 01257

  505 Sheffield Plain, 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
• 

  

  /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
• 

  

  /56

  Est $1,147,919 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,929 Sq Ft

  49 Bow Wow Rd, Sheffield, MA 01257

  49 Bow Wow Rd, 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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  /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
• 

  

  /36

  Est $796,716 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
• 

  

  /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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