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Sheffield, MA Homes for Sale

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  • 64 Hewins St, Sheffield, MA 01257
    64 Hewins St, Sheffield, MA 01257
    64 Hewins St, 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

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 296-3500

    64 Hewins St, Sheffield, MA 01257
  • 119 S Main St, Sheffield, MA 01257
    119 S Main St, Sheffield, MA 01257
    119 S Main St, Sheffield, MA 01257
    /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

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 481-1637

    119 S Main St, Sheffield, MA 01257
  • 1291 Ashley Falls Rd, Sheffield, MA 01222
    1291 Ashley Falls Rd, Sheffield, MA 01222
    1291 Ashley Falls Rd, Sheffield, MA 01222
    /32

    $425,000

    • 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

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 728-1649

    1291 Ashley Falls Rd, Sheffield, MA 01222
  • 339 Alum Hill Rd, Sheffield, MA 01257
    339 Alum Hill Rd, Sheffield, MA 01257
    339 Alum Hill Rd, Sheffield, MA 01257
    /22

    $285,000

    • 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,

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 600-0094

    339 Alum Hill Rd, Sheffield, MA 01257
  • 0 S Main St, Sheffield, MA 01257
    0 S Main St, Sheffield, MA 01257
    0 S Main St, Sheffield, MA 01257
    /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 made up

    Grace Golden Equine Homes Real Estate, LLC

    0 S Main St, Sheffield, MA 01257
  • 1166 Rannapo Rd, Sheffield, MA 01257
    1166 Rannapo Rd, Sheffield, MA 01257
    1166 Rannapo Rd, Sheffield, MA 01257
    /40

    $999,000

    • 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 room

    Grace Golden Equine Homes Real Estate, LLC

    1166 Rannapo Rd, Sheffield, MA 01257
  • 662 Foley Rd, Sheffield, MA 01257
    662 Foley Rd, Sheffield, MA 01257
    662 Foley Rd, Sheffield, MA 01257
    /34

    $775,000 Open Sun 2PM - 3:30PM

    • 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
  • 20 Hillside Ln, Sheffield, MA 01222
    20 Hillside Ln, Sheffield, MA 01222
    20 Hillside Ln, Sheffield, MA 01222
    /47

    $895,000

    • 3 Beds
    • 2 Baths
    • 2,057 Sq Ft

    20 Hillside Ln, Sheffield, MA 01222

    Beautiful, light and bright open concept chalet style home with floor to ceiling windows, cathedral ceilings, woodstove, renovated kitchen with new energy efficient appliances and adjacent dining area. Main floor has 2 bedrooms and a lovely renovated full bath with a walk-in shower, and a large mudroom to store all your outdoor gear. Second floor has the primary suite with vaulted ceilings,

    Sarah Dixon LANCE VERMEULEN RE, INC

    20 Hillside Ln, Sheffield, MA 01222
  • 1900 Home Rd, Great Barrington, MA 01230
    1900 Home Rd, Great Barrington, MA 01230
    1900 Home Rd, Great Barrington, MA 01230
    /27

    $765,000

    • 4 Beds
    • 2.5 Baths
    • 2,389 Sq Ft

    1900 Home Rd, Great Barrington, MA 01230

    Nestled in one of the most desirable areas of Western Massachusetts, this spacious 4-bedroom, 3-bathroom post-and-beam home offers the perfect blend of rustic charm and modern efficiency. Thoughtfully designed with exposed wood beams, cathedral ceilings, and skylights that flood the interior with natural light, this property exudes warmth and character throughout. Set on a serene lot that abuts

    Andrew Gates Houlihan Lawrence

    1900 Home Rd, Great Barrington, MA 01230
  • 60 Parsley Ln, Sheffield, MA 01257
    60 Parsley Ln, Sheffield, MA 01257
    60 Parsley Ln, Sheffield, MA 01257
    /40

    $995,000

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

    60 Parsley Ln, Sheffield, MA 01257

    This newly constructed 5-bedroom farmhouse is priced well below the current cost to build per square foot--truly an exceptional value! Tucked away in a well-established neighborhood convenient to both the Berkshires and Litchfield Connecticut, this energy-efficient home features spray foam insulation and a ductless AC/heat pump system. The open kitchen/dining area is filled with natural light,

    Vashti Poor LANCE VERMEULEN RE, INC

    60 Parsley Ln, Sheffield, MA 01257
  • 567 S Main St, Sheffield, MA 01257
    567 S Main St, Sheffield, MA 01257
    567 S Main St, Sheffield, MA 01257
    /75

    $949,000

    • 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
  • 1786 S Undermountain Rd, Sheffield, MA 01257
    1786 S Undermountain Rd, Sheffield, MA 01257
    1786 S Undermountain Rd, Sheffield, MA 01257
    /17

    $895,000

    • 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
  • 360 Brush Hill Rd, Sheffield, MA 01257
    360 Brush Hill Rd, Sheffield, MA 01257
    360 Brush Hill Rd, Sheffield, MA 01257
    /58

    $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
  • 405 S Undermountain Rd, Sheffield, MA 01257
    405 S Undermountain Rd, Sheffield, MA 01257
    405 S Undermountain Rd, Sheffield, MA 01257
    /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
  • 594 Shunpike Rd, Sheffield, MA 01257
    594 Shunpike Rd, Sheffield, MA 01257
    594 Shunpike Rd, 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
  • 86 Main St, Sheffield, MA 01257
    86 Main St, Sheffield, MA 01257
    86 Main 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
  • 481 Shunpike Rd, Sheffield, MA 01257
    481 Shunpike Rd, Sheffield, MA 01257
    481 Shunpike Rd, Sheffield, MA 01257
    /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
  • 856 Barnum St, Sheffield, MA 01257
    856 Barnum St, Sheffield, MA 01257
    856 Barnum St, Sheffield, MA 01257
    /60

    $998,000

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

    856 Barnum St, Sheffield, MA 01257

    Modern Meets Pastoral - Architectural Gem Designed by Deby Reiser. Where cutting edge design meets countryside charm. Welcome to this stunning three bedroom, three bath modern masterpiece down a quiet dirt road, right beside a serene eco-farm where sheep and geese graze just outside your window. This reimagined 1,800 sq ft home is a rare blend of sleek sophistication and bucolic tranquility.

    Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

    856 Barnum St, Sheffield, MA 01257
  • 1669 Silver St, Sheffield, MA 01257
    1669 Silver St, Sheffield, MA 01257
    1669 Silver St, Sheffield, MA 01257
    /39

    $1,275,000

    • 4 Beds
    • 5 Baths
    • 3,528 Sq Ft

    1669 Silver St, Sheffield, MA 01257

    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

    Elyse Morris ELYSE HARNEY REAL ESTATE

    1669 Silver St, Sheffield, MA 01257
  • 52 Cooper Hill Rd, Salisbury, CT 06068
    52 Cooper Hill Rd, Salisbury, CT 06068
    52 Cooper Hill Rd, Salisbury, CT 06068
    /31

    $1,499,000

    • 3 Beds
    • 2.5 Baths
    • 3,038 Sq Ft

    52 Cooper Hill Rd, Salisbury, CT 06068

    This is a unique chance to enjoy stunning views of Bear Mountain from a contemporary home featuring expansive windows that showcase the scenery, set on nearly 20 acres that stretch across Salisbury, CT, and Sheffield, MA. The bright sunshine and lofty ceilings, along with a screened porch and two upper-level decks, seamlessly blend indoor and outdoor living in this lovely residence. The

    Holly Leibrock Elyse Harney Real Estate

    52 Cooper Hill Rd, Salisbury, CT 06068
  • 168 Main St, Sheffield, MA 01257
    168 Main St, Sheffield, MA 01257
    168 Main St, Sheffield, MA 01257
    /54

    $649,000

    • 5 Beds
    • 2.5 Baths
    • 2,750 Sq Ft

    168 Main St, Sheffield, MA 01257

    Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra

    Tony Segalla LANCE VERMEULEN RE, INC

    168 Main St, Sheffield, MA 01257
  • 2049 S Undermountain Rd, Sheffield, MA 01257
    2049 S Undermountain Rd, Sheffield, MA 01257
    2049 S Undermountain Rd, Sheffield, MA 01257
    /44

    $1,600,000

    • 9 Beds
    • 4.5 Baths
    • 8,406 Sq Ft

    2049 S Undermountain Rd, Sheffield, MA 01257

    An exceptional opportunity awaits on 11 private acres in Sheffield. This unique property, currently utilized as a functional therapy facility, offers a massive footprint and a flexible canvas for your next venture. The centerpiece is an 8,000+ sq. ft. building comprised of over 10 offices, multiple conference rooms, common areas, and three residential apartments, creating an ideal setup for a

    Tony Segalla LANCE VERMEULEN RE, INC

    2049 S Undermountain Rd, Sheffield, MA 01257
  • 1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
    1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
    1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
    /30

    $695,000

    • 3 Beds
    • 6 Baths
    • 4,044 Sq Ft

    1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222

    Old Historic Village downtown location! The centrally located Post Office building constructed in 1860, presents a unique opportunity for both residential and commercial use. Its strategic location ensures consistent foot traffic, making it an invaluable cornerstone of village life. With no mail delivery service in Ashley Falls, the Post Office attracts local residents daily. This building is

    Tony Segalla LANCE VERMEULEN RE, INC

    1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
  • 771 West Rd, Sheffield, MA 01257
    771 West Rd, Sheffield, MA 01257
    771 West Rd, Sheffield, MA 01257
    /69

    $2,450,000

    • 6 Beds
    • 8.5 Baths
    • 5,219 Sq Ft

    771 West Rd, Sheffield, MA 01257

    Down West Road, just past Wyantenuck CC, a 1,500-ft drive climbs through towering trees. At the crest of Broken Hill, where the forest gives way to wide rolling lawns, sits one of the Berkshires' finest examples of American Shingle Style architecture--5,219 sf of cedar and stone. For those who know that real luxury is quality of life, Broken Hill offers space to breathe, room to gather, and peace

    Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    771 West Rd, Sheffield, MA 01257
  • 232 Giberson Rd, Sheffield, MA 01257
    232 Giberson Rd, Sheffield, MA 01257
    232 Giberson Rd, Sheffield, MA 01257
    /53

    $3,250,000

    • 4 Beds
    • 3.5 Baths
    • 3,459 Sq Ft

    232 Giberson Rd, Sheffield, MA 01257

    The Quarry - A One-of-a-Kind Berkshire Estate on 60 Private Acres!Singular, stunning, and secluded--the quarry pool at the heart of this 60-acre Berkshire estate is truly one of its kind: the culmination of geology, industry, and artistry. Carved into a reclaimed limestone quarry and framed by towering stone walls and a 16-foot waterfall, the quarry pool is a marvel in and of itself--equal parts

    Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    232 Giberson Rd, Sheffield, MA 01257
  • 0 Amory Ln, Southfield, MA 01259
    0 Amory Ln, Southfield, MA 01259
    0 Amory Ln, Southfield, MA 01259
    /9

    $139,000

    • Land
    • 6 Acres
    • $22,720 per Acre

    0 Amory Ln, Southfield, MA 01259

    Discover the perfect setting for your custom retreat on this expansive 6+ acre lot nestled on a tranquil cul-de-sac off a scenic Berkshire country road. Located in New Marlborough, with a small portion extending into Sheffield, this beautiful parcel offers endless possibilities for your vision. Enjoy the serenity of nature, the charm of rural living, and the potential for lovely views. Whether

    Kate Lascar COMPASS MASSACHUSETTS , LLC GB

    0 Amory Ln, Southfield, MA 01259
  • 381 Egremont Rd, Sheffield, MA 01257
    381 Egremont Rd, Sheffield, MA 01257
    381 Egremont Rd, Sheffield, MA 01257
    /52

    $5,250,000

    • 4 Beds
    • 3 Baths
    • 5,000 Sq Ft

    381 Egremont Rd, Sheffield, MA 01257

    Perfect for a family compound in the Berkshires with room for expansion. Gracious historic estate on 66 beautiful acres The property including views of the Mt. Everett range. The property includes the north end of Mill Pond, a 100 lake and frontage on Hubbard Brook. Another small pond could be stocked. Restored Adirondack barn with soaring ceilings and views with two guest apartments (sleeps 10)

    Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    381 Egremont Rd, Sheffield, MA 01257
  • 649 Hewins St, Sheffield, MA 01257
    649 Hewins St, Sheffield, MA 01257
    649 Hewins St, Sheffield, MA 01257
    /59

    $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
  • 0 Bunce Rd Unit 245787, Sheffield, MA 01257
    0 Bunce Rd Unit 245787, Sheffield, MA 01257
    0 Bunce Rd Unit 245787, 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
  • 1373 Boardman St, Sheffield, MA 01257
    1373 Boardman St, Sheffield, MA 01257
    1373 Boardman St, Sheffield, MA 01257
    /61

    $2,500,000

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

    1373 Boardman St, Sheffield, MA 01257

    The ULTIMATE LIVE-WORK-PLAY RETREATStep onto a property as striking as the Berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''The Factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked

    Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    1373 Boardman St, Sheffield, MA 01257
  • 355 Clayton Rd, Sheffield, MA 01222
    355 Clayton Rd, Sheffield, MA 01222
    355 Clayton Rd, Sheffield, MA 01222
    /20

    $449,000

    • 3 Beds
    • 3 Baths
    • 6,420 Sq Ft

    355 Clayton Rd, Sheffield, MA 01222

    Opportunities and Potential abound. Set back on 6+- acres in Rural Ashley Falls. Presently Greenwoods Church, can now be yours to live and work from. The large bright and open main room is 42' x 70' with a concrete floor and forced air heat. Create the space you've envisioned for yourself and your business, the ideas are endless from continuing a place of worship, a grand home, a car collectors

    Mark Rosengren LANCE VERMEULEN RE, INC

    355 Clayton Rd, Sheffield, MA 01222
  • 1114 County Rd, Great Barrington, MA 01230
    1114 County Rd, Great Barrington, MA 01230
    1114 County Rd, Great Barrington, MA 01230
    /21

    $295,000

    • 4 Beds
    • 1 Bath
    • 1,704 Sq Ft

    1114 County Rd, Great Barrington, MA 01230

    1950's Cape on 7.5 acres along a country road. This 4 bedroom home has a main floor with nice size kitchen, dining room, living room with fireplace, 2 bedrooms and a full bath. Upstairs there are two more bedrooms and a small office and good attic storage. Screened in porch off the living room, wood floors and beautiful yard. Roof is old (estimate attached in docs), Title V failed and seller is

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    1114 County Rd, Great Barrington, MA 01230
  • 0 Bull Hill Rd, Sheffield, MA 01257
    0 Bull Hill Rd, Sheffield, MA 01257
    0 Bull Hill Rd, Sheffield, MA 01257
    /11

    $795,000

    • Land
    • 18 Acres
    • $44,167 per Acre

    0 Bull Hill Rd, Sheffield, MA 01257

    Eighteen acres on the quitest dirt road with its own exceptional landscape feature: a boulder-strewn, mossy-rocked cobble. The cobble bisects a flat, three acre cleared field to the east, and a wooded forest with old stone wall remnants to the west. Live amongst the ancient spirits in whatever beautiful house you build. Fifteen wooded acres in Chapter 61A.

    Stephanie McNair WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    0 Bull Hill Rd, Sheffield, MA 01257
  • 1699 N Main St, Sheffield, MA 01257
    1699 N Main St, Sheffield, MA 01257
    1699 N Main St, Sheffield, MA 01257
    /9

    $199,000

    • Land
    • 1.30 Acres
    • $153,077 per Acre

    1699 N Main St, Sheffield, MA 01257

    COMMERCIAL AREA ON THE SHEFFIELD/GREAT BARRINGTON LINE OFF OF BUSY ROUTE 7. SOME WETLANDS BUT A WORTHY LOCATION. NICE WITH LEVEL LAWN. THERE ARE NOT MANY LOTS LEFT ALONG THIS POPULAR COMMERCIAL CORRIDOR.

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    1699 N Main St, Sheffield, MA 01257
  • 179 S Main St, Sheffield, MA 01257
    179 S Main St, Sheffield, MA 01257
    179 S Main St, Sheffield, MA 01257
    /30

    $345,000

    • 3 Beds
    • 2.5 Baths
    • 1,536 Sq Ft

    179 S Main St, Sheffield, MA 01257

    Step back in time with this charming 1826 gem, nestled in the quiet village of Sheffield on Main Street. Featuring 3 bedrooms, 3 bathrooms, and a first-floor ensuite, this home offers classic simplicity and historical integrity. The screened-in porch is perfect for enjoying the peaceful surroundings, while the 1-car garage adds convenience. Untouched by modern trends, this property is a blank

    Tony Segalla LANCE VERMEULEN RE, INC

    179 S Main St, Sheffield, MA 01257
  • 454 Sheffield Plain, Sheffield, MA 01257
    454 Sheffield Plain, Sheffield, MA 01257
    454 Sheffield Plain, Sheffield, MA 01257
    /43

    $414,900

    • 3 Beds
    • 1.5 Baths
    • 1,617 Sq Ft

    454 Sheffield Plain, Sheffield, MA 01257

    Beautifully restored New England Farmhouse located in the quaint town of Sheffield. Exterior features fresh paint, new vinyl windows, and a new roof. Stepping inside this home has retained most of the original wide-plank hardwood flooring that has been restored on the first and second levels. Throughout the first floor there are custom updates in the half bathroom with new ceramic tiles, a new

    Cory Evangelisto NOCHER REALTY

    454 Sheffield Plain, Sheffield, MA 01257
  • 339 Clayton Rd, Sheffield, MA 01222
    339 Clayton Rd, Sheffield, MA 01222
    339 Clayton Rd, Sheffield, MA 01222
    /21

    $220,000

    • 2 Beds
    • 1 Bath
    • 1,096 Sq Ft

    339 Clayton Rd, Sheffield, MA 01222

    Fantastic Opportunity to own in well established South Berkshire neighborhood. This homes good bones and newer roof make it a perfect candidate for a fresh makeover. Level 1 acre lot and oversized 2 car garage !

    Eric Steuernagle FAIRGROUND REAL ESTATE, INC

    339 Clayton Rd, Sheffield, MA 01222
  • 730 Clayton Rd, Sheffield, MA 01222
    730 Clayton Rd, Sheffield, MA 01222
    730 Clayton Rd, Sheffield, MA 01222
    /21

    $110,000

    • Land
    • 7 Acres
    • $15,559 per Acre

    730 Clayton Rd, Sheffield, MA 01222

    This property contains a wetland suggested by some to be an official BOG; full of a bog's normal wildlife depending on the season. All earlier permits for building have expired, so new ones are required before building, including location, building, septic, and well permits. The probable building zone is an area adjacent to the bog shoreline, estimated to be around 2.5 acres, or less, as shown on

    Robin Leech Robinson Leech Real Estate

    730 Clayton Rd, Sheffield, MA 01222
  • 321 Salisbury Rd, Sheffield, MA 01257
    321 Salisbury Rd, Sheffield, MA 01257
    /2

    $249,000

    • 4 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    321 Salisbury Rd, Sheffield, MA 01257

    Attention investors! This property features a primary bedroom with a half bath, along with three additional bedrooms, offering plenty of living space. The combined two lots total 7.99 acres, providing ample room for expansion. Having been vacant for several years, this property presents a blank canvas, ready for someone with a vision to restore it to its former glory. Potential buyers should be

    Diane McDougald Berkshire Hathaway Home Service New England Properties

    321 Salisbury Rd, Sheffield, MA 01257
  • 175 Main St, Sheffield, MA 01257
    175 Main St, Sheffield, MA 01257
    175 Main St, Sheffield, MA 01257
    /24

    $339,000

    • 6 Beds
    • 5.5 Baths
    • 3,683 Sq Ft

    175 Main St, Sheffield, MA 01257

    Come this charming 1820 colonial located in Downtown Sheffield! This unique property features 6 bedrooms and 5 and half bathrooms. Lovely hardwood showcasing wide plank and parquet style floors encompass 3,683 square feet of living space. Plenty of off street parking due to the oversized driveway and 2 car attached garage with loft space. Full, unfinished basement can provide additional storage

    Nicholas Decaro Property Works New England

    175 Main St, Sheffield, MA 01257

Showing Results 1 - 40, Page 1 of 2

Massachusetts Sheffield

Real Estate & Homes for Sale in Sheffield, MA

Why Live in Sheffield

Sheffield, a rural community in Western Massachusetts, offers tranquility and historical charm. Bordering Connecticut and 9 miles from the New York state line, Sheffield is nestled in the Housatonic River Valley within the Berkshires. The area is known for its scenic beauty, with rolling green hills, winding creeks, and the Taconic Mountains. Outdoor enthusiasts can enjoy four-season recreation, including hiking the Appalachian Trail and exploring Mount Washington State Forest. Skiing is popular at Catamount Mountain Resort and Ski Butternut, which features a terrain park and tubing hill. Sheffield Town Park provides Little League fields, a basketball court, and a pavilion, while Bushnell-Sage Library offers a playground and unique items for borrowing. The architectural landscape spans over 250 years, with Cape Cod, ranch-style, and contemporary homes set on spacious lots. Southern Berkshire Public Schools serve the community, with Berkshire School being a highly regarded private boarding school. Dining options include The Marketplace Kitchen and Café and the Stagecoach Tavern at Race Brook Lodge, while the Sheffield Farmers Market offers year-round shopping. Sheffield is conveniently located along U.S. Route 7, with Fairview Hospital nearby in Great Barrington. A notable point of interest is the Historic Upper Sheffield Covered Bridge, known for the first government-verified UFO encounter in the country.
Learn more about living in Sheffield

Frequently Asked Questions

What is the average home price in Sheffield, MA?
Homes for sale in Sheffield, MA have an average home price of $1,534,897.
How many homes have sold over the last 12 months in Sheffield, MA?
19 homes have sold in Sheffield, MA over the last 12 months.
What are the most popular zip codes in Sheffield, MA?
The most popular zip codes in Sheffield, MA include 01230, 01223, 06790, 12529 and 06098.
How much do you need to make to afford a house in Sheffield?
The median home price in Sheffield is $765,000. If you put a 20% down payment of $153,000 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $3,980 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $171K a year to afford the median home price in Sheffield.
How are the schools in Sheffield, MA?
Sheffield, MA has highly rated public and private schools. Some of the best schools in Sheffield based on Niche Grades are Berkshire School, North Canaan Elementary School and New Marlborough Central School. Browse all the schools in Sheffield, MA to learn more.

Home Trends in Sheffield, MA

On average, homes in Sheffield, MA sell after 218 days on the market compared to the national average of 50 days. The median sale price for homes in Sheffield, MA over the last 12 months is $650,000, up 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$650,000
Median Single Family Sale Price
$777,500
Average Price Per Sq Ft
$397
Number of Homes for Sale
16
Last 12 months Home Sales
19
Months of Supply
10.10
Median List Price
$765,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
18%
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