32

Homes for Sale in 01257

Section Image Section Image
  • /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
  • /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
  • /32

    $449,000

    • 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
  • /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
  • /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
  • /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
  • /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 tucked away in a well-established Sheffield neighborhood convenient to both the Berkshires and Litchfield Connecticut. This energy-efficient home features spray foam insulation and a ductless AC/heat pump HVAC system. The open kitchen/dining area is filled with natural light, with Pella windows and sliding doors throughout. The Living Room features a

    Vashti Poor LANCE VERMEULEN RE, INC

    60 Parsley Ln, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /52

    $4,500,000

    • 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.Elegant historic estate on 66 beautiful acres 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) and game room

    Martha Piper WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    381 Egremont Rd, 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
  • /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
  • /33

    $798,000 Open Sat 11AM - 1PM

    • 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
  • /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
  • /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.

    Martha Piper WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    0 Bull Hill Rd, 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
  • /30

    $369,000

    • 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
  • /43

    $419,900

    • 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
  • /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
  • /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
  • /48

    $3,750,000

    • 4 Beds
    • 4.5 Baths
    • 5,300 Sq Ft

    116 Brush Hill Rd, Great Barrington, MA 01230

    Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout

    Mark Rosengren LANCE VERMEULEN RE, INC

    116 Brush Hill Rd, Great Barrington, MA 01230
  • /38

    $279,000

    • 2 Beds
    • 2 Baths
    • 1,659 Sq Ft

    52 Shunpike Rd, Southfield, MA 01259

    Attention investors!! Nestled on a peaceful 1-acre lot, this 2-bedroom, 2-bath Cape offers warmth, character, and SO MUCH OPPORTUNITY! A spacious kitchen with adjoining pantry and dining area provides plenty of room for gathering. The inviting living room features a chunky staircase, exposed beams and a brick hearth, perfect for a wood or pellet stove. The first floor includes a bedroom, laundry

    Chris LaPatin LAMACCHIA REALTY, INC

    52 Shunpike Rd, Southfield, MA 01259
How to Buy a Home How to Finance a Home How to Sell a Home