31

Homes for Sale in 01257

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  • /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
  • /35

    $395,000

    • 3 Beds
    • 2.5 Baths
    • 3,217 Sq Ft

    2105 S Undermountain Rd, Sheffield, MA 01257

    Originally part of the Sage family farm, this 1796 Colonial offers nearly 8 acres along Sage's Ravine on the MA/CT line. With over 3,200 sq ft, 3 bedrooms, 21/2 baths, post-and-beam structure, wide-plank floors, fireplaces, and classic Colonial proportions, the home is rich with character and history. Partial updates exist, but the property is a true restoration opportunity, inviting its next

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 393-2038

    2105 S Undermountain Rd, Sheffield, MA 01257
  • /45

    $999,000

    • Land
    • 17.29 Acres
    • $57,779 per Acre

    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
  • /37

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,256 Sq Ft

    414 S Undermountain Rd, Sheffield, MA 01257

    Custom modern home with open plan living area, high ceilings and oversized windows everywhere bringing in tremendous natural light. One level living with large gorgeous marble kitchen, great working island and wall pantry. Guest wing off entry with two bedrooms and a hall bath. Entry hall has a powder room, hooks for coats and closet. The primary suite, on the south side, has french doors to

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    414 S Undermountain Rd, Sheffield, MA 01257
  • /63

    $730,000

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    461 Hulett Hill Rd, Sheffield, MA 01257

    Views galore define this Sheffield gem, situated on 1.4 acres overlooking rolling pastures, hills, and a winding stream. Built in 1990, the home exudes Shaker charm with wide plank wood floors and special touches throughout. First floor features sunny living room with wood burning fireplace and peek-a-boo TV cabinet, farm kitchen/dining area off expansive deck, powder room, boot room entry, and

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    461 Hulett Hill Rd, Sheffield, MA 01257
  • /35

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 1,866 Sq Ft

    1460 Ashley Falls Rd, Sheffield, MA 01257

    Stunning contemporary sanctuary in Ashley Falls offering perfect blend of modern design & natural surroundings. 3BR/2.5BA residence bathed in natural light. The first floor features a comfortable den, eat-in kitchen and gracious living room with marble wood burning fireplace. A thoughtfully designed floor plan flows seamlessly to outdoor spaces including large deck for al fresco dining &

    Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    1460 Ashley Falls Rd, Sheffield, MA 01257
  • /25

    $795,000

    • 3 Beds
    • 2 Baths
    • 1,730 Sq Ft

    1427 Hewins St, Sheffield, MA 01257

    Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a local custom builder, this 3-bedroom, 2-bath home sits on 1.64 private acres. The open-concept living, dining, and kitchen area flows seamlessly to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful

    Claire Pollart LANCE VERMEULEN RE, INC

    1427 Hewins St, Sheffield, MA 01257
  • /40

    $995,000

    • 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
  • /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
  • /33

    $763,000

    • 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
  • /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

    Modernist delight in a Berkshire pastoral setting. A refined retreat where every detail reflects quality and style. Designed by acclaimed architect Deby Reiser, this light-filled three-bedroom, three-bath home blends the sophistication of urban design with the calm of Berkshire countryside living. Tucked away on a quiet country road beside Moon In the Pond Farm an eco-friendly farm with peaceful

    Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

    856 Barnum St, Sheffield, MA 01257
  • /41

    $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
  • /23

    $495,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2 Baths
    • 1,531 Sq Ft

    95 Water Farm Rd, Sheffield, MA 01257

    Open House 10-11-25, 11:00-1:00. Inside pictures to follow soon. Experience the perfect blend of modern comfort and historical charm in this beautifully maintained home. Featuring 4 spacious bedrooms and 2 baths, this home offers over 1,500 sq. ft. of living space. Enjoy the character of the 1850s with updates, including new mechanicals. Freshly painted inside and out, this home is truly move-in

    Suzann Ward HOUSATONIC REAL ESTATE

    95 Water Farm Rd, Sheffield, MA 01257
  • /43

    $469,000

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

    166 Berkshire School Rd, Sheffield, MA 01257

    Nestled in Sheffield Village on 8+ acres, this charming New England farmhouse blends rustic character with modern comfort. Featuring 3 bedrooms, 2 baths, wood floors, beams, Great Room with a gas stove offers a warm inviting space Enjoy a country kitchen with a pantry. Screened in porch with outdoor patio, gardens, and two sheds for storage or hobbies. Perfect as a private sanctuary or Airbnb,

    Suzann Ward HOUSATONIC REAL ESTATE

    166 Berkshire School Rd, Sheffield, MA 01257
  • /2

    $57,900

    • Land
    • 3 Acres
    • $19,300 per Acre

    0 Alum Hill Unit 73415610, Sheffield, MA 01257

    OWNER FINANCING AVAILABLE! This 3.00-acre wooded parcel in peaceful Sheffield, MA offers the perfect setting for your Berkshires retreat or year-round home. Surrounded by natural beauty, you'll enjoy nearby attractions like Bartholomew’s Cobble, the Appalachian Trail, and the cultural gems of Great Barrington just minutes away. Sheffield is known for its small-town charm, farm-to-table dining,

    Derek Greene The Greene Realty Group

    0 Alum Hill Unit 73415610, Sheffield, MA 01257
  • /34

    $749,000 Open Sat 1PM - 2:30PM

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

    483 Home Rd, Great Barrington, MA 01230

    A Berkshire dream home! Nestled in a quiet private setting to enjoy the outdoors. This 3 bedroom 3 full bath home is empty and ready to go. Great lighting nice open kitchen dining/living area. Additional room can be used as a den or 1st floor bedroom. Wood stove insert for chilly fall nights while enjoying your 3 seasoned screened porch. Oversized 2 car garage. Full basement could be completed as

    Suzann Ward HOUSATONIC REAL ESTATE

    483 Home Rd, Great Barrington, MA 01230
  • /13

    $297,500

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft

    412 Berkshire School Rd, Sheffield, MA 01257

    1995 split level home on .50 acres walking distance to the village of Sheffield. 3 bedrooms 1 full bath....eat in kitchen, living room....unfinished lower level....electric and forced hot air propane fired heat, vinal siding......septic.(Title 5 completed)....private water company

    Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    412 Berkshire School Rd, Sheffield, MA 01257
  • /44

    $650,000

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

    649 Hewins St, Sheffield, MA 01257

    Located on a pastoral country road in Sheffield, this thoughtfully updated early 1900s farmhouse with carriage house sits on 1 open acre with sweeping views to the west of conservation land. The home blends original character withmodern touches--vaulted ceilings, exposed beams, hard wood floors, and high-end finishes throughout. In the main house a sunlit kitchen anchors the home featuring custom

    Lauren Molk ELYSE HARNEY REAL ESTATE

    649 Hewins St, Sheffield, MA 01257
  • /78

    $4,500,000

    • 4 Beds
    • 3 Baths
    • 5,256 Sq Ft

    381 Sheffield-Egremont Rd, Sheffield, MA 01257

    SPECTACULAR ONE OF A KIND BERKSHIRE PROPERTY! This compound includes an elegant and updated 4 bedroom 1759 Colonial home and fabulous RED BARN with 2 separate guest spaces. Mill pond for fishing, heated pool, patios and screen porch, 66 protected SUBDIVIDABLE ACRES...with views of Mount Washington. The perfect place to entertain friends and family. An incredible opportunity for additional

    Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    381 Sheffield-Egremont Rd, 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
  • /44

    $1,200,000

    • 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
  • /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
  • /9

    $125,000

    • Land
    • 6.12 Acres
    • $20,432 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
  • /70

    $895,000

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

    567 S Main St, Sheffield, MA 01257

    Investment opportunity in Sheffield. Versatile investment opportunity set on 11 private acres. This multi-building property, held by the same family for four decades, offers strong income potential with flexible configurations across three separate structures. Main House with (4) 1BR and (1) 2BR apartment, a second 3 BR home, and a three-bay garage. Just 15 minutes from GB and 10 minutes to

    Claire Pollart LANCE VERMEULEN RE, INC

    567 S 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

    $695,000

    • Land
    • 18 Acres
    • $38,611 per Acre

    0 Bull Hill Rd, Sheffield, MA 01257

    SIGNIFICANT PRICE REDUCTION! OWNER FINANCING AVAILABLE! Eighteen acres on the quietest 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

    Kristin Clayborne WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    0 Bull Hill Rd, 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
  • /48

    $385,000

    • 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
  • /24

    $299,900

    • 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

    $2,995,000

    • 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
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