1,939

Sheffield, MA Homes

Section Image
    • /50

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,508 Sq Ft

      250 E Main St, Ashley Falls, MA 01222

      250 E Main St, Ashley Falls, MA 01222
  • /5

    $297,000

    • Land
    • 36 Acres
    • $8,303 per Acre

    0 County Rd, Sheffield, MA 01257

    Sheffield Woodland with Potential Views - Located off Bucolic County Road, just minutes from Sheffield Center this lovely 35.77-acre wooded parcel has a substantial elevation of over 1000 ft. The property is currently wooded with multiple hardwoods perfect for timbering to clear a home site. The property with clearing has south and western exposure. The well-drained soil has been perc'd and will

    Elyse Morris ELYSE HARNEY REAL ESTATE

    0 County Rd, Sheffield, MA 01257
  • /46

    $2,300,000 Sold Aug 20, 2024

    • 3,000 Sq Ft
    • $767/SF
    • 88 Days On Market
    • 3 Beds
    • 4.5 Baths
    • Built 2016

    403 S Undermountain Rd, Sheffield, MA 01257

    UNDERMOUNTAIN HOUSE. Nestled beneath majestic views of Mt. Everett, this stunning modern barn-style home floats above the landscape. A boulder strewn rain garden creates a covered bridge effect. Clad in ebony stained cypress and stone with a standing seam metal roof, this award winning house has wonderful privacy with views of a wildlife pond and a fruit orchard. The house has an open

    Tom Lynch COMPASS MASSACHUSETTS , LLC GB

    403 S Undermountain Rd, Sheffield, MA 01257
  • /39

    $1,495,000

    • 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

    $980,000 Sold Aug 15, 2024

    • 2,289 Sq Ft
    • $428/SF
    • 116 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1764

    960 S Undermountain Rd, Sheffield, MA 01257

    Own a piece of History in this pristine setting. A Charming 4-Bedroom 3-Bathroom home situated adjacent to hundreds of preserved land on one of Southern Berkshires most revered scenic roads. The current owners have preserved and updated the property with Marvin triple-grazed windows, new cotton insulation, energy efficient heat pumps and 2-zone forced air furnace. The exterior has new cedar clap

    Mark Rosengren LANCE VERMEULEN RE, INC

    960 S Undermountain Rd, Sheffield, MA 01257
    • /24

      Est $315,403 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,412 Sq Ft

      269 E Main St, Ashley Falls, MA 01222

      269 E Main St, Ashley Falls, MA 01222
  • /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
  • /56

    $1,120,000 Sold Jul 31, 2024

    • 2,929 Sq Ft
    • $382/SF
    • 15 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1941

    49 Bow Wow Rd, Sheffield, MA 01257

    49 Bow Wow - A Gilligan Brothers Masterpiece on 30+ Acres!Set on over 30 acres of stunning meadows, mountain, pond access, and forest, the Gilligan family home at 49 Bow Wow Rd comes to the market for the first time.In the second half of the 20th century, the Gilligan Brothers name was synonymous in southern Berkshire County with a quality built home. Founded by three brothers - Matthew, William,

    Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    49 Bow Wow Rd, Sheffield, MA 01257
    • /33

      Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 5,000 Sq Ft

      554 Sheffield Egremont Rd, Sheffield, MA 01257

      554 Sheffield Egremont Rd, Sheffield, MA 01257
  • /33

    $695,000 Pending

    • 3 Beds
    • 3.5 Baths
    • 2,576 Sq Ft

    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
  • /39

    $5,350,000 Sold Jul 31, 2024

    • 5,850 Sq Ft
    • $915/SF
    • 1149 Days On Market
    • 11 Beds
    • 5.5 Baths
    • Built 1983

    2080 S Undermountain Rd, Sheffield, MA 01257

    This spectacular 85+/- acre property is a destination Educational Center. It offers a magnificent 1880 Manor House, with spectacular distant Views, a Pond, and 11 additional buildings which house an Auditorium, Group Meeting Areas, Breakout Private Offices, a Fitness Center, Pondside Cottage, huge Dining Hall with Commercial Kitchen, and accommodations in over 56 Guest Rooms. The land is made up

    Juliet Moore ELYSE HARNEY REAL ESTATE

    2080 S Undermountain Rd, Sheffield, MA 01257
    • /26

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,879 Sq Ft

      1720 Home Rd, Sheffield, MA 01257

      1720 Home Rd, Sheffield, MA 01257
  • /3

    $39,000 Pending

    • Land
    • 1.00 Acre
    • $39,000 per Acre

    Unlisted Address

    Sandra Preston FAIRGROUND REAL ESTATE, INC

    Unlisted Address
  • /48

    $1,540,000 Sold Jul 26, 2024

    • 2,800 Sq Ft
    • $550/SF
    • 25 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1986

    452 Shunpike Rd, Sheffield, MA 01257

    This timeless and well-loved residence offers 3 spacious bedrooms and 3.5 luxurious bathrooms, all set against the backdrop of breathtaking views and spectacular sunsets. The beautifully landscaped property features a large variety of flora and charming stone walls and details, creating an inviting and serene atmosphere. Step inside the main living area, where you'll find a convenient mudroom

    Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    452 Shunpike Rd, Sheffield, MA 01257
    • /42

      Est $298,477 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,193 Sq Ft

      272 Clayton Rd, Ashley Falls, MA 01222

      272 Clayton Rd, Ashley Falls, MA 01222
  • /59

    $2,295,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,150 Sq Ft

    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
  • /44

    $1,300,000 Sold Jul 16, 2024

    • 2,644 Sq Ft
    • $492/SF
    • 41 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1969

    42 Valley View Rd, Sheffield, MA 01222

    An idyllic setting on 8.34 acres w/panoramic views of lush meadows and protected land. With frontage on the Konkapot River, this is a serene retreat just 15 min from Great Barrington and the rolling hills of Litchfield County. The one level home has a thoughtful layout with a dedicated primary wing and 2 guest bedrooms conveniently located on the opposite side of the house. The heart of the home

    Kate Lascar COMPASS MASSACHUSETTS , LLC GB

    42 Valley View Rd, Sheffield, MA 01222
    • /20

      Est $318,033 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft

      44 Woodedge Ln, Sheffield, MA 01257

      44 Woodedge Ln, Sheffield, MA 01257
  • /40

    $1,250,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 2,100 Sq Ft

    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
  • /19

    $486,000 Sold Jul 15, 2024

    • 2,220 Sq Ft
    • $219/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    285 Salisbury Rd, Sheffield, MA 01257

    Privately situated, a property offering plenty of sunny open space, in a most convenient location. The sprawling floor plan maintains a cozy feel, extending to the outdoors whether relaxing on the deck or enjoying the natural surroundings from your screened porch. Open concept living, with an updated kitchen, Dining Room with pellet stove, and a Living area with vaulted ceiling. 3 Bedrooms, 1.5

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    285 Salisbury Rd, Sheffield, MA 01257
    • /37

      Est $499,043 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,225 Sq Ft

      88 Hillside Ln, Ashley Falls, MA 01222

      88 Hillside Ln, Ashley Falls, MA 01222
  • /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
  • /40

    $695,000 Sold Jul 03, 2024

    • 1,792 Sq Ft
    • $388/SF
    • 171 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1991

    647 Silver St, Sheffield, MA 01257

    Welcome to your dream retreat on one of the prettiest roads in south Berkshire. This charming log cabin exudes warmth and character, featuring two inviting porches with breathtaking views of the surrounding landscape. The large kitchen boasts lovely views, handmade cabinetry, granite tops and ample built in storage. The Updated baths seamlessly blend modern convenience with rustic charm. With 2

    Tony Segalla LANCE VERMEULEN RE, INC

    647 Silver St, Sheffield, MA 01257
    • /19

      Est $599,075 Not Listed For Sale

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

      20 Hillside Ln, Sheffield, MA 01222

      20 Hillside Ln, Sheffield, MA 01222
  • /54

    $1,550,000 Sold Jun 26, 2024

    • 3,500 Sq Ft
    • $443/SF
    • 75 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1989

    199 Hickey Hill Rd, Sheffield, MA 01257

    At the end of a long tree lined driveway, you'll find a fabulous 4 bedroom, 5 bath Dutch Gambrel with detached garage only minutes to Great Barrington. This spacious home is set on almost 5 sunny acres, which include a possible abutting building lot. This place has it all - great entertaining spaces, perfect cook's kitchen, fireplaces and private and peaceful outdoor gardens, along with a

    Claire Pollart LANCE VERMEULEN RE, INC

    199 Hickey Hill Rd, Sheffield, MA 01257
    • /28

      Est $565,409 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,664 Sq Ft

      1741 Home Rd, Great Barrington, MA 01230

      1741 Home Rd, Great Barrington, MA 01230
  • /87

    $525,000 Sold Jun 25, 2024

    • 6,105 Sq Ft
    • $86/SF
    • 283 Days On Market
    • 8 Beds
    • 4.5 Baths
    • Built 1774

    616 Sheffield Plain, Sheffield, MA 01257

    This Pre Revolutionary War home is one of the oldest estates in Sheffield (1774) It has been expanded over the years to 6000 sqft. There is also a very charming carriage house on the property as well. This magical property has tons of potential. Zoned mixed use, this home consists of 6 bedrooms, 8 fireplaces with 20 rooms. The lower level was recently opened up to expose the brickwork and post &

    Lawrence Reilly BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    616 Sheffield Plain, Sheffield, MA 01257
    • /62

      Est $1,121,614 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,886 Sq Ft

      1194 Ashley Falls Rd, Sheffield, MA 01222

      1194 Ashley Falls Rd, Sheffield, MA 01222
  • /31

    $426,650 Sold Jun 24, 2024

    • 1,670 Sq Ft
    • $255/SF
    • 7 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    166 Berkshire School Rd, Sheffield, MA 01257

    Enter the front door through a quaint front porch, into a front parlor with a beautiful picture-frame oak floor. Nearby is the kitchen with pantry and adjoining dining room, as well as a generously sized full bath with both shower and separate soaking tub. At the rear of the house down a small staircase is a spacious Family room with a propane stove hearth, perfect for entertaining. Three

    Mary Naylor LANCE VERMEULEN RE, INC

    166 Berkshire School Rd, Sheffield, MA 01257
    • /71

      Est $526,104 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,500 Sq Ft

      1354 County Rd, Great Barrington, MA 01230

      1354 County Rd, Great Barrington, MA 01230
  • /2

    $90,000 Sold Jun 10, 2024

    • Land
    • 3.60 Acres
    • $25,000 per Acre
    • 11 Days On Market

    Unlisted Address

    3.6 surveyed , level, mostly open fields.Lovely building lot!

    Sandra Preston FAIRGROUND REAL ESTATE, INC

    Unlisted Address
    • /28

      Est $548,219 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,156 Sq Ft

      508 Polikoff Rd, Sheffield, MA 01222

      508 Polikoff Rd, Sheffield, MA 01222
    • /28

      Est $533,866 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,224 Sq Ft

      467 Berkshire School Rd, Sheffield, MA 01257

      467 Berkshire School Rd, Sheffield, MA 01257
    • /47

      Est $883,316 Not Listed For Sale

      • 9 Beds
      • 8.5 Baths
      • 5,358 Sq Ft

      59 Main St, Sheffield, MA 01257

      59 Main St, Sheffield, MA 01257
    • /28

      Est $441,969 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,232 Sq Ft

      90 Cobble Ln, Sheffield, MA 01257

      90 Cobble Ln, Sheffield, MA 01257
    • /13

      Est $422,025 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,572 Sq Ft

      118 Clayton Rd, Sheffield, MA 01222

      118 Clayton Rd, Sheffield, MA 01222
    • /17

      Est $685,882 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft

      974 Berkshire School Rd, Sheffield, MA 01257

      974 Berkshire School Rd, Sheffield, MA 01257
    • /10

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
    • /42

      Est $380,727 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,476 Sq Ft

      106 Blair Ln, Sheffield, MA 01257

      106 Blair Ln, Sheffield, MA 01257

Showing Results 81 - 120, Page 3 of 18

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