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Sheffield, MA Houses for Sale

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  • /36

    $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
  • /33

    $775,000

    • 3 Beds
    • 2.5 Baths
    • 3,082 Sq Ft

    86 Main St, Sheffield, MA 01257

    SOUTH BERKSHIRE COUNTY, UPDATED VILLAGE CENTER HOME & OFFICEThis graciously restored vintage house has all the benefits of an ideal Sheffield setting with walkability to restaurants, Bushnell-Sage Library, Dewey Hall, post office, bank, and churches. With residential/commercial zoning, the house features an above-garage private large office/studio, a 1,000 sq. ft. outbuilding with plumbing and

    David Taylor ELYSE HARNEY REAL ESTATE

    86 Main St, Sheffield, MA 01257
  • /45

    $899,000

    • 3 Beds
    • 3.5 Baths
    • 2,748 Sq Ft

    594 Shunpike Rd, Sheffield, MA 01257

    The Ultimate Berkshire Retreat: Designer Luxury with Versatile Income Potential.Experience the pinnacle of refined living in this ''essentially brand new'' masterpiece by Wingate Ltd. Spanning 2,748 sq. ft. across three levels, this reimagined residence sits on one of the Berkshires' most scenic corridors, surrounded by rolling dairy farms and dramatic mountain vistas.Designed for Luxury &

    John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    594 Shunpike Rd, Sheffield, MA 01257
  • /28

    $495,000

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

    95 Water Farm Rd, Sheffield, MA 01257

    New roof, siding, and house fully painted. Newer heating system. 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 mechanics. This home is truly move-in ready. The stonework patio

    Suzann Ward HOUSATONIC REAL ESTATE

    95 Water Farm Rd, Sheffield, MA 01257
  • /60

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft

    905 West Rd, Great Barrington, MA 01230

    Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road.

    William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    905 West Rd, Great Barrington, MA 01230
  • /43

    $429,000

    • 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
  • /29

    $365,000

    • 3 Beds
    • 1.5 Baths
    • 1,482 Sq Ft

    153 E Main St, Ashley Falls, MA 01222

    TITLE V PASSED. Mid-1960s ranch on a quiet street with nearly 1/2 acre! A perfect family home to settle down in Southern Berkshire County. Semi-finished basement is a huge bonus, plus garage and additional detached barn/workshop. Sunny, spacious and ripe with potential. Some thoughtful updates will be needed -- or move in today and make it yours!

    John Segalla HOUSATONIC REAL ESTATE

    153 E Main St, Ashley Falls, MA 01222
  • /55

    $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 WILLIAM RAVEIS - BERKSHIRE

    168 Main St, Sheffield, MA 01257
  • /40

    $970,000

    • 5 Beds
    • 4.5 Baths
    • 3,024 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 WILLIAM RAVEIS - BERKSHIRE

    60 Parsley Ln, Sheffield, MA 01257
  • /24

    $479,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 3 Baths
    • 1,765 Sq Ft

    107 S Main St, Sheffield, MA 01257

    OPEN HOUSE SAT 4/11 12-2PMStep into history with this iconic property known as ''The Hatfield's,'' a beloved antique landmark in Sheffield. Built in 1793, the original home showcases timeless charm and classic architecture. A late-1990s addition created a flexible two-family layout with a one-bedroom, easily converted back to a spacious 3-bedroom, 3-bath single-family home. Recent updates include

    Judi Panzano HOUSATONIC REAL ESTATE

    107 S Main St, 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

Why Live in Sheffield

Sheffield, Massachusetts, a rural community in the Berkshires, offers tranquility and scenic beauty with its rolling green hills and the Housatonic River Valley. Bordering Connecticut and 9 miles from the New York state line, Sheffield is known for its historic charm, including homes dating back to the 1700s. The area is ideal for outdoor enthusiasts, with attractions such as the Appalachian Trail, Mount Washington State Forest, and Race Brook Falls providing ample hiking opportunities. Winter sports are available at nearby Catamount Mountain Resort and Ski Butternut. Sheffield Town Park features Little League fields, a basketball court, and a pavilion, while the Bushnell-Sage Library offers a playground and a wildflower garden. The residential landscape includes Cape Cod, ranch-style, and contemporary homes, with properties ranging from the 1760s to modern builds. Sheffield students attend Southern Berkshire Public Schools, with the highly regarded Berkshire School also available. Dining options include the Marketplace Kitchen and Café and the Sheffield Farmers Market, which operates year-round. Sheffield is conveniently located along U.S. Route 7, providing access to Great Barrington's amenities and an hour's drive to Springfield, Hartford, or Albany. The town is also notable for the Historic Upper Sheffield Covered Bridge, the site of a government-verified UFO encounter in 1969.

Home Trends in Sheffield, MA

Housing Trends

Median Sale Price
$677,500
Median Single Family Sale Price
$677,500
Median Townhouse Sale Price
$649,000
Average Price Per Sq Ft
$330
Number of Homes for Sale
9
Last 12 months Home Sales
32
Months of Supply
3.40
Median List Price
$729,000
Median Change From 1st List Price
15%
Median Home Sale Price YoY Change
19%
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