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Sheffield, MA Homes for Sale

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  • /68

    $949,000

    • 5 Beds
    • 5 Baths
    • 5,466 Sq Ft

    130 S Main St, Sheffield, MA 01257

    A rare opportunity to become the next steward of a remarkable piece of Sheffield history. Dating to 1819 and prominently located on South Main Street in Sheffield's Historic District, this extraordinary antique is filled with the character, warmth and craftsmanship of another era. 16 rooms, 5 bedrooms, multiple baths and 4 fireplaces, the home features beautiful wide-board floors, period details,

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    130 S Main St, Sheffield, MA 01257
  • /40

    $1,050,000

    • 3 Beds
    • 2 Baths
    • 2,800 Sq Ft

    128 Rannapo Rd, Sheffield, MA 01257

    Privately set on just under 7 acres, this beautifully renovated home offers the perfect combination of tranquility, privacy, and convenience. A meticulously paved circular driveway leads through elegant, iron fencing to the level, beautifully landscaped property. The home offers approximately 2,800 square feet of thoughtfully updated living space, with 3 to 4 bedrooms and 2 full baths across two

    Suzann Ward HOUSATONIC REAL ESTATE

    128 Rannapo Rd, Sheffield, MA 01257
  • /2

    $1,200,000

    • Land
    • 3.69 Acres
    • $325,203 per Acre

    Lot 2 W Sheffield Rd, Great Barrington, MA 01230

    Own a part of history..."Blue Stone Manor". Available for the first time in over twenty years. Create your own 'one of a kind' estate on a piece of the land houses the "Gilded Age Tudor" mansion that is associated with McKim, Mead & White. West Sheffield Road is one of Great Barrington's most picturesque country Road. Offering a quintessential Berskhires landscape of rolling meadows, mature

    Shelly Tretter Lynch Kinlin Grover Compass

    Lot 2 W Sheffield Rd, Great Barrington, MA 01230
  • /27

    $449,000

    $30K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,765 Sq Ft

    107 S Main St, Sheffield, MA 01257

    The Hatfield House : A rare 1793 Sheffield antique offering a unique renovated live/work opportunity, move-in ready; the main residence blends historic character including a sealed basement, new 3 bedroom Septic.. A separate one-bedroom apartment with its own entrance provides income or guest flexibility.Set on 1.5 acres with protected wetland views, commercial/residential zoning allows

    Judi Panzano HOUSATONIC REAL ESTATE

    107 S Main St, Sheffield, MA 01257
  • /35

    $599,000

    $26K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,822 Sq Ft

    1862 Home Rd, Great Barrington, MA 01230

    Bordering protected land and moments from the Appalachian Trail, this light-filled contemporary offers privacy, comfort, and an easy connection to the natural beauty of the Berkshires. Set on one acre in a peaceful Sheffield location, the home features vaulted ceilings, open gathering spaces, and a flexible layout designed for both everyday living and entertaining.The spacious kitchen

    Lisa Crawford BIRCH PROPERTIES

    1862 Home Rd, Great Barrington, MA 01230
  • /21

    $110,000

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

    730 Clayton Rd, Sheffield, MA 01222

    Set along A rural country Town road, this parcel is a mixture of lightly wooded flat ground adjacent to/with a bog which is home to a mixture of frogs, a heron or two and other 'seasonal' visitors. Of the 7.2+- acres (the parcels total size) approximately 2.5 acres is a mostly flat zone in within which a home could be located. While approved for same back around the turn of tis century, all

    Robin Leech Robinson Leech Real Estate

    730 Clayton Rd, Sheffield, MA 01222
  • /6

    $1,750

    • 1 Bed
    • 1 Bath

    150 Water Farm Rd, Sheffield, MA 01257

    Terrific One Bedroom Garage Apartment in Sheffield. Nice neighborhood. You pick it; furnished or unfurnished. Minimum Lease Period is six (6) months.

    George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    150 Water Farm Rd, Sheffield, MA 01257
  • /30

    $649,000

    • 5 Beds
    • 3 Baths
    • 2,710 Sq Ft

    6 Redwood Ln, Sheffield, MA 01257

    A compelling multi-family opportunity in move-in condition, offering comfortable living space with the added flexibility of rental income or accommodations for extended family. The property also features a barn and access to a nearby pond for fishing and kayaking. Sheffield Center is approximately two miles away, offering local restaurants, the Bushnell-Sage Library, the Sheffield Historical

    Timothy Wighton STONE HOUSE PROPERTIES, LLC

    6 Redwood Ln, Sheffield, MA 01257
  • /30

    $673,000

    $22K PRICE DROP
    • 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

    Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

    1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
  • /72

    $1,185,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    249 Boardman St, Sheffield, MA 01257

    Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the

    Claudia Laslie WILLIAM RAVEIS - BERKSHIRE

    249 Boardman St, Sheffield, MA 01257
  • /55

    $549,000

    $100K PRICE DROP
    • 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

    Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

    168 Main St, Sheffield, MA 01257
  • /26

    $429,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,258 Sq Ft

    689 N Main St, Sheffield, MA 01257

    Completely renovated and exceptionally versatile, this spacious 3-bedroom ranch is located in desirable Sheffield, MA. Set on a .50-acre commercially zoned lot just a 5 minute drive to downtown GB, the property offers outstanding live/work, investment, or business potential.The 2,258 sq. ft. main residence features 3 spacious bedrooms, a large new kitchen, full bath, washer/dryer, and

    Judi Panzano HOUSATONIC REAL ESTATE

    689 N Main St, Sheffield, MA 01257
  • /65

    $2,095,000

    $55K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,461 Sq Ft

    304 Hickey Hill Rd, Sheffield, MA 01257

    This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added.Step inside to find timeless Colonial charm--exposed beams, three original fireplaces, and

    Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

    304 Hickey Hill Rd, Sheffield, MA 01257
  • /51

    $639,000

    • 3 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    1741 Home Rd, Sheffield, MA 01257

    This charming Colonial is set back from the road and perched on a hill overlooking a beautiful, sun-filled yard. The private setting features mature landscaping, including apple, peach, and cherry trees, a lovely garden, and a wonderful patio perfect for relaxing or entertaining. Inside, enjoy the open living, kitchen and dining , heated sunroom, bonus room off the kitchen for an office, playroom

    Matt Carlino MACCARO REAL ESTATE

    1741 Home Rd, Sheffield, MA 01257
  • /13

    $325,000

    $4K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,485 Sq Ft

    254 Main St, Sheffield, MA 01257

    Step into a canvas of timeless character in this Historic Colonial, originally built and occupied by Nathaniel Austin,a surveyor who was instrumental in mapping and settling Berkshire County, situated in the town of Sheffield. This 5-bedroom, 2-bathroom residence offers a rare opportunity to restore a piece of Berkshire County history while imprinting your own vision on its enduring architecture.

    Eric Steuernagle FAIRGROUND REAL ESTATE, INC

    254 Main St, Sheffield, MA 01257
  • /66

    $4,500,000

    • 5 Beds
    • 5 Baths
    • 4,700 Sq Ft

    729 Hewins St, Sheffield, MA 01257

    Marcel Breuer partner Tician Papachristou designed this home as a private paradise for his three-generation family: a long driveway leads past a tennis court, guest house, swimming pool, gazebo, and gym shed to a three-level modern house evoking the New England barn. From the third-floor master loft suite with private terrace and kitchenette, a skylit central stair leads to the mid-level

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    729 Hewins St, Sheffield, MA 01257
  • /45

    $849,000

    $50K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,748 Sq Ft

    594 Shunpike Rd, Sheffield, MA 01257

    Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access to a wrap-around

    John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    594 Shunpike Rd, Sheffield, MA 01257
  • /33

    $775,000

    Open Sun 12PM - 3PM
    • 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

    David Taylor ELYSE HARNEY REAL ESTATE

    86 Main St, Sheffield, MA 01257
  • /37

    $2,595,000

    • 5 Beds
    • 4.5 Baths
    • 6,906 Sq Ft

    547 Under Mountain Rd, Salisbury, CT 06068

    The Yellow House is a warm and gracious country retreat set amid an extraordinary natural landscape at the gateway to the Berkshires. Just minutes from the charming villages of Salisbury, Lakeville, Norfolk, Sheffield and Great Barrington, the property offers easy access to the exceptional cultural, culinary, and recreational offerings of the Massachusetts-Connecticut border. Set against a

    Stacey Matthews W. Raveis Lifestyles Realty

    547 Under Mountain Rd, Salisbury, CT 06068

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.

Sheffield, MA Home Prices

Sheffield, MA
Median Home Price
$775,000
Median Sale Price
$720,000
+26% YoY
Avg. Price per Square Foot
$335
Median Single Family Price
$787,500
Median Townhouse Price
$749,000
Total Active Listings
19 listings
Market Conditions
5 Months of Supply
Balanced Market

Frequently Asked Questions

What is the average home price in Sheffield, MA?
Homes for sale in Sheffield, MA have an average home price of $987,070.
How many homes have sold over the last 12 months in Sheffield, MA?
29 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 01257, 01230, 01259, 01258 and 06068.
How much do you need to make to afford a house in Sheffield?
The median home price in Sheffield is $775,000. If you put a 20% down payment of $155,000 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $4,100 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $176K a year to afford the median home price in Sheffield. Learn how much home you can afford with our Home Affordability Calculator.
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 Muddy Brook Regional Elementary School. Browse all the schools in Sheffield, MA to learn more.
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