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Cheshire, MA Homes for Sale

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  • /29

    $389,900

    • 3 Beds
    • 2 Baths
    • 2,747 Sq Ft

    18 W Mountain Rd, Cheshire, MA 01225

    Discover the warmth and character of this inviting post and beam home, showcasing wood floors and cozy fireplaces that create the perfect setting for comfortable living. A walk-up attic offers exciting potential for additional space, while the oversized garage provides ample storage for vehicles, hobbies, and equipment. Set on just over an acre, the property also features a seasonal cabin with

    Robin Moore 413 REAL ESTATE

    18 W Mountain Rd, Cheshire, MA 01225
  • /2

    $599,000

    • Land
    • 1.7 Acres
    • $352,353 per Acre

    12 South St, Cheshire, MA 01225

    Property on corner of busy 4 way stoplight in the heart of town with 256 ft of frontage. High visibility and high traffic count: 11,777 on average. Multi-zoned for multiple different uses & possibilities. The source of all representations are from the seller or a public source; broker has not verified same. It is recommended that buyer independently verify all information.

    Pat Roberts STEEPLEVIEW REALTY - N. ADAMS

    12 South St, Cheshire, MA 01225
  • /37

    $539,900

    • 5 Beds
    • 3.5 Baths
    • 3,307 Sq Ft

    867 Notch Rd, Cheshire, MA 01225

    Home on a dream lot--over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous

    Mariah Worth LAMACCHIA REALTY, INC

    867 Notch Rd, Cheshire, MA 01225
  • /43

    $335,900

    • 3 Beds
    • 2 Baths
    • 1,567 Sq Ft

    1020 Sandmill Rd, Adams, MA 01220

    Welcome to this expansive ranch style home set on a peaceful acre with scenic views of a babbling brook and beautiful woodlands. Designed for easy one-level living, this home features two bedrooms and full bath in addition to a spacious primary en-suite with sliders that open to the outdoors-perfect for enjoying morning coffee or wine under the stars. The living and dinning room combination

    Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    1020 Sandmill Rd, Adams, MA 01220
  • /16

    $599,000

    • Land
    • 1.7 Acres
    • $352,353 per Acre

    12 South St, Cheshire, MA 01225

    Property on corner of busy 4 way stoplight in the heart of town with 256 ft of frontage. High visibility and high traffic count: 11,777 on average. Multi-zoned for multiple different uses & possibilities. The source of all representations are from the seller or a public source; broker has not verified same. It is recommended that buyer independently verify all information.

    Deb Trzcinski Steepleview Realty - Mass

    12 South St, Cheshire, MA 01225
  • /6

    $119,900

    • Land
    • 1.38 Acres
    • $87,047 per Acre

    Lot 9E Stewart White Rd, Cheshire, MA 01225

    Discover the perfect setting for your dream home on this gently sloping, 1.4 acre lot located in the rural countryside of Cheshire. With breathtaking views and a cleared, ready-to-build landscape, this property offers the ideal blend of privacy and natural beauty. Situated on a town-maintained road and includes drilled well and perc test.

    Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

    Lot 9E Stewart White Rd, Cheshire, MA 01225
  • /50

    $519,000

    • 4 Beds
    • 2.5 Baths
    • 2,892 Sq Ft

    268 Devonshire Dr, Cheshire, MA 01225

    Super spacious Colonial with amazing mountain views! This 4 bedroom / 3 bath home will check all of your boxes. Located towards the top of the Hutchinson Development this home boasts, an enormous primary bedroom, a wood burning fireplace, a completely finished lower level which contains the family room along with a full bath, Granite kitchen countertops, 2892 sq ft of living space, a large 2 bay

    Timothy Johnson NOCHER REALTY

    268 Devonshire Dr, Cheshire, MA 01225
  • /37

    $209,900

    • 3 Beds
    • 2 Baths
    • 2,326 Sq Ft

    971 N State Rd, Cheshire, MA 01225

    Bring your vision and restore this spacious home to its full potential. Offering 7+ rooms set on almost 1 acre of land with a wraparound front porch in the heart of Berkshire County. The generous layout offers flexibility for 3-4 bedrooms, home office space or expanded living areas. Plus, a large, detached garage. Original features and ample square footage create the perfect canvas for

    Cindy Carrigan LAMACCHIA REALTY, INC

    971 N State Rd, Cheshire, MA 01225

Why Live in Cheshire

Cheshire, Massachusetts, nestled in the scenic Berkshires, offers a quaint small-town experience with a rich history dating back to its 18th-century dairy farming roots. Known for its outdoor recreation, Cheshire is a haven for nature enthusiasts, featuring the nearly 13-mile Ashuwillticook Rail Trail and sections of the Appalachian Trail. Mount Greylock, the state's highest peak, is an 8-mile hike away, while The Cobbles offers views of the Taconic Mountains. The town hosts community events like the Appalachian Trail Community Celebration Day, enhancing its close-knit atmosphere. Housing in Cheshire includes classic New England styles such as farmhouses, Colonial Revivals, and midcentury ranches, with competitive prices lower than the state median. The Hoosac Valley Regional School District serves the area, though schools receive average ratings. Shopping and dining options are limited, with a few local businesses like Cheshire Glassworks and Common Table, a popular eatery. For more variety, residents often travel to nearby Pittsfield. Massachusetts Route 8 connects Cheshire to Pittsfield and Adams, with Albany International Airport about 50 miles away. While cell phone service can be spotty, the town's charm lies in its natural beauty and community spirit.

Frequently Asked Questions

What is the average home price in Cheshire, MA?
Homes for sale in Cheshire, MA have an average home price of $423,688.
How many homes have sold over the last 12 months in Cheshire, MA?
39 homes have sold in Cheshire, MA over the last 12 months.
What are the most popular zip codes in Cheshire, MA?
The most popular zip codes in Cheshire, MA include 01225, 01220, 01237, 01226 and 01267.
How much do you need to make to afford a house in Cheshire?
The median home price in Cheshire is $419,900. If you put a 20% down payment of $84,000 and had a 30-year fixed mortgage with an interest rate of 6%, your estimated principal and interest payment would be $2,010 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $86K a year to afford the median home price in Cheshire. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Cheshire, MA?
Cheshire, MA has highly rated public and private schools. Some of the best schools in Cheshire based on Niche Grades are Lanesborough Elementary School, Mt. Greylock Regional High School and Wahconah Regional High School. Browse all the schools in Cheshire, MA to learn more.

Home Trends in Cheshire, MA

Housing Trends

Median Sale Price
$397,000
Median Single Family Sale Price
$389,900
Average Price Per Sq Ft
$201
Number of Homes for Sale
4
Last 12 months Home Sales
39
Months of Supply
1.20
Median List Price
$419,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
4%
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