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Cheshire, MA Multifamily Homes & Duplexes for Sale

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  • /26

    $159,000

    • 4 Beds
    • 2 Baths
    • 1,850 Sq Ft

    108 Church St, Cheshire, MA 01225

    Welcome to the quaint town of Cheshire, this 2-unit rental is situated in center of town convenient to coffee shop, town hall, post office, Ashuwillticook Rail Trail, local activities & more. Lower level unit is vacant - easy to show. Some charming details remain in the 2nd floor unit - tin ceiling in living room, spacious eat in kitchen. New septic system installed 2025, certificate of

    Agent Photo

    Nadine Hiser

    KRG - Key Realty Group

    (413) 481-1596

    108 Church St, Cheshire, MA 01225
  • /28

    $239,000

    • 3 Beds
    • 2 Baths
    • 1,503 Sq Ft

    139-141 Main St, Cheshire, MA 01225

    This two family is perfect for investors or those looking for a multi-generational living arrangement. Lower apartment offers two bedrooms; one full bath and the upstairs apartment offers one bedroom and one full bath all on almost an acre of land, walking distance to the Ashuwillticook Rail Trail. Don't miss out on this rare opportunity to own in the town of Cheshire where taxes are low.

    Michelle Picard NOCHER REALTY

    139-141 Main St, 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.

Home Trends in Cheshire, MA

Housing Trends

Median Sale Price
$347,525
Median Single Family Sale Price
$328,000
Median Townhouse Sale Price
$312,500
Average Price Per Sq Ft
$204
Number of Homes for Sale
2
Last 12 months Home Sales
26
Months of Supply
0.90
Median List Price
$367,500
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
20%
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