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Explore Similar Condos Within 2 Miles of Cheshire, MA

  • /19

    $819,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    5 Aspen Way, Pittsfield, MA 01201

    Great opportunity to design your 2000 sq ft free-standing condo home at Berkshire Country Meadows! This is one of only three remaining homesites in this established condo community. Select from a several floor plans with contemporary design, featuring one-level living. Primary suite, one-two additional bedrooms, central a/c, gas heat, screened porch, two car garage. On-site amenities include

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    5 Aspen Way, Pittsfield, MA 01201
  • /46

    $649,000

    • 3 Beds
    • 2 Baths
    • 2,030 Sq Ft

    14 Sunrise Cir, Pittsfield, MA 01201

    Immaculate and beautifully updated free-standing home offering effortless one-level living. The open-concept floor plan seamlessly connects the living, dining, kitchen, and den areas, all enhanced by abundant windows that fill the space with natural light. The chef's kitchen features quartz countertops, stainless steel appliances, and a generous center island ideal for entertaining. Three

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    14 Sunrise Cir, Pittsfield, MA 01201
  • /35

    $249,500

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft

    580 S Main St Unit Building 1, Unit 6, Lanesborough, MA 01237

    Unmatched stunning lake and mountain views! This renovated second-level one-bedroom, one-bath unit boasts easy living with open common spaces and private condo association dock spaces on Pontoosuc Lake. Great central location to enjoy cultural attractions here in the Berkshires! The owner has already taken care of the $20,000 special assessment and will be gifting a boat dock to the new owner.

    Brandon White COHEN & WHITE ASSOCIATES

    580 S Main St Unit Building 1, Unit 6, Lanesborough, MA 01237
  • /31

    $799,000 New Construction

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    15 Cherry Hill Dr, Pittsfield, MA 01201

    Berkshire Country Meadows single-family condo almost ready for occupancy. Seeking single level living? Compare this for value! 2000 sq ft, 3 br, 2 bath, central a/c, natural gas heat, gas fireplace hardwood flooring, screened porch, large basement offers expansion possibilities, and a two-car garage. Still time to make some custom finishes. Established condo community with pool, tennis, and

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    15 Cherry Hill Dr, Pittsfield, MA 01201

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
$416,500
Median Single Family Sale Price
$389,900
Average Price Per Sq Ft
$196
Number of Homes for Sale
4
Last 12 months Home Sales
37
Months of Supply
1.30
Median List Price
$425,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
10%
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