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Explore Similar Condos Within 2 Miles of Cheshire, MA

  • 580 S Main St Unit 210, Lanesborough, MA 01237
    580 S Main St Unit 210, Lanesborough, MA 01237
    580 S Main St Unit 210, Lanesborough, MA 01237
    /43

    $169,900

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft

    580 S Main St Unit 210, Lanesborough, MA 01237

    Whether you're looking for a full time residence or a weekend getaway, you can look forward to enjoying beautiful views of the lake, mountains and sunsets from the deck of this desirable second floor ''End Unit''. It features an open floor plan for a comfortable relaxed lifestyle. Upgrades include Kitchen countertop and flooring. Access door is right at the foot of your back stairs to your

    Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

    580 S Main St Unit 210, Lanesborough, MA 01237
  • 15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201
    15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201
    15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201
    /31

    $799,000

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

    15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201

    Looking to have your new home in the new year? This Berkshire Country Meadows single-level living condo will be ready for summer 2025 occupancy! Construction is well underway for this 2000sf, 3 bedroom, 2 bath stand-alone condo, but there is still time to make your own personalized selections! Central a/c, natural gas heat, gas fireplace, hardwood floors, two car garage. The condo community

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    15 Cherry Hill Dr Unit Lot 12, Pittsfield, MA 01201
  • 5 Aspen Way Unit 17, Pittsfield, MA 01201
    5 Aspen Way Unit 17, Pittsfield, MA 01201
    5 Aspen Way Unit 17, Pittsfield, MA 01201
    /19

    $799,000

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

    5 Aspen Way Unit 17, Pittsfield, MA 01201

    Great opportunity to custom design your 2000 square foot free-standing condo home at Berkshire Country Meadows! This is one of only a few remaining sites in this established community. Close to Pontoosuc Lake and centrally located for all Berkshire attractions. Association has a club house with fitness equipment, pool and tennis. Select from several floor plans which feature a contemporary

    Pamela Roberts ROBERTS & ASSOC. REALTY, INC

    5 Aspen Way Unit 17, Pittsfield, MA 01201
Massachusetts Berkshire County Cheshire

Condos for Sale in Cheshire, MA

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.

Learn more about living in Cheshire

Home Trends in Cheshire, MA

On average, homes in Cheshire, MA sell after 44 days on the market compared to the national average of 53 days. The median sale price for homes in Cheshire, MA over the last 12 months is $376,025, up 21% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$376,025
Median Single Family Sale Price
$387,931
Average Price Per Sq Ft
$195
Number of Homes for Sale
5
Last 12 months Home Sales
40
Months of Supply
1.50
Median List Price
$399,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
21%
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