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Explore Similar Condos Within 2 Miles of Cheshire, MA

  • 580 S Main St Unit 2-1, Lanesborough, MA 01237
    580 S Main St Unit 2-1, Lanesborough, MA 01237
    580 S Main St Unit 2-1, Lanesborough, MA 01237
    /19

    $159,900

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft

    580 S Main St Unit 2-1, Lanesborough, MA 01237

    Affordable Lakeside Living, 1st Floor, Corner Unit Condo on Beautiful Pontoosuc Lake! Ideally Situated in Building 2, Unit 1, Offers an Open-Concept Layout with Modern Updates for Easy, Low-Maintenance Living. This 1 Bedroom, 1 Bath Unit Includes Extra Bonuses Like a Convenient In-Unit Washer & Dryer Plus 2 Private Storage Units & Semi-Furnished. Relax on the Expansive Back Deck (9'x24') with

    Kim Gordnier RE/MAX COMPASS

    580 S Main St Unit 2-1, Lanesborough, MA 01237
  • 19 Aspen Way, Pittsfield, MA 01201
    19 Aspen Way, Pittsfield, MA 01201
    19 Aspen Way, Pittsfield, MA 01201
    /41

    $965,000

    • 3 Beds
    • 3 Baths
    • 4,024 Sq Ft

    19 Aspen Way, Pittsfield, MA 01201

    Live the lifestyle you deserve in this stunning 4-year-young detached single family condominium offering over 4,000 square feet of luxury! This 3-bed, 3-bath home features a gourmet kitchen with quartz counters, custom cooktop and hood and double ovens. Perfect for the Chef of the family. The home gym with sauna, and a spacious walkout lower level with game room and bar is the perfect space for

    Victoria Standring LAMACCHIA REALTY, INC

    19 Aspen Way, Pittsfield, MA 01201
  • 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
    /18

    $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

    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
    /20

    $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 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
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