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Cheshire, MA Houses for Sale

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  • 1008 N State Rd, Cheshire, MA 01225
    1008 N State Rd, Cheshire, MA 01225
    1008 N State Rd, Cheshire, MA 01225
    /52

    $309,000

    • 3 Beds
    • 1 Bath
    • 1,297 Sq Ft

    1008 N State Rd, Cheshire, MA 01225

    Welcome to 1008 North State Road, a beautifully updated home offering the perfect blend of modern convenience and rustic charm. This recently renovated property boasts a spacious layout, updated finishes, and ample outdoor space for relaxation and recreation.Inside, you'll find a tastefully renovated kitchen featuring stainless steel appliances, granite countertops, and shaker-style cabinetry.

    Marci Levesque BISHOP WEST REAL ESTATE

    1008 N State Rd, Cheshire, MA 01225
  • 74 South St, Cheshire, MA 01225
    74 South St, Cheshire, MA 01225
    74 South St, Cheshire, MA 01225
    /39

    $315,000

    • 3 Beds
    • 2 Baths
    • 2,010 Sq Ft

    74 South St, Cheshire, MA 01225

    This spacious home has a nice size kitchen with quartz counters, lots of cabinets, dining room, fireplace living room and 3 large bedrooms. The addition on the first floor is being used as 4th bedroom with an ensuite bathroom, it can also be used for a large family room or in-law suite/guest room since it has private door entrance. Enjoy all the natural bright light coming through the many

    Toni Marie Gage SIGNATURE ASSOCIATES

    74 South St, Cheshire, MA 01225
  • 20 Pleasant View Dr, Cheshire, MA 01225
    20 Pleasant View Dr, Cheshire, MA 01225
    20 Pleasant View Dr, Cheshire, MA 01225
    /48

    $879,000

    • 4 Beds
    • 2.5 Baths
    • 2,438 Sq Ft

    20 Pleasant View Dr, Cheshire, MA 01225

    Unique home overlooking Mount Greylock range. Early morning, afternoon and evening sun fill this 4 bedroom 2.5 bathroom, open floor plan home with light all year round.The entire first floor has been renovated and now has an open floor plan with a new doublesided propane fireplace. Opportunity for single floor living exists since primary bedroom and laundry are on first floor in addition to a

    Sean Taylor MORESI REAL ESTATE PARTNERS

    20 Pleasant View Dr, Cheshire, MA 01225
  • 192 Curran Rd, Cheshire, MA 01225
    192 Curran Rd, Cheshire, MA 01225
    192 Curran Rd, Cheshire, MA 01225
    /38

    $299,999

    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    192 Curran Rd, Cheshire, MA 01225

    Artful Country Retreat! Prime Berkshire Location. Tucked away on a quiet country road in Cheshire, this turnkey 3-bedroom, 1.5-bath home offers peace, privacy, & a deep connection to nature-yet it's just a short drive to both North & South County amenities. Set on nearly 2 acres of parklike grounds featuring meandering trails, woods, perennial flowers & berry bushes, grapes & a young pear &

    Dennis D'Arcangelo MONARCH REALTY, INC.

    192 Curran Rd, Cheshire, MA 01225
  • 57 Church St, Cheshire, MA 01225
    57 Church St, Cheshire, MA 01225
    57 Church St, Cheshire, MA 01225
    /9

    $125,000

    • 3 Beds
    • 1 Bath
    • 1,681 Sq Ft

    57 Church St, Cheshire, MA 01225

    An exceptional investment property nestled in the heart of Cheshire MA. The Property has 7 rooms total . 3 bedrooms and 1 full bath. Whether you're looking to expand your rental portfolio or embark on a fix-and-flip project, this property caters to a variety of investment strategies. With its flexible layout and potential for customization there is possibility to add 4th bed and 2nd bath if town

    Letizia Dutra Cameron Real Estate Group

    57 Church St, Cheshire, MA 01225
Massachusetts Berkshire County Cheshire

Houses 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
How to Buy a Home How to Finance a Home How to Sell a Home

In Cheshire, there are currently 5 houses for sale, offering an array of options for potential buyers. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Cheshire, MA and find the perfect place to call home.

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