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Cheshire, MA Homes for Sale

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  • /32

    $169,000

    • 5 Beds
    • 3 Baths
    • 2,250 Sq Ft

    136 Church St Unit 142, Cheshire, MA 01225

    Situated in the heart of the quaint town of Cheshire, this 3 family offers potential for the new owner as an investment or owner occupied. First floor has 2 bedrooms, primary is large, living room and kitchen are also spacious and kitchen offers pantry w/ potential laundry hook ups. Upstairs back unit is 2 bedroom, Upstairs front unit is 1 bedrooms & currently vacant. Long term tenants &

    Agent Photo

    Nadine Hiser

    KRG - Key Realty Group

    (413) 475-9494

    136 Church St Unit 142, Cheshire, MA 01225
  • /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
  • /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
  • /24

    $569,000

    • 5 Beds
    • 3.5 Baths
    • 3,307 Sq Ft

    867 Notch Rd, Cheshire, MA 01225

    A charming, spacious Colonial with privacy, and lovely grounds. Breathtaking mountain views. Built in 2005 and set on 7.25 acres, this 5-bedroom, 4.5-bathroom residence offers 3,307 square feet of living space. Two primary suites, one up and one down. The open-concept kitchen flows seamlessly into a great room, perfect for entertaining. This home does need work but is priced accordingly. Make

    Marnie Garzone THE KINDERHOOK GROUP - PITTSFIELD

    867 Notch Rd, Cheshire, MA 01225
  • /40

    $299,999

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

    192 Curran Rd, Cheshire, MA 01225

    Tucked away on a quiet country road in central Cheshire, this charming 3-bedroom, 1.5-bath home offers peace, privacy, and a connection to nature--yet it's just a short drive to both North and South County amenities. Set on nearly 2 acres bordered by woods and state land, enjoy walking trails, wildflowers, and young pear and apple trees right outside your door. The home is neat and well-kept,

    Dennis D'Arcangelo MONARCH REALTY, INC.

    192 Curran Rd, 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
  • /10

    $799,000

    • Land
    • 1.70 Acres
    • $470,000 per Acre

    12 South St, Cheshire, MA 01225

    Property on corner of busy 4 way stoplight in the heart of town with 256 ft of frontage. High visibility and high traffic count: 11,777 on average. Multi-zoned for multiple different uses & possibilities. The source of all representations are from the seller or a public source; broker has not verified same. It is recommended that buyer independently verify all information.

    Pat Roberts STEEPLEVIEW REALTY - N. ADAMS

    12 South 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.

Frequently Asked Questions

What are the most popular zip codes in Cheshire, MA?
The most popular zip codes in Cheshire, MA include 01225, 01237, 01220, 01226 and 01267.
How are the schools in Cheshire, MA?
Cheshire, MA has highly rated public and private schools. Some of the best schools in Cheshire based on Niche Grades are Lanesborough Elementary School, Mt. Greylock Regional High School and Wahconah Regional High School. Browse all the schools in Cheshire, MA to learn more.
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