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Cheshire, MA Homes for Sale

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  • /33

    $485,000

    • 3 Beds
    • 2 Baths
    • 2,670 Sq Ft

    40 Curran Rd, Cheshire, MA 01225

    Beautifully updated home situated on over an acre of land in the Berkshires! This well maintained home offers 3 bedrooms, 2 full baths, and a bright open concept layout designed for comfortable living and entertaining. Featuring a wood burning fireplace (chimney has recently been cleaned). Updated kitchen with stainless steal appliances Private primary bedroom with large en-suite bath. The lower

    Agent Photo

    Laura Arseneau

    PAULA MCLEAN REALTORS INC.

    (413) 288-5638

    40 Curran Rd, Cheshire, MA 01225
  • /8

    $53,000

    • 2 Beds
    • 1 Bath
    • 980 Sq Ft

    4 1st, Cheshire, MA 01225

    Great single wide manufactured home with lovely living room and nice sized bedrooms.Very well maintained and priced.

    Agent Photo

    Byron R. Ford, Jr.

    Berkshire Hathaway HomeServices Robert Paul Properties

    (413) 344-2297

    4 1st, Cheshire, MA 01225
  • /2

    $599,000

    • Land
    • 1.7 Acres
    • $352,353 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 Lamacchia Realty, Inc. - North Adams

    12 South St, Cheshire, MA 01225
  • /33

    $499,900

    $40K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,307 Sq Ft

    867 Notch Rd, Cheshire, MA 01225

    Home on a dream lot--over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous

    Mariah Worth Lamacchia Realty, Inc. - Dalton

    867 Notch Rd, Cheshire, MA 01225
  • /53

    $299,900

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

    192 Curran Rd, Cheshire, MA 01225

    This beautifully maintained one-level manufactured home is a true reflection of pride of ownership and years of meticulous care. Warm, welcoming, and completely move-in ready, the property offers a peaceful lifestyle surrounded by almost 2 acres of stunning, lush park-like grounds filled with natural beauty and privacy. The expansive deck provides the perfect place to relax, entertain, or simply

    Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    192 Curran Rd, Cheshire, MA 01225
  • /19

    $89,000

    • Land
    • 37,462 Sq Ft
    • $103,487 per Acre

    0 Horns Beach Rd, Cheshire, MA 01225

    Build your dream home on this rare, fully cleared 0.86-acre lot offering stunning, elevated views of Cheshire Lake. Located on a quiet, private road that enjoys the convenience of being town-maintained, this property perfectly balances serenity with accessibility. This lot is truly ''shovel-ready'' with significant infrastructure already in place. A 3-bedroom septic system is already on-site.

    Timothy Johnson NOCHER REALTY

    0 Horns Beach Rd, Cheshire, MA 01225
  • /16

    $599,000

    $501K PRICE DROP
    • Land
    • 1.7 Acres
    • $352,353 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.

    Deb Trzcinski Lamacchia Realty, Inc.

    12 South St, Cheshire, MA 01225
  • /6

    $119,900

    • Land
    • 1.38 Acres
    • $87,047 per Acre

    Lot 9E Stewart White Rd, Cheshire, MA 01225

    Discover the perfect setting for your dream home on this gently sloping, 1.4 acre lot located in the rural countryside of Cheshire. With breathtaking views and a cleared, ready-to-build landscape, this property offers the ideal blend of privacy and natural beauty. Situated on a town-maintained road and includes drilled well and perc test.

    Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

    Lot 9E Stewart White Rd, Cheshire, MA 01225
  • /15

    $397,000

    • 2 Beds
    • 1 Bath
    • 699 Sq Ft

    115 Lake Shore Dr, Cheshire, MA 01225

    Cozy four season home with incredible views. 2 bedroom, one bath, on the water with new dock on beautiful Hoosac Lake. Large two-level deck. Near popular lake-side bike trail. Town water, natural gas heat. Perfect for all-season living or summer weekend getaway.

    John Garber

    115 Lake Shore Dr, Cheshire, MA 01225
  • /6

    $115,000

    • 3 Beds
    • 1 Bath
    • 1,281 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
  • /46

    $615,000

    • 3 Beds
    • 4 Baths
    • 1,776 Sq Ft

    222 Brough Rd, Cheshire, MA 01225

    This beautifully positioned Berkshire retreat offers the perfect blend of privacy, comfort and natural beauty. Nestled on a peaceful country road, this inviting home is surrounded by scenic woodlands and mountain views while remaining conveniently close to the cultural attractions, outdoor recreation, and vibrant communities that make Berkshire County so desirable. Inside, you'll find warm and

    Paula McLean PAULA MCLEAN REALTORS INC.

    222 Brough Rd, 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 is the average home price in Cheshire, MA?
Homes for sale in Cheshire, MA have an average home price of $419,923.
How many homes have sold over the last 12 months in Cheshire, MA?
33 homes have sold in Cheshire, MA over the last 12 months.
What is the average household income in Cheshire, MA?
The average household income in Cheshire, MA is $90K.
What are the most popular zip codes in Cheshire, MA?
The most popular zip codes in Cheshire, MA include 01225, 01220, 01237, 01226 and 01201.
How much do you need to make to afford a house in Cheshire?
The median home price in Cheshire is $425,000. If you put a 20% down payment of $85,000 and had a 30-year fixed mortgage with an interest rate of 6.48%, your estimated principal and interest payment would be $2,140 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $92K a year to afford the median home price in Cheshire. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Cheshire is $90K.
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, Emma L. Miller Memorial Elementary School and Mt. Greylock Regional High School. Browse all the schools in Cheshire, MA to learn more.

Home Prices in Cheshire, MA

Home Price Trends

Median Sale Price
$416,500
Median Single Family Sale Price
$397,000
Median 2 Bedroom Sale Price
$304,000
Average Price Per Sq Ft
$210
Number of Homes for Sale
6
Last 12 months Home Sales
33
Months of Supply
2.20
Median List Price
$425,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
12%
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