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Cheshire, MA Homes for Sale

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  • 31 2nd Ave, Cheshire, MA 01225
    31 2nd Ave, Cheshire, MA 01225
    31 2nd Ave, Cheshire, MA 01225
    /18

    $119,900

    • 2 Beds
    • 2 Baths
    • 773 Sq Ft

    31 2nd Ave, Cheshire, MA 01225

    Built in 2023 and impeccably maintained, this move-in ready home offers modern comfort with an open, bright layout designed for easy living. The spacious kitchen flows seamlessly into the living area, creating the perfect space for entertaining or relaxing. A practical mudroom adds everyday convenience, while two full bathrooms and comfortable bedrooms provide flexibility for family or guests.

    Agent Photo

    Corey Bishop

    BISHOP WEST REAL ESTATE

    31 2nd Ave, Cheshire, MA 01225
  • 7 3rd Ave, Cheshire, MA 01225
    7 3rd Ave, Cheshire, MA 01225
    7 3rd Ave, Cheshire, MA 01225
    /12

    $124,900

    • 2 Beds
    • 1 Bath
    • 896 Sq Ft

    7 3rd Ave, Cheshire, MA 01225

    Move right into this immaculately maintained 2022 home in Berkshire Village, where everything still feels fresh and new. The open-concept design is centered around a beautiful oversized kitchen island--perfect for gathering, entertaining, or everyday living--and features abundant cabinetry, modern finishes, and Frigidaire appliances, including a dishwasher that has never been used. Two spacious

    THE KAHN TEAM BISHOP WEST REAL ESTATE

    7 3rd Ave, Cheshire, MA 01225
  • 487 Jenks Rd, Cheshire, MA 01225
    487 Jenks Rd, Cheshire, MA 01225
    487 Jenks Rd, Cheshire, MA 01225
    /8

    $225,000

    • Land
    • 9.7 Acres
    • $23,196 per Acre

    487 Jenks Rd, Cheshire, MA 01225

    Build your dream home on this exceptional 9.7 acre parcel, already prepared for your vision! This beautiful property features a completed septic system, drilled well, 100-amp electrical service, and a 10' x 20' storage shed-saving you time and expense. With much of the groundwork already completed, this lot is ready for construction. Enjoy the privacy and space of nearly 10 acres while still

    Darcy Reid MOCKINGBIRD REAL ESTATE

    487 Jenks Rd, Cheshire, MA 01225
  • 12 South St, Cheshire, MA 01225
    12 South St, 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
  • 40 Willow Cove Rd, Cheshire, MA 01225
    40 Willow Cove Rd, Cheshire, MA 01225
    40 Willow Cove Rd, Cheshire, MA 01225
    /59

    $649,900

    • 2 Beds
    • 3 Baths
    • 2,481 Sq Ft

    40 Willow Cove Rd, Cheshire, MA 01225

    Nestled on a picturesque 2 acre lot and set well back from the road for added privacy, this beautiful 2 bedroom, 2 bath home offers both comfort, character and outdoor living. Step inside to a sunken livingroom centered around a stunning fieldstone fireplace. A large den offers flexible living space, and the finished lower level features a bedroom and full bath. French doors lead to an

    Robin Moore 413 REAL ESTATE

    40 Willow Cove Rd, Cheshire, MA 01225
  • 14 Richardson St Unit 14, Cheshire, MA 01225
    14 Richardson St Unit 14, Cheshire, MA 01225
    14 Richardson St Unit 14, Cheshire, MA 01225
    /32

    $3,000

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    14 Richardson St Unit 14, Cheshire, MA 01225

    Welcome to 14 Richardson Street, Cheshire, MA, a beautifully maintained fully furnished long-term rental offering approximately 1,800 square feet of thoughtfully designed living space. Built in 2006, this spacious 3-bedroom, 2.5-bath home comes fully furnished, including furniture, cookware, dishes, silverware, towels, linens, and other household essentials.Designed with ADA accessibility in

    Christian Garner NOCHER REALTY

    14 Richardson St Unit 14, Cheshire, MA 01225
  • 867 Notch Rd, Cheshire, MA 01225
    867 Notch Rd, Cheshire, MA 01225
    867 Notch Rd, Cheshire, MA 01225
    /33

    $450,000

    $90K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,307 Sq Ft

    867 Notch Rd, Cheshire, MA 01225

    Home on 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 counter space

    Mariah Worth Lamacchia Realty, Inc. - Dalton

    867 Notch Rd, Cheshire, MA 01225
  • 477 N State Rd, Cheshire, MA 01225
    477 N State Rd, Cheshire, MA 01225
    477 N State Rd, Cheshire, MA 01225
    /25

    $349,900

    • 3 Beds
    • 1.5 Baths
    • 2,063 Sq Ft

    477 N State Rd, Cheshire, MA 01225

    Escape to your own private, wooded 2.36-acre sanctuary with this rare property that directly abuts protected Appalachian Trail land, giving you instant access to miles of world-class hiking, wildlife viewing, and pristine natural beauty right from your back door. Offering ultimate peace of mind, this home features a newer roof and newer windows, both complete with guarantees that protect your

    Cheryl Ryan BISHOP WEST REAL ESTATE

    477 N State Rd, Cheshire, MA 01225
  • 335 North St, Cheshire, MA 01225
    335 North St, Cheshire, MA 01225
    335 North St, Cheshire, MA 01225
    /29

    $415,000

    • 3 Beds
    • 3 Baths
    • 2,584 Sq Ft

    335 North St, Cheshire, MA 01225

    Modern ranch home perched high above North Street offering views to the east and bordering the approximate 370,000 acre Appalachian trail on two sides! Enjoy direct access for hiking right off your property! Offering 3 bedrooms, 3 full baths and extremely nice mechanicals updated in recent years. The lower level consists of a one bay garage/storage area and a beautiful in-law accommodations. The

    Jeffrey Loholdt ENGEL & VOLKERS WELLESLEY

    335 North St, Cheshire, MA 01225
  • 0 Outlook Ave Unit 249990, Cheshire, MA 01225
    0 Outlook Ave Unit 249990, Cheshire, MA 01225
    /2

    $205,000

    • Land
    • 31.66 Acres
    • $6,475 per Acre

    0 Outlook Ave Unit 249990, Cheshire, MA 01225

    Build your dream home on this stunning 31 -acre wooded parcel abutting Mount Greylock. Enjoy privacy, natural beauty, and endless opportunities for outdoors recreation, all while being surrounded by the peaceful charm of the Berkshires.

    Thane Yorke CARRIAGE HOUSE REAL ESTATE

    0 Outlook Ave Unit 249990, Cheshire, MA 01225
  • 192 Curran Rd, Cheshire, MA 01225
    192 Curran Rd, Cheshire, MA 01225
    192 Curran Rd, Cheshire, MA 01225
    /50

    $289,900

    $10K PRICE DROP
    • 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
  • 0 Horns Beach Rd, Cheshire, MA 01225
    0 Horns Beach Rd, Cheshire, MA 01225
    0 Horns Beach Rd, Cheshire, MA 01225
    /19

    $89,000

    • Land
    • 37,461 Sq Ft
    • $103,488 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
  • 12 South St, Cheshire, MA 01225
    12 South St, Cheshire, MA 01225
    12 South St, 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
  • Lot 9E Stewart White Rd, Cheshire, MA 01225
    Lot 9E Stewart White Rd, Cheshire, MA 01225
    Lot 9E Stewart White Rd, 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
  • 115 Lake Shore Dr, Cheshire, MA 01225
    115 Lake Shore Dr, Cheshire, MA 01225
    115 Lake Shore Dr, 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 John Garber

    115 Lake Shore Dr, Cheshire, MA 01225
  • 221 North St Unit 222, Cheshire, MA 01225
    221 North St Unit 222, Cheshire, MA 01225
    221 North St Unit 222, Cheshire, MA 01225
    /11

    $1,500

    • 2 Beds
    • 1 Bath

    221 North St Unit 222, Cheshire, MA 01225

    Discover the perfect blend of small-town peace and sprawling living space! Nestled in the wonderfully quiet, quaint heart of downtown Cheshire, this beautiful second-floor apartment offers a serene escape from the hustle and bustle while remaining just a short drive from all the culture and dining of the northern Berkshires.Inside, you will find an exceptionally large, sun-drenched layout

    Jason Nocher NOCHER REALTY

    221 North St Unit 222, Cheshire, MA 01225
  • 57 Church St, Cheshire, MA 01225
    57 Church St, Cheshire, MA 01225
    57 Church St, Cheshire, MA 01225
    /6

    $110,000

    $5K PRICE DROP
    • 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
Massachusetts Berkshire County

Real Estate & Homes 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

Frequently Asked Questions

What is the average home price in Cheshire, MA?
Homes for sale in Cheshire, MA have an average home price of $421,722.
How many homes have sold over the last 12 months in Cheshire, MA?
36 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, 01256 and 01270.
How much do you need to make to afford a house in Cheshire?
The median home price in Cheshire is $415,000. If you put a 20% down payment of $83,000 and had a 30-year fixed mortgage with an interest rate of 6.55%, your estimated principal and interest payment would be $2,110 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $90K 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, Mt. Greylock Regional High School and Emma L. Miller Memorial Elementary School. Browse all the schools in Cheshire, MA to learn more.

Home Prices in Cheshire, MA

The median home sale price in Cheshire, MA is $417,000, up 14% year-over-year. Homes in Cheshire sell in 46 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$417,000
Median Single Family Sale Price
$415,000
Median Townhouse Sale Price
$165,000
Median 2 Bedroom Sale Price
$397,000
Average Price Per Sq Ft
$199
Number of Homes for Sale
7
Last 12 months Home Sales
36
Months of Supply
2.30
Median List Price
$415,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
14%
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