9

Cheshire Homes for Sale

Section Image Section Image
  • 136 Church St Unit 142, Cheshire, MA 01225
    136 Church St Unit 142, Cheshire, MA 01225
    136 Church St Unit 142, Cheshire, MA 01225
    /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
  • 108 Church St, Cheshire, MA 01225
    108 Church St, Cheshire, MA 01225
    108 Church St, 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
  • 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
  • 867 Notch Rd, Cheshire, MA 01225
    867 Notch Rd, Cheshire, MA 01225
    867 Notch Rd, 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
  • 192 Curran Rd, Cheshire, MA 01225
    192 Curran Rd, Cheshire, MA 01225
    192 Curran 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
  • 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
  • 12 South St, Cheshire, MA 01225
    12 South St, Cheshire, MA 01225
    12 South 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
Massachusetts Berkshire County Cheshire Cheshire

Real Estate & Homes for Sale in Cheshire, Cheshire

Frequently Asked Questions Why Live in Cheshire

Is Cheshire a good place to live?
Cheshire is a good place to live. Cheshire is considered very car-dependent and somewhat bikeable. Cheshire is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. It has a median age of 51. The average household income is $89,913 which is below the national average. College graduates make up 33.7% of residents. A majority of residents in Cheshire are home owners, with 14.1% of residents renting and 85.9% of residents owning their home. A local real estate agent serving Cheshire can help you decide if this neighborhood is the right one for you. Learn more on our Cheshire neighborhood guide.
Is Cheshire, MA a safe neighborhood?
Cheshire, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
What are the best public schools in Cheshire?
The best public schools that serve Cheshire are:
What are the most popular zip codes in Cheshire, Cheshire, MA?
The most popular zip codes in Cheshire, Cheshire, MA include 01225, 01237, 01220, 01270 and 01226.
Learn more about living in Cheshire
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group