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Cheshire, MA Homes for Sale

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  • /26

    $149,000

    • 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
  • /32

    $149,900

    • 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
  • /67

    $770,000

    • 4 Beds
    • 3.5 Baths
    • 2,952 Sq Ft

    39 N Mountain Rd, Lanesborough, MA 01237

    Take in the peace and tranquility at this wonderful Lanesboro home. Step onto the wrap around porch and enter into the thoughtfully laid out floor plan. Perfect for everyday living or entertaining. Open kitchen and living room design overlook the private backyard. Walk onto the deck that overlooks 3.3 acres of manicured lawn and an inground pool. 1st floor has a 1/2 bath as well as a 3/4

    Janet Benoit MOCKINGBIRD REAL ESTATE

    39 N Mountain Rd, Lanesborough, MA 01237
  • /21

    $295,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,359 Sq Ft

    19 Fisk St, Cheshire, MA 01225

    Located in the heart of desirable Cheshire, this cozy Colonial is just a short walk from the Ashuwillticook Trail. The outside offers a newly installed shed 20'x12' with plenty of storage surrounded by a fenced in yard. The foyer to the home is spacious to accommodate a small home office or for additional storage. Entertain guests in an open dining room / living room with a good flow to the

    Diane Dandurand-Burdick STEEPLEVIEW REALTY - ADAMS BRANCH

    19 Fisk St, Cheshire, MA 01225
  • /33

    $500,000 Open Sun 10AM - 12PM

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

    40 Curran Rd, Cheshire, MA 01225

    Welcome to 40 Curran Rd. This beautifully updated modern home sits on over an acre of private land. This turnkey home offers 3 bedrooms, 2 full baths, an open-flow layout filled with natural light. The inviting living room features a cozy wood-burning fireplace, perfect for gathering on cool fall evenings with pumpkin spice everything! Primary bedroom includes private en-suite bath. Updated

    Laura Arseneau PAULA MCLEAN REALTORS INC.

    40 Curran Rd, Cheshire, MA 01225
  • /46

    $439,000

    • 3 Beds
    • 1.5 Baths
    • 2,254 Sq Ft

    136 Ingalls Rd, Cheshire, MA 01225

    Experience refined living in this beautifully renovated and thoughtfully designed home in the heart of Cheshire! This turnkey property offers the perfect blend of comfort, style, and functionality. Step outside to your private backyard oasis, complete with a recently upgraded in-ground pool, ideal for summer entertaining or relaxing evenings while watching the sunset. Inside, you'll find

    Laiken Rapisarda LAMACCHIA REALTY, INC

    136 Ingalls Rd, Cheshire, MA 01225
  • /36

    $329,900

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft

    83 Devonshire Dr, Cheshire, MA 01225

    This inviting 3-bedroom, 2-bath ranch offers comfortable living in a desirable neighborhood. Inside, you'll find a bright and open layout with a mix of oak, tile, and vinyl flooring for both warmth and easy care. The home features a 2-car attached garage for convenience and plenty of storage. Recent updates include a new septic system installed in 2017, giving peace of mind for years to come.

    Jim Thurston LAMACCHIA REALTY, INC

    83 Devonshire Dr, Cheshire, MA 01225
  • /6

    $114,900

    • Land
    • 1.38 Acres
    • $83,417 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, perc test and septic design. Additional 1.4 acre adjacent lot available.

    Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

    Lot 9E Stewart White Rd, Cheshire, MA 01225
  • /6

    $119,900

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

    Lot 10E 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, perc test and septic design. Additional 1.4 acre adjacent lot available.

    Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

    Lot 10E Stewart White Rd, Cheshire, MA 01225
  • /39

    $549,000

    • 3 Beds
    • 2 Baths
    • 2,184 Sq Ft

    230 Curran Rd, Cheshire, MA 01225

    Welcome to this beautifully crafted, move-in ready chalet-style home, set on over 4 private acres with a spacious cleared backyard, wooded surroundings, and stunning mountain views. Inside, you're greeted by a welcoming mudroom and convenient first-floor laundry. The open-concept living area features vaulted ceilings, hardwood floors, and large windows that fill the space with natural light and

    Laiken Rapisarda LAMACCHIA REALTY, INC

    230 Curran Rd, Cheshire, MA 01225
  • /51

    $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
  • /40

    $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
  • /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

    $120,000

    • 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 is the average home price in Cheshire, MA?
Homes for sale in Cheshire, MA have an average home price of $395,059.
How many homes have sold over the last 12 months in Cheshire, MA?
48 homes have sold in Cheshire, MA over the last 12 months.
What are the most popular zip codes in Cheshire, MA?
The most popular zip codes in Cheshire, MA include 01225, 01237, 01220, 01270 and 01256.
How much do you need to make to afford a house in Cheshire?
The median home price in Cheshire is $397,000. If you put a 20% down payment of $79,400 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $2,020 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $87K a year to afford the median home price in Cheshire.
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.

Home Trends in Cheshire, MA

Housing Trends

Median Sale Price
$373,525
Median Single Family Sale Price
$348,475
Median Townhouse Sale Price
$312,500
Average Price Per Sq Ft
$195
Number of Homes for Sale
11
Last 12 months Home Sales
48
Months of Supply
2.80
Median List Price
$397,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
20%
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