Cheshire, MA Homes for Sale

Q: What are the most popular zip codes in Cheshire, MA?

The most popular zip codes in Cheshire, MA include 01225 , 01220 , 01237 , 01270 and 01226 .

/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 multi- 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 &

Nadine Hiser

KRG - Key Realty Group

(413) 475-9494

136 Church St Unit 142, Cheshire, MA 01225
Explore Cheshire
/44
$539,900
- 4 Beds
- 1.5 Baths
- 1,865 Sq Ft
573 Stafford Hill Rd, Cheshire, MA 01225

Welcome to this spacious 4-bedroom, 2-bathroom home offering 1,865 sq ft. of comfortable living space on a generous 1.42 acre lot in the beautiful town of Cheshire. This property features a bright and inviting layout, well-sized bedrooms, and ample room for everyday living or entertaining. New vinyl siding, gutters & awnings added in the most recent years. Enjoy the privacy and outdoor

Sara Bresett NOCHER REALTY

573 Stafford Hill Rd, Cheshire, MA 01225
/16
$389,900
- 3 Beds
- 1.5 Baths
- 2,747 Sq Ft
18 W Mountain Rd, Cheshire, MA 01225

Center of town 1820s colonial home with natural sunlight throughout. Oversized garage with attic storage/access. Seasonal Cabin with own septic, water, gas and electric (needs updates/repair). Irregular lot with privacy, fencing and wooded boundaries to neighbors.

Chris Warner CHRISTOPHER A WARNER REALTY

18 W Mountain Rd, Cheshire, MA 01225
/22
$399,900
- 3 Beds
- 2 Baths
- 1,756 Sq Ft
53 Depot St, Cheshire, MA 01225

Nestled in the heart of downtown Cheshire, this beautifully updated New England farmhouse blends classic charm with modern comforts. Featuring a convenient first-floor bedroom and full bath, plus two additional bedrooms and a second full bath upstairs. The recently renovated kitchen boasts granite countertops, abundant cabinet space, stainless steel appliances, and an abundance of natural light.

Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

53 Depot St, Cheshire, MA 01225
/33
$489,999
- 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
/5
$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 and perc test. Additional 1.4 acre adjacent lot available.

Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

Lot 9E Stewart White Rd, Cheshire, MA 01225
/16
$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.

Deb Trzcinski Steepleview Realty - Mass

12 South St, Cheshire, MA 01225

Massachusetts Berkshire County Cheshire

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 $407,353.

How many homes have sold over the last 12 months in Cheshire, MA?

41 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, 01220, 01237, 01270 and 01226.

How much do you need to make to afford a house in Cheshire?

The median home price in Cheshire is $399,000. If you put a 20% down payment of $79,800 and had a 30-year fixed mortgage with an interest rate of 6.19%, your estimated principal and interest payment would be $1,950 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $84K a year to afford the median home price in Cheshire. Learn how much home you can afford with our Home Affordability Calculator.

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

On average, homes in Cheshire, MA sell after 44 days on the market compared to the national average of 53 days. The median sale price for homes in Cheshire, MA over the last 12 months is $385,963, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$385,963

Median Single Family Sale Price

$389,900

Average Price Per Sq Ft

$195

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

1.20

Median List Price

$399,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

How to Buy a Home How to Finance a Home How to Sell a Home

More About Living in Cheshire

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