Homes, values and local insight for Cheshire, Berkshire County, Massachusetts. Typical home value $363,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Cheshire is a residential town in Berkshire County providing living with strong Mountain setting and Rural character. The community develops civic pride and family values.
The housing market reflects regional positioning with diverse home types. Properties range from modest to premium estates. Buyer pool includes families, commuters and professionals seeking quality living.
Winslow Homes serves this town's buyers and sellers across FL, MA, CT, and RI. Ryan and Megan Winslow provide both brokerage and mortgage services (Ryan Winslow NMLS #2426605 | Megan Winslow NMLS #2692933). Get pre-approved at www.winslowloan.com or call 386-690-5858.
The typical home in Cheshire is worth $363,000, 7% below the Berkshire County typical value of $392,000 and 45% below the Massachusetts typical value of $662,000.
Zillow Home Value Index for Cheshire, August 2026. The middle of the market for single family homes and condos.
Home values in Cheshire moved +34.7% over five years and +88.1% over ten.
Median gross rent in Cheshire. Useful for investors running rental numbers.
Share of occupied homes in Cheshire lived in by the owner.
Older homes often need inspection focus on roof, systems and windows.
Median household income in Cheshire.
Ryan and Megan are mortgage bankers with The Federal Savings Bank, lending in all 50 states. You get the home and the loan from one team. On a typical Cheshire home of $363,000:
Ryan and Megan price Cheshire homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $271,000 · 7,992 residents
Area guide →3,004 residents
Area guide →249 residents
Area guide →Typical value $348,000 · 6,198 residents
Area guide →Typical value $362,000 · 817 residents
Area guide →Typical value $326,000 · 655 residents
Area guide →See the full Berkshire County real estate guide or the Massachusetts real estate guide.
The Zillow Home Value Index for Cheshire was $363,000 in August 2026, +2.4% over the past year.
Cheshire is in Berkshire County, Massachusetts.
About 3,190 people as of the 2024 Census Bureau estimate, compared with 3,259 in 2020.
Ryan and Megan Winslow of Winslow Homes have sold over 3,000 homes since 2009 and are licensed in Florida, Massachusetts, Connecticut and Rhode Island. Call or text 386-690-5858.
Apply at www.winslowloan.com. Ryan and Megan are mortgage bankers with The Federal Savings Bank and lend in all 50 states, including FHA, VA and conventional loans.
87% of occupied homes in Cheshire are owner occupied, based on the 2019 to 2023 American Community Survey.
17 years, over 3,000 homes sold, and one team for the home and the loan. Call or text 386-690-5858.
Sources: U.S. Census Bureau 2024 population estimates and 2019 to 2023 American Community Survey; Zillow Home Value Index, August 2026. Numbers update as new data is released. Talk to Ryan and Megan for current sold prices on your street.
No in-person meeting or phone call needed for most addresses. See your estimated value, price range and value trend in seconds.
Get coming-soon homes, pocket listings and price drops in Cheshire, MA before they hit the big home search sites.
The typical home in Cheshire is worth $361,842 as of August 2026 in ZIP code 01225. Values moved +2.5% over the last 12 months at the middle ZIP code.
| ZIP | Typical value | 12 months | 5 years | Median sale, Mar to May 2026 | Days on market |
|---|---|---|---|---|---|
| 01225 | $361,842 | +2.5% | +34.7% |
Sources: Zillow Home Value Index through August 2026 and the Redfin Data Center ZIP code tracker, March to May 2026. Ask Ryan and Megan for a value for your own home.
