Windsor, Massachusetts.
Typical home $360,903 (+1.6% in a year). Pittsfield, MA metro.
to buy the typical home at today's mortgage rate — +$1,092 (+136%) since Jan 2020.
- 1 year
- Up $5,787 +2%
- $355,116$360,903 since Sep 2025
- 5 years
- Up $81,020 +29%
- $279,882$360,903 since Sep 2021
Monthly payment to buy the typical home
Home value × that month's 30-year mortgage rate, 20% down, principal and interest. This is the line households feel: prices and rates compound each other.
- Windsor$1,894
- Massachusetts$3,439
- United States$1,922
At the last five years' pace, a typical home here doubles in price every 14 years.
Typical home values in Windsor, MA rose 1.6% over the past year — faster than the nation's +1.2%.
Living in Windsor, Berkshire County, Massachusetts
Windsor is a town of 831 people in Berkshire County. Half its households earn more than $115,563 a year and half less, against $76,013 across Berkshire County; 4% of its people live below the poverty line. 96% of its homes are lived in by their owners and 4% are rented. Unemployment in Berkshire County was 4.1% in August 2026, and the county had 0.2% fewer jobs in 2025 than the year before. The most residents work in schools and health care, then professional services.
Written by AI Claude Sonnet 5.5 wrote this on 23 October 2026 from the figures here, a list of nearby places and what it knows. It can be wrong or out of date.
What it’s like
The place. Windsor is a very small hill town in Berkshire County, with far fewer residents than most towns. Nearly everyone owns the home they live in, and household incomes run well above the county's, with fewer people living below the poverty line than you might expect. A good share of adults hold a four-year degree, and winters are cold, with January highs staying below freezing and summer warm but mild.
Work. Residents work mostly in schools, hospitals and social care, with others in professional and business services, manufacturing and shops. Across Berkshire County, some of the largest workplaces are Berkshire Medical Center, Williams College and the Pittsfield school district. Commutes are on the long side, and a fair number of people work from home.
Things to do. Notchview, a ski area, is in or beside town, which suits the long cold season. A short drive away are Mount Greylock State Reservation, Wahconah Falls State Park and Savoy Mountain State Forest, all protected areas for walking and time outdoors. For a museum visit, the William Cullen Bryant Homestead is also a short drive away.
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- 453households
- 42%of adults have a degree
- 4%below the poverty line
- 37 mintypical commute
- 21%work from home
What residents work in
Employed residents by industry, from the Census survey. Berkshire County had 57,806 jobs in 2025, 0.2% fewer than the year before (Bureau of Labor Statistics).
Weather through the year
Coldest in January, with highs near 28° and lows near 9°; warmest in July, with highs near 75° and lows near 53°.
Average daily high and low, 1991–2020, at the East Hawley weather station, 10 miles away (NOAA).
Largest workplaces in Berkshire County
- Berkshire Medical CenterGeneral hospital2,275FTE
- Williams CollegeUniversity or college1,351
- Pittsfield SchoolsSchool district944FTE
- Berkshire County ArcGroup homes, intellectual and developmental disability792
- General Dynamics Mission SystemsSearch, detection, navigation, guidance, aeronautical, and nautical systems and instrument manufacturing530
- Butternut BasinAlpine skiing facilities without accommodations425
- THE Brien Center for Mental Health and Substance Abuse ServicesMental health centers and clinics, outpatient417
- General Dynamics Mission SystemsSearch, detection, navigation, guidance, aeronautical, and nautical systems and instrument manufacturing405
Staff on average in 2025, as each workplace reported it to OSHA with its injury records: 99 workplaces with 20 or more staff, 11,288 people in all across the county; Windsor has none of its own. Hospitals come from their Medicare cost reports (CMS, 2023), colleges from IPEDS (NCES, 2023–24) and school districts from the Common Core of Data (NCES, 2023–24); FTE marks full-time equivalent staff. Not listed: many offices and banks, which need not report to OSHA; military bases, whose staff OPM withholds; and, in about half the states, city and county governments.
Natural hazards
- Inland floodingRelatively moderate
- HurricanesRelatively moderate
- Strong windRelatively moderate
- Ice stormsRelatively moderate
- Cold wavesRelatively moderate
- LightningRelatively moderate
FEMA’s National Risk Index (December 2025) rates the risk each natural hazard poses to the people, buildings and farms across Berkshire County, against the rest of the country; all of them together, relatively moderate. It is meant for planning, not a substitute for a local risk assessment or a flood map: FEMA’s index.
From the U.S. Census Bureau’s 2020 census and its American Community Survey (2020–2024 five-year estimates), and the Bureau of Labor Statistics. A survey, so each figure has a margin of error, and figures it is not sure of are left out. More on Berkshire County and the Pittsfield, MA metro.
Windsor home values
Zillow measures a city over its municipal boundary. Against the state and national figures, mid-tier homes, smoothed and seasonally adjusted.
- Windsor$360,903
- Massachusetts$655,219
- United States$366,157
When this market ran hot
Each cell is that month's year-on-year home-value growth. Read left to right, top row is the latest year — the 2021–22 band is the boom.
Market heat, inside the city limits
Homes for sale
Active for-sale inventory. More supply hands power to buyers.
- Windsor6
Zip codes with a Windsor address
A different geography, not a breakdown. The figure above covers the municipality; these zips cover everywhere the Post Office calls Windsor — often including townships beyond the city limits. Both come straight from Zillow, and they are not expected to average out.