Winchester, Massachusetts.
Typical home $1,530,404 (+2.6% in a year), asking rent $3,191 (-0.5%). Boston-Cambridge-Newton, MA-NH metro.
to buy the typical home at today's mortgage rate — +$4,260 (+113%) since Jan 2020.
- 1 year
- Up $39,307 +3%
- $1,491,097$1,530,404 since Sep 2025
- 5 years
- Up $329,888 +27%
- $1,200,516$1,530,404 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.
- Winchester$8,033
- 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 Winchester, MA rose 2.6% over the past year — faster than the nation's +1.2%.
Asking rents in Winchester, MA fell 0.5% over the past year — slower than the nation's +2.7%.
Owning the typical home in Winchester runs $7,794/mo more than renting one — the widest that gap has been in this data.
That is $10,986 a month against $3,191 rent: a $8,033 mortgage payment, plus $1,314 property tax and $1,638 insurance & upkeep.
Owning vs renting — Winchester
The owning line is the typical home's monthly payment at that month's rate, plus property tax and insurance & upkeep; the renting line is the typical asking rent; the grey line is the mortgage payment on its own. Same homes, same months, both ways of paying for a roof.
- Owning all in$10,986
- Renting$3,191
- Mortgage only$8,033
Property tax · $1,314/mo 1.03% of value a year — the ACS 2020-2024 median bill over the median home value for Middlesex County, MA
Insurance & upkeep · $1,638/mo insurance, maintenance and repairs together, from the BLS Consumer Expenditure Survey — the national figure for mortgaged homeowners, scaled to this market's home value. BLS publishes the three bundled and they cannot be split.
Both are priced off the same month's home value, so they rise with the market. Neither is a quote — a specific home's bill depends on its assessment, its age and its insurer.
Living in Winchester, Middlesex County, Massachusetts
Winchester, in Middlesex County, had 22,970 people in the 2020 census. Half its households earn more than $230,198 a year and half less, against $130,847 across Middlesex County; 5% of its people live below the poverty line. 82% of its homes are lived in by their owners and 18% are rented. Unemployment in Middlesex County was 4.0% in August 2026, and the county had 2.4% fewer jobs in 2025 than the year before. The most residents work in professional services, then schools and health care.
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. Winchester is a town of homeowners, with far more owner-occupied homes than renters. Incomes run well above the county's, and very few households live below the poverty line. Home values and rents are both high. The population skews middle-aged, and nearly all adults hold a four-year degree. Winters are cold and snowy, with January the coldest month, while summers turn warm, and precipitation is steady through the year.
Work. Residents work mainly in professional and business services, in schools, hospitals and social care, in banks, insurance and property, and in manufacturing. Winchester Hospital and the Winchester Schools are among the largest workplaces in town, along with Winchester Rehabilitation and Nursing Center. Commutes are fairly long, and a good many people work from home. Across Middlesex County, jobs have slipped a little over the past year.
Things to do. Boston is a short drive away, and its museums are the nearest draw: the Museum of Fine Arts Boston and the Isabella Stewart Gardner Museum are both close by, and Fenway Park, the baseball stadium, is a short drive as well. For a quieter day, Walden Pond is a reservoir a longer drive away.
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- 8,340households
- 80%of adults have a degree
- 5%below the poverty line
- 31 mintypical commute
- 34%work from home
What residents work in
Employed residents by industry, from the Census survey. Middlesex County had 903,942 jobs in 2025, 2.4% fewer than the year before (Bureau of Labor Statistics).
Weather through the year
Coldest in January, with highs near 38° and lows near 18°; warmest in July, with highs near 84° and lows near 63°. About 64 inches of snow and 50 inches of rain and melted snow a year.
Average daily high and low, 1991–2020, at the Reading weather station, 5 miles away (NOAA).
Largest workplaces in Winchester
- Winchester HospitalGeneral hospital1,494FTE
- Winchester SchoolsSchool district608FTE
- Winchester Rehabilitation and Nursing CenterSkilled nursing facilities225
- Mahoney's Rocky LedgeGarden power equipment stores168
- John Moriarty & Associates, Inc. (MA)Addition, alteration and renovation for-sale builders, commercial and institutional building119
- Wise ConstructionAddition, alteration and renovation for-sale builders, commercial and institutional building114
- Stop & ShopGrocery stores98
- Gentle Giant Moving Company Office HeadquartersOffice administration services96
Staff on average in 2025, as each workplace reported it to OSHA with its injury records: 12 workplaces with 20 or more staff, 3,072 people in all. Hospitals come from their Medicare cost reports (CMS, 2023) 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 high
- Ice stormsrelatively high in parts of WinchesterRelatively moderate
FEMA’s National Risk Index (December 2025) rates the risk each natural hazard poses to the people, buildings and farms in Winchester’s census tracts, against the rest of the country; all of them together, relatively low. 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 Middlesex County and the Boston-Cambridge-Newton, MA-NH metro.
Winchester home values
Zillow measures a city over its municipal boundary. Against the state and national figures, mid-tier homes, smoothed and seasonally adjusted.
- Winchester$1,530,404
- Massachusetts$655,219
- United States$366,157
Sellers are cutting prices on about 1 in 4 Winchester listings — the market is cooling.
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
Share of listings with a price cut
The early-warning dial: sellers cut when buyers stop reaching. Rising cuts cool a market months before prices notice.
- Winchester27.43%
- United States26.90%
Homes for sale
Active for-sale inventory. More supply hands power to buyers.
- Winchester68
New listings per month
Sellers arriving at the market.
- Winchester22
Median sale price
What buyers actually paid — closed sales, not asking prices.
- Winchester$1,470,004
- United States$371,553
Sale-to-list ratio
Above 100%, homes sell over asking; below, buyers negotiate wins.
- Winchester101.90%
Zip codes with a Winchester address
A different geography, not a breakdown. The figure above covers the municipality; these zips cover everywhere the Post Office calls Winchester — often including townships beyond the city limits. Both come straight from Zillow, and they are not expected to average out.