Chester, New York.
Typical home $538,036 (+3.2% in a year). Poughkeepsie-Newburgh-Middletown, NY metro.
to buy the typical home at today's mortgage rate — +$322 (+13%) since Jan 2024.
- 1 year
- Up $16,534 +3%
- $521,502$538,036 since Sep 2025
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.
- Chester$2,824
- New York$2,755
- United States$1,922
Typical home values in Chester, NY rose 3.2% over the past year — faster than the nation's +1.2%.
Living in Chester, Orange County, New York
Chester is a village of 3,993 people in Orange County. Unemployment in Orange County was 4.3% in August 2026, and the county had 0.4% fewer jobs in 2025 than the year before. The most residents work in shops, 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 It can be wrong or out of date.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. Chester is a small village in Orange County, New York. Household incomes in the county run on the high side, and a typical home here is worth a good deal. Winters are cold, with January the coldest month, and summers are warm, with July the warmest. Rain and melted snow add up to a fair amount over the year.
Work. Many residents work in shops, in schools, hospitals and social care, in restaurants, hotels and entertainment, and in transport, warehouses and utilities. Some of the largest workplaces in Chester are distribution and trucking operations, among them Wakefern, L.P. Transportation and JB Hunt. Getting to work takes a long commute for many, and only a small share work from home.
Things to do. Legoland New York, an amusement park, is in or beside town, as is Goosepond Mountain State Park, a protected area for walking and being outdoors. Tomahawk Lake is a short drive away for time by the water. For a longer outing, the United States Military Academy, which houses a museum, is a longer drive away.
Report a mistake
- 1,552households
- 35%of adults have a degree
- 7%below the poverty line
- 40 mintypical commute
- 10%work from home
What residents work in
Employed residents by industry, from the Census survey. Orange County had 154,905 jobs in 2025, 0.4% fewer than the year before (Bureau of Labor Statistics).
Weather through the year
Coldest in January, with highs near 35° and lows near 17°; warmest in July, with highs near 84° and lows near 61°. About 41 inches of rain and melted snow a year.
Average daily high and low, 1991–2020, at the Montgomery Orange Airport weather station, 10 miles away (NOAA).
Largest workplaces in Chester
- CS Wholesale Grocers Chester NY PDC311
- WakefernGrocery stores194
- L.P. TransportationBulk liquids trucking, local112
- JB Hunt107
- Trinity SolarInstallation of photovoltaic panels103
- ADUSA Dist DC 59 Chester80
- Satin Fine FoodsConfectionery, nonchocolate, manufacturing70
- Brakewell SteelStructural steel, fabricated, manufacturing47
Staff on average in 2025, as each workplace reported it to OSHA with its injury records: 13 workplaces with 20 or more staff, 1,139 people in all. 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
- Winter weatherRelatively high
- HurricanesRelatively moderate
- Strong windRelatively moderate
- Inland floodingRelatively 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 in Chester’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 Orange County and the Poughkeepsie-Newburgh-Middletown, NY metro.
Chester home values
Zillow measures a city over its municipal boundary. Against the state and national figures, mid-tier homes, smoothed and seasonally adjusted.
- Chester$538,036
- New York$524,942
- United States$366,157
Levy by levy, and a check of one home’s own bill, the site covers Ohio’s property tax.
Sellers are cutting prices on about 1 in 6 Chester listings — the market is roughly in balance.
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.
- Chester17.30%
- United States26.90%
Homes for sale
Active for-sale inventory. More supply hands power to buyers.
- Chester77
New listings per month
Sellers arriving at the market.
- Chester22
Zip codes with a Chester address
A different geography, not a breakdown. The figure above covers the municipality; these zips cover everywhere the Post Office calls Chester — often including townships beyond the city limits. Both come straight from Zillow, and they are not expected to average out.