Poughkeepsie metro, NY relocation guide
Moving to Chester, NY
$699,995Median listing price
OrangeArea
Commuter-friendlyCommute profile
About Chester
The Village of Chester sits within the Town of Chester in southeastern Orange County, a classic Hudson Valley village with a walkable Main Street. Housing is village colonials, capes, and newer infill near the center.
Home prices in Chester
The median listing price in Chester is $699,995.
Top places in Chester
- Main Street — village shops, cafes, and restaurants.
- Sugar Loaf hamlet (nearby in the town) — artisan shops.
- Village parks and the Chester Commons area.
- Goosepond Mountain State Park (nearby) — hiking.
- Chester railway heritage — the former Erie station area.
Commuting from Chester
- No in-village rail station; nearest Port Jervis Line stations are Harriman and Salisbury Mills–Cornwall, each about 10–15 minutes away.
- Typical weekday rail trip to Hoboken from Harriman: approximately 1 hour 20 minutes (approximate).
- Approximate drive to Midtown Manhattan: ~65 minutes (NY-17/I-87; longer with traffic).
Schools in Chester
Public schools: Chester Union Free School District. For enrollment and performance data, see the state report card in Town links below. Confirm school assignment for any address directly with the district.
Chester FAQs
- What is the housing market like in Chester, NY?
The median listing price in Chester is $699,995. Median listing price · Realtor.com · September 24, 2026 - How is the commute from Chester, NY?
No in-village rail station; nearest Port Jervis Line stations are Harriman and Salisbury Mills–Cornwall, each about 10–15 minutes away. - Which school district serves Chester, NY?
Chester is served by Chester Union Free School District. See the state report card in Town links, and confirm school assignment for a specific address with the district.
Town links
Schools
Transit
Official town resources. School report cards via the New York State Education Department.