Poughkeepsie metro, NY relocation guide
Moving to Chester, NY
$699,995Median listing price
OrangeArea
Commuter-friendlyCommute profile
About Chester
The Town of Chester surrounds its namesake village in southeastern Orange County, blending the storybook hamlet of Sugar Loaf — famous for its artisan shops — with suburban subdivisions and rural roads. Housing ranges from village colonials to newer developments near the Route 17 corridor.
Home prices in Chester
The median listing price in Chester is $699,995.
Top places in Chester
- Sugar Loaf — historic 18th-century hamlet known for its craft and artisan shops.
- Downtown Chester village — Main Street shops and restaurants (shared with the village).
- Chester Commons — local shopping and dining hub.
- Goosepond Mountain State Park (nearby) — hiking and views.
- Purgatory Road and rural back roads — classic Orange County countryside.
Commuting from Chester
- No in-town 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).
- Short Line bus service to Port Authority serves the Chester area.
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-town rail station; nearest Port Jervis Line stations are Harriman and Salisbury Mills–Cornwall, each about 10–15 minutes away.
Town links
Schools
Transit
Official town resources. School report cards via the New York State Education Department.