Yes, New Castle Residents can purchase up to two permits per household. You are not guaranteed a spot, however there have not been complaints to the Town Clerk about this. Most commuters find a spot closer to the station if they arrive between 7-7:15am. Otherwise there are lot places toward Washington St. and there should be a spot. (5 min walk). Residents can also purchase a Meter Spot for approx. $5 and then put quarters into the meter between the hours of 7am-7pm, after those hours it is free (with resident meter sticker).

Here is the link and all the info that you need for parking at the Chappaqua train station.

http://as0.mta.info/mnr/stations/station_detail.cfm?key=148