Ossining, NY
Ossining is a perfect example of a 19th century Hudson Valley waterfront community.
Main Street leads up the hill from the river and train station to Ossining’s bustling downtown area, which has a mix of street-level shops and restaurants with apartments, offices and artists’ lofts on the upper floors. The surrounding residential neighborhoods provide homes ranging from modest multifamily homes, rentals and townhouses to grand Victorian homes and mansions overlooking the river.
Ossining, which refers to the town and the village it surrounds, dates back to the Dutch colonial era and now is primarily a bedroom community. Shops, restaurants and services are clustered downtown and along Route 9, and there still are some light-industrial employers scattered around town, particularly along the waterfront.
Ossining was ranked the second-best community to live in Westchester by Westchester Magazine, based on criteria such as diversity, housing costs, parks, recreation, property taxes, proximity to the city, safety, schools, proximity to water, nightlife, shopping and downtown amenities.







