Image from Ossining
Image courtesy of Mark Wyman. Used by permission under CC BY 2.0. License Info Photo has been cropped.
Image from Ossining
Image courtesy of Mark Wyman. Used by permission under CC BY 2.0. License Info Photo has been cropped.

Living In: Ossining

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Ossining, New York, is a small town on the west side of Westchester County that directly borders the Hudson River to the west and the Croton River to the north. It is a popular residence for commuters to New York City, as it is approximately 25 miles away and provided commuter rail service to Grand Central Terminal, Croton-Harmon and Poughkeepsie via the Metro-North Railroad's Hudson Line from the Ossining Train Station. Its early history involves settlement by the Mohegan Tribe, who referred to the area as Sint Sinck, which translates to stone upon stone and refers to the multiple layers of limestone found in parts of the town. In 1685, the Sint Sinks sold their land to the Manor of Philipsburg, whose family held the land until the end of the Revolutionary War when the lord of the manor was imprisoned for being a Loyalist and the land was forfeited to the State of New York and sold at an auction. Many parts of the manor were sold to tenant farmers who had worked the land during and long before the war. After the war, the area became known as Sing Sing. In 1825, the state began the construction of the Sing Sing Prison. The town flourished from industrial growth, which relied heavily on convict labor from the penitentiary. However, as the prison became notorious, the town officially changed its name to Ossining in 1901 to try and distance itself from the prison's reputation. Ossining's public schools are highly regarded throughout New York- specifically the Ossining High School was in the list of the country's top 250 best schools in the year 2000. In addition to the public schools, there are three parochial schools that serve students from kindergarten through eighth grade. The Ossining Public Library is one of the town's prized buildings and houses over 110,000 books, 25,000 non-print items and 300 newspaper and magazine titles. As part of the Westchester Library System, the library also offers patrons access to millions of other listings across the libraries. The library also offers patrons over 50 public internet terminals, a 250-seat theater, an art gallery, a café and the country's first radio frequency circulation system. Ossining is home to a mid-to-upper middle class population, considerably less expensive than its surrounding neighbors in Westchester County. Renting is also more popular in Ossining than in greater Westchester.

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Neighborhood Information




  • Anne M. Dorner Ms
  • Brookside School
  • Claremont School
  • Ossining Shs
  • Park School
  • Roosevelt Educ Ctr

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