The village of Ossining is located within the town of Ossining in Westchester County, New York.  It is located on the eastern shore of the Hudson River at its widest point, Haverstraw Bay.  The area was inhabited by the Sint Sinck, members of the Mohegan Indian tribe, and their name is literally translated to mean “stone upon stone”, referring to the large beds of limestone found in southern Ossining.

Frederick Philipse purchased their land and used it to build his Manor of Philipsburg, a 165,000 acre estate.  He then leased his land out to tenant farmers from Holland, France, and England.  The land was later confiscated by the state during the American Revolution because the owner was a loyalist.  It was sold at auction, and many of the tenant farmers, who were supporters for America purchased the land they were working.

At the time, the area was known as Sing Sing and was, in 1813, the first incorporated village in Westchester County to be chartered by the state.  However, in 1825, construction began on Sing Sing prison, and it was decided that the name of the village should be changed to avoid confusion.  Finally, in 1901, it became the village of Ossining.

Because of its extensive history, many structures within the village of Ossining are listed on the National Register of Historic Places.  It is one of only 14 villages included in the Urban Cultural Park System, an acknowledgement for its role in New York’s heritage.  The population is diverse, and the homes range from modest in size and amenities to extremely luxurious estates with plenty of perks.