The Village of Ossining was ranked eighth in the list of the top 10 places to live in New York State for 2014 according to the national online real estate brokerage Movoto.
Frederick Philipse bought the area which presently constitutes the Town of Ossining from the Sint Sinck Indians in 1685. The Sint Sinck are members of the Matinecock (Algonquin) tribe, who originally resided in the area of Cow Neck Peninsula on Long Island, New York. His Manor extended from Spuyten Duyvil Creek on the border between present day Manhattan and the Bronx to the Croton River. The last Lord of the Manor, Frederick III, was a Loyalist in the American Revolutionary War who fled to England, so the State of New York confiscated the manor in 1779.
In 1838 Benjamin Brandreth built a manufacturing facility for his Vegetable Universal Pills which became one of the most successful patent medicines in the United States. Brandreth's business became very successful and his firm was at one point the nation's leading proprietary advertiser. Brandreth became President of the village for many years.
Due to the history of the village, a number of Ossining structures are on the National Register of Historic Places, and the downtown shopping area is listed as the Downtown Ossining Historic District. In addition, the Sparta neighborhood has been designated a local historic district. Ossining’s role in New York’s heritage has been recognized by its inclusion, as one of only 14 areas, in an Urban Cultural Park System designed to attract visitors to the State. Also listed on the National Register of Historic Places are the Richard Austin House, Brandreth Pill Factory, First Baptist Church of Ossining, Highland Cottage, St. Paul's Episcopal Church and Rectory, and Washington School.