Living in Ossining, NY

Ossining NY Real Estate and Homes for Sale


With a population near 40,000, Ossining is one of Westchester County’s larger towns. It stretches along the spectacular Hudson River on the county’s western edge, with several miles of waterfront and incredible scenic vistas. It extends just over 15 square miles, and is bounded to the north by the Croton River.

The countryside where Ossining sits is classic Hudson River Valley scenery. Majestic hills cloaked by thick forests, quiet lakes, hidden streams, and abundant wildlife. These may lead you to think that you’ve stepped back in time or at least far from the everyday world, but the city is actually less than 40 miles away! The city’s rail station is right on the waterfront. Route 9 passes right through town and is an excellent connection to points south.

Living in Ossining

The town center of Ossining features a collection of interesting and beautiful historic buildings. The downtown is listed on the National Register of Historic Places. Interesting sites include the Old Croton Aqueduct, which used the force of gravity to move water 41 miles to Manhattan, and the beautiful Olive Opera House.

Originally a river port, Ossining was first developed at the waterfront, and the traditional business center, called The Crescent, is near the Hudson River.

One readily recognized local landmark is Sing-Sing prison, a maximum-security facility that opened in 1826. It was the 3rd prison constructed in the United States, and today houses about 2000 inmates. Ossining is also home to many prominent people in entertainment and business, and is the fictional home of Don Draper’s character from the popular Mad Men television series.

Today, the lifestyle in Ossining reflects an appreciation for the area’s rich history and natural treasures. Recreation opportunities abound and natural areas and waterways are carefully protected. Parks and nature preserves are ubiquitous in Ossining and residents can take advantage of miles of scenic trails in local woodlands and along the Hudson. At Crawbuckie Park and preserve they enjoy a stunning, accessible riverside trail.

Ossining Real Estate

Homes in Ossining range from convenient apartments to impressive properties with commanding views of the Hudson. Median prices for single-family homes sit at about $400,000, with larger colonials commanding $2 million or more.

Learn more about this community and the real estate available in Ossining by connecting with our team of professionals at GioHomes. We look forward to hearing from you soon.

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