Ossining Real Estate

With New York City and Long Island Sound to the south, Putnam County on the north and Connecticut to the east, Westchester County holds the distinction of being the world’s first large-scale suburb. Major interstate highways constructed during the 1950s and ‘60s and the construction of the Tappan Zee Bridge encouraged major corporations to build their headquarters here. A sweet spot for commuters traveling by car or by the Metro-North Commuter Railroad, today’s Westchester is one of the nation’s most affluent counties and the location of many of New York City's most desirable suburban communities.

With roots that go as far back as 1685, the town of Ossining, NY, is made up of two villages, Ossining and Briarcliff Manor. One of Westchester’s “rivertowns,” Ossining is situated on a series of hilltops overlooking the mighty Hudson. Just 30 minutes away, the Manhattan skyline is visible on clear days. Ossining is the hometown of the fictional Draper family of Mad Men television series fame as well as infamous maximum security prison Sing-Sing. Sparta is the town’s oldest surviving settlement.

The historic town has kept a great deal of its original character while becoming a vital community with a variety of housing options, from modest single-family homes to luxurious estates. Westchester Magazine ranked Ossining as the No. 2 best community in Westchester based on criteria like diversity, housing cost, parks and recreation, proximity to NYC, safety, schools, shopping, nightlife and proximitiy to water. Green spaces and parks–like Cedar Lane Park and Teatown Reservation–keep outdoor enthusiasts happy, and there are several boating clubs for lovers of water sports.