Ossining Village

To Americans who came of age during the era of Peak TV, Ossining Village is known as the home of perhaps television’s most enduring advertising executive, Don Draper. But long before Jon Hamm achieved superstardom in his portrayal of the whiskey-soaked, rakish and debonair Clio award-winning creative director in Mad Men, Ossining was the peaceful staging point for individuals and families looking for an Upstate quality of life while moving forward along a New York City career track.

Home buyers usually leave New York City for these northern river towns for various reasons, including home prices, space, schools and a more straightforward and slower lifestyle. Julie Alcée, a local associate real estate broker with Berkshire Hathaway and resident of Westchester County, says, “When the pandemic happened, people began to move up and further up, and then they just kept coming when the remote work continued.”

In the southern part of this 6-square-mile neighborhood, there are several postwar brick cooperative apartment buildings where home buyers may find one-bedroom units for as little as $100,000. Prices start at $400,000 for Ossining’s ubiquitous three-bedroom colonial revivals. The village was founded in 1813, and many homes date back to the early 19th century. Saltbox homes from the late 19th century less than a mile from the Hudson River, or America’s Rhine as it’s sometimes called, can be found in well-preserved condition for under $450,000. Many homes in this hilly neighborhood on the water have a storybook quality, standing like quaint if sometimes ramshackle monuments to the early American Republic. Prices generally top out well under $1 million.

Louis Engel Waterfront Park edges the Hudson River on the far western section of Ossining Village, opening up before commuters as they step off the next-door Metro-North Rail Road. With kayak racks and boat launches, commuters coming home after a hard day at work in New York City “can get off the train and go kayaking,” says Alcée. Or you can grab a beer and some fish and chips and stare at the slate-blue water drifting by at The Boathouse restaurant, which occupies prime riverfront real estate next to the train station. A bit inland, Snowden Park features an ample green space and a new skatepark.

Ossining’s historic downtown shopping district, revitalized in recent years and consistently featuring new shops and restaurants, begins at the water and leads east. It’s charming and walkable, with a view of the New Jersey Palisades and the river to the east and hills rising up in the west. Prewar storefronts belie the diverse citizenry of this neighborhood, housing restaurants serving cuisine from all four corners of the globe. The newly constructed Ossining Library is evidence of the public spiritedness of the town government. A large Stop & Shop serves residents from all walks of life.

The Ossining Union Free School District received an A-minus for overall performance on the school rankings website Niche. The Park School is a kindergarten through first-grade school that received a B-plus on Niche. Nearby Claremont Elementary School received a B. Anne M. Dorner Middle School received a B-plus, and Ossining High School, with an excellent student-teacher ratio of 13 to 1, received an A-minus and is ranked among the top 500 Standout High Schools in America by Niche. Private school St. Augustine has a vast campus by the river. Commuters can reach Midtown Manhattan from the Ossining station on the Metro-North Rail Road in one hour. With river views the whole way, Ossining Village offers the best of the country and the city in one beautiful and historic place.

Written By

Abbot Street

Photography Contributed By

Deawell Adair

Video By

Syd Silberman