Best Places to Live: The Old Village, Ossining

Those who like activities and the sublime beauty of the river will be happy calling this home.

Blueprint: In the early 1800s, the Old Village of Ossining was the shipping, commercial, and industrial hub for Northern Westchester. Captains of ships, commerce, and industry built homes with the finest river views on the higher elevations of Ossining and built many of the surrounding homes for associates and employees.

​Façade: The Old Village is a diverse, developing, and evolving community with exceptional river views and is still affordable compared with its Rivertown neighbors to the south. Walkable to the train, it’s just 42 minutes to 42nd Street.  

Foundation: The Old Village of Ossining features stunning National Historic Registry buildings and beautifully repurposed old structures. Main Street and the Market Square have 16 delis, restaurants, and cafés like Melike’s and First Village Coffee. Food offerings include Cravin’ Jamaican and new restaurants, like the vegetarian Good Choice Kitchen. Seasons are marked by a host of festivals, events, and activities, such as the Ossining Village Fair, Portuguese Fair, the Family Fall Festival, along with the Ossining Farmer’s Market. “The Old Village is the beating heart of this community,” says real estate agent Eric Schatz. “It has an amazing diversity of homes and people, parks, cultural activities, festivals and performances, preserves and trailways.” 

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Recent Reno: Parks are being added and improved, including the Crawbuckie Nature Preserve and the Sing Sing Kill Park.

Trending: “As people are discovering this area and what it has to offer, they are finding so many things to appreciate, right at their doorsteps,” says Schatz. “Prices of homes are moving up but still amazingly affordable compared with those of our neighbors.”

Selling Points: Within easy walking distance to the train station, The Old Village remains affordable, with amazing natural amenities, striking architecture, and diverse activities. The Ossining High School Science Team has sent more finalists to the State Science Symposium than any other school in Westchester. 

Trade-off: While it offers a great quality of life, Ossining is not yet a status symbol.

Starting Point: $325,000 for a 1,400 sq ft single-family home

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Topping Out: $1 million or so for a 6,000 sq ft antique hilltop mansion

Best For: those who like activities and those who like the sublime beauty of the river, including kayakers, birdwatchers, and sunset worshipers

Need to Know: Most area homes have been renovated, but some are still in need of TLC.

Fast Fact: Home to the infamous Sing Sing Prison, Ossining, like Rome, was built on seven hilltops. 

Assessment: dining and architectural diversity, along with stunning views, at great value

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Best Thing About Living Here: “Ossining is great. It is becoming more diverse and interesting, with ethnic restaurants, a new coffee shop, vegan restaurant, and a black-box theater.” —James Finger, longtime resident


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