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The imposing brick buildings in Ossining’s shopping district are on the National Register of Historic Places, as are many of the ample homes scattered about this sprawling village. Colonials, Cape Cods, and Victorians sit side-by-side on the downtown streets.


Miles of Waterfront

Compared to its neighbors to the north and south, the river town of Ossining is a major metropolis. Its population is three times that of Croton-On-Hudson or Tarrytown. Its broad streets and imposing brick buildings are a clue to how it compares to nearby communities. But size does matter, at least in terms of the housing stock. There is an unusually wide range of homes available, from one- and two-bedroom co-ops to four- and five-bedrooms houses with views of the river. And prices tend to be more reasonable than in the adjacent villages — at least until the word gets out about Ossining and its miles of waterfront.

Where to Get Your Bearings

If you’re here early in the day, stop by First Village on Main Street. This storefront café is the opposite of a Starbucks — the beans are ground locally, and the pastries are homemade. On top of that, owners Kathryn and Luis Corena are thrilled to share their eclectic playlist with you. If it’s afternoon, Bigfoot Creamery has a charming little kiosk on the waterfront that serves hand-scooped ice cream.

What Locals Recommend 

Starting at Gerlach Park, take a hike along the Old Croton Aqueduct Trail. This is one of the most unspoiled sections of the entire trail, with much of it looking like it did in the 19th century.

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The Local Market at a Glance

Notable Information
35 mile drive north of Midtown Manhattan. 45 minute train ride via Metro-North from Grand Central at peak.
Because of its size, Ossining isn’t quite as walkable as most of the nearby river towns. If you’re here for the day, you might want to focus on the village’s breezy waterfront.
Honest Answers to Your



What are the top 3 reasons to consider buying in Ossining?

1. A massive supply of homes. Ossining is three times the size of neighboring Tarrytown or Croton-On-Hudson, so there’s always quite a few houses on the market. 2. Less sticker shock. The median price for a single-family home is still significantly less in Ossining than in the rest of Westchester County. That means you get more house for your money. 3. Great place for a starter home. If you’re looking to buy your first home, or downsize from the one you have, Ossining has more condos per capita than any other community.

What’s the vibe like in Ossining?

In Ossining, there’s literally dancing in the streets at the river town’s long list of annual celebrations. The best known is June’s Ossining Village Fair, which draws thousands of people for the live bands, children’s activities, and food from around the globe. July and August bring Ossining Riverjam, which transforms the usually quiet waterfront park into a music festival.

Where can I get the basics in and around Ossining?

If you’re in search of organic produce, you have plenty of choices in Ossining. Besides the Ossining Farmers’ Market, open spring to fall, there’s a Green’s Natural Foods on the edge of Briarwood Village and a Whole Foods a few miles away in Chappaqua. There are several other chain supermarkets as well. For home renovations, Melrose Lumber has had devotees since it first opened in 1922.

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