Briarcliff Manor

The hilly, tree-lined streets of this thriving village, which occupies 70 percent of the combined areas of Ossining and Mount Pleasant, are dotted with the mansions of millionaires who came to the village after the turn of the century. Some are still privately owned but many have been subdivided into housing developments. Briarcliff is highly conducive to an active lifestyle, sitting at a crossroads of Westchester County’s extensive trail network. There’s the 12-mile Briarcliff-Peekskill Trailway, which winds northward through Teatown Lake Reservation. The North County Trailway, which replaced the old Putnam Division train line through town, provides a paved bicycle link from Brewster to the Bronx, a span of 43.7 miles. While the tracks through Briarcliff proper were torn up decades ago, commuters can still hop a ride to Grand Central from Scarborough station on Metro North’s Hudson Line, or at neighboring Pleasantville station on the Harlem Line.

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