RIARCLIFF MANOR, a village of 8,000 people less than thirty miles north of New York
City, looks a lot like what one might picture a
place called Briarcliff Manor to look like.
Situated on just under six square miles of
land in Westchester County, between Ossining and Mount Pleasant, Briarcliff is home to
the Sleepy Hollow Country Club and a Trump
National golf course. The median home value
is around $750,000. And the time it takes
to walk from one end of Pleasantville Road
to the other—that’s the main drag with the
bank, the hardware store and the café where
the owner handed an entire jar of Nutella
and a spoon to a young customer one day this
summer—is just over three minutes.
“Briarcliff is like, kind of a little
picture of perfection,” says Jenny
Rosen, 21, a senior at Bucknell
University who grew up across the
street from the Briarcliff Manor
schools. With only 150 students
per class, the high school is small
enough to share its property with
the middle school.
Briarcliff Manor Union Free
School District, offering one of
the nation’s top high schools,
is an important reason people
choose to settle here. Many residents pay $20,000 a year or
more in property taxes, a large
chunk of which funds the public
school system.
And 20 years ago if you told
some of those parents—who
patted their kids on their heads
and kissed them goodbye before
sending them off on the bus—that
one day they’d consider suing their