Best Places to Live: In-Town, Chappaqua

Lovely homes, a close-knit community, and fabulous schools all within walking distance are what defines this area the most.


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Blueprint: Founded by a group Quakers in the 1730s, Chappaqua was the home of New-York Tribune editor and US Congressman Horace Greeley. Since the late 1990s, Bill and Hillary Clinton have called Chappaqua home.

Chappaqua’s a lot more than Bill & Hill. Located between Pleasantville and Mount Kisco, it’s considered the southernmost Northern Westchester town. It’s beautiful, walkable, upscale and has a fabulous location.

‚ÄčFaçade: Housing inventory is plummeting as buyers seek homes with land in a woodsy setting that’s also walkable to this bucolic hamlet in the southernmost part of Northern Westchester.

Foundation: Chappaqua, about 39 miles from Manhattan, is a hamlet in the town of New Castle. Its hotness is nothing new, but these days it’s for reasons other than a chance to rub elbows with Bill and Hill. Chappaqua is not “Scarsdale North,” as some would like to believe; people don’t choose Chappaqua because they can’t afford upscale Southern Westchester towns. People buy here because the location is fabulous and accessible in its own right; the schools are among the best in the region; the downtown is walkable and cheerful; and there’s lots to do and see. There’s a popular farmers’ market and classic dining at establishments like Le Jardin du Roi. With a newly renovated Metro-North station and the debut of the farm-to-table café Chappaqua Station, commuters can unwind with a glass of wine or enjoy dinner as soon as they step off the train.

Recent Reno: An infrastructure project is making upgrades and widening sidewalks.

Trending: Up at the lower price points. In the $700,000 to $1M price point, inventory is down 42 percent compared with last year, according to Houlihan Lawrence brokerage manager Brian Murray.


Best Thing About Living Here: “We love that we are within walking distance of the town, train, library, and the elementary and middle schools.” —Chris Madden, longtime resident


Selling Points: lovely homes, close-knit community, fabulous schools, proximity to Greenwich, NYC, and points north and south

Trade-off: temporary inconvenience due the construction and infrastructure effort 

Starting Point: $500,000

Topping Out: $5M

Best For: families, empty nesters, retirees

Need to Know: High taxes in return for a high level of services

Fast Fact: Governor Andrew Cuomo and TV chef Sandra Lee have a house in Chappaqua.

Assessment: sophistication, cachet, and urban amenities in a town-and-country setting

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