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.

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.

​Façade: 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.

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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

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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

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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

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

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