Chappaqua

A leafy hamlet that’s sleepy, but polished.

Though it’s recently become a popular suburban outpost for New York City’s Upper East Siders who crave meticulously restored antique homes on wooded lots and exceptional schools, Chappaqua has retained its country charm with its rolling hills, centuries-old stone walls, and idyllic American flag-lined downtown streets.

The name of this picturesque wooded hamlet comes from tribes of the Mohegan Confederation, who called it “Shepequa” because of its plentiful water sources. Today, Chappaqua’s abundance of natural beauty—parks, trails, and nature preserves—continues to nourish its long-time residents and lure newcomers.

What to Expect

Bucolic vistas and easily walkable downtown.

Chappaqua is compact at just under one-half of a square mile. Fanning out from the quaint downtown—which houses the train station, shops, restaurants, and a gazebo that holds summer concerts—are side streets with houses on small lots. As you get further from the epicenter, the lots and homes get significantly larger.

The Lifestyle

A friendly, small-town vibe is less than an hour from New York City.

With just under 1,500 residents, most neighbors in this close-knit community know each other by name. The main drag in the heart of the hamlet, South Greeley, is lined with mom-and-pop shops that close their doors in time for everyone to get home for dinner.

Unexpected Appeal

Celebrity homeowners who are just like us.

While grabbing a bite, walking along the local trails, or attending the local Strawberry Festival, you might spot some famous faces engaged in casual conversation with their neighbors. Past and present residents include Hillary and Bill Clinton, Vanessa Williams, and Ben Stiller.

The Market

Antique gems with original details.

Early 20th-century classic Colonials and farmhouses abound—whether on small lots within walking distance to the train or multi-acre plots on the outskirts. Newer construction will also soon be available. Just shy of 100 luxury Georgian-style townhomes are being built in an upscale retail village called Chappaqua Crossing at the northern end of town.

You'll Fall in Love With

The farm-to-table ethos.

Chappaqua’s expertly curated farmers’ market—where you’ll find everything from local beer to hot sauce to dumplings—draws foodies from all over Westchester. Even the train station cafe boasts a seasonal menu, which includes protein bowls topped with farm-fresh eggs and smoothies made from local produce. And gourmet restaurants and food markets abound.