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.
Bucolic vistas and an 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.
A friendly, small-town vibe 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.
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.
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.
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.
A sophisticated Westchester suburb surrounded by nature.
Just under 5,000 people live in Armonk’s 6.1 square miles of rolling hills. Its lack of a train station keeps it from being overrun by commuters (the nearest is a 10-minute drive away), but the village’s walkable business district, new restaurants, and first-rate schools increasingly draw young families from Manhattan.
Named by the Siwanoy Native Americans of the Wappinger Confederacy in the mid-1800s, this Central Westchester village began to boom after IBM’s global headquarters came to town in the 1960s. Today, the hamlet still doesn’t have the same name recognition of some of its bigger or fancier neighbors, but its bucolic charm and plethora of amenities continues to lure New York City transplants.
A dizzying spectrum of retail and real estate options.
Main Street, studded with mom-and-pop shops, offers everything from doughnuts to bicycles. Nearby lies Armonk Square—a relatively new retail hub with a mix of restaurants, specialty shops, and residences, including apartments, gated communities and free-standing homes on lots up to a half-acre. Farther from the town center, you’ll find multi-acre estates.
Unpretentious luxury living in the country.
The pristine downtown has more of a Hamptons than Westchester vibe with its high-end fashion boutiques and gourmet food shops. And if you want a highly private 10-acre property with a pool, a tennis court, and gated security, you can find it. But the community is still close-knit, reliably coming together for charming events like Frosty Day with cocoa and face painting every winter.
The hamlet’s Revolutionary War–era history.
The iconic Smith’s Tavern, on Bedford Road, was the wartime headquarters for the local militia and is now a museum. Benedict Arnold’s co-conspirator, Major John André, was even held in a local barn before his hanging in 1780 in nearby Tappan, N.Y.
Lots of square footage and relatively new construction.
Occasionally buyers can find modest properties, like a 1960s split-level ranch. But the market tends to be dominated by sprawling colonials built sometime during the past few decades.
The burgeoning food and cultural scene.
Armonk offers a wood-fired Neopolitan pizzeria, a premium grocer with a craft beer bar, innovative farm-to-table and New American restaurants (one with a James Beard award), a wine store from the former Blue Hill at Stone Barns wine director, plus a top-notch theater company and nationally famous fall arts festival.
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