With an urbanely quaint downtown, sprawling homes, a topnotch school district, and a 50-minute ride to GCT, Chappaqua has long been a name-brand suburban address. Long before before evolving into a veritable who’s who of politicians, CEOs, and Hollywood elite, locals knew they had one of the best-kept secrets in Westchester.
The farming Quakers who settled here around 1730 called it shah-pah-ka, the Native American term for “rustling land,” or a place where nothing is heard but the rustling of the wind in the leaves. That may be the case on the meandering trails of the 126-acre Gedney Park just outside the downtown, but it’s a far cry from the Chappaqua of today, where the main thoroughfare is bustling at lunch time, rush hour, and any hour in between.
The area around the Quaker’s meeting house, which still hosts weekly gatherings, is on the National Register of Historic Places, though many early establishments were destroyed in the 1904 Chappaqua tornado. (The New York Times then reported severe lightening made the ladies faint.) The house New-York Tribune founder and Congressman Horace Greeley built around 1820 still stands, and is now home to the local historical society.
Some of today’s residents stroll to the chic shops and upmarket eateries that dot the downtown streets, though most drive from grand homes that rest on an acre plus. Jardin du Roi is a longtime local favorite for everything from escargots to all day breakfast, best enjoyed on the patio. Gourmet food shop Susan Lawrence, part-market and part-European sidewalk cafe, is another staple for coffee meet-ups or a grab-and-go duck burrito. The newer Chappaqua Station serves up seasonal fare in the town’s fieldstone train depot, bringing excitement to the commuter routine that’s just part of daily life in this bustling “rustling land.”
Chappaqua boasts an incredibly diverse housing stock, represented by virtually every architectural style.
“People appreciate that we’re socially aware and that we give back—and, that we’re not all tutus and pink,” said longtime Chappaqua resident Trish Kallman, who owns fashion-forward, globally conscious Hip Kid, a clothing boutique where nothing but organic, fair trade, eco-friendly, or mindfully manufactured brands are on sale. She says the concept works in a small town like Chappaqua where the sense of community—and style—is strong.
“That feel of Brooklyn edginess really resonates here,” she added.
It’s a community we’ve got deep roots in. In the 1920s, our company acquired more than 1,000 acres in New Castle and embarked on one of the most ambitious developments in Westchester history: Lawrence Farms. The project brought Reader’s Digest to the area, for years headquartered in a sprawling complex on Roaring Brook Road, and many properties in the subdivision were sold to employees looking to live nearby. Repeating the success of their Hotel Gramatan in Bronxville, the Lawrences even restored an old boarding house into a country inn and restaurant for prospective homebuyers, still thriving today as the acclaimed Crabtree’s Kittle House. Two decades later, A.T. Houlihan opened a sales office in town, and we’re still there today.
In recent news, the Reader’s Digest site, now Chappaqua Crossing, is being redeveloped as a mixed-use community of residential, retail, and commercial space, and will soon welcome Northern Westchester’s first Whole Foods.
“It’s as southern as Northern Westchester gets,” said Brian Murray, our Chappaqua brokerage manager. “We offer a comparable product to what you can achieve down-county—a downtown, a train station, walkability—at an up-county price point. We’re hopeful the new development will excite buyers all the more.”
Stop in and visit us at 45 S. Greeley Avenue, right next door to Squires.