The first time I drove down South Greeley, the main drag running through the center of Chappaqua, I felt like I was in Vermont. It was summer, the trees were lush with bright green foliage, and there were forested hills in the distance. Rows of adorable shops and restaurants lined the streets with American flags waving out front. Kids licked ice cream cones while their parents ducked in and out of the hardware store, the bakery, the corner Starbucks.
Anyone looking for a true country village will find it in Chappaqua. While tastes here are certainly urbane – most local residents do the 55-minute commute into Manhattan and you can get your banana kale raw almond smoothie at Chappaqua Station, the “farm to town” café in the old train station – the draw of the town is its rural, community-centric vibe. A passionate group of foodies meet at the Chappaqua Farmer’s Market every Saturday. There’s a Strawberry Festival every spring, and a Children’s Book Festival in the fall.
Don’t expect an abundance of nightlife. Chappaqua is sleepy; most shops are shuttered by 6 or 7pm. Still, during the daytime, the town is a vibrant meeting place in an area where houses tend to sit further apart with big sprawling yards in between.
“People who live here value its country chic vibe,” says Harriet Libov, a broker with Houlihan Lawrence in Armonk, who works with families in the town frequently. “They want to support the mom and pop shops. They get a good feeling when they visit because it’s a quiet, safe family-friendly town. It checks off lots of boxes like charm, value, education, local train station, and strong sense of community.”
Case in point: The village of Chappaqua recently hired a project manager to give the downtown a makeover, with plans to improve the village’s walkability and increase outdoor gathering spaces. There’s already a unique assortment of businesses in place: Chappaqua resident Trish Kallman opened her shop Hip Kid in 2015, which sells hipster clothes and toys (most of the wares are also raising money for causes Kallman believes in), while Adam Strahl and Danielle Zinaich, also residents, founded LOCAL, a gourmet healthy eats café in 2011. Since there wasn’t a local bookshop, Laura Schaefer opened Scattered Thoughts on King Street in 2016. We’ve named the brie burger at Le Jardin de Roi our favorite in the county, and the chocolate chip cookies at bakery Sherry B are delicious.
If new residents are lured by the top-rated schools, then they’re often sold by the unique antique houses common in this area. You’ll find many early 20th century classic colonials with original period details – whether they’re on smaller lots and walking distance to town or on sprawling acreage a quick drive away. There are townhomes close to town that typically start around $400,000, and if you prefer newer construction, Random Farms, developed in the 1990s, has a community pool, tennis courts, a playground and clubhouse; houses price at over one million. While the area, like most of Westchester, is expensive, you can get more for your dollar in Chappaqua than in some of the southern Westchester suburbs, like Scarsdale; In 2016, the median sales price in Chappaqua was $914,500.
Chappaqua Crossing, a large shopping center on the outskirts of town that used to house the headquarters of Reader’s Digest, is currently being developed into a combination of luxury townhouses, retail and restaurants. Ground has already been broken for a 40,000-square-foot Whole Foods, the first in Northern Westchester, and mega-gym Lifetime Fitness.
The local children’s room at the Chappaqua Library has one of the most impressive free event line-ups in the county; there are multiple story hours a day. Many moms bring their kids to play at Gedney Park on Millwood Road, and there is an Over the Moon Music program in Chappaqua.
Says Libov: “The quality of life, natural beauty and easy commute to NYC offer an exceptional lifestyle for my buyers and sellers and they feel fortunate to live here..”