What It’s Really Like Living in Chappaqua and Northern Westchester County

By Ted Holmes

Edward “Ted” Holmes is a Licensed Associate Real Estate Broker and founder of The Holmes Team at William Raveis Real Estate, serving Chappaqua and Northern Westchester County, NY. With 25 years licensed, 456 career transactions, and consistent top-ranking production statewide, he is a recognized expert in residential, luxury, and commercial real estate.

Before you pack a single box, there’s something I want you to know about living here. The best part of Chappaqua? It’s not the beautiful homes you see in the listing photos. It’s the little, unexpected moments. It’s walking into the train station and seeing three people you know. It’s having a yard where the kids can actually run around, and realizing you’re just a quick train ride from Manhattan, or a short drive from a hike that feels a world away.

If you’re thinking about moving to Chappaqua or anywhere in Northern Westchester, you’re probably doing the same math everyone does. You’re looking at the school ratings, you’re calculating the commute, and you’re dreaming of more space. Those are the right reasons to start looking. But honestly? They’re not the real reasons people put down roots here.

So, if you’re trying to decide whether this area is the right fit, here are the six things I’d want you to know.

1. You feel the community quickly. People here actually show up for each other. The farmers market on Saturday morning, the little league games, the street fair in the fall—these aren’t just things on a to-do list. They’re the heartbeat of the town. Pretty soon, you’re not just going to the parade, you’re waving at people you know. You see the same families at the playground and the same faces at the school drop-off. It’s that feeling of connection that’s really hard to explain until you’ve lived it.

2. You get your own space, without being stranded. You know that feeling when you can finally hear yourself think? That’s what it’s like here. You have privacy and a quieter pace, but you’re minutes from everything you actually need. And the best part? Every little town around here, like Chappaqua, Armonk, Bedford, has its own personality. So you get a real sense of place, not just another cookie-cutter suburb.

3. The school districts support long-term stability. Let’s be real, the schools are why so many families land here. And it’s not just about the education, though that’s obviously top-notch. When you have really strong public schools, they do something else: they stabilize the whole community. It’s one of the biggest reasons home values here have held up so well, year after year. It’s an investment in your kids and in your home at the same time.

4. Good healthcare is a bigger deal than you think. It’s one of those things you don’t really appreciate until you need it. Having Northern Westchester Hospital right up the road in Mount Kisco, and being close to the Westchester Medical Center network, is a huge weight off your shoulders. As your family grows or your needs change, knowing that world-class care is 15 minutes away is a gift.

5. The commute works, and the region stays close. The commute really works here. You’ve got multiple train stations with direct lines to Grand Central, with trains running all the time. But it’s not just for the 9-to-5 crowd. It means you can decide on a whim to grab dinner in the city, see a show, or hit a museum, and it doesn’t feel like an expedition. You just… go.

6. The lifestyle is active, local, and truly four seasons. We have these incredible Westchester County parks with trails for biking and hiking, great golf courses, and even places to camp. I take my boys camping every year, not far from here, and I swear, it feels like we’re upstate. When you want more of a city buzz, White Plains is right there with The Westchester for shopping and some really good restaurants. And the seasons? Spring and fall are absolutely gorgeous. Summer and winter are just long enough to enjoy before you’re ready for the next one. It keeps things fresh.

So, what does this mean for you? If you’re relocating, you’re probably starting with the checklist: commute, schools, square footage. And that’s smart. But then you get here, and you realize it’s about so much more. It’s about finding a place where the lifestyle actually fits. Whether you’re upsizing, downsizing, or just starting to explore, the trick is finding the right town and the right home for your rhythm.

People come here for the schools and the space. They stay because they fall in love with the pace of life and the people in it.

If you have any questions about living in Chappaqua or Northern Westchester, whether you’re just starting to look, thinking about a change, or want to know what a specific town is really like, just reach out.

Call or text me at (914) 548-6179, email me at ted.holmes@raveis.com, or check out http://www.theholmesteamny.com. I’m happy to be a resource and help you figure out what makes the most sense for you and your family.