You’ve probably heard of Chappaqua. If you haven't, you definitely know its most famous residents. But tucked away on a quiet, winding cul-de-sac sits 15 Old House Ln Chappaqua NY 10514, a property that represents everything people love—and occasionally find frustrating—about Westchester luxury real estate. It's not just a house. It’s a specific vibe.
Chappaqua has this reputation for being buttoned-up. Elite. Maybe even a little bit stiff. But when you get onto Old House Lane, that feeling shifts into something much more private and, frankly, secluded. We aren't talking about a suburban tract home here. We are talking about the kind of acreage that makes you forget you're less than an hour from Grand Central.
The Reality of 15 Old House Ln Chappaqua NY 10514
Most people looking up this address are doing it for one of two reasons. One, they are interested in the high-end real estate market in the Town of New Castle. Two, they are curious about the "Clinton effect." Bill and Hillary Clinton moved into number 15 back in 1999, right as he was wrapping up his presidency and she was eyeing a Senate run.
It changed the neighborhood. Forever.
The house itself is a Dutch Colonial. It dates back to the late 19th century—1889, to be exact. It’s got that classic white wood siding and black shutters that look like they were pulled straight from a Ralph Lauren catalog. With 11 rooms spread across roughly 5,200 square feet, it's big, sure, but it isn't a "McMansion." It has soul. It has squeaky floorboards and history.
Honestly, the "Old House" part of the street name is literal.
The property sits on about 1.1 acres. In this part of Westchester, that’s a decent sized lot, though not massive. However, it feels much larger because of the surrounding woods and the way the road terminates. There’s no through traffic. You don't just "end up" on Old House Lane. You have to mean to be there.
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The Security Bubble and Privacy
If you try to drive past 15 Old House Ln Chappaqua NY 10514 today, you’ll notice something immediately. It’s quiet. Eerily quiet. But you’re also being watched.
Since the late 90s, the Secret Service presence has been a permanent fixture of this specific block. This isn't just a fun trivia fact; it fundamentally changes the living experience for everyone on the street. Neighbors have to deal with checkpoints during high-profile visits. There’s a guard booth. It’s the safest cul-de-sac in America, but it comes with the trade-off of never truly being "alone."
Local real estate experts often debate if this adds or subtracts value. On one hand, you have 24/7 professional security for the whole street. On the other, your friends might have to show ID just to come over for a barbecue. It's a weird niche.
Why Chappaqua Real Estate Stays Resilient
Why do people pay millions to live here? It’s the schools. Always the schools.
The Chappaqua Central School District, specifically Horace Greeley High School, is consistently ranked among the top in New York State and the entire country. People move to 15 Old House Ln Chappaqua NY 10514 and the surrounding area specifically to get their kids into these classrooms.
The market here doesn't crash like other places. It dips, it plateaus, but it rarely bottoms out.
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- Property Taxes: They are high. No way around it. Expect to pay a significant five-figure sum annually.
- Commuting: The Metro-North Harlem Line is the lifeline. It’s about a 45-to-50-minute express ride to the city.
- Vibe: It’s "stealth wealth." People have money, but they wear Patagonia and drive Volvos.
The architecture on Old House Lane is a mix. You have these older, renovated Colonials sitting near more modern, expanded estates. It’s a microcosm of the Hudson Valley’s transition from rural weekend getaway to power-broker suburbia.
Beyond the Clinton Fame
Let’s get away from the politics for a second. What is the actual house like?
Records show a structure that has been meticulously maintained. It’s got three stories, a pool, and a barn that was converted into a guest house/office. It’s the kind of place where you can host a formal dinner for twenty people or just sit on the porch with a book and hear nothing but crickets.
The kitchen was renovated years ago to handle the needs of a modern family (and a modern security detail), but it kept the traditional aesthetic. Think granite, high-end stainless steel, and plenty of hardwood.
The "Secret" Backyard of Westchester
One thing people get wrong about this area is thinking it’s all paved over. It’s not.
Living near 15 Old House Ln Chappaqua NY 10514 means you’re minutes away from the Pruyn Sanctuary. There are miles of hiking trails. You’ve got Gedney Park nearby for soccer and sledding in the winter.
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It’s surprisingly rugged. You’ll see deer every single day. You might even see a black bear or a coyote. It’s a strange juxtaposition—one of the most famous homes in the world, surrounded by literal wilderness and the occasional wild animal roaming the driveway.
The town center of Chappaqua is charming, if a bit small. You have the iconic Lange’s Little Store where the locals get coffee. You have the local library which is basically a community hub. It’s a town that tries very hard to feel like a village, even though the net worth of the residents says otherwise.
Is It Worth the Hype?
If you’re looking at a home in this 10514 zip code, you have to ask what you value.
If you want a modern glass box with no neighbors, this isn't it. The houses here are close enough to wave to each other, even with the acreage. But if you want a piece of American history—and the prestige that comes with the most famous address in town—then Old House Lane is the pinnacle.
Prices in this specific pocket of Chappaqua have remained high because of the scarcity. There are only so many homes on this specific street. They don't come up for sale often. When they do, they are usually "pocket listings" or they move fast to buyers who want the security and the status.
Steps for Potential Buyers in 10514
If you are actually looking to buy in this neighborhood, don't just look at Zillow. The best properties here often move through word-of-mouth among Westchester’s elite brokers.
- Get a local specialist. You need someone who knows the New Castle building codes. They are strict. If you want to add a pool or an ADU, you're going to face a lot of red tape.
- Check the tax assessments. Chappaqua taxes are no joke. Make sure the "Star" exemptions or any local abatements are factored into your monthly carry.
- Visit at different times. Drive by on a weekday morning to see the commuter rush, then on a weekend to see how quiet it actually gets.
- Understand the security. If you are buying on Old House Lane specifically, talk to your agent about what the Secret Service presence means for your daily life. It’s a unique living situation that requires a certain temperament.
The allure of 15 Old House Ln Chappaqua NY 10514 isn't going away. Whether it’s the history, the schools, or the sheer privacy of the lot, it remains a cornerstone of Westchester’s luxury identity. It’s a quiet life, guarded by gates and trees, just far enough from the city to breathe.