Real estate in New York City is a weird, high-stakes game of chicken where everyone is trying to figure out if the neighborhood they’re eyeing is actually worth the hype or just a relic of a bygone era. If you’ve spent any time looking at the high-end market in the outer boroughs, you’ve probably seen 110 Longfellow Road Staten Island NY pop up. It’s a massive property. It sits right in the heart of Todt Hill, which is arguably the most exclusive enclave in the entire five boroughs.
People talk about Todt Hill with a sort of hushed reverence. It's the highest natural point on the Atlantic seaboard south of Maine. That’s a cool bit of trivia, but for the people living there, it’s mostly about the privacy and the sheer scale of the homes.
The Reality of 110 Longfellow Road Staten Island NY
When you look at a place like 110 Longfellow Road, you aren't just looking at a house. You're looking at a statement. This isn't your typical Staten Island semi-attached or a cookie-cutter colonial. Built in the late 1990s—1997 to be exact—the property spans over 8,000 square feet of living space on a lot that’s nearly half an acre.
It’s big.
Most people in NYC live in boxes. This is a fortress.
The architecture is that classic, sprawling brick style that defines the neighborhood’s "Gold Coast" vibe. You’ve got a massive circular driveway, which is basically the suburban equivalent of a velvet rope. It tells the world that you don’t park on the street. You don't even think about street parking here.
Inside, the layout is designed for a specific kind of lifestyle that feels very "old-school New York wealth." We’re talking grand entryways, high ceilings, and a finished basement that is probably larger than most Manhattan apartments. It’s got five bedrooms and seven bathrooms. Think about that for a second. You could go a whole week using a different bathroom every day.
Why the Location Matters (More Than the House)
Location is a cliché for a reason. 110 Longfellow Road Staten Island NY is situated in a spot that feels completely disconnected from the noise of the city, despite being a 20-minute drive from the Verrazzano-Narrows Bridge.
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Todt Hill is unique. It’s wooded. It’s quiet.
The Richmond County Country Club is just around the corner. If you’re into golf or high-end social networking, that’s the hub. But there’s also a certain level of isolation that comes with living on Longfellow Road. You aren't walking to a bodega for a sandwich. You aren't hopping on the subway. You are car-dependent, and for the people who buy here, that is a feature, not a bug.
Honestly, the "hill" part is no joke. The elevation changes in this part of Staten Island are dramatic. It gives the neighborhood a geographic "buffer" from the rest of the borough. When you’re up there, looking out over the Raritan Bay or the New York Harbor, you feel like you’ve escaped.
The Market Context: Is It a Good Investment?
Staten Island real estate is a different beast than Brooklyn or Queens. In those boroughs, you’re paying for proximity to Manhattan and "cool" factors like craft breweries or artisanal bakeries. On the Hill, you’re paying for square footage and seclusion.
Properties like 110 Longfellow Road don't hit the market every day. When they do, the price tag usually reflects the rarity. However, the market for ultra-luxury on Staten Island is smaller than it is in, say, the Upper East Side. Your pool of buyers is limited to a very specific demographic: surgeons, high-level executives, and families who want the "mansion lifestyle" without moving to Westchester or Jersey.
The value of these homes stays relatively stable because the land itself is so scarce. You can’t exactly build more "highest points on the Atlantic seaboard."
One thing to keep in mind is the tax situation. New York City property taxes are a nightmare, but compared to similar-sized estates in Nassau County or Alpine, NJ, Staten Island can sometimes be—dare I say—a "bargain" in the context of the ultra-wealthy. That’s a relative term, obviously. We’re still talking about millions of dollars.
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Understanding the Architecture and Upkeep
Maintenance on a house like this is a full-time job.
If you’re looking at 110 Longfellow Road, you have to account for the "hidden" costs. Brick needs repointing. Large roofs need inspection. The HVAC systems required to heat and cool 8,000 square feet are massive and expensive.
The aesthetic is very much of its time. While many owners have updated the interiors with modern smart home tech and contemporary finishes, the bones of the house are traditional. You’ll find lots of marble, hardwood, and custom millwork. It’s built to last, but it’s not "modern minimalist." It’s "stately."
What Most People Get Wrong About Todt Hill
There’s a misconception that Staten Island is just one big suburb. That’s wrong. There are pockets of the borough that feel like the Hamptons and pockets that feel like the Bronx.
Todt Hill is its own universe.
People think everyone here is a caricature from a mob movie. In reality, the neighborhood is incredibly diverse in terms of professional backgrounds. You have people who have lived there for 40 years and young families who are moving out of the city because they realized they could get a pool and a yard for the price of a three-bedroom condo in DUMBO.
The schools in the area, particularly private options like Staten Island Academy, are a huge draw. If you’re living at 110 Longfellow Road, you’re likely looking at these institutions.
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The Lifestyle Trade-offs
Let's be real for a second.
Living here means you’re commuting. If you work in Financial District, it’s manageable. If you work in Midtown or LIC, you’re going to spend a lot of time in your car.
But the payoff? Coming home to a quiet street where you can actually hear the wind in the trees. You have a backyard that isn't shared with sixteen other neighbors. You have a garage. A real one.
110 Longfellow Road Staten Island NY represents a very specific New York dream. It’s the dream of "making it" and then getting away from the very chaos that helped you make it in the first place.
Actionable Insights for Potential Buyers
If you’re seriously looking at this property or others like it on Longfellow Road, don’t just look at the Zillow history. Here is what you actually need to do:
- Check the Elevation: Because it’s a hill, drainage can be an issue. Ensure the property has proper grading and that the basement—massive as it is—has no history of moisture issues.
- Survey the Land: Todt Hill has strict zoning laws. If you plan on adding a pool or an extension, you need to know exactly where your property lines and "greenbelt" restrictions lie.
- Audit the Utilities: Ask for the last two years of heating and cooling bills. A house of this size can easily run several thousand dollars a month in utility costs during a New York winter.
- Evaluate the Commute: Do the drive at 7:30 AM on a Tuesday. Don't rely on Google Maps. See what the bridge traffic actually feels like before you commit.
- Private School Deadlines: If you’re moving for the schools, check the enrollment windows for nearby private academies immediately. They often fill up a year in advance.
The appeal of 110 Longfellow Road isn't just the bricks and mortar. It’s the quiet. It’s the space. It’s the fact that you’re in New York City, but you’d never know it by looking out the window. For the right person, that’s worth every penny of the asking price.