You’ve probably seen the headlines about the most expensive house on Long Island NY. It’s usually some grainy aerial shot of a sprawling Hamptons estate that looks more like a small village than a place where someone actually sleeps. But honestly? The numbers are getting weird. We aren't just talking about "rich" anymore. We are talking about "generational wealth that rivals the GDP of a small nation" territory.
Currently, if you want the absolute crown for the highest asking price on the market in 2026, you’re looking at the Mylora estate in Water Mill. It’s listed for a cool $125 million.
Think about that for a second. $125,000,000.
For that price, you get an 80-acre equestrian compound at 165 Cooks Lane. It’s got an 8-bedroom main house, sure, but the real flex is the land. In the Hamptons, land is the only thing they aren't making more of, and 80 acres is basically a kingdom. It’s owned (or was developed) by Jeffrey Collé, a name you’ll hear a lot if you hang around East End real estate circles long enough.
What $125 Million Actually Buys You
Most people think a hundred-million-dollar house is just about gold faucets. It’s not. It’s about the sheer, exhausting scale of the thing.
At the Mylora estate, you’ve got a 20,000-square-foot main residence. That’s about ten times the size of a "normal" suburban home. But the amenities are what really differentiate the most expensive house on Long Island NY from a regular luxury mansion. We are talking about:
- A private farm with boarding stables.
- Professional-grade training facilities for horses.
- A sunken tennis court (because why would you want to see the fence?).
- Sunset views over protected farmland that—legally—can never be built on.
That last part is key. In the Hamptons, "protected" is the sexiest word a billionaire can hear. It means no one is ever going to put a McMansion in your line of sight. You are paying for the silence. You’re paying for the fact that your neighbors are essentially a mile away.
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The Ghost of Jule Pond
We can't talk about the most expensive house on Long Island NY without mentioning 90 Jule Pond Drive. For a long time, this was the undisputed heavyweight champion. Originally part of the Henry Ford II estate (Fordune), it sat on 42 acres with 1,200 feet of ocean frontage.
It sold a few years back for $105 million, which at the time felt like the ceiling.
Funny how ceilings work. Now, $105 million feels like a "fair deal" compared to the $125 million and $150 million whispers we hear today. Jule Pond had 12 bedrooms and 12 bathrooms. It was a relic of the Gilded Age brought into the modern era. But the market has shifted. Buyers in 2026 aren't just looking for history; they want turn-key, hyper-modern compounds where the Wi-Fi works in the middle of a 5-acre garden and the security system is basically a private NSA hub.
Why the North Shore is Different
While the Hamptons (the South Shore) gets all the Instagram fame, the North Shore—the "Gold Coast"—plays a different game. This is the land of The Great Gatsby.
In places like Old Westbury and Sands Point, you’ll find estates that don't always hit the public Zillow listings. They trade in "whisper listings." For example, there’s a 110-acre estate in Old Westbury that features its own 9-hole golf course. Yes, a private golf course.
The construction costs on these places often exceed $90 million.
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The vibe on the North Shore is "old money." It’s brick, it’s ivy, and it’s very quiet. While a $100 million house in Southampton is meant to be seen from a helicopter, a $100 million house in Glen Cove is usually buried behind three gates and a mile of forest.
The Reality of the "Most Expensive" Title
Here’s the thing most people get wrong: the most expensive listed house is rarely the most valuable house.
If we are talking about the true most expensive house on Long Island NY, we have to look at Fair Field in Sagaponack. Owned by billionaire Ira Rennert, this place is legendary. It’s not for sale. It likely never will be.
Fair Field is roughly 64,000 square feet. The total floor area of all buildings on the 63-acre property is over 110,000 square feet. It has:
- A 164-seat theater.
- Two bowling alleys.
- A garage that holds 100 cars.
- Its own power plant.
Tax assessments have valued it anywhere from $267 million to $500 million. It’s so big that the Town of Southampton actually changed the law after it was built, limiting new homes to 20,000 square feet. So, in a way, Fair Field is the last of the true dinosaurs. You literally cannot build a house that big anymore.
Is it a Good Investment?
You’d think a $100 million house would be a nightmare to sell. And you’d be right.
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These properties stay on the market for years. 165 Cooks Lane has been floating around for a while. Why? Because the buyer pool for the most expensive house on Long Island NY is about the size of a dinner party. You are looking for a literal billionaire who specifically wants to be in Water Mill, specifically wants an equestrian setup, and doesn't want to build their own.
However, the "ultra-luxury" segment (homes over $10 million) actually grew by about 30% in 2025. People are moving capital out of volatile markets and into "hard" assets like Hamptons dirt.
What You Should Do Next
If you’re actually in the market for a trophy property (or just like to window shop with purpose), here’s how to track the real movers:
- Watch the Transfers: Follow the Suffolk County deed transfers rather than Zillow. The biggest sales are often off-market.
- Look at the Acreage: In 2026, the house is secondary. The "most expensive" title always follows the land. Look for parcels over 10 acres with water access.
- Check the Architect: Names like Peter Marino, Shope Reno Wharton, or Jeffrey Collé add a 20-30% premium to the price just because of the "brand" of the build.
The market for the most expensive house on Long Island NY is basically a game of high-stakes poker. Whether it's a $125 million horse farm or a $500 million private kingdom, these houses are more than just "homes." They are monuments to ego, architecture, and the weird, wild world of New York real estate.
If you’re tracking these listings, keep an eye on Sagaponack and Water Mill specifically. These two zip codes are currently cannibalizing the top end of the market, leaving even traditional hotspots like East Hampton Village in the rearview mirror.