Take A Video Tour Of Billy Joel's $50 Million 26-Acre Waterfront Island Compound (With Helipad)

Last night, HBO debuted the first of its two-part Billy Joel documentary. If you love Billy, you're clearly going to love this doc. If you're just ok with Billy Joel, maybe skip it. FYI, part 1 is over two hours.

In the first part, Billy tells the story of a time when he was a teenager working on a fishing boat off the coast of Long Island. One day, as the boat was returning to the harbor, he spotted an enormous mansion on a private island. He was annoyed at the time. He thought to himself, "Damn rich people. They've probably never worked a day in their life."

A couple of decades later, after Billy had become an extremely rich person (current net worth of $250 million), he bought the house.

Known as "Middlesea," the home is located in Oyster Bay, New York, on an island on Long Island called Centre Island (say that five times fast)! Middlesea is technically three parcels that Joel pieced together over three transactions. The first transaction occurred back in 2002 when Billy paid $22.5 million for the first 14 acres of what became 26 waterfront acres.

Back in 2002, Middlesea's primary mansion spanned 14,000 square feet. After a few upgrades and additions, today the primary mansion is 20,000 square feet. There's a multi-room beach house, a floating dock, two pools, two guest houses, and a beach house that has a bowling alley! Oh, if you live in Manhattan and don't want to deal with traffic getting to and from Middlesea, no problem. The property has a helipad.

Billy listed Middlesea for sale back in March 2023 for $49 MILLION. Here's a video tour from when it was first listed:

In March 2025, Billy sold five of Middlesea's 26 acres for $8.5 million. Those five acres feature the property's 5,600-square-foot guest house, which you can see off to the left in the thumbnail of the video above.

And "guest house" isn't really a good description. It's more of a "guest mansion." The guest mansion has five bedrooms, four bathrooms, two kitchens, a heated pool, AND its own three-bedroom guest house!

After that sale, Billy reduced the price for the rest of the estate to $39.9 million.

"Realtor to the Stars"

Billy is a prolific real estate buyer and seller. He has jokingly referred to himself as the "realtor to the stars" because he has sold a number of homes to celebrities. For example, in 2000, Billy sold his enormous oceanfront estate in Amagansett, New York, to Jerry Seinfeld for a then-record $32 million. He also sold a duplex apartment in Manhattan to the singer Sting.

Here's a quick summary of his other purchases and sales:

In 2015, he paid around $22 million for a stunning oceanfront compound in Manalapan, Florida, just south of Palm Beach. After listing the property for as much as $64.9 million, he ultimately sold it in late 2024 for $42.6 million. The estate featured a Mediterranean-style main house, guest quarters, a private dock, and more than 13,000 square feet of living space. In 2023, he purchased a new $10.7 million equestrian estate in East Hampton, expanding his presence in the Hamptons. He's also known to own a home in Sag Harbor and recently picked up a $29 million waterfront mansion in Boca Raton's exclusive Sanctuary community.