Want To Own Your Own Private Island And Commute To NYC? Here’s How

A cluster of private islands close to NYC—and rarely for sale—have just appeared on the market.

By Jeff Vasishta March 27, 2017
Photo courtesy of Sotheby's International Realty

Think of owning an island and you’ll more that likely imagine some tranquil Caribbean get away owned by an A-list celeb.  However, if you can afford it, it is possible to own your own private island and still commute to Manhattan each day. The Long Island Sound, off the coast of Connecticut is where you can grab your own slice of island life without jumping on a plane to get there.

The NY Post reports that a 7.1-acre island capped with a single 8,332-square-foot residence is currently available near Darien, Ct. for $17.5 million. This car-accessible estate at 20 Juniper Road includes five bedrooms with Long Island Sound views, a pool and a dock.

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Too pricey? There’s another 50 miles farther east, an 1.1-acre private isle named Potato Island accessible only by boat. Listed for $6.5 million, it holds a renovated 3,871-square-foot four-bedroom home with views of the surrounding Thimble Islands. And on the islands themselves—located just off Branford, Ct, near New Haven, there are a cluster of homes relisted by Douglas Elliman’s Melissa Frank Lutz for $50 million. They’re also available as individual plots for $1.7 million. Perfect for swimming, fishing and BBQ’s in the summer — but in the winter when a Northeaster blows into town they may not be such a good experience.

Brokers concur: “It’s a very adventurous kind of lifestyle,” says Willard Finkle, of Page Taft Christie’s International Real Estate, who is marketing Potato Island. “If you want a quart of milk, you need to get in your boat.”

Still, as alternative for whooping it up with the Hamptons crowd, a private summer Island retreat has been the preferred choice for a several long term owners who have handed these properties down over the generations. Now, aging owners are realizing that no man (or woman) is, in fact, an island and maintenance and the lack convenience are finally forcing them to sell. Thus, several have found their way on to the market. There are currently at least four active listings, with prices starting at roughly $2 million and rising above $100 million.

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“It’s unusual that [this many] islands come up for sale,” Finkle says. “Most of these are in families that get handed down from generation to generation.”

And he means unusual. The last time Darien’s Great Island—a 63-acre car-accessible island estate—was available was in 1902 but it is available now. That doesn’t mean it will sell anytime soon. With a price tag of $175 million, despite stunning views and amenities, taking the title for the most expensive house ever sold in the US is not something that happens on a regular basis.

With fears of catastrophic terrorism or economic collapse fueling a desire for urban dwellers to take flight, many retirees are consulting websites such as International Living, which promises the opportunity for full or part time retirement overseas. However, for those who don’t wish to be so far from their families but still far enough away from the mainland to have a modicum of autonomy, offers a slew of island living opportunities at various price ranges.

The good news is that even with a tight budget, owning your own private island may actually be cheaper than buying a house, with many available for under a $100,000 and more under $200,000. So what are waiting for? Pack your bags and grab a bucket and spade. But first see if you can afford a boat to get you there.

Jeff Vasishta



Jeff is a writer, husband and father but not necessarily in that order. As a music journalist he counts Prince, Beyonce and Quincy Jones amongst those he’s interviewed. He's also owned and flipped homes in Brooklyn, NJ, CT and PA.

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