
Daniel Milstein
Even private islands come with problems.
One is the hassle of ferrying family members, guests, and goods back and forth from the mainland.
The new $30 million listing for Rogers Island off the coast of Connecticut, owned by Bridgewater Associates’ co-chief investment officer Greg Jensen, offers a solution.
The island, which is $5 million cheaper than when it first listed last year, comes with a five-bedroom home on the mainland that has a private dock.
“This gives you the perfect launching point to get to the island,” said Leslie McElwreath, of Sotheby’s, who now has the listing with her colleague Joseph Barbieri.
Typically, Rogers and other nearby islands, all part of the Thimble Islands, are serviced by a public ferry that makes multiple stops throughout the day. Now, Rogers Islands’ new owner can get to the island directly and seamlessly.
Property records show Rogers Island was purchased by an LLC for $21.5 million in 2018; The Wall Street Journal later identified Jensen as the buyer. Jensen first listed the island in June of 2024 for $35 million.
Rogers Island has multiple houses, a pool, a tennis court, and a putting green designed by famed golfer Jack Nicklaus.
The New York area’s financial elite have long had trophy homes in Connecticut. Bridgewater founder Ray Dalio and hedge fund boss Steve Cohen own palatial estates in Greenwich, which is a ferry ride and 60 miles from the Thimble Islands.
Take a look around Rogers Island.
Rogers Islands is part of the Thimble Islands, a smattering of 365 tiny islands off the coast of Branford, Connecticut, in the Long Island Sound.

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A 1.1-acre property on nearby Potato Island sold for over $4 million in 2020. In 2017, eight of the islands were listed altogether for $50 million, the New Haven Independent reported.
The main house on Rogers Island was built in 1902.

Daniel Milstein
The home is perched on a bluff 45 feet above sea level.
The sprawling mansion totals 8,746 square feet.

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Jensen renovated the main house in 2024, adding Calacatta marble countertops, luxury kitchen appliances, and a new wet bar.
The main house has 10 bedrooms.

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The main house also has six bathrooms and two half-bathrooms.
Rogers Island also has a four-bedroom guesthouse, an artist’s studio, a tennis court, and a pool.

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The artist’s studio has its own outdoor shower.
The pergola beside the pool is intended for seaside dining.

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There is also island-wide internet access.
Many of the island’s 7.7 acres are meticulously landscaped.

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There are three private beaches on the island.
The putting green was designed by famous golfer Jack Nicklaus.

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Golf legend Jack Nicklaus won 18 major championships throughout his career and now runs a successful course-designing business.
The mainland house last sold for $4.3 million on its own, according to McElwreath, the listing agent.

Daniel Milstein
The mainland home with a dock allows for easy boat parking and direct access to Rogers Island. The house, which last traded hands for $4.3 million, is now a deal-sweetener of sorts for the $30 million private island.
The post A Bridgewater exec is still trying to sell his private island. He cut its price — and threw in a mainland house with a dock. appeared first on Business Insider.