Ahoy! A Sea Captain Once Owned This $35M Private Island in Connecticut

A private escape known as Roger’s Island recently landed on the market for an impressive $35 million, making it one of the week’s most expensive listings on Realtor.com® when it hit the market.

The 7.6-acre island in Branford, CT, was last sold in 2018 for $21.5 million. It comes with a renovated, 10-bedroom, 6.5-bath, 8,746-square-foot main residence; a four-bedroom, waterfront guesthouse; and a fascinating history.

“The island was once home to Captain John Jay Phelps, a well known financier and revered yachtsman who built the island in the early-1900s,” says listing agent Jennifer Leahy. “He sailed his yacht around the world—which is rumored to have been the first trip of its kind by an American yacht.”

The 1902 home was built in a traditional Tudor style and features a beautiful stucco-and-brick facade and a covered, wraparound porch.

“The kitchen was just completed in 2024,” Leahy says. “It features an oversized island with calacatta marble countertops and top-of-the-line appliances. Almost every bathroom in the house was redone, including the primary bathroom which comes with an oversized shower and sauna.”

The private island offers plenty of resortlike amenities—a pool and spa, cabana, gazebo, tennis court, putting green, and some pretty spectacular gardens. The luxury property is just 15 minutes from downtown Branford, which can be reached by boat and a short car ride. And it’s only an hour-long drive to Greenwich, CT, or a two-hour drive to Manhattan.

“This is an incredible opportunity for a buyer who wants the privacy of being somewhere far away but is easily accessible to NYC, Boston, the Hamptons, and beyond,” Leahy says.