A Glimpse into Private Island Living: Greg Jensen’s Rogers Island Listing

Private islands possess an allure that can entice even the most grounded of individuals, combining seclusion, luxury, and the tranquility of nature. One such gem on the market is Rogers Island, situated off the coast of Connecticut and boasting an impressive listing price of $30 million. Owned by Greg Jensen, the co-chief investment officer of Bridgewater Associates, the island provides a unique escape that now comes bundled with a mainland house—an attractive proposition for any potential buyer.

The island’s charm

Rogers Island is part of the Thimble Islands, a picturesque collection of over 365 tiny islands nestled in the Long Island Sound. The new price reflects a $5 million reduction from its original listing of $35 million, incorporating a five-bedroom home on the mainland that features a private dock. This addition not only sweetens the deal but also provides a seamless transition to island living, cutting down on the logistical hassles of ferry transport.

Leslie McElwreath, the listing agent from Sotheby’s, highlights the strategic nature of this inclusion, stating, “This gives you the perfect launching point to get to the island.” By coupling the island with the mainland residence, buyers can now enjoy the convenience of direct access without relying on the public ferry services.

A brief history

Jensen acquired Rogers Island in 2018 for $21.5 million». The island first hit the market in June 2024, reflecting the steep demand for exclusive properties among the financial elite. It boasts multiple residences**, luxurious amenities, and a backdrop that has long attracted notable figures in finance and beyond.

Luxury at every corner

Rogers Island isn’t just about its real estate; it offers a lavish lifestyle. The properties on the island include:

• A primary residence with 10 bedrooms, renovated in 2024 to provide modern conveniences paired with classic architectural elements. The main house spans an impressive 8,746 square feet and features Calacatta marble countertops and a sophisticated wet bar.

• Additional amenities such as a tennis court, a pool, and even a putting green, designed by golf legend Jack Nicklaus, cater to the whims of outdoor enthusiasts and entertainers alike. Jensen’s attention to detail ensures that every corner of the island speaks to opulence and leisure.

• A four-bedroom guesthouse and an artist’s studio add additional dimensions of functionality to the property, making the island an engaging locale for family gatherings and social events.

• The beautifully landscaped 7.7 acres feature three private beaches, enhancing the idyllic coastal experience. Outdoor lovers will appreciate the gardens that accompany these beaches alongside a dazzling waterfall pond.

A mainland escape

The mainland home adds considerable value to the listing. Sold separately for $4.3 million before being bundled with the island, this house provides a necessary connection to the mainland conveniences. With a private dock, it facilitates smooth boating access, allowing for easy transportation of guests and goods—an especially coveted feature for island dwellers. Whether it’s grocery runs or hosting family and friends, this access makes life significantly more enjoyable.

Lifestyle and Elite Living

Rogers Island contributes to a trend in which the New York area’s financial elite seek out properties in Connecticut—a state known for its serene landscapes and affluent communities. The likes of hedge fund moguls Ray Dalio and Steve Cohen own luxurious estates nearby, often requiring only a ferry ride to reach their retreats. They represent a lifestyle that blends high finance with nature-infused leisure, all while maintaining a sense of exclusivity.

Final thoughts

With its rich history, lavish amenities, and strategic location, Rogers Island stands as an epitome of luxury living. The combination of island life alongside a mainland residence creates an appealing lifestyle that few can resist. Whether as a permanent home or a summer escape, it offers a unique opportunity to redefine the boundaries of leisure living in a spectacular coastal setting.