Francis York

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Private Island in Connecticut: $35M Old Money New England Estate for Sale

This property is on the market for $35,000,000, listed with Jennifer Leahy of Douglas Elliman.

Located in the exclusive Thimble Islands region of Connecticut, this private island spans 7.65 acres of meticulously landscaped grounds. Highlights include a resort-style swimming pool, sunken formal gardens, a Home Depot-sized greenhouse, three private beaches, a four-bedroom guest house, a full-size tennis court, and a private putting green with a driving range.

At the heart of Rogers Island is an 8,746-square-foot Tudor-style mansion, built in 1902 by Captain John Jay Phelps. A celebrated yachtsman and financier, Phelps designed this remarkable home as the ultimate summer escape.

Renowned as the first American to sail around the world, Phelps’s adventurous spirit is reflected in every detail of this breathtaking estate. Today, Rogers Island is celebrated as a historic and architectural landmark on Long Island Sound, offering unparalleled luxury and exclusivity, and has been recently renovated and updated.

With 10 bedrooms, six full baths, and two half baths, the home offers ocean-facing bedrooms, a fully customized kitchen, and spacious living areas adorned with large windows and fireplaces.

Complementing the main house is a 1,866-square-foot waterfront guest cottage. This charming retreat features four bedrooms, two full baths, and a wraparound porch—perfect for visitors seeking their own slice of paradise.

The property also includes staff quarters with two bedrooms and two baths, ensuring seamless hospitality for residents and guests alike.

Rogers Island is more than a home; it’s a private resort, with resort-style amenities, including:

  • Three private beaches: Enjoy the pristine shoreline and uninterrupted ocean views.

  • Tennis court and putting green: Ideal for recreation and leisure.

  • Pool and cabana: A tranquil poolside haven surrounded by lush landscaping and a gazebo perched above the water.

  • Formal gardens and koi pond: Stroll through meticulously landscaped grounds and serene natural beauty.

  • Greenhouse and trails: Explore meandering paths or tend to plants in the expansive greenhouse.

  • Artist’s studio: Create or display your masterpieces in this inspiring space.

  • Despite its secluded ambiance, Rogers Island is remarkably accessible.

This quintessential New England summer escape is just a five-minute boat ride from the mainland, and a mere 15 minutes from downtown Branford.

The island is also conveniently located within a two-hour drive of Manhattan, Boston, and the Hamptons, making it an ideal weekend getaway or full-time residence.

All photos belong to the listing agency.