One of the largest Thimble Islands off the coast of Connecticut is being floated on the market for $35M

The 7.65-acre Rogers Island is anchored by a stunning Tudor-style mansion originally developed in 1902 by John Jay Phelps, a notable railroad baron and yachtsman.

Georgie Mihaila
8 Min Read
Photo credit: Daniel Milstein Photography

Get ready to update your vision board, folks.

Because today, we’re taking a tour of an idyllic private island with a fully renovated, century-old mansion, a waterside guest cottage, a putting green, a tennis court, a resort-like pool, and formal gardens, among other desirable features.

Rogers Island, one of the largest Thimble Islands off the coast of Branford, Connecticut, offers all that for a hefty $35 million.

This 7.65-acre gem, featuring a circa 1902 Tudor mansion built by railroad baron John Jay Phelps and a host of luxurious amenities, promises unparalleled privacy and comfort, all just a short boat ride from the mainland.

Part of the Thimble Islands archipelago, the same one where Davis Island is located — and where President William Taft established his “Summer White House” for two years — the private island is reportedly owned by a hedge fund executive with ties to Ray Dalio’s Bridgewater Associates.

The Thimble Islands: A Connecticut treasure

Photo credit: Daniel Milstein Photography

The Thimble Islands are a picturesque archipelago located in Long Island Sound, off the coast of Branford, Connecticut. Comprising around 365 small islands, only 23 of which are inhabited, the Thimble Islands offer a unique blend of natural beauty and historical significance. These islands were named by early settlers who thought they resembled thimbles sticking out of the water.

The Thimble Islands have a storied past, with some dating back to the 17th century. They have been used for various purposes over the years, including farming, quarrying, and as private retreats. Today, they are known for their serene landscapes, charming cottages, and luxurious private estates.

Rogers Island is one of the largest in the archipelago

Photo credit: Daniel Milstein Photography

Each island has its own character and charm, making the Thimble Islands a sought-after destination for those seeking tranquility and seclusion, just a short boat ride from the mainland.

Rogers Island stands out from the other 364 small islands for several reasons. At 7.75 acres, it’s one of the largest in the archipelago, surpassed only by the 17-acre Horse Island (owned by Yale University), the 12-acre Money Island, a village in itself with 32 houses and a library, and the 10-acre Governor Island. It’s also one of the few inhabited, and one of the most expensive.

The Tudor-style property that anchors it

Photo credit: Daniel Milstein Photography

This island isn’t just about breathtaking views and seclusion; Rogers Island is anchored by a stunning Tudor-style mansion originally developed in 1902 by John Jay Phelps, a notable railroad baron and yachtsman.

The main house, measuring nearly 8,750 square feet, offers a blend of century-old architecture and modern design, featuring 10 bedrooms, 6 bathrooms, and 2 half-baths.

Heavily updated by the current owner

Photo credit: Daniel Milstein Photography

Several news outlets have identified the current owner as Greg Jensen, co-chief investment officer at Ray Dalio’s Bridgewater Associates, one of the largest hedge funds in the world.

Jensen purchased the island in 2018 for $21,500,000 from Edmund and Christine Stoecklein (nicknamed the Thimbles Lady, and known for collecting several islands — and trying to offload 8 of them all at once in 2017).

Under his ownership, Jensen has extensively renovated the mansion’s interiors and updated the island’s electrical systems, bringing modern convenience to this historic property. Known for his financial acumen, Jensen has transformed Rogers Island into a luxurious retreat, blending its rich history with contemporary comforts.

Luxurious living spaces abound

Photo credit: Daniel Milstein Photography

The main residence showcases spacious living areas with large windows and numerous fireplaces, giving it a warm and inviting ambiance.

The modern kitchen, renovated by Jensen, includes custom cabinetry, an eat-in island, and a daybed by the window, making it perfect for casual family meals or entertaining guests. The bedrooms, many of which are ocean-facing, provide serene views and a peaceful retreat.

See also: $16.5M miniature private island in the heart of Florida Keys

The many other buildings on the island

Photo credit: Daniel Milstein Photography

Beyond the main Tudor mansion, Rogers Island has several other impressive structures that add to its appeal. A 4-bedroom waterfront guest cottage with a charming wraparound porch offers additional accommodations for visitors.

For those who enjoy artistic pursuits, a dedicated artist’s studio provides a serene space to create.

The pool house complements the resort-like pool area, which is surrounded by stone terracing perfect for lounging and outdoor dining. A picturesque gazebo, perched directly on the rocks above the water, provides an ideal spot for relaxation and taking in the stunning views.

Amenities make the most of the idyllic location

Photo credit: Daniel Milstein Photography

The island’s amenities cater to every whim and desire. Sports enthusiasts will appreciate the fenced-in tennis court with a basketball hoop and the Jack Nicklaus-designed putting green.

Nature lovers can explore the lush formal gardens, meandering trails, and a serene koi pond. For those who love the water, there are three private beaches and two docks, perfect for swimming, boating, or simply relaxing by the sea.

Practical perks

Photo credit: Daniel Milstein Photography

Despite its seclusion, Rogers Island is fully equipped for modern living. The island has three septic systems, a generator, and a recently updated electrical system connected to the mainland.

Practical amenities include a greenhouse, staff quarters, three private beaches, and two docks, making Rogers Island a fully equipped and self-sufficient haven.

Currently listed for $35,000,000

Photo credit: Daniel Milstein Photography

Jennifer Leahy of Douglas Elliman, who holds the listing, emphasizes the unique appeal of Rogers Island. “Rogers Island is such a unique offering because you have almost every amenity imaginable at your fingertips,” she told the New York Post.

Relax poolside, play a game of tennis, perfect your putting skills, or explore the incredible gardens and mature trees that adorn this 7.65-acre retreat.”

Neighboring islands for sale

Photo credit: Daniel Milstein Photography

Leahy is also selling several other islands in the Thimble Islands archipelago, including Belden Island for $2.75 million, Jepson Island for $1.5 million, and Burr Island for $1.3 million. Each offers its own slice of paradise, but Rogers Island stands out as the ultimate trophy property for those seeking a luxurious, secluded escape with endless amenities.

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With a decade-long career as a digital content creator, Georgie started out as a real estate journalist for Multi-Housing News & CPExecutive. She later transitioned into digital marketing, working with leading real estate websites like PropertyShark, RENTCafé and Point2Homes. After a brief but impactful stint in the start-up world, where she led the marketing divisions of fintech company NestReady and media publisher Goalcast, Georgie returned to her first passion, real estate, and founded