These Eight Gorgeous New England Islands Are All for Sale
Welcome to the Thimble Islands!
The Thimble Islands, just offshore of Branford, Connecticut, in Long Island Sound, make a perfect seaside escape—and several of them are for sale. Grouped together as a single property, these eight islands (plus one waterfront Victorian home on the mainland) are listed by Shelly Tretter Lynch of Sotheby International Realty’s Greenwich Brokerage for an impressive $78 million. You can see the full listing here, or tour the whole collection by drone.
Want to step inside? Here, an up close and personal look at the houses on four of these islands and at the classic Victorian mansion on the shore.
Cut in Two
The first island on this tour is aptly named: This pair of islands is connected only by a sturdy bridge, like a single island cut into two.
Cut in Two House
On one side of the island is this charming Victorian-style home, which boasts panoramic seaside views and a striking corner tower. Sharing its rocky perch is a shingled bungalow situated on the very edge of the island. On the other side of the island, trees surround a third house, shielding it from the eyes of passing boaters and visitors.
Cut in Two Kitchen
In Cut in Two's Victorian-style house, the traditional exterior gives way to a contemporary interior, including this open-concept kitchen, which boasts striking white cabinetry and a large center island.
As the centerpiece of the collection, Rogers Island offers beautiful vistas—and even more beautiful accommodations.
Rogers Island Main House
This Tudor Revival–style mansion sits near the center of Rogers Island. It's surrounded by a grove of towering trees, groomed gardens, and, of course, the waters of the Sound.
Rogers Island Interior
The interior of the house is a colorful surprise: Decked out in bright hues with charming coastal accents, it offers a playful contrast to the staid gray and white exterior.
Rogers Island Pool
A beautiful pool is an exterior focal point, along with an architecturally sensitive (and charming) pool house and big views of Long Island Sound.
Rogers Island Gardens
The landscaping on Rogers Island is almost as beautiful as the water beyond—bright flowers and carefully groomed walkways abound, and a commercial-scale greenhouse promises year-round blooms. The island also boasts a Nicklaus-designed golf hole overlooking the water.
The lone mainland property included in this Thimble Islands portfolio, Prospect Hill holds a stunning historic Victorian abode, guest and staff quarters, and a private commercial-grade dock.
Prospect Hill Victorian
Beautifully maintained, this Victorian offers a scenic transition from the main land to the islands.
Prospect Hill Interior
The interior retains original Victorian décor such as dark wood floors, ornate ceilings, and graceful chandeliers.
Jepson Island, also part of this dream-island parcel, is just big enough to be home to an old-school fishing shack.
Jepson Island House
This wood-paneled cabin has two bedrooms, one bathroom, and a wide deck. Its perch atop a small rock island ensures almost complete privacy.
Last on this tour is green Wheeler Island, which boasts a thick patch of beautiful green grass atop a dramatic rock outcrop.
Wheeler Island House
The star of Wheeler Island is this classic shingled beach house, which has wide wraparound porches and narrow railings that don't obscure the view. A balcony on the top floor offers even more breathtaking vistas.
Wheeler Island Interior
High ceilings, large windows, and neutral walls—enlivened by brightly colored décor—fill the interior of the 8-bed, 4-bath Wheeler Island house with natural light.