Connecticut's Very Own Private Islands

There aren’t many displays of extreme wealth more upper class than owning a private island. Although that fact remains, there’s a group of eight private islands in Connecticut, all listed for a collective $78 million. The properties, located among the Thimble archipelago off the coast of Connecticut, showcase a broad array of architectural styles and top-notch amenities. Check out these luxurious private island estates.

Photography: Sotheby's Homes

Central to the Thimble archipelago is the eight-acre Rogers Island. At its highest point, this island houses a 13,000-square-foot residence with ten bedrooms. Expansive lawns, expertly-manicured gardens, and towering trees fill the private paradise with loads of natural beauty. Rogers island even includes a four-bedroom guesthouse in case visitors want a more private space to enjoy.

Wheeler Island measures in at just under one acre of land. Its massive eight-bedroom residence features a widow’s walk and multiple landscaped gardens.

Aptly named, Cut-in-Two, this island is divided into two sections that are linked to each other by a pedestrian bridge. Both the eastern and western sections of the island feature a main residence and guesthouse.

The main residence among this group of islands is the mainland waterfront property — a historic Victorian-style manor with guest and staff quarters. This property also features a commercial-grade dock and landing. In true luxurious fashion, the easiest way to travel from the Thimble Islands to nearby Manhattan or New Haven, Connecticut is by helicopter.

Recommended For You.

New Balance Grey Days: A Monochrome Movement
Sneakers
7 Must See Places to Visit in Italy
Travel
Shrubs You Should Never Prune in Spring
Home & Garden
6 Reasons Quinoa is Good for You
Food & Drink
9 Queer Characters from the Best Animated TV Shows
TV & Film
7 Ways to Stimulate Your Brain as You Age
Health
Most Popular Lap Dogs in the U.S.
Lifestyle
Self-seeding Fruits That Cause Less Work For You
Home & Garden
Gorgeous African National Parks to Visit this Summer
Travel
Hottest Sneaker Releases | Made for Outside
Sneakers
Unusual Ingredients You Can Add to Potato Salad
Food & Drink
Master the Trend | Trench Coats for Men
Fashion
MSCHF x Mercedes-AMG Limited Edition Furniture Collection
Art & Design
Unusual Skincare Hacks for Healthier Looking Skin
Lifestyle
Jordan Tatum 3: Continuing Greatness
Sneakers
11 Must See Summer Movies
TV & Film
How to Get Rid of Fleas in Your House
Home & Garden
10 Food Focused Cities to Visit in Latin America
Travel
The Most Handy Gadgets to Buy for Your Home
Shopping
Master The Trend | Retro Athleisure
Fashion
Mesmerizing Views of the Night Sky
Photography
Business Casual Work Clothes for Travel or the Office
Shopping
11 Products that Promote Your Mental Wellness
Wellness
Weekly Celebrity Birthday Roundup | 6/16 - 6/22
Celebrities
Hottest Sneaker Releases | Inspired By Culture
Sneakers
How to Add Protein to Your Smoothies
Food & Drink
Fascinating Tidbits About Independence Day
Lifestyle
Nike A'One: A Superstar's Arrival
Sneakers
More than You Ever Wanted to Know About Dragonflies
Home & Garden
Never Miss on a Fit with These Kicks
Sneakers
Consider These Eastern European Travel Destinations
Travel
Hottest Sneaker Releases | Artwork on Footwear
Sneakers
Nike Air Max Craze: Brought Back to Life
Sneakers
7 Herbs You Probably Never Thought to Grow
Home & Garden
Adidas x Kith SS25: Football for the Streets
Fashion
Pistachio: The Color Defining Spring
Fashion
Ways to Enjoy a Long July 4th Weekend
Lifestyle
Best Workout Equipment for Small Spaces
Wellness
7 Kitchen Gadgets you Can Toss Right Now
Home & Garden
Incredible Gift Ideas for the Moms in Your Life
Lifestyle
6 Ways to Enjoy Green Tea
Food & Drink
The Pros Skip these Tools and So Can You
Home & Garden
7 Fun Memorial Day Weekend Activities
Lifestyle
How to Keep Your Dog Out of the Garden
Home & Garden
9 Quick Trips to Take from Latin American Cities
Travel
7 of the Most Nutrient-Dense Foods
Food & Drink
The Types of Volcanoes That Frame Landscapes
Photography
7 Common Uses for Tea Tree Oil
Home & Garden
Smart Gadgets on Amazon That Simplify Pet Care
Shopping
Hottest Sneaker Releases | Neutral But Bold
Sneakers