Have Your Own Private Island in the Hudson Valley
Live an endless summer camp lifestyle at this private island getaway, just two hours north of Manhattan in New York’s Dutchess County.
Poet John Donne wrote that no man is an island, but what person could truly resist owning a private piece of paradise? Tucked away in tranquil Pine Plains, New York, is 71 Lake Shore Drive, an islet that’s sized just right for a solo or two-person glamping getaway and is one of the two islands in the aptly named Twin Island Lake.
One might not normally associate the phrase “15 minutes away from the Taconic Parkway” with directions to an island escape, but this private island has more surprises than a pirate’s buried treasure. The property’s centerpiece is a .25-acre island and is being sold along with a companion .85-acre parcel on the mainland, complete with a floating dock and a 1,152-square-foot, two-story barn. (There is a Board of Health approval in progress for the barn to be converted into a residence if desired.) On the other side of the lake, a third 20 x 20-foot parcel of land is included in the sale and could be used as a parking space or a location for a second dock.
“It’s really tranquil,” says Rebecca Hanlon, the Corcoran Country Living agent handling the sale. “You have this beautiful mountain on one side and the lake surrounding you, when you look out at the view. And you’ll see swans, eagles, red-tailed hawks, and fish jumping out of the water. It’s really neat.”
Pine Plains, along with neighboring Millbrook and Amenia, forms a bucolic enclave of rolling hills, delightful old farmhouses, and sprawling equestrian estates, all interspersed with cultured boutiques and astoundingly good restaurants. This storied hunt country sits in the interior of the Hudson Valley, but is closer in spirit and geography to the pastoral villages of Connecticut’s Litchfield County. However, the buzz of the river towns remains just a short drive away.
Though the vibes are understated, the cultural tide is strong. Stissing House, the Colonial-era tavern at the center of town, snagged a James Beard nomination for “Best New Restaurant” in 2023 and is helmed by four-time nominated chef Clare DeBoer. There’s also Chaseholm Farms, with its grass-fed cheeses and beef, and Champêtre, with its craft cocktails and French classics like escargot and duck confit. Ronnybrook Farms, whose organic milk can be found everywhere from the shelves of Whole Foods to hip espresso bars, is headquartered in nearby Ancramdale.
In addition to the unexpectedly large selection of high-end dining and antiquing hidden amid acres of farmland, this pocket of the Hudson Valley is known for its gorgeous hiking trails, with its views of the mountains, lakes, and wide-open sky. The Stissing Mountain Fire Tower hike in Pine Plains is particularly popular, about a 45-minute hike from the parking lot to the tower. And for those willing to brave the many, many stairs to the top of the 90-foot tower that sits at an elevation of 1,402 feet, you’ll be rewarded with stunning views of Connecticut, Massachusetts, Vermont, Pennsylvania, and all the way north to New York’s capital, Albany.
But back to the private island — it’s a completely exclusive spot, only accessible by boat, where no one can disturb your days and nights of peaceful reflection. The island is currently a successful Airbnb rental, and it is outfitted with everything necessary for glamping: a platform safari-style tent with a queen-sized bed, a gazebo, a full outdoor kitchen with a propane grill, a fire pit, and a camping toilet and a camp shower with propane-heated hot water in a stylish outhouse. The island also boasts solar- and battery-operated lighting, a 150-watt battery-operated inverter to charge electronics, and excellent cell phone service coverage.
To get to the island, start by driving to Pine Plains — about two hours from New York City — and park on the mainland. Then, row in a canoe or kayak (three boats are included in the sale) for five minutes to arrive on the island. Surrounded by the spectacular peak of Sissing Mountain and the lake’s calm waters, this short journey feels like a portal to another time and place as you dock on the secluded isle and climb a staircase to the glamping grounds.
Once you’re on the island — accessible during spring, summer, and fall — all of civilization feels very far away. After dinner, drinks, and s’mores, fall asleep under a night sky filled with stars and wake up to birdsongs and rustling wind.