'Treetop' Harborview Studio, with Balcony, in the Heart of Shelter Island

Second-story one-bedroom apartment, with balcony, surveying a lush, tranquil, seven-acre property overlooking Dering Harbor, mere steps from the North Ferry and bustling Bridge Street thoroughfare. Part of the 1960s-vintage Winthrop Manor (aka The Dering Harbor Inn), the island’s only co-op, shared amenities include heated outdoor pool, tennis courts, fitness center, cafe and communal patio. The apartment itself has full kitchen and bathroom, while its living room and bedroom—complete with an eight-foot desk—are in full view of the water (and brilliant pastel sunsets). Laundry facility (washers/dryers) two floors below, in the cellar storage area. High-speed wifi included.

All within a short walk, jog, bike or drive to the island’s many special attractions and landmarks: beaches, restaurants, miles of hiking trails, farmers markets, and the incomparable Sylvester Manor and Mashomack Nature Preserve. Even more to be discovered, from a vibrant food scene to dozens of wineries, throughout Greenport and the North Fork—a few minutes' ferry trip across the Peconic—with the Hamptons and Montauk but a quick jaunt in the opposite direction.

The North Ferry terminal in Greenport offers simple, fast connection to the Hampton Jitney and Long Island Railroad.