With quiet, tree-shaded lanes, sweeping bay views, and an emphasis on seclusion and relaxation, this quiet isle blends some of the best aspects of the Hamptons and the North Fork.
A destination for families and fun-lovers alike
Shelter Island, which sits between the North and South forks of Long Island, can only be reached by boat or a short car ferry ride at each end, a quirk that’s helped preserve its lush, unhurried feel. The island has just one supermarket and one gas station to serve its 2,400 year-round residents, and the lone drug store still has a no-frills lunch counter tucked to one side. But if you know where to look, more happens on Shelter Island than meets the eye.
Vintage victorians, spectacular estates and classic bungalows
For well under $1 million, you can find a nice Craftsman home, or perhaps even land one of the colorfully painted gingerbread cottages in the Heights district. But prices for the stunning waterfront estates of Dering Harbor, Little Ram Island and the Nostrand Parkway can easily top $10 million. Co-op buyers with just under half a million to spare should investigate the spacious units at the full-service Dering Harbor Inn. But be prepared for the common charges, which are significant.
The go-to place for lattes, fresh-baked goods worthy of a Parisian patisserie, terrific rotisserie chicken, and other prepared foods and groceries. Seating inside and out, including on a back dock with views of Dering Harbor.
Celebrity hotelier André Balazs created this perennial hotspot, which features a restaurant, hotel, lively beach scene, fire pit and bar with a European flair. You can also book an open-air massage in their beach tent.
This adorable cottage serves exceptional seafood, steaks and pasta — all of it cooked from scratch — in a romantic, fine-dining setting. It also has a food truck, if you want takeaway.