Get to Know Osterville

Osterville, one of Barnstable’s seven villages, is a secluded enclave of epic waterfront estates — the ultimate embodiment of quiet luxury. Osterville is technically a neighborhood within Barnstable but has several smaller neighborhoods within its borders. There’s a picturesque downtown area, with a mix of independent boutiques and branches of preppy brands like J. McLaughlin and Island Outfitters, as well a few eateries and Fancy’s Market, a gourmet grocery store that’s been in town since 1839. Besides the shops on Main Street, Osterville is mostly residential, and includes Oyster Harbors, a private island that’s connected to the mainland via a steel drawbridge. Oyster Harbors was developed as a summer resort for the Boston elite, with its landscaping designed in the 1920s by the Olmstead brothers, architects of New York City’s Central Park. Today, Oyster Harbors remains a very private place and home to grand properties with spectacular gardens and grounds.

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Living on Cape Cod, Martha’s Vineyard, and Nantucket

Cape Cod and the islands of Martha’s Vineyard and Nantucket have been synonymous with summer for generations, the epitome of a New England escape. The siren call of this region has beckoned to a wide swath of visitors, from day trippers to Presidents, with the promise of relaxed days and nights spent in a magical world of beaches, lighthouses, and shingled cottages both big and small. There’s space for everyone here: Kids ride the same valiant steeds as their grandparents did at the carousel in Oak Bluffs, while boldfaced names, wealthy financiers, and first-time visitors all pile into local clam shacks for deep-fried seafood and just caught lobster. There’s also a significantly smaller population that lives here year-round — these are the residents that pride themselves on knowing all the secret spots when the highways and beaches clear out and the Cape and the islands return to their meditative, foggy, winter selves.