As you might have surmised, this quiet village was once a center for oystering. Its original Native American name was Cotacheset. It remains a relatively obscure village that has a stupendously charming Main Street enclave of white clapboard buildings housing an upscale collection of shops, boutiques, galleries, eateries and banks. Cape Cod Academy, a private school, calls the village home. Along its shady byways are some of Cape Cod’s most impressive and lavish homes. Many of these, and yet larger estates, remain unseen within gated community at Oyster Harbors as well as Seapuit, Wianno and other parts of the village exclusively the domains of wealthy seasonal residents summer. Osterville has two private country clubs, the Wianno Club and Oyster Harbors, both features private 18-hole golf courses, tennis facilities and beaches. Crosby Boat Yard, port to renowned Crosby catboats and Wianno seniors, is located here. The latter was a favorite of President John F. Kennedy. Dowses Beach is the only semi-public, resident-only beach. This lovely beach fronts Nantucket Sound and rears up to tranquil East Bay, a favorite of families with children.
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