Osterville

With a rich history dating back to the late 1800s, the Wianno Club is a true Osterville historic landmark. Now the site of frequent gatherings, celebrations and even weddings, the club celebrates more than a century overlooking Nantucket Sound and even has a spot on the National Register of Historic Places.

The Cotocheset House, now the main clubhouse of the Wianno Club, sits on land once purchased by Plymouth settlers from the Native Americans, later used as the site of a grand summer hotel for wealthy vacationers. While modernized over the years, the charm of yesteryear is still evident at the Wianno Club. After all, the private and seasonal member-owned club has served its guests for a period that now spans four generations.

Members of the Wianno Club

Home to some of the most expensive properties on Cape Cod, Oyster Harbors offers pure luxury for those searching for an estate on Nantucket Sound. The home of billionaires and philanthropists, the gated, waterfront community features its own golf course and extreme privacy.

Formerly known as Grand Island, the location became the setting for the summer homes of prominent Boston families around the turn-of-the-century. The 1920s ushered in a new offering, with construction of the stylish Oyster Harbors Club and golf course. It wasn’t long before the summer resort turned into an exclusive country club, with a coveted Donald Ross-designed golf course and neighborhood.

Along with views of the golf course, many of the sprawling estates of Oyster Harbors