The tiny seaside village of Osterville was settled in the 1700s by hardy Colonists determined to make a living harvesting oysters. The village is home to the Crosby Yacht Yard, which has been turning out superior craft since the 1840s. Pres. John F. Kennedy often sailed his Crosby Wianno Senior on Nantucket Sound when he vacationed at his Cape Cod home. Osterville follows this town’s evolution, from a haven for captains of great merchant ships to a summer playground for such storied families as the Mellons and DuPonts. Today, Osterville’s superb beaches and laid-back lifestyle attract not only the rich and famous but also year-round residents who enjoy a relaxed and sophisticated lifestyle.