A wealthy Barnstable enclave 5 mi east of Cotuit, Osterville is lined with elegant waterfront houses, some of which are large "cottages" built in the 19th century when the area became popular with the monied set. You'll find that most beaches in the village, including the impressive Dowses Beach, are restricted to residents-only parking. Despite its haute homes, the village of Osterville retains the small-town charm that permeates the Cape; its Main Street and Wianno Avenue area has a collection of trendy boutiques and jewelry shops mixed with a library, a post office, and country stores. The village's festivals of Daff O'ville Day (late April) and Christmas Stroll (mid-December) are heavily attended.
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