Welcome to Osterville, Cape Cod Massachusetts

We are the local experts in Osterville Real Estate, Osterville luxury real estate, and Cape Cod waterfront homes. Our estate agents have over 60 years of combined experience in real estate transactions. Our strength is based on the in-depth training of our employees, on constantly updated information and on continuous knowledge transfer within our company. Our estate agents are here to serve your needs for buying and selling Osterville real estate. Although Osterville luxury real estate is considered one of the premier villages for Cape Cod, there are other towns and village to consider including Cotuit, Marstons Mills, Barnstable, Chatham, and Orleans.

The attractive seaside village of Osterville, rich in history and cultural heritage, was founded in 1648 as “Cotacheset”. It was primarily a seafaring village, the home of sea captains, shipbuilders, salt-workers, cranberry growers and oyster men. The name of Osterville did not come into use until 1815. Ostervilles popularity evolved from its location, the extensive coastline, charming convenient village center and attractive neighborhoods and resort areas. Today Ostervilles 5.8 square miles preserves its association with the sea and its traditional summer resort quality. Ostervilles distinct areas include the more rural northern area along Bumps River Road, Tower Hill, East Bay, the village center, Seapuit, Osterville Harbor and the historic area of Wianno as well as the island communities of Little and Grand Island (Oyster Harbors). The village attributes include the 5 mile Nantucket Sound coastline and the 17 mile shoreline along the coastal bays and river estuaries. The shoreline encircles 1300 acres of protected waters and the coastline has 102 acres of protected barrier beaches. Thirteen inland ponds and lakes total 75 acres of surface water. Two private golf courses retain 228 acres of open space. The village center provides a blend of retail commercial, professional services, institutional and community uses, banking, and a collection of small quality shops, galleries and offices. Three select clubs, the Wianno Club, the Oyster Harbors Club and the Wianno Yacht Club keep the residents active.

Armstrong-Kelley Park, the oldest and largest privately-owned park on Cape Cod, is located in Osterville. Crosby Boat Yard is the home of the famous Crosby catboat, and the Wianno senior, both renowed in the sailing field and the latter a favorite of nearby Hyannisport resident President John F. Kennedy.

A drawbridge connects the town to Little Island and Grand Island (also known as Oyster Harbors), a gated community featuring many luxury homes and a country club. The neighborhood of Wianno abuts the East Bay section of Osterville, and is home to the Wianno Inn, a longtime inn and function hall. One of the legends about the Inn tells of Robert F. Kennedy riding a donkey up the front stairs of the hotel entrance during a wedding reception.