Sitting in the village of Osterville, Oyster Harbors is perhaps Cape Cod's most exclusive neighborhood. This exclusivity is mainly because the resort community takes up all of Grand Island, which is surrounded by Cotuit Bay, West Bay, and North Bay and overlooks Nantucket Sound.

There is only one road in and one way out of Oyster Harbors, and its gates prevent non-residents or those without club membership from even getting onto the island. As a result, those who buy a home in Oyster Harbors don't have to worry about tourist crowds in the summers, as everything on the island is just for them.

Buying property in Oyster Harbors puts you on a private island on the shores of Cape Cod, providing you with perhaps the nation's most ideal living situation.

The Oyster Harbors way of life

While Oyster Harbors only has one neighborhood, there are a few different elements to it that you'll want to be aware of when choosing a home to buy.

Most of the houses on the island's shores feature docks, providing you with the ideal place to store your boat. The majority of these docks are in deep water so that they can support large vessels. Keep in mind that if you buy a home without dock access, there is a marina just off the island in Osterville.

Another thing to consider is that many homes overlook the golf course or sit along its fairways. If you're into living right on the golf course, look into buying one of those properties.

The history of Cape Cod's Oyster Harbors

Despite being such a small, private community, Oyster Harbors has an intriguing history.

The Wampanoag tribe originally inhabited the area before the arrival of Europeans. Although legends state that Captain Kidd spent some time there in the late 1600s, the land was reserved for the Wampanoags until 1737 when they sold it to the Lovell family.

Over the next 200 years, there were no efforts to develop this land, as the only things present were pastureland and salt works.

It wasn't until 1904 that Pulitzer Prize winner and Harvard University professor Edward Channing built a hunting lodge on the island. In the coming years, wealthy families from Boston began constructing summer homes on the land, and in 1925, seeing the island's potential, Forris W. Norris purchased it for about $500,000.

Shortly after, the Olmstead brothers, who designed New York's Central Park, came to Grand Island to develop its roads and homesites, while Donald Ross was put in charge of building the golf course.

Oyster Harbors was officially established in 1926 as a gated community and golf resort.

From the time Oyster Harbors opened until 1967, there were no initiation fees for new members. Instead, there was an invite-only system where the club had to extend invitations to new members and current members had to pay their annual dues every year by April 1. When fees weren't paid, the club assumed the members had given up their spot.

The majority stockholder at this time was Kenneth Boyd, but when he died in 1960, the club was losing money, and his family had no interest in continuing. Numerous investors came forward in an attempt to purchase the shares, some of whom wanted to turn the club into a commercial resort.

Two residents, Harry Hoyt and Paul Mellon, heard about these plans and purchased the shares themselves, ensuring that the area stayed a private island club, rather than becoming a public resort.

Living in Oyster Harbors

Buying a home in Oyster Harbors puts you in one of Cape Cod's most exclusive private neighborhoods.

This exclusiveness is a side of the Cape that most people don't have the opportunity to see, as you'll be away from the crowds and get to enjoy activities like golfing and boating in peace.

Kinlin Grover Real Estate can let you know the details of living in Oyster Harbors so you can see if the island a good fit. Contact us for more information on this ultra-private community.

Show More

Let Us Help You Find the Perfect Home

Tell us what you're looking for and we'll send you an email update anytime a new home matching your criteria is listed.

Other Golf Communities

Ballymeade Estates

Cummaquid Heights

Kings Way

New Seabury

Ocean Edge - The Villa

Oyster Harbors



The Ridge Club

The Villages at Brookside