Cape Cod, MA
Osterville
About Osterville
Living in Osterville
Osterville is one of Cape Cod's most prestigious villages, known for its stunning waterfront estates, world-class sailing, and charming boutiques along Main Street.
Whether you are searching for a waterfront estate, a charming Cape Cod cottage, or a year-round home in one of the most desirable communities on the East Coast, the Freitas Monteforte Group brings unparalleled local knowledge and Compass's world-class marketing to every transaction.
Search Osterville ListingsAt a Glance
Active Listings
Osterville Homes For Sale
Private Communities
Gated Communities & Enclaves
Oyster Harbors
$2M – $20M+A private gated island community accessible by drawbridge, offering harborfront estates, a yacht club, and tennis courts. One of Cape Cod's most exclusive addresses.
Wianno
$1.5M – $8MAn historic enclave centered around the Wianno Club, renowned for its Wianno Senior sailboat class and century-old shingle-style cottages overlooking Nantucket Sound.
Lifestyle
Parks, Activities & Things To Do
Dowses Beach
A sheltered, family-friendly beach on Nantucket Sound with calm waters and spectacular sunsets.
Wianno Club
A historic private club offering sailing, golf, and tennis in an idyllic waterfront setting.
Osterville Village
A charming village center with boutique shops, art galleries, and waterfront dining along Main Street.
West Bay Boating
West Bay and North Bay offer exceptional boating, kayaking, and stand-up paddleboarding surrounded by estuaries.
Lowell Park
A scenic town park with tennis courts, a playground, and walking paths in the heart of the village.
Location
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