Cape Cod, a hook-shaped peninsula that extends off Massachusetts into the Atlantic Ocean, is the quintessential picture of New England, with its boat-filled harbors, tranquil marshlands, pristine beaches, and sprawling, shingle-style homes. The Cape, as it’s often referred to, is probably most famous as the base of the Kennedy family at their waterfront compound in Hyannis Port, where John F. Kennedy and Jackie Kennedy would summer with their family.
Located on the “elbow” of the peninsula, 20 miles east of Hyannis Port, is the seaside town of Chatham. First settled in the middle of the 17th century and today one of the wealthiest enclaves on all of the peninsula, Chatham also has a relaxed lifestyle that includes clam bakes and local fish markets. Now listed for $13 million, 552 Shore Road is a rare opportunity to live among the charming cottages and multi-million-dollar mansions along what is widely considered one of the most prestigious streets in Chatham.

A row of curving row of mullioned windows gives the pastel-hued living room a panoramic coastal view.
Jack Vatcher Photography
The rambling, shingle-style bluff-top estate is listed for the first time in more than 50 years, and it is currently the most expensive home on the market in Chatham. Situated on a 2.86-acre lot, the 5,868-square-foot home has seven bedrooms, six full bathrooms, and one powder room spread over two floors. Each room seamlessly flows from one to another and retains the charm of a bygone era through reclaimed wood floors, paneled walls, beamed ceilings, and French windows. Each room is flooded with natural light and has a mix of classic pastel hues, apt for a region where a light color palette and nautical design elements are frequent decorative motifs.
The home feels as though you’ve stepped into a different era. The spacious living room features…