58 Oyster BluffChatham, MA 02633Price: $5,750,000

Perched high above Oyster Pond, this generational estate-first known as “The Beach Plum House” and later as “Adsamore”-is one of Chatham's rarest offerings. Set on a .93-acre parcel with expansive frontage, it captures sweeping views of town and Oyster Pond, a lifestyle both connected and secluded. Originally built in Wellfleet as the Captain Holbrook House, it has been preserved and expanded over generations while modernized for gatherings. Seven bedrooms include a first-floor primary suite, while a Good Morning staircase with a hand-painted Chatham mural leads to additional bedrooms. Historic character endures throughout: the celebrated wood room with elements from the Plymouth Cordage Co. ropewalk (c.1824), hand-hewn beams, herringbone brick floors, central hearths, and built-ins. Outside, brick patios, sycamore trees, granite steps, and rock walls frame lawns rolling to the water's edge, where a private catwalk and moorings await. A legacy property, ready for its next steward.