Rarely does a property of such storied provenance and grand scale grace the Key West market. This is a residence where history breathes. Commanding nearly half a city block in the prestigious Casa Marina district, 1101 Casa Marina Court is an architectural masterwork built by A. Maitland Adams in the early 1930s. Adams was said to be a partner of Charles Thompson, Ernest Hemingway's fishing companion. If the walls could talk at this iconic residence, it would tell you that this is the very home where renowned author Philip Caputo penned ''Indian Country'' and where Gregory Peck and Harry Truman played cards in the dining room. The 20,000 square foot estate seamlessly marries Palm Beach sophistication with island charm, commanding attention with its vast landscaped grounds of unparalleled beauty, sweeping open spaces, and stunning resort-style pool. Tucked behind the walls, awaits a vast courtyard complete with its own meditation garden--perfect for grand entertaining or peaceful relaxation. Along with gated off-street parking for two, the home features five bedrooms and four and a half bathrooms, including a second-story guest apartment that offers privacy and versatility. Recent updates to the home include travertine marble floors, new roof (2025), impact windows and doors, a chef's kitchen, and welcoming fireplace. Enjoy breathtaking open-water views and sunsets from the home's private widow's walk- an elevated retreat perfect for unwinding above it all. Moments away from waterfront dining, beaches, and pickleball courts, this corner estate offers an unparalleled lifestyle for those seeking a piece of island history redefined for modern luxury.