Nestled within the prestigious Tokeneke Association, this exceptional Mediterranean-inspired waterfront residence offers sweeping southern views toward Contentment Island and an unparalleled coastal lifestyle. Complete with a seasonal dock, the property is ideal for boating, paddle boarding, kayaking, and waterfront entertaining. An oversized covered breezeway welcomes you into a private rear courtyard or the beautifully appointed interior, where arched openings frame sunlit living spaces and captivating water views. The main level features a dramatic sunken living room, wood-paneled library, formal dining area, and a stunning chef's kitchen with custom full-height cabinetry, quartz countertops, professional-grade appliances, and expansive prep space. Upstairs, the luxurious waterfront primary suite offers a wood-burning fireplace, four closets, and a spa-like bath. Two additional en suite guest bedrooms include walk-in closets and private balconies designed to capture refreshing coastal breezes. Rich oak detailing, arched-top windows, and timeless Mediterranean architecture blend seamlessly with modern finishes throughout. Additional highlights include a walk-in cedar closet, spacious laundry room, oversized two-car garage, and exceptional privacy. Impeccably maintained and thoughtfully designed for both elegant entertaining and everyday living, this extraordinary waterfront home offers a rare opportunity to experience the very best of Darien coastal living.