Classic coastal charm meets modern luxury in this exceptional waterfront estate overlooking Milford Harbor. Built in 1915 by famed inventor Simon Lake, the stately Georgian style main residence blends original hardwood floors, antique windows, and gracious architectural character with thoughtful updates. The formal living room features a fireplace, the den offers a cozy retreat, and the open concept kitchen and family room addition boasts a large island, dining area, generous pantry, fireplace, and walls of windows framing bluestone patios and harbor views. Upstairs, the serene primary suite includes a full bath and private harbor view deck, plus two additional bedrooms and a third level guest suite or bonus room that includes a full bath. A finished basement adds storage, and recreation space. Behind the main home, a Nantucket inspired guest house added in 1995 features a three car garage, spacious entertainment room with wet bar, full bath, and patio with outdoor shower and hot tub setup possibilities. The upper level offers professional office space, ideal for a private business with staff, including a large harbor view office with gas fireplace and balcony, a common area with kitchenette, and two additional offices easily convertible to extra living space or bedrooms. Surrounded by lush gardens, stone walls, this rare property is minutes to the Milford Yacht Club, downtown, train, and beaches, an extraordinary blend of history, luxury, and waterfront lifestyle.