An exceptional coastal compound overlooking Milford Harbor, this one-of-a-kind waterfront estate features a main residence with thoughtful updates plus a fully detached Nantucket inspired guest house and three-car garage. Just two blocks from Fort Trumbull Beach and the Milford Yacht Club, and minutes to town shops, restaurants and Metro North, the property offers private beach access and direct harbor views creating an unmatched blend of lifestyle, location, and flexibility. The main home showcases timeless architecture, high ceilings, a formal living room w/fireplace and a den with harbor views. Modern updates include an expansive open concept kitchen/family room with fireplace, large island, dining area and sliders to a new waterfront deck. The spacious covered front porch overlooking the harbor is perfect for summer evenings. Upstairs, the harbor-facing primary suite offers a private deck and full bath. Two additional bedrooms and a third-floor guest/bonus suite w/full bath complete the home. The guest house spans 1768 SF and features a first floor rec room with wet bar, full bath, patio with hot tub hookup and outdoor shower. Located on the upper level is a large harbor view room with fireplace and balcony, two additional rooms, a common area and full bath ideal for guests or extended family. Bluestone patios connect both residences creating seamless indoor-outdoor living along the harbor. A RARE coastal retreat with unmatched versatility. This property is a MUST SEE!