A one of kind waterfront compound on Milford Harbor, perfect for multi-generational living or professionals needing a private office with space for a small team. This exceptional coastal estate features a beautifully updated main residence plus a fully detached, Nantucket inspired guest house/office with three car garage. Just two blocks from Fort Trumbull Beach and the Milford Yacht Club, and minutes to Milford Green's shops and restaurants. With private beach access and direct harbor views, this property offers an unmatched blend of lifestyle, location, and flexibility. The main home showcases timeless architecture, high ceilings, and thoughtful updates, including a formal living room with fireplace, den with harbor views, and open concept kitchen/family room with fireplace, large island, dining area, and sliders to a new waterfront deck. Upstairs is a harbor facing primary suite with private deck and full bath, two additional bedrooms, and a third-floor guest or bonus suite with full bath. The guest house/office spans 1,768 sqft with a spacious rec room, wet bar, full bath, patio with hot tub hookup, and outdoor shower. Upper level boasts a large harbor view office with fireplace and balcony, two rooms, common area, and full bath can potentially function as a private guest residence, in-law suite, or professional office setup. Bluestone patios connect both buildings for seamless indoor outdoor living on the harbor. A RARE coastal retreat with unmatched versatility.