Welcome to Windward on the Bay; a distinctive waterfront property where a spacious main residence and separate guest cottage overlook Penobscot Bay. With two independent homes, 275' of shoreline, multiple garages, and an established rental history, this property creates exceptional flexibility for family, guests, or income potential, all in a private setting just minutes from Belfast. The main residence features more than 3,600 square feet of finished living space, plus 946 square feet in the finished walk-out lower level. Expansive windows capture views of the bay, while custom woodwork, wood floors, and a grand open staircase bring warmth and character throughout. The custom kitchen connects to inviting gathering spaces, including a dining room with wood-burning stove, library with built-ins, and living room opening to a screened porch overlooking the grounds. A spacious first-floor primary ensuite provides comfortable one-floor living. Three additional bedrooms are located upstairs, including one with a private deck overlooking the water. The third floor features a dedicated office with custom built-ins and bay views, while the finished lower level includes a family room, home gym, and full bath. The detached guest cottage lives like a home of its own, with separate heat and utilities, a galley kitchen, open living area, laundry/utility room, three bathrooms, and a spacious studio-style bedroom upstairs. Expansive lawns, mature landscaping, and wooded surroundings lead toward the bay, while two detached garages provide abundant space for vehicles, boats, storage, and hobbies. Windward on the Bay brings together two residences, privacy, and a beautiful Penobscot Bay setting in one remarkable coastal Maine property.