Sitting on 1.74 acres on Black Pond, this is a truly unique and meticulously maintained Chatham compound that offers a variety of possibilities. Whether you're looking for an investment property, a retirement home, a second home, or the potential for expansion, this property has it all. The main home features 4 bedrooms and 4.5 bathrooms. Two of the bedrooms are recently renovated first -floor primary and the remaining two bedrooms are located on the 2nd floor and share a full bathroom. The kitchen is fully equipped and opens up to a large patio fitted with an awning. One of the highlights of this property is the unique Pilot House with its circular design and window lined walls. From here, you can enjoy breathtaking views of the sprawling lawn and Black Pond. In addition to the main house, there is a charming guest cottage located next door which features 3 bedrooms and a recently renovated full bath, sitting area and updated kitchen. Adjacent to both the cottage and main house is a carriage house with additional living space. Ideally situated close to both town and the Atlantic, this property is conveniently close to various activities and attractions, including the Chatham Fish Pier, Chatham A's games, pickleball courts, Seaside Links golf course, and swimming spots. Additionally Downtown Chatham with all it has to offer is just moments away: fine & casual dining, galleries, shops and the beach are within easy reach. Overall, this Chatham pond-front compound is a highly desirable property that combines versatility & beauty in a prime Chatham location. See attached for amenities, improvements and rental history.