Nestled on 1.85 acres along Pleasant Bay, this extraordinary waterfront estate offers refined craftsmanship, comfort, and sweeping water views. The home features a striking post-and-beam addition with soaring ceilings and walls of glass framing views of the bay and Eastward Ho! Golf Course. Designed for relaxed living and entertaining, the kitchen boasts a dramatic vaulted ceiling, custom cabinetry, and seamless flow to dining and living areas. French doors and oversized windows open to expansive decks and porches, ideal for enjoying the scenery. With over 5,500 sq ft of living space, the home includes spacious bedrooms, inviting gathering areas, and a spectacular primary suite. An additional 2-car garage with a former caretaker's cottage attached provides endless possibilities. Set among mature trees with a private path to the shore, this rare coastal retreat is minutes from Wequassett Resort, Chatham Village, and all the natural beauty and recreation the area has to offer.