2079 Head of the Bay Road Nestled on 1.85 acres along the pristine shores of Pleasant Bay, this extraordinary waterfront estate offers an elegant blend of craftsmanship, comfort, and sweeping water views. Thoughtfully updated and expanded over the years, the home showcases a stunning post-and-beam addition with soaring cathedral ceilings, exposed trusses, and walls of windows that frame captivating views of the bay and the Eastward Ho! Golf Course. Designed for relaxed living and gracious entertaining, the heart of the home features a sun-splashed kitchen with a dramatic vaulted ceiling, custom cabinetry, and an open flow to both dining and casual living areas. French doors and wide windows seamlessly connect the interior to outdoor decks and porches, offering multiple vantage points for enjoying the breathtaking scenery. With over 5, 500 square feet of finished living space, the home includes generously sized bedrooms, inviting gathering spaces, and a spectacular primary suite with a private balcony. An additional two-car garage with a former caretaker's cottage attached provides endless possibilities. Set amidst mature trees and plantings with a private path to the water's edge, this rare coastal retreat is minutes from Wequassett Resort, Chatham Village, and everything the area has to offe