187 Penzance RoadMA 02543Sale Price: $20,000,000

This irreplaceable 9.6-acre estate in Woods Hole is a once-in-a-lifetime offering including a timeless six-bedroom home, a charming two-bedroom guesthouse, verdant grounds, a pool, a workshop dating to 1911, a boathouse, a deepwater dock, and two beach areas-all enveloped by the waters of Great Harbor and Buzzard's Bay. The main residence features a chef's kitchen, a formal dining room with a built-in pine china cabinet, a living room with a wood-burning fireplace and French doors to a deck overlooking the water, a library with reclaimed chestnut paneling, an office or study, a family room with a dramatic wood ceiling and French doors on two sides, and the estate's original sunroom. The master suite is a serene retreat boasting a water-view balcony, dual baths, and a dressing room with a fireplace. Each of the three guest bedrooms on the upper floor has an en suite bath, and two enjoy balconies overlooking the water. The lower level, accessed via a stairway from the kitchen, offers a laundry area, storage, the garage, and two additional bedrooms. The guesthouse includes a living area with a fireplace, a kitchen with a dining area, a patio, a waterfront deck, and a two-car garage.