19,300,000

From its rise above Capaum Pond - near the site of Nantucket's first settlement - this shingled residence looks north over the pond to the open water of Nantucket Sound. Eight en-suite bedrooms span three finished levels, joined by a two-story great room, a granite-and-butcher-block kitchen, and a paneled study. Covered porches on two sides step down to stone-walled gardens, a pergola-shaded dining terrace, and an infinity-edge pool with spa; a roof deck with a fire pit faces the sunset. A separate guest cottage with its own kitchen, den, and bedroom stands beside the circular drive. The lower level adds a theater, bar, and games room. The property is minutes from Town and the north-shore beaches.