Vermont lumber baron William Barrett built this Italian villa-style mansion on a Sausalito hillside in 1885, part of a wave of wealthy San Franciscans buying property across the bay after a developer began marketing the town as an upscale ferry-commute suburb. Barrett’s family lived there until 1902, when the house was converted into a guesthouse, and attorney John P. Gallagher bought it outright in 1910, running it as the Casa Madrona Hotel and, later, the Gallagher Inn.
Local rumor holds that it also operated as a bordello for a stretch, though records on that chapter are thin. The property served as temporary lodging for military families during World War II before falling into disrepair, and a French immigrant family restored it starting in 1959. It’s listed on the National Register of Historic Places and has hosted guests including Dick Van Dyke.