House at 1254–1256 Montgomery Street

The house at twelve fifty-four to twelve fifty-six Montgomery Street is a flat-fronted Italianate building distinguished by its large corner windows, pilasters, and a bracketed roofline. Constructed around eighteen sixty-five on a secondary summit of Telegraph Hill, it sits on land once occupied by Hudson’s Windmill, which burned down in eighteen sixty-one. Originally built as a twenty-five-room boarding house, it was designed with interior doors that allowed for flexible, connected living spaces.