Scholars disagree on the exact provenance of the Captain Leal House, but it is certainly one of the oldest residences in the Cow Hollow neighborhood of Pacific Heights.

The structure was originally the main house for a dairy farm and may have been built as early as 1853. Captain Leale, a ferry boat captain, bought the house in 1883, and either he or the previous owner remodeled the facade with a false front in the popular Italianate style. In the back garden, the Captain built a little study, nautically furnished and fitted to resemble a pilot house.