As one of the oldest dwellings in the area,[2][3] the exact origin of the Captain Leale House has been a subject of debate among scholars. Originally serving as the main house for a dairy farm, it is believed to have been constructed as early as 1853.[4][5]
The building was originally used as a farm house for a 25 acres (10 ha) dairy ranch.[5] Captain Leale, a ferry boat captain, purchased the house in 1883. It is unclear whether he or the previous owner was responsible, but at some point, the facade was remodeled with a false front in the popular Italianate architectural style. Adjacent to the house, Captain Leale constructed a small study in the backyard, which was furnished and designed to resemble a pilot house, reflecting his nautical background.[6]