Mortimer Fleishhacker Sr. was a San Francisco banker and civic leader whose family controlled the Anglo California National Bank. The wealth that built Green Gables came from banking, hydroelectric power, and paper manufacturing. The estate's English manor style reflected the Fleishhacker family's aspirations: not the Spanish Colonial Revival popular elsewhere in California but a deliberate evocation of the English country house tradition. The building campaign stretched over decades as the house was expanded and refined, growing from a modest country retreat into a substantial estate with formal gardens.

The house sits in the wooded hills of Woodside, a community that has long attracted the Peninsula's wealthiest families. The area's combination of privacy, natural beauty, and proximity to San Francisco made it ideal for the kind of gentleman's estate that European aristocrats would recognize. Green Gables exemplifies this ambition: its English manor design, unusual for California, creates a sense of transplanted tradition among the native oaks and redwoods. The National Register listing recognizes both the architectural significance and the historical importance of the estate as a document of early twentieth-century Peninsula wealth.

Green Gables belongs to a layer of Peninsula history that Silicon Valley has largely buried under office parks and subdivisions. Before venture capitalists and tech founders colonized these hills, banking families, railroad barons, and industrialists built estates that reflected East Coast and European sensibilities transplanted to California soil. The Fleishhacker House is one of the finest surviving examples of that era -- a reminder that wealth has shaped these hills for more than a century, even if the source of that wealth has changed from gold and banking to code and equity.