Crocker hired architect Willis Polk to design the home in the style of a neo-classical Renaissance palazzo, although Porter Garnett called it "more a varied, free, and personal interpretation of classic architecture than a rendering of the neoclassic", adding that "Mr. Polk proves that he can be at once daring and discreet, reckless and restrained" in 1915.

[5] Completion was delayed by the onset of World War I and suspension of merchant shipping services.

[2]: 64–65  In 1915, Crocker added 20 acres (8.1 ha) of land adjoining the site to preserve his views.

[8] It was occupied intermittently — most notably by Soviet Ambassador Andrei Gromyko and his delegation to the 1951 Japanese Peace conference[4][9] for a week and a half[10] — and the estate was subdivided, reducing the site to 10 acres (4.0 ha).

The 2005 and 2006 Crystal Springs Uplands baseball teams won North Coast Section Class B Championships.

[18] Following a North Coast Section record 27–3 victory in the 2006 championship game, the San Francisco Chronicle named Crystal Springs Uplands one of the top 20 high school teams in the San Francisco Bay area.

Nick Neely, class of '03, won the NCS individual cross country title in 2002.

Benjamin Bouie, class of '25, won the CCS individual title in 2023 and also finished 2nd at the state meet Division V race.

After a couple of years and a few additions, the girls' team won the NCS Class A meet in 2004 and 2005.

That same year, the 400m relay team (Madeleine Evans, Sydney Blankers, Imani McElroy and Caroline Scanlan) qualified for the state meet with their third-place finish.