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Hillbrook, originally known as the Children's Country School, was founded by Mary Orem, Elizabeth Glassford, Nathalie Wollin, and Ann Boge. Hillbrook once extended as far as Shannon and Kennedy Roads to the North and South, but the property has since been subdivided to create the current 15-acre (61,000 m2) campus.
A boarding school during its earliest years, Hillbrook became a day school in 1960, at which point the TCCS name was dropped. Robin Clements was headmaster from 1976–97, followed by Sarah Bayne from 1999-2009, with an interim headmaster serving in 1998. Hillbrook's motto is "Educate, Nurture, Inspire".
There are approximately 315 students in junior kindergarten through 8th grade. Mark Silver was appointed as current Head of School in 2009. Silver was recruited from Francis Parker School in San Diego, California.
- "Best of Picture from the Past". Los Gatos Weekly Times. February 20, 2002. Retrieved August 23, 2007.
- "Hillbrook headmistress leaves school 'on a high note'". San Jose Mercury News. Retrieved June 13, 2009.