Conceived and founded by Konrad "Chip" Kruger, the former Co-Head of Greenwich Capital, the Waterside School opened its doors on September 10, 2001 with a Kindergarten and First Grade, five teachers, twenty-seven students and modest means but an ambition anything but. The School, drawing principally from Stamford's most economically challenged communities, seeks to provide its children a rigorous classroom experience blending the important lessons of the classroom with the requisite lessons of character and the lasting lessons of the heart. Waterside School was purposefully designed to offer an alternative to the region's standardized public school experience and to provide a direct path for admission to the area's more traditional and most competitive independent schools. Simply, the School aims to provide better lives for its students and families and to plant meaningful seeds of promise and hope in their communities.

Waterside was reinvented in 2004 with the recruitment of new leadership, Jody Visage, the rebuilding of the teaching faculty and a renewed and heightened commitment from each of the School's constituencies. The School now spans grades PK-5 and serves over one hundred fifty students with one hundred thirty families from thirty-one different countries.

Waterside School was fully accredited by CAIS (Connecticut Association of Independent Schools) in 2008 and 2018.