Ranked 29th among Massachusetts High Schools,[3] close to 98% of students graduated in 2023, with about 96% of those continuing to higher education.

[3] A major three-phase reconstruction and expansion of the school started in 2014 and was completed in September 2017.

After the complete redesign of the interior of the building, approximately 75% of classrooms now have exterior windows and direct day-lighting versus 25% in 1972.

The original internal courtyard was enclosed to create the 2-story dining commons and assembly space.

[5] Winchester High School fields teams in the following sports: