The current high school, designed by Newman Architects of New Haven, was constructed from 2003 to 2005, opening in the fall of 2005.

[citation needed] The girls' lacrosse team won the 2007, 2008, 2009, 2011, 2013, and 2014 CIAC Division I state championship.

[citation needed] The girls' volleyball team maintains a 100+ game winning streak in addition to numerous FCIAC and state championships.

][citation needed] The boys' track team won state class championships in the Indoor 2005 and 2006 seasons.

[citation needed] The boys' swim and dive team won the state championships in 2018.

[16] After years of public debate with school neighbors,[17] stadium lights were turned on for evening game play on September 14, 2017.

The DHS Baseball Field Project raised almost $1 million for the field (along with $1.08 appropriated by the Representative Town Meeting, $306,000 provided by the school district and $20,000 donated by the Darien High School Building Committee).

The Fall Drama is intellectual, contemplative, and intimate, while the Spring Musical is often a large-scale production targeted at the broader Darien community.

The Drama is especially well known for its use of extensive original music composition, direction, and live performance in many of its past shows.

Its shows, ranging from Kiss Me Kate to Metamorphoses to Chicago to The Curious Incident of the Dog in the Night-Time, are beloved by the Darien public and widely attended.