The student numbers continued to increase as families moved from Boston, Massachusetts, further out to the suburbs, and by the mid-1990s the school again became overcrowded.

Several new classrooms were added, the sizes of the cafeteria and gymnasium were increased, and a ventilation system was installed.

In addition to its traditional academic offerings, Timberlane allows students to take vocational classes at Salem High School and Pinkerton Academy.

[9] In 2020, Christopher Gempp was arrested for attempting to meet up with a 15 year old boy he met off the popular LGBTQ+ dating app Grindr.

The whole thing ended up being a sting operation from his local police department and he got caught and arrested.

Russell was previously placed on administrative leave in November 2021 pending the outcome of the districts investigation.

[11] In June 2023, a non-student juvenile entered the building intoxicated after having taken the school bus from a different home.