The Upper School serves grades 9 through 12, and it houses its administration in the Leggett building and the Campus Center.

[5] The principal educational facilities are: Leggett Hall - 21 Upper-School Classrooms - Middle School Drama & Latin Classes - Headmaster's Office - Upper School Principal and Deans Offices - Hulst House - Wireless Internet Access Campus Center - Hajjar Auditorium - Shenck Auditiorium - 9 General Classrooms - Student Coop and Bookstore - Cafeteria - Student Lounges - Bells Classroom - Choir Room - Arts Display Spaces - Wireless Internet Access Hajjar STEM Center - Wireless Internet Access- 8 Science Labs with Fume Hoods, Chemical Working Surfaces, etc.

- 7 classrooms - Math and Science Department Offices- Massoud Steps Meeting Area- Robotics Lab Imperatore Library - 35,000+ Volumes - Computer Workspaces - Student Lounge - 4 Language Classrooms - Taub Technology Center - Wireless Internet Access Swartley Art Center - Photography Studio - Ceramics - Art History - 2 Studio Arts Classrooms - Music Practice - Art Gallery - Printmaking Facilities - Wireless Internet Access Khubani Performing Arts Center - Theatre - Music Instruction Rooms - 1 Sound and Lighting Booth - 1 Projection Booth Modell's Sports Complex 2 Gymnasiums - Dance/Aerobic Studio - Weight Room - 2 On-Campus Fields - 2 Additional Fields - 5 Tennis Courts Lower School Building 15 Classrooms - Cafeteria - Gymnasium - Library - Computer Room - Wireless Internet Access Umpleby Hall - 28 Middle-School Classrooms - 2 Science Labs - Wireless Internet Access Graham House - Admissions Office - Alumni Office - Business Office - Development Office Middle School Building A 10,910 square feet (1,014 m2) Middle School facility was built, replacing the Library Circle area of the campus and the now-demolished Generoso Pope Science Hall.

Within the schools, there are departments for Math, English, History, Science, Language, Physical Education, Technology, Human Development, and Arts.

[13][14][15] Prior to the realignment that took effect in the fall of 2010, Dwight-Englewood was a member of the Bergen County Scholastic League.

[19] The boys' tennis team won the 2002 Non-Public B state championship and was the runner-up to Holmdel High School in the Tournament of Champions, falling by the score of 3-2 in the finals.

[21] The team's only loss was in the Tournament of Champions semi-finals to ultimate runner-up Westfield High School by the score of 3-2.

[22] In 2010 the boys' team won the North Jersey Group B sectional, knocking off tournament favorite Newark Academy 3-2, and won the Group B title once again, against Moorestown Friends 4-1,[23] before falling in the Tournament of Champions semifinal to Westfield, 31⁄2-11⁄2, t finish the season with a record of 26-4.

[26] The girls tennis team won the Non-Public A state championship in 2001 (vs. Red Bank Catholic High School).

They form an opera company and go through all the steps necessary to stage a full production—script writing, libretto, costumes and makeup, set design, lighting, and publicity.

In May 2021, the Foundation Against Intolerance and Racism (FAIR) sent a letter to the school criticizing their lessons on gender identity and race.

[31] In June, FAIR started a campaign to support Dana Stangel-Plowe, who resigned from the Dwight-Englewood School due to what she called "essentialist, racialist thinking".

"[34] In an email to parents and students, Board President Robert E. Miller stated, "Dr. De Jarnett's resignation follows conduct inconsistent with Dwight-Englewood School's values and standards of behavior."