Introduction Research has shown that mental health issues are prevalent among university students and healthcare professionals. Dental practitioners are particularly at risk due to the demanding nature of their profession. Our study aims to survey dental students and faculty to assess their psychological well-being and identify key stressors and potential interventions. Methodology A cross-sectional study examined the psychological well-being, depression, anxiety, and stress of undergraduate (UG) and postgraduate (PG) dental studentsand faculty from the School of Dental Sciences. A questionnaire was distributed via email and WhatsApp to 350 participants. The questionnaire contained a unique set of items for each study group related to factors affecting psychological well-being among students, and a separate questionnaire was used to assess depression, anxiety, and stress (DASS-21) in the same population. Results A cross-sectional study of 350 dental students and educators found no significant changes in depression, anxiety, and stress (DASS) levels between age groups. Females, however, reported greater levels of these difficulties than men (D=71.5%, A=71.9%, S=76.7% for females vs. D=28.5%, A=28.1%, S=23.3% for men, with p-values for D=0.014, A=0.001, and S=0.031). Overall, 67.3% of UG students study away from home and live in hostels or flats, with academic and financial demands (30.6% and 33.5%, p-values: 0.014 and 0.098, respectively). Many people find their workload unpleasant (40.8%, p-value=0.143) and feel overwhelmed by academic obligations (47.9%, p-value=0.002), with 20%-25% worried about examinations, failure, and balancing well-being with academics (p-values: 0.001, 0.006, and 0.002, respectively). In total, 57.1% suffer severe social isolation (p-value=0.045), and more than 40% have mental health issues (p=0.003). While the mentor-mentee program is rated as helpful (p-value=0.68), 35% of students are ignorant of mental health options (p-value=0.006). Financial concerns are a big worry, with 38.7% seeking assistance, and second- and third-year students suffer more challenges than first-year students. Overall, 41.2% of instructors are perceived as extremely accessible, whereas 34.3% and 31.4% feel that scheduled breaks are required due to stress (38.2%, p=0.053). Most instructors (51.4%) encourage counseling and interact with students (76.5%), while 77.1% discuss mental health. Among the PGs, 74.2% of participants are content with the college's amenities, but 90.3% are stressed because of the PG seat departing bond, demonstrating widespread concern over this issue. To cope, 22.6% seek help from loved ones, while 19.4% pursue hobbies, emphasizing the value of personal support networks and leisure activities. Conclusion The study found that females perceive more stress than males. Most UG students live with supportive families and only experience academic helplessness on rare occasions. First-year students find academic effort more demanding than their peers at higher educational levels. Overall academic load gradually decreases from the first to the third year but rises significantly in the final year before declining during internships. As academic load increases, students tend to isolate themselves socially. Engaging in leisure activities can help mitigate the negative effects of stress on physical and psychological health. Faculty members recommend college counseling services to help students cope with stress.