This study aimed to assess the prevalence of dens invaginatus (DI) and its association with periapical lesions (PLs) in a Western Indian population by means of cone-beam computed tomography (CBCT). CBCT volumes of 5201 subjects were evaluated. Associations among gender, tooth type, DI type (Oehler's classification), and presence of PL were investigated. PL was codified using Estrela's Cone Beam Computed Tomography Periapical Index (CBCTPAI). Chi-square tests and descriptive statistics were used at p = 0.05. Overall, 7048 CBCTs were assessed, containing 19,798 maxillary and mandibular anteriors, of which 77 maxillary teeth demonstrated DI (0.39% of all anteriors). Of all 5201 subjects, 57 had DI (1.1%). Bilateral DI was more common in females than in males (p = 0.046). DI type distribution was as follows: type I (22.1%), type II (61.03%), type IIIa (10.4%), and type IIIb (6.5%), which was significantly different (p < 0.001). Maxillary lateral incisors were the most associated with PL (p < 0.001). Type I was frequently associated with CBCTPAI scores 1 and 2 (absence of PL), whereas types II, IIIa, and IIIb were associated with CBCTPAI scores 3, 4, and 5 (presence of PL). A prevalence of 1.1% identifies DI as a common developmental tooth anomaly in a Western Indian subpopulation. The percentage of maxillary anteriors affected by DI and associated PLs should be considered before diagnosis and treatment planning. Knowledge about the prevalence of DI and its subtypes, and their association with/without periapical pathosis may aid clinicians in treatment planning and execution to improve patient outcomes.