Objectives: To assess the impact of the presence or position (buccal/palatal) of impacted canines on trabecular bone density using fractal analysis (FA) on cone-beam computed tomography (CBCT) images, and to compare the results with a control group without impacted canines. Methods: This retrospective study included 41 patients with unilateral impacted canines (30 palatal, 11 buccal) and a control group of 39 patients who underwent surgically assisted rapid maxillary expansion. All patients had CBCT images recorded for diagnostic and treatment purposes. Cross-sectional CBCT images were obtained between the first and second premolars on both sides of the patients’ maxilla. From these images, fractal dimension (FD) was measured in a 20 × 20 pixel region of interest in the trabecular bone using the ImageJ software. Results: The FD values were significantly higher on the impacted side in the impacted canine group (p = 0.02). Within the impacted canine group, a significant increase in FD was observed on the impacted side in the buccal-impacted subgroup (p = 0.02), while no significant difference was observed in the palatal-impacted subgroup (p > 0.05). Conclusions: According to the results of our study, there is an association between the position of the impacted canine and trabecular bone density. An increased trabecular bone density may play a role in the etiology of buccally impacted canines. Clinicians should consider anchorage planning, and appropriate force level, during the forced eruption of buccally impacted canines with high surrounding bone density, to minimize undesirable movements and achieve optimal treatment outcomes.