Background Chondroblastoma is an uncommon benign cartilaginous tumor of young adults and adolescents, accounting for 1% of all bone tumors. We aim to analyze the imaging characteristics of pathologically proven chondroblastoma, measure the incidence rate of local recurrence of this tumor, and identify factors that may influence its local recurrence. Materials and methods The details of a total of 44 patients with pathologically proven chondroblastoma who underwent surgery and followed up by cross-sectional imaging between January 2006 and March 2021 at the KFSHRC in Riyadh were retrieved from our archive. All available modalities, including plain radiography, CT, and magnetic resonance imaging (MRI), performed at baseline and on follow-up were reviewed and correlated with the histopathological diagnosis. Recurrence was calculated from the date of surgery to the date of recurrence or the date of being lost to follow-up depending on the date of recurrence. The statistical software STATA was used to analyze the data. Results The tumor recurrence rate was 4.55% (n = 2). Similarly, the residual tumor rate was 4.55% (n = 2). No metastases were documented. The recurrence-free survival was 93.8% at the 722-day follow-up. More than 95% of lesions demonstrated typical imaging features including: a well-defined lobulated margin, intermediate-to-low signal on T2-weighted images, and perilesional edema. Conclusions This study emphasizes the imaging findings of chondroblastoma, which classically affects skeletally immature patients. Although imaging findings cannot be used to predict recurrence or survival, we obtained excellent prognosis following surgical treatment at our institution.