Introduction: Cystic lesions are one the most common pathologies in the oral and maxillofacial region. A number of software are available to assess the progress of bone healing following their surgical management. Aim and objective: The aim and objective of this study was to assess the changes in size and bone density following treatment (either marsupialization or enucleation) of benign odontogenic cystic lesions in eight patients using computer analysis on pre- and postoperative panoramic radiographs. Materials and methods: The study was undertaken in 8 patients with mean age of 35.37 years (range = 11–50 years). The male–female ratio was 3:5. All lesions (n = 7) were present in the mandible except one that involved right maxilla. Out of the total eight cystic lesions, six cystic lesions were treated by marsupialization, and two cystic lesions were treated by enucleation. Results: There was a significant decrease in cystic volume postoperatively in all patients treated by marsupialization (n = 6) and also decrease in size of radiolucent (in all 8 patients) area radiographically, with progressive increase in bone density when compared to contralateral healthy side. The mean difference in bone density between preoperative and postoperative values was highly significant in the first 2 months, significant in third, fourth, and fifth month, and nonsignificant in the last 3 months. It was observed that the mean postoperative speed of shrinkage of the radiolucent areas was almost similar in the first 5 months and then decreased progressively over the next 4 months. The average speed of shrinkage was maximum for odontogenic keratocyst (OKC) (n = 3), followed by unicystic ameloblastoma (UAB) (n = 1), dentigerous cyst (DC) (n = 1), and was the least for residual cyst (n = 1). Conclusion: The study noted that there might be a direct relation between size of primary radiolucent area and postoperative speed of shrinkage. Hence, digitalized orthopantomograph can be considered as an economical alternative to assess postoperative bone regeneration along with the added benefit of reduced radiation exposure to the patient.