Objective No studies have yet evaluated linear alveolar bone levels and extraction socket dimensions on dry skulls using different techniques. We aimed to investigate the accuracy of cone-beam computed tomography (CBCT), digital radiography, and digital photography. Methods Circumferential linear alveolar bone level measurements were performed at six sites on the examined teeth using gutta-percha points placed for reference at the cementoenamel junction and alveolar bone crest. Dimensions of the extraction socket were evaluated by linear measurements in the mesiodistal and buccolingual directions. Groups were formed according to the following imaging and estimation techniques: (1) direct measurement using digital calipers under loupe magnification (gold standard); (2) direct measurement using only digital calipers; (3) digital photographs/ImageJ (Photo/I); (4) digital paralleling long-cone periapical radiographs/ImageJ (Periapical/I); (5) digital panoramic radiographs/digital calipers; (6) digital panoramic radiographs/digital calipers and loupe magnification; (7) digital panoramic radiographs/ImageJ; and (8) CBCT/ImageJ (CBCT/I).Results Statistical analyses showed significant differences for all panoramic radiography subgroups in all examined regions compared with the gold standard (p \ 0.001). Results of the CBCT/I (r = 0.930, p \ 0.01), periapical/I (r = 0.939, p \ 0.01), and Photo/I (r = 0.978, p \ 0.01) techniques showed high correlation with the gold standard. Reliability of repeated measurements was higher with loupe magnification and the image-processing program.Conclusions Periapical/I and CBCT provide promising results in analyses of the dimensions and relations of periodontal tissues. Routine clinical digital photographs can be converted to scaled images and applied to treatment planning and preoperative-postoperative comparisons.