Background: Radiographic evaluation of bone regeneration following maxillary sinus floor elevation commonly emphasizes volumetric gains. However, the qualitative microarchitecture of the regenerated bone, particularly when assessed via two-dimensional imaging modalities, such as panoramic radiographs, remains insufficiently explored. This study aimed to evaluate early trabecular changes in grafted maxillary sinus regions using fractal dimension, first-order statistics, and gray-level co-occurrence matrix analysis. Methods: This retrospective study included 150 patients who underwent maxillary sinus floor augmentation with bovine-derived xenohybrid grafts. Postoperative panoramic radiographs were analyzed at 6 months to assess early healing. Four standardized regions of interest representing grafted sinus floors and adjacent tuberosity regions were analyzed. Image processing and quantitative analyses were performed to extract fractal dimension (FD), first-order statistics (FOS), and gray-level co-occurrence matrix (GLCM) features (contrast, homogeneity, energy, correlation). Results: A total of 150 grafted sites and 150 control tuberosity sites were analyzed. Fractal dimension (FD) and contrast values were significantly lower in grafted areas than in native tuberosity bone (p < 0.001 for both), suggesting reduced trabecular complexity and less distinct transitions. In contrast, higher homogeneity (p < 0.001) and mean gray-level intensity values (p < 0.001) were observed in the grafted regions, reflecting a more uniform but immature trabecular pattern during the early healing phase. Energy and correlation values also differed significantly between groups (p < 0.001). No postoperative complications were reported, and resorbable collagen membranes appeared to support graft stability. Conclusions: Although the grafted sites demonstrated radiographic volume stability, their trabecular architecture remained immature at 6 months, implying that volumetric measurements alone may be insufficient to assess biological bone maturation. These results support the utility of advanced textural and fractal analysis in routine imaging to optimize clinical decision-making regarding implant placement timing in grafted sinuses.