(1) Background: The use of multiscale prediction or the optimal scaling of predictors can enhance soil maps by applying pixel size in digital soil mapping (DSM). (2) Methods: A total of 200, 50, and 129 surface soil samples (0–30 cm) were collected by the CLHS method in three different areas, namely, the Marvdasht, Bandamir, and Lapuee plains in southwest Iran. Then, four soil properties—soil organic matter (SOM), bulk density (BD), soil shear strength (SS), and mean weighted diameter (MWD)—were measured at each sampling point as representative attributes of soil physical and chemical quality. This study examined different-scale scenarios ranging from resampling the original 30 m digital elevation model and remote sensing indices to various pixel sizes, including 60 × 60, 90 × 90, 120 × 120, and up to 2100 × 2100 m. (3) Results: After evaluating 22 environmental covariates, 11 of them were identified as the most suitable candidates for predicting soil properties based on recursive feature elimination (RFE) and expert opinion methods. Furthermore, among different pixel size scenarios for SOM, BD, SS, and MWD, the highest accuracy was achieved at 1200 × 1200 m (R2 = 0.35), 180 × 180 m (R2 = 0.67), 1200 × 1200 m (R2 = 0.42), and 2100 × 2100 m (R2 = 0.34), respectively, in Marvdasht plain. (4) Conclusions: Adjusting the pixel size improves the capture of soil property variability, enhancing mapping precision and supporting effective decision making for crop management, irrigation, and land use planning.