Monitoring soil water content (SWC) is vital for various applications, particularly in agriculture. This study compares SWC estimated by means of SCATSAR-SWI remote sensing (RS) at different depths (T-values) with Cosmic Ray Neutron Sensing (CRNS) across four agricultural sites in northern Italy. Additionally, it examines the spatial mismatch and representativeness of SWC products’ footprints based on different factors within the following areas: the Normalized Difference Vegetation Index (NDVI), soil properties (sand, silt, clay, Soil Organic Carbon (SOC)), and irrigation information. The results reveal that RS-derived SWC, particularly at T = 2 depth, exhibits moderate positive linear correlation (mean Pearson correlation coefficient, R = 0.6) and a mean unbiased Root–Mean–Square Difference (ubRMSD) of 14.90%SR. However, lower agreement is observed during summer and autumn, attributed to factors such as high biomass growth. Sites with less variation in vegetation and soil properties within RS pixels rank better in comparing SWC products. Although a weak correlation (mean R = 0.35) exists between median NDVI differences of footprints and disparities in SWC product performance metrics, the influence of vegetation greenness on the results is clearly identified. Additionally, RS pixels with a lower percentage of sand and SOC and silt loam soil type correlate to decreased agreement between SWC products. Finally, localized irrigation practices also partially explain some differences in the SWC products. Overall, the results highlight how RS pixel variability of the different factors can explain differences between SWC products and how this information should be considered when selecting optimal ground-based measurement locations for remote sensing comparison.