Accurate surface soil moisture (SM) data are crucial for agricultural management in Jiangsu Province, one of the major agricultural regions in China. However, the seasonal performance of different SM products in Jiangsu is still unknown. To address this, this study aims to evaluate the applicability of four L-band microwave remotely sensed SM products, namely, the Soil Moisture Active Passive Single-Channel Algorithm at Vertical Polarization Level 3 (SMAP SCA-V L3, hereafter SMAP-L3), SMOS-SMAP-INRAE-BORDEAUX (SMOSMAP-IB), Soil Moisture and Ocean Salinity in version IC (SMOS-IC), and SMAP-INRAE-BORDEAUX (SMAP-IB) in Jiangsu at the seasonal scale. In addition, the effects of dynamic environmental variables such as the leaf vegetation index (LAI), mean surface soil temperature (MSST), and mean surface soil wetness (MSSM) on the performance of the above products are investigated. The results indicate that all four SM products exhibit significant seasonal differences when evaluated against in situ observations between 2016 and 2022, with most products achieving their highest correlation (R) and unbiased root-mean-square difference (ubRMSD) scores during the autumn. Conversely, their performance significantly deteriorates in the summer, with ubRMSD values exceeding 0.06 m3/m3. SMOS-IC generally achieves better R values across all seasons but has limited temporal availability, while SMAP-IB typically has the lowest ubRMSD values, even reaching 0.03 m3/m3 during morning observation in the winter. Additionally, the sensitivity of different products’ skill metrics to environmental factors varies across seasons. For ubRMSD, SMAP-L3 shows a general increase with LAI across all four seasons, while SMAP-IB exhibits a notable increase as the soil becomes wetter in the summer. Conversely, wet conditions notably reduce the R values during autumn for most products. These findings are expected to offer valuable insights for the appropriate selection of products and the enhancement of SM retrieval algorithms.