The goal of this study was to estimate the areas under willow cultivation by farmers, as well as their growth and health status. Due to the extremely small patch size of land cover types in the study area, Sentinel-2 data were used to conduct supervised classification based on the random forest machine learning technique, and a large training dataset was produced from PlanetScope satellite imagery. The results of image classification using Google Earth Engine indicated that the Sentinel data were suitable for identifying willow-cultivated areas. It was found that these areas declined from 875.32 ha in 2017 to 288.41 ha in 2022. The analysis of the growth and health conditions of willow-cultivated plots also revealed that the temporal variations in the NDVI in these plots decreased significantly in 2022 as compared to previous years (p < 0.05). An in-depth analysis revealed a significant positive correlation between NDVI, precipitation, and temperature. It was found that the most efficient components explaining the process of browning the vegetation in the planted willow plots were the increasing temperature and decreasing precipitation. This research may be used to document the national and global monitoring efforts for climate change adaptation.