Characterizing soil moisture (SM) around drip irrigation pipes is crucial for precise and optimized farming. Machine learning (ML) approaches are particularly suitable for this task as they can reduce uncertainties caused by soil conditions and the drip pipe positions, using features extracted from relevant datasets. This letter addresses local moisture detection in the vicinity of dripping pipes using a portable microwave imaging system. The employed ML approach is fed with two dimensional images generated by two different microwave imaging techniques based on spatio-temporal measurements at various frequency bands. The study investigates the performance of K-Nearest Neighbor (KNN) and Convolutional Neural Networks (CNN) algorithms for moisture classification based on these images in three scenarios: before clutter removal, after clutter removal, and after applying imaging techniques such as back projection and the Born approximation. We also explore the potentials of CNN and KNN for moisture estimation around the plant roots and in the presence of pebbles. The results demonstrate the more accurate moisture estimation using CNN when it is applied after clutter reduction considering back projection algorithm (BPA) as the imaging technique. The results indicate that using the Back Projection technique for image formation, combined with CNN for classification, improves leak detection accuracy by approximately 20% compared to other methods.