Aboveground biomass (AGB) is an important indicator for characterizing crop growth conditions. A rapid and accurate estimation of AGB is critical for guiding the management of farmland and achieving production potential, and it can also provide vital data for ensuring food security. In this study, by applying different water and nitrogen treatments, an unmanned aerial vehicle (UAV) equipped with a multispectral imaging spectrometer was used to acquire images of winter wheat during critical growth stages. Then, the plant height (Hdsm) extracted from the digital surface model (DSM) information was used to establish and improve the estimation model of AGB, using the backpropagation (BP) neural network, a machine learning method. The results show that (1) the R2, root-mean-square error (RMSE), and relative predictive deviation (RPD) of the AGB estimation model, constructed directly using the Hdsm, are 0.58, 4528.23 kg/hm2, and 1.25, respectively. The estimated mean AGB (16,198.27 kg/hm2) is slightly smaller than the measured mean AGB (16,960.23 kg/hm2). (2) The R2, RMSE, and RPD of the improved AGB estimation model, based on AGB/Hdsm, are 0.88, 2291.90 kg/hm2, and 2.75, respectively, and the estimated mean AGB (17,478.21 kg/hm2) is more similar to the measured mean AGB (17,222.59 kg/hm2). The improved AGB estimation model boosts the accuracy by 51.72% compared with the AGB directly estimated using the Hdsm. Moreover, the improved AGB estimation model shows strong transferability in regard to different water treatments and different year scenarios, but there are differences in the transferability for different N-level scenarios. (3) Differences in the characteristics of the data are the key factors that lead to the different transferability of the AGB estimation model. This study provides an antecedent in regard to model construction and transferability estimation of AGB for winter wheat. We confirm that, when different datasets have similar histogram characteristics, the model is applicable to new scenarios.