Accurate and timely crop areas monitoring and yield modeling are of great significance for food security and sustainability of agro-ecosystems. This study provides a rapid and robust method for planted area monitoring and yield modeling of winter wheat based on Moderate Resolution Imaging Spectroradiometer (MODIS) data from 2001 to 2016 in the Huang-Huai-Hai Plain of China. Statistical data at the prefecture level are used for accuracy assessment of MODIS-derived winter wheat planted area and yield. The results show that the overall accuracy of estimated winter wheat planted area is 96.5% from 2001 to 2016. Besides, the winter wheat planted area presents an increasing trend in the Huang-Huai-Hai Plain, especially from 2009 to 2013. In terms of yield modeling, the coefficients of determination (R²) between the estimated yield and statistical data are all higher than 0.86, and the relative errors (RE) are <5%. The models can accurately estimate yield, with adequate NDVI data, before the harvesting dates. The rapid and robust method has the potential to be applied to winter wheat planted area monitoring and yield modeling in other regions.