A timely and comprehensive understanding of winter wheat maturity is crucial for deploying large-scale harvesters within a region, ensuring timely winter wheat harvesting, and maintaining grain quality. Winter wheat maturity prediction is limited by two key issues: accurate extraction of wheat planting areas and effective maturity prediction methods. The primary aim of this study is to propose a method for predicting winter wheat maturity. The method comprises three parts: (i) winter wheat planting area extraction via phenological characteristics across multiple growth stages; (ii) extraction of winter wheat maturity features via vegetation indices (VIs, such as NDVI, NDRE, NDII1, and NDII2) and box plot analysis; and (iii) winter wheat maturity data prediction via the selected VIs. The key findings of this work are as follows: (i) Combining multispectral remote sensing data from the winter wheat jointing-filling and maturity-harvest stages can provide high-precision extraction of winter wheat planting areas (OA = 95.67%, PA = 91.67%, UA = 99.64%, and Kappa = 0.9133). (ii) The proposed method can offer the highest accuracy in predicting maturity at the winter wheat flowering stage (R2 = 0.802, RMSE = 1.56 days), aiding in a timely and comprehensive understanding of winter wheat maturity and in deploying large-scale harvesters within the region. (iii) The study’s validation was only conducted for winter wheat maturity prediction in the North China Plain wheat production area, and the accuracy of harvesting progress information extraction for other regions’ wheat still requires further testing. The method proposed in this study can provide accurate predictions of winter wheat maturity, helping agricultural management departments adopt information-based measures to improve the efficiency of monitoring winter wheat maturation and harvesting, thus promoting the efficiency of precision agricultural operations and informatization efforts.