Land Use Land Cover (LULC) segmentation is a famous application of remote sensing in an urban environment. Up-to-date and complete data are of major importance in this field. Although with some success, pixel-based segmentation remains challenging because of class variability. Due to the increasing popularity of crowd-sourcing projects, like OpenStreetMap, the need for user-generated content has also increased, providing a new prospect for LULC segmentation. We propose a deep-learning approach to segment objects in high-resolution imagery by using semantic crowdsource information. Due to satellite imagery and crowdsource database complexity, deep learning frameworks perform a significant role. This integration reduces computation and labor costs. Our methods are based on a fully convolutional neural network (CNN) that has been adapted for multi-source data processing. We discuss the use of data augmentation techniques and improvements to the training pipeline. We applied semantic (U-Net) and instance segmentation (Mask R-CNN) methods and, Mask R–CNN showed a significantly higher segmentation accuracy from both qualitative and quantitative viewpoints. The conducted methods reach 91% and 96% overall accuracy in building segmentation and 90% in road segmentation, demonstrating OSM and remote sensing complementarity and potential for city sensing applications.