Processing single high-resolution satellite images may provide a lot of important information about the urban landscape or other applications related to the inventory of high-altitude objects. Unfortunately, the direct extraction of specific features from single satellite scenes can be difficult. However, the appropriate use of advanced processing methods based on deep learning algorithms allows us to obtain valuable information from these images. The height of buildings, for example, may be determined based on the extraction of shadows from an image and taking into account other metadata, e.g., the sun elevation angle and satellite azimuth angle. Classic methods of processing satellite imagery based on thresholding or simple segmentation are not sufficient because, in most cases, satellite scenes are not spectrally heterogenous. Therefore, the use of classical shadow detection methods is difficult. The authors of this article explore the possibility of using high-resolution optical satellite data to develop a universal algorithm for a fully automated estimation of object heights within the land cover by calculating the length of the shadow of each founded object. Finally, a set of algorithms allowing for a fully automatic detection of objects and shadows from satellite and aerial imagery and an iterative analysis of the relationships between them to calculate the heights of typical objects (such as buildings) and atypical objects (such as wind turbines) is proposed. The city of Warsaw (Poland) was used as the test area. LiDAR data were adopted as the reference measurement. As a result of final analyses based on measurements from several hundred thousand objects, the global accuracy obtained was ±4.66 m.