Recently, remote sensing satellite image analysis has received significant attention from geo-information scientists. However, the current geo-information systems lack automatic detection of several building characteristics inside the high-resolution satellite images. The accurate extraction of buildings characteristics helps the decision-makers to optimize urban planning and achieve better decisions. Furthermore, Building orientation angle is a very critical parameter in the accuracy of automated building detection algorithms. However, the traditional computer vision techniques lack accuracy, scalability, and robustness for building orientation angle detection. This paper proposes two different approaches to deep building orientation angle estimation in the high-resolution satellite image. Firstly, we propose a transfer deep learning approach for our estimation task. Secondly, we propose a novel optimized DCRN network consisting of pre-processing, scaled gradient layer, deep convolutional units, dropout layers, and regression end layer. The early proposed gradient layer helps the DCRN network to extract more helpful information and increase its performance. We have collected a building benchmark dataset that consists of building images in Riyadh city. The images used in the experiments are 15,190 buildings images. In our experiments, we have compared our proposed approaches and the other approaches in the literature. The proposed system has achieved the lowest root mean square error (RMSE) value of 1.24, the lowest mean absolute error (MAE) of 0.16, and the highest adjusted R-squared value of 0.99 using the RMS optimizer. The cost of processing time of our proposed DCRN architecture is 0.0113 ± 0.0141 s. Our proposed approach has proven its stability with the input building image contrast variation for all orientation angles. Our experimental results are promising, and it is suggested to be utilized in other building characteristics estimation tasks in high-resolution satellite images.