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Automated detection of the content of images remains a challenging problem in artificial intelligence. Hence, continuous manual monitoring of restricted development zones is critical to maintaining territorial integrity and national security. In this regard, local governments of the Republic of Korea conduct four periodic inspections per year to preserve national territories from illegal encroachments and unauthorized developments in restricted zones. The considerable expense makes responding to illegal developments difficult for local governments. To address this challenge, we propose a deep-learning-based Cascade Mask region-based convolutional neural network (R-CNN) algorithm designed to perform automated detection of greenhouses in aerial photographs for efficient and continuous monitoring of restricted development zones in the Republic of Korea. Our proposed model is regional-based because it was optimized for the Republic of Korea via transfer learning and hyperparameter tuning, which improved the efficiency of the automated detection of greenhouse facilities. The experimental results demonstrated that the mAP value of the proposed Cascade Mask R-CNN model was 83.6, which was 12.83 higher than baseline mask R-CNN, and 0.9 higher than Mask R-CNN with hyperparameter tuning and transfer learning considered. Similarly, the F1-score of the proposed Cascade Mask R-CNN model was 62.07, which outperformed those of the baseline mask R-CNN and the Mask R-CNN with hyperparameter tuning and transfer learning considered (i.e., the F1-score 52.33 and 59.13, respectively). The proposed improved Cascade Mask R-CNN model is expected to facilitate efficient and continuous monitoring of restricted development zones through routine screening procedures. Moreover, this work provides a baseline for developing an integrated management system for national-scale land-use planning and development infrastructure by synergizing geographical information systems, remote sensing, and deep learning models.