Accurate urban green space (UGS) measurement has become crucial for landscape analysis. This paper reviews the recent technological breakthroughs in deep learning (DL)-based semantic segmentation, emphasizing efficient landscape analysis, and integrating greenness measurements. It explores quantitative greenness measures applied through semantic segmentation, categorized into the plan view- and the perspective view-based methods, like the Land Class Classification (LCC) with green objects and the Green View Index (GVI) based on street photographs. This review navigates from traditional to modern DL-based semantic segmentation models, illuminating the evolution of the urban greenness measures and segmentation tasks for advanced landscape analysis. It also presents the typical performance metrics and explores public datasets for constructing these measures. The results show that accurate (semantic) segmentation is inevitable not only for fine-grained greenness measures but also for the qualitative evaluation of landscape analyses for planning amidst the incomplete explainability of the DL model. Also, the unsupervised domain adaptation (UDA) in aerial images is addressed to overcome the scale changes and lack of labeled data for fine-grained greenness measures. This review contributes to helping researchers understand the recent breakthroughs in DL-based segmentation technology for challenging topics in UGS research.