Demands for three-dimensional GIS modeling are increasing rapidly with the new evolving and supporting technologies for various applications. It is charting the new trend/direction for our Geo-Spatial community. Threedimensional modeling is the true Simulation of Reality, especially if it is relatively accurate. On the other hand, using 3D modeling in GIS environment offers a flexible interactive system for providing the best visual interpretation, planning and decision making process. The built 3D models are becoming one of the most efficient technologies for spatial data management and analysis. The objective of this work is to elaborate on the demand and usefulness of three-dimensional modeling, and also, explore the capabilities of current technologies via several pilot projects. Through this, one can discuss the corresponding required production workflow for building three-dimensional GIS Model of a complex site of interest using Digital Photogrammetry techniques, other techniques and GIS modeling. Several case studies are presented: first for a university campus; second for city modeling; and for the country level; and finally for cadastral application. Another important aspect one should consider in 3D modeling is to add true texture to your model to provide better prospective and clearer view of the required scenario. This is very important, especially for decision maker and valuators who are not familiar with geo-informatics analysis. Presentations of two procedures followed are briefed.