Spaceborne stereoscopic systems have been growing in recent years, and the point cloud extracted from spaceborne stereo imagery has been used to measure forest spatial structures. These systems work on different viewing angles and image spatial resolutions, which are two critical factors determining the quality of the derived point cloud. In addition, the complex terrain is also a great challenge for the regional mapping of forest spatial structures using spaceborne stereo imagery. Although several theoretical models for simulating multi-view spectral features of forest canopies have been developed, there is hardly any report of a stereoscopic analysis using these models due to the limited size of the simulated forest scenes and the lack of a geometric sensory model (i.e., physical relationship between two-dimensional image coordinates and three-dimensional georeferenced coordinates). The stereoscopic features (i.e., parallax) are, as important as the spectral features contained in the multi-view images of a targeted area, the basis for the extraction of a point cloud. In this study, a new model, referred to as LandStereo model, has been proposed, which is capable of simulating the stereoscopic features of forest canopies over mountainous areas at landscape scales. The model comprised five parts, including defining the mountainous forest landscapes, setting the sun-senor observation geometry, simulating images, generating ground control points, and building geometric sensor models. The LandStereo model was validated over three different scenes, including flat forest landscapes, bare mountain landscapes, and mountainous forest landscapes. The results clearly demonstrated that the LandStereo model worked well on simulating stereoscopic features of both terrains and forest canopies at landscape scales. The extracted height of a forest canopy top from simulated stereo imagery was highly correlated to the truth (R2 = 0.96 and RMSE = 0.99 m) over the flat terrains and (R2 = 0.92 and RMSE = 1.15 m) over the mountainous areas. The LandStereo model provided a powerful tool to further our understanding of the relationships between forest spatial structures and point cloud extracted from stereo imagery acquired from different view angles and spatial resolutions under complex terrain conditions.