This paper addresses the problem of prediction of probability of successful radio communication of any mobile or stationary subscriber located in areas of service such as complex urban environments characterized by nonline-of-sight propagation conditions, which limit GPS, Low Earth Orbit, and Medium Earth Orbit services in land-satellite communications. It presents a self-consistent physical-statistical approach for predicting fading phenomena usually occurring in land-satellite communication links caused by influence of the terrain features on radio signal propagation from the ground-based to the satellite antenna. This approach combines (1) the statistical description of the buildings array located on the rough terrain and the buildings' overlay profile, based on special probabilistic distributions of built-up terrain parameters, and (2) the theoretical description of propagation phenomena, taking into account multiple scattering, reflection, and diffraction mechanisms. A new technique is proposed for predicting the probability of fading phenomena occurring in land-satellite links using the so-called stochastic multiparametric model. Results of theoretical predictions are compared with those obtained from the “pure statistical” Lutz model and physical-statistical Saunders-Evans model, and then with experimental data obtained for different European cities. Obtained results show that the proposed stochastic approach can be used as a good predictor of fading phenomena in land-satellite communication links for different satellite constellation scenarios and elevations of satellites during their movement surrounding the Earth, with respect to the ground-based antenna for different land environments: rural, mixed residential, suburban, and urban.