Research Highlights: Modelling species’ distribution and productivity is key to support integrated landscape planning, species’ afforestation, and sustainable forest management. Background and Objectives: Maritime pine (Pinus pinaster Aiton) forests in Portugal were lately affected by wildfires and measures to overcome this situation are needed. The aims of this study were: (1) to model species’ spatial distribution and productivity using a machine learning (ML) regression approach to produce current species’ distribution and productivity maps; (2) to model the species’ spatial productivity using a stochastic sequential simulation approach to produce the species’ current productivity map; (3) to produce the species’ potential distribution map, by using a ML classification approach to define species’ ecological envelope thresholds; and (4) to identify present and future key factors for the species’ afforestation and management. Materials and Methods: Spatial land cover/land use data, inventory, and environmental data (climate, topography, and soil) were used in a coupled ML regression and stochastic sequential simulation approaches to model species’ current and potential distributions and productivity. Results: Maritime pine spatial distribution modelling by the ML approach provided 69% fitting efficiency, while species productivity modelling achieved only 43%. The species’ potential area covered 60% of the country’s area, where 78% of the species’ forest inventory plots (1995) were found. The change in the Maritime pine stands’ age structure observed in the last decades is causing the species’ recovery by natural regeneration to be at risk. Conclusions: The maps produced allow for best site identification for species afforestation, wood production regulation support, landscape planning considering species’ diversity, and fire hazard mitigation. These maps were obtained by modelling using environmental covariates, such as climate attributes, so their projection in future climate change scenarios can be performed.