Connectivity and affluence provide communities on small islands with opportunities and challenges. Both factors drive the expansion of material stocks which in turn determines future waste generation. For islands with limited waste treatment options an effective waste management strategy is inevitable. For the Greek island of Samothraki, construction and demolition waste (CDW) represents a new phenomenon. The advent of tourism, EU funding, labor migration and the construction of a new port in the 1960s led to an expansion of the built environment unprecedented on the island. As a consequence, new types and expanding quantities of CDW put the island community increasingly in the need for action. The European Waste Framework Directive, reinforced in 2018 with the Circular Economy Package, demands from EU member states at least 70% recycling and recovery rate of CDW until 2020. In this study, a mixed methods approach enabled the integration of data from official statistics, field surveys and interviews into a dynamic stock-driven model for different infrastructure and buildings types on Samothraki from 1971 to 2016. Our results show that the material stock expanded from 175 t/cap to 350 t/cap in the given period, leading to a 15-fold increase of annual CDW generation. With a recycling rate of only 14%, the island is currently far away from meeting the recycling and recovery targets of the EU-WFD. This study provides a systematic and dynamic analysis for developing policy and management options on reducing, re-using and recycling of CDW on islands where waste treatment options are limited.