The colonization of artificial structures by benthic organisms in the marine realm is known to be affected by the general trophic patterns of the biogeographical zone and the prevailing environmental traits at the local scale. The present work aims to present quantitative data on the early settlement progress of macrofaunal benthic assemblages developing on artificial reefs (ARs) deployed at the Underwater Biotechnological Park of Crete (UBPC) in the oligotrophic Eastern Mediterranean. Visual census and subsequent image analysis combined with scraped quadrats were used to describe the establishment of the communities and their development over three consecutive campaigns, spanning 5 years post-deployment. Macroalgae consistently dominated in terms of coverage, while sessile invertebrates displayed different patterns over the years. Polychaeta and Bryozoa were gradually replaced by Cnidaria, while Porifera and Mollusca displayed an increasing trend over the years. Motile benthos was mainly represented by Mollusca, while the abundance of Polychaeta increased in contrast to that of Crustacea. For both sessile and motile assemblages, significant differences were observed among the years. The results of this study indicate that ecological succession is still ongoing, and further improvement in the monitoring methodology can assist towards a more accurate assessment of the community composition in complex AR structures.