In recent decades, climate change has significantly influenced the frequency and intensity of wildfires across Mediterranean pine forests. The loss of forest cover can bring long-term ecological changes that impact the overall biodiversity and alter species composition. Understanding the long-term impact of wildfires requires effective and cost-efficient methods for monitoring the postfire ecosystem dynamics. Passive acoustic monitoring (PAM) has been increasingly used to monitor the biodiversity of vocal species at large spatial and temporal scales. Using acoustic indices, where the biodiversity of an area is inferred from the overall structure of the soundscape, rather than the more labor-intensive identification of individual species, has yielded mixed results, emphasizing the importance of testing their efficacy at the regional level. In this study, we examined whether widely used acoustic indicators were effective at capturing changes in the avifauna diversity in Pinus halepensis forest stands with different fire burning histories (burnt in 2001, 2009, and 2018 and unburnt for >20 years) on the Sithonia Peninsula, Greece. We recorded the soundscape of each stand using two–three sensors across 11 days of each season from March 2022 to January 2023. We calculated for each site and season the following five acoustic indices: the Acoustic Complexity Index (ACI), Acoustic Diversity Index (ADI), Acoustic Evenness Index (AEI), Normalized Difference Soundscape Index (NDSI), and Bioacoustic Index (BI). Each acoustic index was then assessed in terms of its efficacy at predicting the local avifauna diversity, as estimated via two proxies—the species richness (SR) and the Shannon Diversity Index (SDI) of vocal bird calls. Both the SR and SDI were calculated by having an expert review the species identification of calls detected within the same acoustic dataset by the BirdNET convolutional neural network algorithm. A total of 53 bird species were identified. Our analysis shows that the BI and NDSI have the highest potential for monitoring the postfire biodiversity dynamics in Mediterranean pine forests. We propose the development of regional-scale acoustic observatories at pine and other fire-prone Mediterranean habitats, which will further improve our understanding of how to make the best use of acoustic indices as a tool for rapid biodiversity assessments.