Forest structure has a significant impact on the quality of habitat for various bird communities. In particular, birds that rely on forests, such as woodpeckers, are sensitive to changes in the characteristics of the forest. However, there is limited knowledge on how woodpeckers respond to these changes in forests outside protected areas, and in the highly seasonal Eastern Himalaya. To address this gap, a study was conducted in the differently managed non-protected forests of Darjeeling, Eastern Himalaya, India, spanning an elevation range of 250–2,400 m. The study aimed to identify the key forest characteristics that influence woodpecker diversity at the community and individual species levels. Data on woodpeckers were collected using point counts along transects during the pre-monsoon, monsoon, post-monsoon, and winter seasons. Habitat characteristics were assessed using 20 × 20 m quadrats at each observation point. The study recorded 1,721 individual woodpeckers belonging to 13 species from 3,456 point counts. The results indicated that the basal area and density of snags were the main factors influencing woodpecker diversity. Woodpeckers in the study area showed a significant negative relationship with the basal area, tree density, and tree diameter diversity. This suggests that woodpeckers prefer high snag density but scattered, smaller, and more uniformly sized trees in the study area. Among individual species, the Greater Yellownape Chrysophlegma flavinucha and Grey-capped Pygmy Yungipicus canicapillus Woodpeckers showed a strong preference for high snag density, while Bay Woodpeckers Blythipicus pyrrhotis were closely associated with high canopy cover and denser forests. Seasonal effects had minimal influence on woodpecker diversity in the study area. The study contradicts the typical preference of large woodpeckers for large trees and greater basal areas, despite four large-sized species making up 75% of the woodpecker community in the region. Thus, the findings highlight the importance of considering species-specific, region-specific, and management-specific habitat requirements when developing conservation strategies.