Birdsong can play a critical role in establishing a territory and finding a mate among individuals from local and foreign populations. Variation in birdsong among populations can be influenced by habitat fragmentation and might affect successful dispersal among habitat fragments. We studied variation in great tit song in a long-term study population distributed over nine forest fragments. All individual males recorded had a known dispersal history within the fragmented forest habitat. We found spatial structure of declining song-type sharing with distance, with a marked drop from an individual’s own forest fragment to another across a habitat gap. We also found decreasing song similarity among increasingly distant fragments in terms of temporal and spectral characteristics of shared song types. The change in acoustic structure was more gradual and seemed less affected by habitat discontinuity but also showed a tight correlation with dispersal index among forest fragments. Immigrant birds shared fewer song types with neighbouring birds that were born within the same forest fragment, but not less compared to birds born in another forest fragment within the study area. Our data provide detailed insight into the relationship between song differentiation and male dispersal and contribute to our understanding of the potential role of song in reproductive exchange and avian speciation. The fact that birds in small forest fragments shared more songs than birds in larger forest fragments confirms that song analysis has potential as a tool for conservation in rare species.