Tropical trees often display long distance pollen dispersal, even in highly fragmented landscapes. Understanding how patterns of spatial isolation influence gene flow and interact with background patterns of fine scale spatial genetic structure are critical for evaluating the genetic consequences of habitat fragmentation. In the endangered tropical timber tree Dysoxylum malabaricum (Meliaceae) we apply eleven microsatellite markers with paternity and parentage analysis to directly estimate contemporary gene flow across a large area (216 km2) in a highly fragmented agro-forest landscape. A comparison of genetic diversity and genetic structure in adult and juvenile life stages indicates an increase of differentiation and fine-scale spatial genetic structure (FSGS) over time. Paternity analysis and parentage analysis demonstrate high genetic connectivity across the landscape by pollen dispersal. A comparison between mother trees in forest patches with low and high densities of adult trees shows that the frequency of short distance mating increases, as does average kinship among mates in low density stands. We interpret this as an early warning sign of potentially negative genetic consequences of forest fragmentation. Single isolated trees, in contrast, frequently receive heterogeneous pollen from distances exceeding five kilometres. We discuss the processes leading to the observed patterns of gene flow and the implications of this for conservation management of D. malabaricum and tropical trees more generally.