Bees are important within terrestrial ecosystems, providing pollination, which facilitates plant reproduction. Agricultural regions are large landscapes containing varying proportions of cropland, natural, and semi-natural habitats. Most bees are not restricted to any of these and move freely throughout, exploiting food and nesting resources in favourable locations. Many factors affect bee diversity, and knowledge of these is crucial for promoting healthy bee communities. The main objectives of this study were to compare diversity and guild structure of bee communities across a range of land disturbance levels within the Annapolis Valley, Nova Scotia, Canada, in habitats ranging from managed apple orchards to old fields. The two habitat extremes differed significantly; intensely managed orchards had significantly lower species richness (∼50%) than observed/estimated in old fields, but orchards with intermediate levels of adjacent natural/semi-natural habitat showed affinities to either extreme depending on the metrics used for estimating species richness. Species assemblages in orchards had lower proportions of several guilds, particularly cavity-nesters, bumble bees, and cleptoparasites, than other habitats. These guilds accounted for over 30% of bees collected in old fields but only 3–10% in orchards, increasing with habitat complexity. The use of guilds for assessing the health of bee communities is discussed.