Five experiments performed in a desktop virtual-reality setting investigated the influence of environmental features—that is, noticeable landmarks along the route—on distance estimation. Landmarks were of two types: Either they simply “filled” the route or they “filled” and also segmented it, thereby inducing a hierarchical structuring of the route. Previous research had left the question open of whether a filling or a segmenting feature leads to an overestimation of a distance along the route. Our experiments showed different results dependent on the kind of space: If an environment was learned from a route perspective, filling and segmenting environmental features led to overestimations of distances, while the segmenting of a route induced by a grouping of similar features did not. If the environment was learned from a map that afforded a survey perspective, route structuring induced through a segmenting feature or by phenomenal grouping led to an overestimation of distances, whereas features that merely filled the route did not.