Both because of the good preservation of the historical city center and its particular geography, the town of Oudenaarde, in the south of Flanders (Belgium), offers valuable insights into the use of stone, brick and wood in the medieval and early modern era. The location of Oudenaarde on a navigable waterway (the river Scheldt), the proximity of stone quarries as well as the presence of alluvial clay suitable for making building ceramics enabled a marked resurgence of stone construction, followed in the second half of the 13th century by the sudden appearance of brick, in religious, public and private architecture. Nevertheless, houses in half-timbered construction continued to be built into the 17th century, thus bearing witness to the centuries-long coexistence of stone, brick and wood. The case of Oudenaarde, which to this day is characterized by a wooded hinterland, shows that the increased use of stone and brick in the late Middle Ages does not solely stem from a presumed local shortage of timber. This contribution intends to shed light on the reasons for the use of either stone, brick or wood within the confined space of the city of Oudenaarde. Material-economical, constructive and architectural motivations will be discussed, as well as aspects of medieval urban planning.