The development of a contemporary townscape within the historical urban structures is a phenomenon of this period that has been going on in Lithuania for about 20 years. This is an ongoing process with an uncertain outcome, as the rapidly changing urban design trends require quick responses to current needs. It is necessary to modify, revise, and supplement the concepts and existing legislation accordingly. This article examines the factors leading to the emergence and formation of the modern townscape in Vilnius, as well as the documents governing the city’s development after gaining independence. It presents an evaluation of the newly established urban structures in the central part of Vilnius and identifies the challenges and problems in shaping the contemporary townscape. The results of the study allow us to identify what actions must be taken in order to form a high-quality modern townscape, starting with self-evaluation of what has been done and ending with the creation of a dynamic urban model that would respond to constantly changing needs.