Urban solutions in Vilnius were mostly of a practical rather than aestethical character. After World War II architects of urban design, whose activity used to change substantly historically settled cities, became more active. In Lithuania the conception of heritage developed gradually lagging behind dominating European tendencies; therefore, Vilnius city has been strongly influenced by individual creative works. The most obvious materialized conception of that kind is the idea of “architectural hills“. Currently this conception is widely criticized, and at the same time new restraints protecting the old town are set. These restraints often contradict the development of the city, which is inevitable bearing in mind the status of Vilnius city (the capital) and the size of administrated territory. Due to objective reasons political decisions and the activity of energetic private investors have a strong influence on the development of the city. In the chain an investor–administrator–professional there exists uneven proportion of participation thus spoiling the final result. The paper presents the main contradiction between the city development and heritage supporters and ways of solving it.