This paper is concerned with the structure and dynamics of modern retail facilities in Israel. It presents the first comprehensive quantitative study of the recent trends in Israeli retail. On the basis of an unique database that includes sizes and locations of retailers for a number of years, we test and challenge some of the traditional theories, as well as the latest approaches to the analysis of urban systems. Recent approaches view cities as selforganizing systems and utilize complexity theory and concepts of order. In the case of Israeli retail application of alternate methods of analysis suggests that the conventional regularities such as rank-size rule, as is implied by the central place theory or the more general power law do not hold. The findings reveal that the sizes of modern retailers display an exponential distribution, consistent across time and scale. This signifies a presence of stable regularity in the structure of retail sizes. Exponential distribution of the retail sizes is shown to reflect a lack of interdependence between the existing and the planned retail facilities. The issue of order versus randomness and self-organization in the size distribution of retailers remains debatable and requires further development of tools and universal criteria for analyzing complex systems.