In this book, we argue that different ground plan types have distinct influence on the fundamental three-dimensional characteristics of building fabrics. Each ground plan type in New York expresses the relation of today’s city with a particular physical site and reflects its past existence over different historical periods, from the Lenape and Dutch, to the British and American. Furthermore, each ground plan type constitutes the fundamental structure for the present and future development of main features of the urban landscape. The reading of New York’s ground plan reveals that differences in building arrangements and street systems are more pronounced than those in plot patterns. This is evident if we compare Manhattan and Staten Island. While most of Manhattan is characterized by a high coincidence of building and plot frontages along streets and a highly connected street system, most of Staten Island displays low coincidence of frontages and weaker connectivity. At the core of these differences is density—but not density in a broad, vague sense often used in urban studies and planning. The book focuses on the density of 4-ways nodes, street blocks and plots, and coincident frontages. We claim that it is through this specific density and its variation that a wide range of urban landscapes has been and can continue to be created. Furthermore, this density variation provides a means to address the most significant physical weaknesses of each urban landscape.