Urban heterogeneity, such as the variation of street layouts, building shapes, and building heights, cannot be fully represented by density parameters commonly used in idealized urban environmental analyses. To address this shortcoming and better model flow fields over complex urban neighborhoods, we propose two novel descriptive geometric parameters, alignedness and building facet entropy, which quantify the connectivity of inter‐building spaces along the prevailing wind direction and the variation of building facet orientations, respectively. We then conducted large eddy simulations over 101 urban layouts, including realistic urban configurations with uniform building height as well as idealized building arrays with variable heights, and evaluated the resulting bulk flow properties. Urban canopy flow over realistic neighborhoods resembles staggered building arrays for low urban densities but becomes similar to aligned configurations beyond λp ∼ 0.25 where the realistic flow is less sensitive to changes in density. We further show that compared to traditional density parameters (such as plan and frontal area densities), the mean alignedness, a measure of connectivity of flow paths in street canyons, better predicts canopy‐averaged flow properties. Furthermore, for realistic urban flow, the dispersive momentum flux shows a clear increasing trend with building density, and a decreasing trend with alignedness, which is in contrast with idealized cases that exhibit no clear trend. This distinct behavior further highlights the necessity of evaluating flow over realistic urban layouts for flow parameterization. This study provides an improved method of describing urban layouts for flow characterization that can be applied in neighborhood‐scale urban canopy parameterization.