Though they’re inconvenient for those passing through a community, cul-de-sacs are preferred by those who live on them. Guess which group homebuilders pay more attention to?

The undifferentiated gridiron layout for “additions” to cities was criticized in the early 20th century as insensitive to topography, wasteful, and ill-suited for growing auto traffic. When the Federal Housing Administration was established in 1934 to guarantee mortgages, homebuilders saw it as devoted to ensuring the success of their projects rather than as governmental interference, so were much more receptive to FHA’s underwriting criteria than to local subdivision regulations with similar aims. FHA’s 1935 technical standards suggested that streets should fit the local topography and have widths suited to their requirements (not overbuilt on the assumption that every lot might someday contain a factory or apartment house). FHA standards also promoted the “functional classification” familiar to us (arterials, collectors, local streets) that had been made necessary by the growth of auto traffic. “Best principles” publicized by homebuilder organizations Urban Land Institute and National Association of Home Builders and by planning officials of American Society of Planning Officials and the American Institute of Planners during the 1940s followed similar concepts, recommending loop and cul-de-sac layouts that followed local topography and efficiently subdivided often-irregular parcels. Cul-de-sacs branching off collector streets were promoted as the most attractive layout for single-family dwellings.

Postwar homebuilders initially turned to modified grids to relieve the “monotony” of long, straight local streets, but research in the 1950s by traffic engineers seemed to show dramatically lower accident rates for T intersections and bending streets. By the 1970s, homebuilders increasingly favored cul-de-sacs even in places where the terrain was completely flat. Residents of cul-de-sacs praise their safety and neighborliness: the street is a place where older children can safely play; one where everyone knows who “belongs” there. Developers found that houses built on cul-de-sacs sold for a premium. They also saved builders a lot of money, requiring less pavement and shorter utility runs. Naturally, that’s what they began to build more of.

From the late 1980s, planners began to note the drawbacks for pedestrians and cyclists of cul-de-sacs and the functional classification system. The movement initially known as neotraditional development (later the New Urbanism) promoted permeable networks that didn’t push all traffic onto collectors and arterials, and that allowed pedestrians and cyclists to take reasonably direct paths through neighborhoods.

While the older, tourist districts of European cities don’t have cul-de-sacs, they do have dead end lanes and courts, and new subdivisions frequently include hammerhead streets and other configurations that are functionally similar to cul-de-sacs. Development patterns in East and Southeast Asia have gone along similar lines, but with an exaggerated street hierarchy. Districts of big cities are connected by 10- or 12-lane arterials not easy for pedestrians to cross, while housing districts behind and between those boulevards may have dendritic street patterns with almost no through routes, and very narrow (2- 4-meter lanes that are shared by autos, motorbikes, and pedestrians.

Probably the best source on this subject is Michael Southworth and Eran Ben-Joseph, Streets and the Shaping of Towns and Cities, though it can be instructive to look at ASPO/AIP/APA publications for city planners, and at 20th century editions of the ULI's Community Builder’s Handbook and Residential Streets.