When I said “slice” up the land, I meant to infer that it doesn’t necessarily need to be used as a roadway. Perhaps they could agree to divide the former cul-de-sac into pieces and each could use it as a lawn, or whatever each chooses.

Although it probably depends on roads to exist, such a cooperative property would still be adjacent to an existing road at the nearest nodal intersection. Residents probably don’t necessarily need to be mobile with an automobile within the cooperative. Perhaps, it could be developed as a large apartment complex with underground parking. But, property rights would have to be allowed such that the cul-de-sac itself does not need to stay in-tact.

You are right that it’s not as simple as just privatizing and deregulating, without re-examining property rights. Without getting into anarchist theories, government probably needs some regulatory role in land use, even in the most free-market setting. This would be necessary to prevent situations like you mention, where one person owns the land surrounding a neighbor. That situation is referred to as “forestalling”, and is considered an act of coercion, even by the staunchest proponents of property rights. At a minimum, I would imagine property rights regulations would have to stipulate that one property owner could not hamper the use of an other’s property through forestalling or other acts of coercion.

Nonetheless, I consider such discussions somewhat utopian in this day and age, but I think it’s worthwhile to liberalize what we can, and shift the dialogue in the direction towards a more free society.

This results from the fact that “land” in a urban setting is fundamentally different from land as it is historically understood. Land to our grandparents was something that one lived from in a homestead. It could be divided because it was mostly autonomous. In an urban setting, one lives from the roads, meaning we are renting land from a much larger landowner. The plot that a house sits on is not autonomous, the road that leads up to it is its sole reason to exist.

Although a cul-de-sac can be turned into a cooperative like any condominium (courtyard housing in Paris has such an organisation), it cannot be subdivided like homestead land. And anyway the cooperative would still be depending on the roads to exist, and would still have to pay rent for that right.

In an economy a enterprise has to exist at the scale of its largest indivisible good. A road is an indivisible good, and all the plots that exist from it are necessarily part of the same indivisible unit of land.

By the way, anytime I hear someone declare confidently that a truly free market would lead to a suburban driving utopia, I send them your way.

Cul-de-sacs transferred from communal ownership (the misplaced term “government”) to house owners wouldn’t be in private ownership, they would have to be in some form of cooperative ownership since they are shared between multiple homes.

It would still be private, although probably in the form of some cooperative or other collective ownership. But they could slice the land up among themselves if they wanted.

The market works well organizing some pretty complex systems incrementally through millions of private decisions, but roads are tied closely to land, which has monopolistic qualities. I have hard time imagining how the market would organize this effectively.

Land does not have monopolistic quality. It is just big, like oil or automobile companies. However there are literally thousands of cities and counties (land estates) competing with each other. The solution would be to create a market for land at the scale of cities and end the communal ownership of land.

Think if the cul-de-sac where privatized and zoning were liberalized. Maybe a developer could buy the homes and the cul-de-sac and build a new, more urban development on the assemblage.

The transportation network is a massive and complex system that would seem to need some centralized coordination.

Complexity is a reason to decentralize control, as opposed to centralize it. Complex systems of interactions are better handled in a bottom-up manner, such as with the internet. Trying to manage such a complex system centrally will result in “knowledge problems“, such as those which led to the collapse of the Soviet Union. These knowledge problems occur because central planners cannot know and understand all the subtle complexities of the system, and cannot make decisions as well as individual agents that have local knowledge of their situation.

Where a top-down public roadway system fails is in the signaling of needed resource allocation. This signaling breakdown can be seen in congestion of the commons, over-reliance on socialized services, and road overbuilding. In a publicly owned and managed system, needs are signaled by voters complaining of congestion and by lobbyists pushing certain projects, creating an unhealthy positive feedback loop. While in a private system, needs can be be signaled through pricing. Entrepreneurs pick up those signals, and supply more roads if prices indicate profit potential.

I’d argue that the private system is more versatile and nimble; adjusting to changes more quickly and efficiently in the long-run.