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A great many subdivisions fall into the "planned community" category where the streets curve for no reason and there are cul de sacs everywhere and you can't really get around without a map and you never meet a neighbor more than a house or two away.
I communities that have a more rectilinear grid and sidewalks it is more likely that you will walk around more and see more neighbors and the streets might actually lead to something like a train station or a downtown shopping district.
In a handful of towns the streets curve becuase there is a river or creek that flows through the area. Typically such an arrangement will also dictate specific kinds of landscape features as some plants tolerate the flooding that pretty much all rivers or subject to at least occasionally. This is all very different than the phony twisting a developer does to try and make some lots more expensive and the promises of transforming cornfield into tree lined parkways...
When it comes t gated communities you are really talking about a false kind of privacy/security. Organized burglaries happen with about the same frequency in gated communities as open, and there have been numerous incidents of gated communities having a resident suffer a violent crime. I think both of these phenomena can be traced to the nature of gated communities -- they are not tight knit at all. Literally no one knows who lives more than a house or two away. People make too big an effort to keep to themselves and no one actually tends their own yard or does a neighborly thing like wash their cars together. In condo/townhouse developments that are gated it is even more severe, and few people even attend the HOA meetings unless huge assessments are needed as things go unmaintained.
The success and demand that there has been for teardowns should be evidence enough that people will pay a high premium for a town that has an authenticity to it.
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