The 4,500 resident city of North Oaks, MN has demanded that Google remove StreetView imagery of their town. However, they’re not a typical town, in that all of their roads are owned by the residents (meaning they’re private) and the city enforces a trespassing ordinanace.
While it’s certainly unique, since no other city has made a similar request, it seems that they’re well within their rights to request that, since the roads are private.
It makes me wonder if other cities (with public roads) will request this. It would be interesting to see what happens with those.