Charleston is an interesting example to use for historic neighborhoods, because it shares geographic similarities with Manhattan - mainly being landlocked around the peninsula. Since it can’t build out and historic preservation prevents a lot of tall structures. A notable challenge to the city’s restrictions was Sergeant Jasper and the Bennett hotel which fought the Board of Architectural Review and Charleston’s historical preservation approach. The peninsula now sees properties selling for over $1,000/SF because of this scarcity.
Ideally you have a high degree of consistent development/activation in an urban area. When you mention “a bit farther” out of town, you start to require more transit which paves the way for sprawl.