In terms of aesthetics, I'm probably with Jalyha in preferring the first one, but it's a pretty close thing. That opinion encompasses both buildings and the main road (and I think I recognise that cobblestone texture).

Also, I'm not sure the dark yellow/green lanes are working at this stage; perhaps a browner/redder/paler method would look better?

Also, if you want to make it look more crowded (as Scoopz notes) I think you should not only add buildings to the outskirts, but start squeezing more into the inner parts. You're mapping a city over time, which is a cool idea, but that means you have to accept that no city remains unchanged. Cities grow, but they also change internally, just about every generation (the only parts that tend to remain unchanged are the streets). It goes back to the thing I said earlier about the burgage cycle (and as Jalyha points out, people also upgrading their homes). I think it would be good if you started making the existing parts of the city more crowded, but if you have an in-world explanation, than, like last time, stick with that.

THW