Dont know if this is the same thing but when you asked for a tool that fills in a line with a selection of houses then it brought to mind paint shop pro's image pipes. I just did a check for Gimp and it has similar too:

https://www.gimp.org/tutorials/Image_Pipes/

I recall I made a similar feature for my mapping app but mine would only take the one current icon you were holding and randomly size and rotate copies and you moved it. Mine was done more for trees, bushes etc rather than houses. But with a pipe you had a selection of icons lined up and it would drop them in. So maybe that would be useful to try out.