I searched in vein looking for old highway/road maps for my area. I couldn't find anything.Then somehow I came across a antique railroad site. That gave not only railways,roads,but also churches,old farm houses,churches and schools. It's pretty hard to find the places that match with today,But if you look at the rivers and compare that to google earth, Then you can get a basic idea.BTW it took me 3 days to get earth to launch! First I had to have chrome,then my proxy ,etc! I hope this helps! I'm going out tomorrow for my first out of my land search so wish me luck!
Ever thought of checking old Plat information at the county courthouses in your area? That may at least have building info. I know from wife's family background that on the family farm, right in the front 20 field corner was a blacksmith's shop and across the road was the store. These buildings were there up until 1970's when they came down. Those only show up on land maps of the 40's and earlier. And yea, some amatuer idiot (brother-in-law) went half*** searching with a $80 used POS wand...did find a rusty horseshoe...i went into the barn and grabbed a couple really nice mule shoes without the rust!
I found loads of maps at my state college website. Most are printable JPEGs. Some dating back to 1600s. I'd just type "historical maps of [yourstate]" into your preferred internet search engine and sift through it.