What are the Odds?

The odds of a tree located on the edge of a woodlot falling away from the woods and into the road are better than 80%, even if the  direction of fall is into the prevailing winds.  That is because branches will have more sunlight available away from the woods, so they will grow into the open area above the road.  That weights the tree toward the road.

If you own a woodlot with trees along the road, don't risk it.  Cut them down.  You are liable for the danger posed by dead trees and can be sued if they fall and harm someone.