My guess:

"shep hestor."

Probably an amalgamation of

• dutch sheop (sheep).

and

• hayrester (hairester/hayste, a hair-cloth maker, or one who makes garments from livestock hair).

or, less convincing

• haester (from the French kitchen worker who turns the spit (or haste) over the fire, a hasteur).

So Sheophester Rd. is named after s family whose occupation was as shepards, either turning them into clothing or eating them...probably both.

Go see the sheppy we'd say, if we were cold or hungry. Like the time I caught the ferry over to Shelbyville. I needed a new heel for my shoe, so, I decided to go to Morganville, which is what they call Shelbyville in those days, so I tied an onion to my belt, which was the style at the time. So, to take the ferry cost a nickel, and in those days, nickels had pictures of bumblebees on ‘em. Give me five bees for a quarter you’d say. Now where were we? Oh yeah! The important thing was I had an onion on my belt, which was the style at the time. They didn’t have white onions, because of the war. The only thing you could get was those big yellow ones.

Could check land records in the town by name search. Probably turn up a few with the name, could be some around to ask. It's common enough too, maybe search YouTube for someone with that name, maybe they will say it. That would be convincing. Not sure how important this answer is to you. Thanks for sticking this out to the end.