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Your driveway looks fine - it is the road that looks like a mess. The cobblestone edging would look pretty good all the way up each side of the driveway and along the new cobblestone section. Some additional stone dust may help smooth the transition as well.
Is it a private road, or does the town consider it a private road? My town just had some residents of a private road petition the town to make it a public way - as that was how it was years ago - I believe it passed and now the town has to take care of it. Is there a homeowners association that collects money for plowing and road maintenance? Maybe there should be - before the road needs major repairs and not everyone is in agreement.
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