Thanks it’s kind of hard to remember all the nuances of all the tags.
There is definitely no physical access control on any of the relevant roads, but access was already set to private and there is an abundance of private property signs so I was hesitant to change it. But maybe there’s a case for at least switching the main road to access=yes since according to Mass GIS data (if I’m looking at it right), the main road Stiles Pond Road isn’t included in any of the parcels.
Another potential issue is that one of the roads (the right fork at the bottom of the screenshot) appears to go right through one of the property parcels, so I’m not sure what to make of that as far as access goes, especially since I’m pretty sure you need that section to get to a bunch of the properties.
I did however change the main road to highway=residential, since I think it’s a stretch to call it a driveway since it services all the houses like a neighborhood road would. I think there’s a stronger case for pipestem if highway=service + service=* is wanted.
Edit: Access=destination actually sounds like it would make the most sense from what I know about the place. Either for the whole place or using access=yes for the main road and access=destination for any segment that’s shared by multiple property owners.