that totally depends on where you decide to get situated. e.g. it would be easier to set up such a place in a remote town in Baltics, as opposed to England due to the density of the population.
A lot of old yet comfy houses there are inherited, and quite a lot of people from that generation do not have/know their children. So waiting for them to pass and then trying to get the house. would be the most cost effective option. Not to sound heartless, of course. I knew at least 2 elderly women who had the lifestyle I wanted, even though they were not well off. Therefore, as long as you plan on taking care of the property and respecting it, said dream could come true.
At least that's what I've observed.
As for work, they all had chickens and at least one cow, so the lifestyle was semi self sustainable and they traded some of their vegetables,berries, jam etc. for other things, as well as just living in a frugal manner. + pension. I suppose one could manage to work from home, or land a comfy librarian/shop worker job.
I also knew a family who built their own house in the middle of the woods. They were old fashioned, but happy. The mother was a wedding seamstress and the father a pilot (I think). I rarely saw them, but they seemed smart and supportive of their daughter (my friend that hosted a lot of sleepovers that involved just the two of us. Super comfy and I miss being 8 lol)
Remember, this is coming from someone who's still in education(over 18, though) and has only observed random people throughout my life.
I'll update you if I manage to find a place similar to my description and then tell you my master plan.