It might be easy and cheap, or it might be very expensive and just about impossible.
You might have a problem with zoning or other property regulations. In my area, the smallest parcel that they will allow building on is 10 acres, so an owner would not want to leave himself with less than that size of remaining property, because it would not be worth nearly as much as if it could be a building site.
You might be shocked at how much taxes might go up for both the seller and buyer. Years ago, my Dad's next door neighbor about 300 feet away, built a new barn without doing a survey first. My Dad thought the barn was awfully close to the property line, and told his neighbor. But the neighbor built the barn there anyway. When my Dad had the property surveyed a couple of years later, it was determined that the barn was over 1/3 on our land. My Dad, being a nice guy, agreed to sell a strip of land to the neighbor so the barn would all be on his land for $1000 and all of the transfer fees. It only amounted to a little over 1 acre, but then the assessor decided that both properties were worth a whole lot more than they had been before. My Dad's taxes doubled the next year, and both he and the neighbor ended up having to hire attorneys to get the mess straightened out and doing that took more than 2 more years. It would have been cheaper to have GIVEN the neighbor the strip of property.
And the current owner might not want to sell the land at virtually any price, or might not want to subdivide the property, at least like you would like him to. And there is no way that I know of that you could make him do so.
I think if I wanted to buy some of my neighbor's undeveloped property, I would begin by getting to know that neighbor to gain a "feel" for how he thinks of his land and maybe what he is planning to do over the next number of years. At some point, I might let him know that I would like to increase the size of my property, somehow, and maybe he might offer to sell you some land. It could be that the guy is thinking about retiring and is wondering about what to do with his property. Or he could be planning to just live there until he dies...and would not consider doing anything different than he always has. Tact and diplomacy can go a long way. And sometimes, the only thing that will work is the long green.
It might help to have some idea of how much similar property has sold for recently in your area. In my area, land is worth several times it was 10 years ago, and about 10 times what it was when I bought it 30 years ago. I really don't want to sell my land, but if someone came along and offered me $20K/acre, I would sure have to think hard about selling my extra property.
Good luck! Having some privacy is sure nice. As it is, no one can build any closer than they now are, because I own all the land around my building site. But it comes at a price--my property taxes are high!
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