We never seriously considered buying an existing house in Chestertown. We looked at a few old homes, just for fun, but all of them had significant issues. There were a few really nice, well-maintained or restored homes for sale near the waterfront, at astronomical prices. We weren’t at all interested in a tract house, so we decided early on to find a lot to build on.
We looked at some listings to get a feel for building lot availability and prices in and near the town. We quickly learned that there are not very many unbuilt lots left in town, and good ones are expensive. We decided we needed help from a local realtor. We located a real estate agent in the area through a friend who is also an agent, and started looking at lots in Spring 2007.
He showed us one lot in the town, one close by and one farther away. We quickly rejected the last one. Initially I preferred the in-town lot. I liked the idea of being within easy walking distance of the downtown and waterfront areas. It was a typical town lot, deep and narrow, and would have needed a two-story house. It was also not in the greatest neighborhood, with a trailer park on the opposite corner and rental houses next door.
My wife liked the other lot, about a mile south of town and maybe 1/4 mile from the Chester river. It is about 1 acre and flat, with a few mature trees. It also has no on-site water and sewer, and I was hoping to avoid a well and septic tank (our current house has them). The difference in the listed prices of the two lots was not large.