I've found definitive dates for the Howard Gilman (1894 - 1979) of South Stratford, Vermont, who made these and stamped each one on the underside, but that's about it. I sure appreciate the love and labor and detail he put into these small wooden structures, though, which include a varied series of houses--all with chimneys and most with log piles arranged in one configuration or another--as well as a church, a covered bridge, a barn with silo, and a mill. Earnestly sweet but not at all saccharine, I might guess these date to the 1940s or so and were carved of pine, which has acquired a warm dry wood patina. Maybe a sort of Christmas village or maybe made for a model train set, I'm not sure, but good now displayed all sorts of ways.
11 structures in total, all in good shape, with minor losses or repairs here and there, no real matter. For reference, the church measures 3.5” long x 2” wide x 5” tall. Sold as a set.