I’m running out of photos from Berenice Abbott’s “Changing New York” project, which is why there hasn’t been one of these in a while. Her 1938 photo above, labelled “West 18th Street, Nos. 461-463” shows two small commercial buildings with some peculiarities. They’ve been written about before, but I’m not sure that I agree with all of that analysis.
First oddity: the second floor facade of the building on the left, number 463. What is going on with the central arch? And why bricked-in arches on either side? This was not a fancy neighborhood until recently – certainly not in 1938 or in the 1800s when the buildings were constructed – and that seems like a lot of masonry design for such a small building. My pet theory, which is unproveable but also can’t be proven wrong, is that the second floor originally had three narrow arch-top windows, and at some point the two side windows were filled in and the center one expanded. The center panel, which is a 6-over-2 double-hung window, is just about the same width as the blank arches on the sides.
The next oddity comes regarding dates and sequence of construction. The Ephemeral New York blog post I linked to above says that the buildings are twin carriage houses constructed in the 1880s. Here’s a fire-insurance map from 1895, with a big blue rectangle I drew showing the buildings:

461 West 18th Street is an ordinary occupancy, brick-walled, wood-floored building (pink) with a store on the first floor and dwellings above (the open-circle dot), of the “second class” (two dots). It’s three stories high. That sounds a lot like the building on the right as it is visible in Abbott’s photo more then 40 years later, although the third floor is an attic under the gable roof. 463 West 18th Street, on the other hand, is a special occupancy, brick-walled, wood-floored building (green with a solid dot) of construction equivalent to a “first class store or dwelling” (G). One-dot special occupancy is a long list of manufacturing possibilities, all of which present a greater-than-normal fire risk, including commercial bakers, dyeing, and “manufactories of feather dusters.” The presence of a restaurant or bar would not have been enough to get the special-occupancy classification. This could have been a converted carriage house, but 15 years is a very short life from a carriage house to a small-scale factory. Also, note that there’s an areaway west of 463, separating it from the building facing Tenth Avenue. That has been filled in with a one-story extension in the 1938 photo.
Looking at the 1862 map makes things a little clearer (with some minor confusion):

The confusion is that the crosstown streets were renumbered in the 1860s so that each of the original avenues meant another hundred, measured fr0m Fifth Avenue: buildings between Ninth and Tenth Avenues would start at 400 west at Ninth and go up form there. So this map shows the older numbering system. Just follow my blue rectangle…
303 West/461 West looks exactly the same as it did in the map 33 years later. But there’s no building on the 305/463 West lot, just a couple of wood-frame (yellow) sheds. So it seems like 461 was built first. Another reason to suspect that 461 is older than the 1880s is that it has a gable roof with the ridge running parallel to the street, which is typically seen in Manhattan on pre-1850 buildings.
The last bit of evidence regarding sequence is that the front facades appear to have been built at different times. If you zoom way in, you see that the brick coursing does not line up:

One or other could be a replacement facade, but both look quite nineteenth century. Also, if you zoom in on where the one-story addition meets 463, we’ve got some rust-jacking:

My best guess – and it a guess based on the arguments above – is that 461 was built mid-1800s and was always residential above commercial occupancy, and 463 was constructed later (possibly the source of that 1880s date) as an industrial building and then later joined to the Tenth Avenue building and converted to a bar, at which time the second-floor windows were made more fancy. But I wouldn’t be amazed if some or all of that was wrong.
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