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I have these photos I inherited from my father of a building near a water feature that was taken around June 1958 in the New York City area, in a roll of film that is right before some photos of West Point. I tried searching Google Images with a bunch of terms in various combinations and was unsuccessful. The terms I tried included:

  • Botanical Gardens
  • New York
  • Building
  • Historical
  • White
  • Hudson River
  • West Point

There is a building that probably can be used to identify the location:

enter image description here

The next photo shows the same building in the background behind the tree and has a water feature with statue of a human figure, that from prior picture's vantage point appears to be raised above the surrounding area by several feet:

enter image description here

Ideas on how to better search for a building by its appearance?

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FWIW, the Hudson Valley is full of historic mansions with landscaped grounds — many of them white — so your search terms should mention things that are unique about this one (e.g. "white" is unlikely to help, but "Gothic windows" might), and notable (e.g. "Cupid statue" is unlikely to help [even if it were a Cupid, which I guess it's not, ha]).

I just spent... I don't know, probably an hour... down this rabbit hole. Here's my liveblog of how I went about it. I didn't find your location (sorry!), but your question was actually about how one might approach the search, so in that sense, this is a good answer to the question you asked. ;)

The most notable things about the building in the photo are:

  • Gothic windows
  • that stepped roofline
  • that square tower on the left

The first two features are shared with Washington Irving's Sunnyside; the Wikipedia article tells me that the name for the stepped roofline is stepped gable or corbie gable. It's also known as a Dutch gable, which is just more confirmation that we're looking at the Hudson Valley.

At this point I started Google-Image-searching for "stepped gable" mansion and grounds "west point", "dutch gable" mansion and grounds "west point", "corbie" mansion and grounds "west point", gable tower gothic hudson,...

The problem, of course, is that the results for "show me a mansion with a stepped gable and a tower" are overwhelmingly polluted with the stepped-gable-and-tower-having Sunnyside. But we don't want to add -sunnyside to the search because we don't want to exclude a useful page that just happens to say "Notice how the tower and gable on [the mansion we care about] resembles Washington Irving's Sunnyside..."

I ended up on a page for Hudson Valley Ruins, organized by county, which suggested to me that I should find out what county West Point is in: Orange (again with the Dutch!). This is a vague term, but the biggest town in Orange County seems to be Newburgh, so I tried "stepped gable" tower newburgh. This turned up "On the Origins of the American Porch" (2005), which had lots of photos — none of the building we're looking for — and suggested the additional terms parapet or crenellation (on the tower: a distinguishing feature compared to Sunnyside's Spanish-style tower) and enclosed porch. Unfortunately all of those terms are also used for regular single-family houses, so I brought back mansion: now we're somewhere like gable tower parapet mansion "new york", which is too generic.

With dutch "square tower" historic mansion hudson "new york" I found another JSTOR article: "Castles on the Hudson" (1979). As before: lots of photos of other mansions, no luck on yours.

Suppose it was torn down? mansion destroyed 1960s hudson new york, mansion destroyed 1970s hudson new york, etc. Still no luck.

It's possible that the mansion and grounds were open to the public circa 1958 but are no longer public; maybe there's a good way to search for "mansion house tourist attractions in New York circa 1958," but I'm starting to burn out. Tourist attractions might issue postcards: mansion postcard Hudson Valley New York 1950s? The house might be on the Register of Historic Places (but with that ugly enclosed porch I'm not hopeful; and also it'd have to still exist).

Anyway, if you ever find out, maybe you'll come back and update this post with your answer. :)

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