Depending on the device, you can go to the device list, right-click on a book and use "Add to library" (or something like that). If the device and book format supports it, this will do what you want. But, I have no idea if it will work for a Nook, or the purchased books on a Nook. And I have no idea what happens if the book has DRM.
And the restrictions for this are based on the comments they others have made. The book must be somewhere calibre can access. They must be a format that calibre can handle. The information about the book must be accessible and usable by calibre. And DRM has to be handled in some way.
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