See https://drafts.css-houdini.org/css-properties-values-api/#shadow-dom
According to this, @property descriptors work on the flattened tree and don't consider shadow boundaries.
However, no implementation respects this, at least with regards to initial values. See https://css-names-in-the-shadow.glitch.me/property.html: Basically all implementations currently only respect @property declarations that come from the document scope. Perhaps the spec should be amended to reflect that?