Techniques are described for populating visual designs with web content. In implementations, a document design is generated via a digital media application. The document design includes a layout of repeating design elements, such as a grid or table of repeating areas each having various design elements. Web content having a structured arrangement of data elements is accessed through a data panel exposed via the application. The web content data may be linked to the document design to populate elements of the document design with “real-world” data. To do so, the web content is to detect semantically similar repeating data elements by based on element positions, node types, style types, and node hierarchies reflected by structured data defining the web content. Design elements in the layout of the document design are then auto-populated with content of the semantically similar repeating data elements to produce a preview linked to “real-world” data.