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Wuddles' PlanetX Cuberite server had something like this since a long time. I don't know what plugin he used though
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I don't think he used a plugin for it.
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This could be divided into several separate areas. First, a plugin is needed that converts the world block data into the map bitmap files. Then another addition would be all the overlays, such as protected areas, warps etc. And completely separate is the HTML/JS/AJAX rendering engine and live update. Perhaps most of the web engine could be reused from the Bukkit's plugin, only changing the "backend" to match Cuberite. This would be an awesome project, but very large. We'd need someone who's really good with web technologies to make this work.
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I'm working at a Company making web and mobile games. I know a lot about web technologies
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The difference is that Minecraft Overviewer doesn't update live. Dynmap actually renders changes done on the map live, and shows player locations, etc.
If you're indeed going to take his web engine, then you should probably ask the original developers permission.
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On the client side, we could use a websocket for pushing live updates