A Web Service is the "right" way if you want them to communicate directly. However, I've found it easier in some situations to coordinate via database records. For example, my web app has bulk email capability. To make it work, the web app just leaves a database record behind specifying the email to be sent. The WinApp scans periodically for these records and, when it finds one with an "unprocessed" status, it takes the appropriate action. This works like a charm for me in a very high volume environment.
You cannot quite do this in the other direction only because web apps don't generally sit around in a timing loop (there are ways around this but they aren't worth the effort). Thus, you'll require some type of initiating action to let the web app know when to reload the file. To do this, you could use the following code to do a GET on a page:
WebRequest wrContent = WebRequest.Create("http://www.yourUrl.com/yourpage.aspx");
Stream objStream = wrContent.GetResponse().GetResponseStream();
// I don't think you'll need the stream Reader but I include it for completeness
StreamReader objStreamReader = new StreamReader(objStream);
You'll then reload the file in the PageLoad method whenever this page is opened.