Yes, we can, please follow the given steps - 


1. Go to the Mass File Upload Tab and go to the "Records" section, will be displayed where you'll get the following format as shown in the image below. Choose "List Views" in Search mode under the "Records" section, and select List View accordingly in the drop-down.

2. Now, click on the Upload Files Button and upload the files that you want to upload to the selected listview.


PS: View Mass File Upload, Salesforce file upload app, on Salesforce AppExchange: https://appexchange.salesforce.com/appxListingDetail?listingId=82cf236b-1ee8-4ea7-aebf-fd0c89fb93bd