You can yes....
There are a number of proprietary software solutions that can do this for you but they do charge varying fees to use their services of course.
However, there is another way that is FREE but will take quite a bit of work on your part if you have the time available. And you will need to be able to use Microsoft Excel.
You can use the ebay File Exchange process. This is a method of uploading listings using CSV data files.
You can learn about this by reading their instructions in a PDF file.
Google search for Ebay File Exchange Advanced Instructions to locate this booklet.
With regard to images you then choose an external file hosting service (eg PhotoBucket) to host your images then put the URL link to your image files into the CSV upload file. Of course you need to separately upload all your image files to the external server first in the way you mention.
File Exchange is quite complex to figure out (and free to use) but once you do so it makes listing this way much simpler especially uploading product images.
I have developed an Excel app of my own, making extensive use of formulas and VBA code to make myself up a little File Exchange interface. But its been tailored to our own specific products so may not work for yours unless you modify it. Our products are wearable baby accessories and have lots of colour and size variations that I had to account for in the listing process. We have lots of variation and product images.
In short, you can do what you are asking about using this method but it will take some time and learning on your part.
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Further....
You can also host your own images on the same external server and then put the URL links into your description field. This involves the use of a lilttle bit of basic HTML code to set up the URL image links in the item descriptions. But you would still have to have at least one product image on the main listing in the usual way.
