dFactory

<p><a href="http://www.dfactory.co/products/download-attachments/" rel="nofollow ugc">Download Attachments</a> is a new approach to managing downloads in WordPress. Instead of bloated interface it enables simple, drag & drop and AJAX driven metabox where you can insert and manage your Media Library files and automatically or manually display them after, before or inside posts content.</p>
<p>For more information, check out plugin page at <a href="http://www.dfactory.co/" rel="nofollow ugc">dFactory</a> site.</p>
<h4>Features include:</h4>
<ul>
<li>Automatic or manual download links display</li>
<li>Select post types where Download Attachments should be used</li>
<li>Select list, table or sortable, dynamic table display style</li>
<li>Downloads count</li>
<li>Advanced attachments sorting</li>
<li>Most Downloaded Attachments widget</li>
<li>Drag & drop files ordering</li>
<li>Based on Media Library attachments</li>
<li>Easy customisation of Frontend & Backend display</li>
<li>Pretty URLs for download links</li>
<li>Encrypt URLs by default</li>
<li>Customizable tamplates engine</li>
<li>Custom download slug</li>
<li>Custom permission for metabox display</li>
<li>Option to exclude selected attachments from display</li>
<li>Option to select from all Media Library files or only those attached to a post</li>
<li>2 shortcodes</li>
<li>5 functions and multiple filter hooks for developers</li>
<li>Option to use attachment caption and/or description for download links description</li>
<li>Compatible with WPML & Polylang</li>
<li>.pot file for translations included</li>
</ul>
<h4>Get involved</h4>
<p>Feel free to contribute to the source code on the <a href="https://github.com/dfactoryplugins" rel="nofollow ugc">dFactory GitHub Repository</a>.</p>


Download Attachments

Download Attachments is a new approach to managing downloads in WordPress. It allows you to easily add and display download links in any post or page.

Turker YILDIRIM

<p><strong>Be careful when using this plugin.</strong></p>
<p>Sometimes you may need to update files, like product or property photos, without deleting old one before uploading new one. In such cases you can use this plugin to replace old files with new ones.</p>
<p>OverWrite It makes a filename search in <code>wp-content\uploads</code> folder recursively and replaces first matching file with the uploading one.</p>
<p>Keep in mind there is no excluded files, folders or file types so <strong>double check everything before uploading anything</strong> while the plugin is active.</p>
<h3>Languages</h3>
<p>Please consider helping translations at the <a href="https://translate.wordpress.org/projects/wp-plugins/overwrite-it" rel="nofollow ugc">GlotPress project</a>.</p>


OverWrite It

I have been searching for similar plugin, some of them didn't work for me but this one does. Thanks

It works

When you upload files, OverWrite It jumps into the scene to replace old file with uploading one.

Download Attachments vs OverWrite It