"A bad workman always blames his tools" is a known proverb, however, a cool tool is still better than a lame one. To avoid being the proverbial "bad worksman", here's a list of awesome web dev utilities (for Windows) that you can add to your toolbox!
Filezilla is a great, full featured FTP client (and optionally, server). The split pane interface makes it easy to drag and drop local files to your server.
Time Management: Rainlendar
If you find yourself needing to manage your tasks a bit better, Rainlendar is a great and lightweight desktop calendar that has support for events and tasks, allowing you to create due dates for projects, track their progress, and offer you a peek of what's to come with a simple glance or click.
Image Optimization: PNGGauntlet
The majority of your images should be in PNG, which offers great compression most of the time but why not run them through a compressor to make sure you are saving every last KB? PNGGauntlet will let you drag in any number of PNGs and run them through some algorithms to pack those PNGs as tightly as possible, without any sort of distortion or image data loss.
Ever worked on a page, only to realize you accidentally deleted something in it and need to revert back? Or how about trying to sync folders between desktop and laptop to work on the same project on both machines when needed? Dropbox can handle all of this and more. Once installed, you manage it just like any other folder, except this folder is synced to the cloud, readily accessible to you or any other machine you are logged into, with automatic syncing between everything and an incredibly handy 1 month history of all the previously saved versions of your files.
Folder Management: Q-Dir
If you find yourself with a ton of Explorer windows open just to organize your files, may I suggest Q-Dir? It has support for up to 4 different panes, laid out in numerous formats (horizontal panes, vertical, or grid) each one able to contain its own group of tabs. 1 window, and as many folders as you want, Q-Dir will definitely help keep the window count down as you are able to do drag and drop anything and everything within this one app!