Scenarios
The main benefit you would get from using language that is compiled to machine code is that you can do lots of byte and bit-magic. Lets say, modifying image data, transforming audio, analysing indices of a genomic sequence database.
Typical tasks
Serving web-pages you typically have problems if a completely different sort: You will be loading a resource from hard disk, serve them directly if its an image or audio, or you will be executing different transformation steps on a text resource until it becomes the final HTML document. The latter will be using template engines, database queries, and so on.
If you look at that you can see that most of the things, say 90-99% are pretty high-level stuff -- in Python you will use an API that is optimized by many, many users for optimal performance (meaning: time and space). "Open a file" will be almost as fast in C as it is in Python, so is reading from it and serving it to some Socket. Transforming text data could be a bit faster in C++ then it is in Python, but... how fast does it have to be? A use is very likely willing to wait 200ms, isnt't he? And that is a lot of time for a nice high-level template engine to transform a bit of text.
What C++ and Python can do for you
A typical Python web-service is much faster to write and a easier to deploy then a server written in C++. If you would do it in C++ you firstly need to handle sockets and connections -- and for those would either use an existing library or write your own handling. If you use an existing library (which I strongly recommend) you are basically not doing anything differently then Python does. If you write your own handling, you have many, many low-level things you can do wrong that will burn the performance you wish for. No, that is not an option.
If you need speed, and Python and the server and template framework is not enough you should re-think your architectural approach. Then take a look at the c10k-problem and write tiny pieces in C. (Look at this c10k very hot topic, too) But I can not see many reasons not to use a high-level language like Python, if you are only looking for performance in a medium-complex web-serving application.
Summary: The difference
If you are just serving files from the hard-drive I guess your Python program would even be faster then your hand-crafted C++-server. If you use a framework written in C or C++ and just drop in your static pages, I guess you get a boost like 2-5fold against Python. Then again, if your web-application is a bit more complex then serving static content, I estimate that the difference will diminish very quickly and you will get 1-2fold speed gain at most.
It's not all about speed...
One note about another difference between C++ and Python one should not forget: Since C++ is really compiled and not as dynamic as Python you would gain a lot of static error analysis by using Python. Writing correct code is always difficult, but can be done in C++ and Python with good tests and static analysis -- the latter is simpler in C++ (my opinion). If that is an issue for you, you may think again, but you asked about speed.