So here is the rather important system information needed for someone to help and want to make it easier for those to answer my question, so here:

Intel Core 2 Duo 2.33 GHZ (Will upgrade possibly)
PCI-E X16 Slot unsure if it is 1.0, 2.0, or 3.0
1000W PSU
2.00 GB of RAM (Will be upgrading to 4 GB, 6 GBm or 8 GB)
Windows Ultimate SP 1

I am looking to buy a new GPU and have an available PCI-Express Slot so what can you recommend me at this point, the price Im trying to keep to the maximum $300 or less.

I understand my system is kind of old but Ive been upgrading it over the years and its kept somewhat current if this decision to buy a new GPU falls through Iam going to save up to build one on my own i was just wondering if I can get a new GPU slap it in there and play skyrim at somewhat decent settings.

Which GPU do you have now?
Also, the most important thing you can do for faster fps in Skyrim is a CPU upgrade.

Before any discussion of GPUs, not only is an identification of the current one appropriate, but so is an ID and age number for the power supply.

The problem with upgrading CPUs is that often you can not upgrade just your CPU. You probably need to upgrade your motherboard and ram too.

In theory, you could upgrade just the CPU. But only to another CPU that fits into your current motherboard. Is it a "socket 775" motherboard ? You could put in another 775 CPU, the fastest you can find.
http://www.cpu-world.com/Sockets/Socket%20775%20%28LGA775%29.html
For a 2-core CPU that would be a E8600 (3.3GHz).
For a 4-core CPU that would be a Core 2 Q9k-something.

The problem there is that even though those processors are a few years old, the prices for new CPUs have not dropped a lot since then. The E8600 is not for sale since January 2012 anymore. But even then, the last known price was ~250 euros ! Even a brand new i5-3570K is cheaper. The 4-core Q9000 chips seem not available either. And their last prices were over 200 euros too.

If you can score a second hand CPU, for a sweet price, that might be acceptable. But even then, your CPU will go up 25%-30% in performance at most. Not good, when compared to the latest generations of CPUs (Sandy Bridge and Ivy Bridge). It might be worth it for 50 euros/dollars. But if you have to pay 200+ euros/dollars, than I'd certainly consider buying a new CPU+mobo+ram.

That being said, I think your system can take a faster videocard. A gtx560ti might be a good choice. Your CPU might bottleneck it a little bit. But if you care more for eyecandy (let your GPU work hard), then the CPU won't be much of a bottleneck. I am running a gtx680 with a E8500 myself. (I have just ordered a i5-3570K this afternoon myself !).

So a gtx560ti might be good. ~ 200 euros/dollars. Or if you wanna spend a bit more, get one of the latest AMD videocards, e.g. the 7850 for 220-240 euros/dollars. Or a faster/more expensive 7000 series videocard. Note, with those, the risk will be even bigger that your CPU will hamper your videocard. (I also kinda remember somewhere that AMD cards require a faster CPU than nVidia cards do, to get the max performance out of the card. Not sure if that is still true today).

The CPU could bottleneck the new GPU, probably should get an idea on what is the fastest card your CPU can handle and just drop maybe $150 on a card, or maybe $100 on craigs or ebay. Otherwise you could put all $300 in a card and then upgrade the CPU later.