I've asked a somewhat similar question elsewhere. Much of this depends on which laptop/OS (Macs will have optical out, make sure Vista drivers are solid if using that, etc.) Also I don't know if you're requesting a headphone setup too? On the DAC and speaker front you can do everything from suggested Goodwill to watch Audiogon and eBay for vintage equipment. Two approaches I contemplated (both eliminating a separate amp) ...
A) NuForce Icon DAC/amp ($250) and vintage speakers
B) vintage DAC and Audioengine A2 active monitors ($200)
For my solution I'm leaning towards the latter (nearly all my DACs are vintage), but both should get you near your budget. I don't know the current status of E-mu Vista drivers (don't use Windows), but if you want to keep it new...
C) E-mu 0404 USB ($200) and Audioengine A2s ($200)
... should get you a very nice sounding system (said by someone who's never heard the A2s, so ask around. Stereophile though was
impressed).
Finally, another all new option would be ...
D) M-Audio USB Transit or similar cheap DAC ($100) and the Swan M200 MKIII active speakers ($300)
... but I'd probably find that distribution much too weighted away from your source, so would likely consider the other options first.