A mild cam, intake and carb on a 440 will make 400 hp without any issues. Without a stroker kit or aftermarket cylinder heads, the jump to 500 hp is going to require porting the factory heads and probably more camshaft and a looser converter than most people would want in a C-body. You trade off street manners for horsepower if you use mostly factory parts without the stroker kit.
One of the old school 500 hp combos is a 440, 10:1 compression, ported 906 or 452 heads, a single plane intake like a Holley Street Dominator, an 850 cfm carb, 1 7/8" headers, and the .509 hydraulic camshaft. You could put a slightly smaller camshaft in it because the .509 requires 3000+ stall to be effective.
If I wanted to build a relative cheap low compression 440 to make the power you're after, I'd buy a set of higher compression pistons (like Speed Pro L2235F) and change the rod and main bearings and use a set of plain fast iron rings. Use 320 grit sandpaper to knock the glaze of the cylinder walls so the rings will seal quickly. You're looking at about $800 and you have basically a new short block. Then with the stock heads, a Holley Street Dominator intake and the camshaft linked below from Hughes Engines, you'll easily make 450+ HP.
Pistons:
CHRYSLER Sealed Power L2355F Speed-Pro Forged Pistons | Summit Racing
Camshaft:
https://www.hughesengines.com/Index...RmxhdCBUYXBwZXQsIEh5ZHJhdWxpYw==&partid=30252
can I still achieve that with the factory hp rods and pistons ?