What I'm asking is how hard would this be? Maybe thinking of race car or something along those lines.

 

Depends on your skills. Anything is possible. Why go backwards ? Get a late model 5.7/6.1 Hemi for a swap if needed..

 

My reason is that I have my hands on a 440 internally balanced. And it's easy to pick up a wrecked charger and just rebuild it or make it into a circle track car. My main question is if there is enough room under the hood and if the front end would hold a motor that size.

 

It's been done with an early 426 Hemi, so it should fit a 440.

Google the engine external dimensions and that should assure you!