Can I get at 53' into my driveway

If you have a long hood truck my guess would be a big no to being able to get in or out of that drive. Now you might be able to with a short wheelbase daycab but would take some time backing and pulling forward.

Iam able to back in and back out of my drive off of a 16' rd with a ditch on each side but my drive is on the higher side of 50' wide.

 

id say try it...

 

Just watch the overhang of your trailer.

Make your wheel base shorter, slide your tandems up.

 

After looking at your photos....

The 16 feet road is to narrow, your tractor is going to drop off on the other side of the road.

However, you might be able to blind side it, by hugging the mail box and angling in and hugging the tree as close as you can.

It may take several attempts to get it right.

Shorten up that wheel base as much as possible.

YOU will have to watch the height of your trailer.

YOU will have to be extremely careful.

 

You may have to straddle the culvert. It will be close.When your steer tire drops off its possible to get stuck

 

I say it is doable. This assumes you can use every bit of the driveway pictured (looks like it splits) as well as a little bit of the ditch for your steers.

The only issue is the culvert.

Try to picture yourself siting in your truck, in the driveway with a 53, and sitting as far to the right as you can get. Now ask yourself if you can make a left turn out onto the road. If yes, then obviously you should be able to back it in as well.

 

is there a culvert on the other side? or is that just grass and leaves?

i think it can be done...

pull way up and on the far left of the main road and turn the wheel to the right just a tad enough to get the trailer moving then turn the wheel back straight to keep the tractor from moving but the trailer will cont. to go into the hole...
this is probley going to take a few shots, but after a few times yourll be good!