TTM-
The counterpoint is my folks did it. there was lots of back and forth with planners, but they were able to significantly extend a grade II listed cottage and are now beyond happy with their house. It's doable.
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Grade II or II*? As there are differences. We're in a town with an incredible number of listed buildings (and I wanted to buy one! but we didn't move fast enough)*. Lots of people still manage to do interesting things to them, but as others have mentioned it's a bit more involved.
Someone up the road is looking to do a bit of reconfiguring and the planning proposal includes quite detailed historical records and arguments as to the what and the why, but it has been approved. The plus side is there are a lot of trades here that make their living working on historic buildings, so even if the permissions end up being quite restrictive it isn't as challenging as you would expect to jump through the hoops. Just a bit spendy.
* the new owner of this property has planning in for a loft conversion and some heavily glazed ground floor rearranging which has received general support although some of the window positioning and style has got the conservation officer's back up a bit. There is a neighbouring property that's got a load of glass and been done quite sensitively though so they'll likely get away with it after a bit of to and fro.
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owl
6pt
Have you looked at the entry in the list for the property? Is it in a conservation area as well? That would give a better indication of what might be allowed.