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I know... many here think the OP is overreacting as to the grade. Looks like a normal northeast US driveway to me (and mine is a lot steeper!).
I don't know how you miss that when looking at the house...
What a beautiful house! If it were me, I wouldn't change a thing. Steep? Not to me. Just a slight incline. Part of the beauty of the home is that it slopes upward from the street, like sitting on a perch. Lovely.
The carport is also part of the charm of the house. Look at the arched front faschia on it.
However, since you want to do that, what I've seen (and what your neighbors have done) is:
Remove the attached carport. Build a new one set back at back of the lot...IF there's room to make the garage/carport wide enough for two cars.
You can leave the new garage facing toward the road, or sideways behind the house. Whichever gets you the room to make it for two cars.
I will say this, though, for when you go to sell:
1. Removing an attached garage may devalue your home;
2. Taking up a small yard (if the yard is small) to put a structure with concrete on it may also devalue the home; LAND is in demand. There are few nice homes with decent sized yards. That adds value, even if you think it's more valuable with a big garage in the back. It's not, to many people. I would buy right now an awesome old house IF they had left the garage where it was. But the demolished the small garage that used to face the street at the end of the driveway (it was unattached to house), and they built a nice, new two-car garage behind the house, pouring new concrete for it, of course. The result is almost no yard, with concrete and structures covering most of the lot.
Whatever way there is to leave as much land exposed as possible, is the way to go, IMO. Garages facing the street seem to take up less of the lot space, it seems to me.
As for the sidewalk in front, it is CHARMING. I would leave it, if possible. The house wouldn't look as lovely w/o it. If you have to move it, it would be expensive. Besides, I wouldn't pour cement for parking right smack in front of the house, near the sidewalk, anyway. That would NOT look good and would definitely devalue your home.
Whatever you do, I don't see a way around both cars sharing the one-car driveway, which doesn't seem much of a problem, anyway. That's the way it is with old houses. Unless you just wreck the house and put concrete everywhere, which would be a big mistake, IMO. It would look tacky.
You're overthinking this. The solution is easy and cheap if you park 1 car in the garage and 1 car next to the house.
1) spray the side of the house with roundup
2) line your parking spot with landscape fabric
3) lay a brick edging along the perimeter of your new parking spot
4) cover with gravel
Pictures can be deceiving. It looks like a 8' rise over 2 car lengths, and that doesn't even take into consideration the flat area you need right before the garage entrance. Sounds pretty steep to me. Take a picture of your own driveway and post it up. I bet it will look a lot less steep when you look at it in a picture compared to when you stand on it in person.
You're overthinking this. The solution is easy and cheap....
Except that he will be parking RIGHT next to his neighbor's house.
OP, you need to live with this driveway for a little while before you make any major decisions. An architect is expensive, but this is not the kind of thing you want to do half-*ss. Besides the setback questions, there are MANY grading, drainage, and design issues to consider.
At minimum I would get a landscape architect to help navigate the city permitting process and design.
Here in our historic district we have lots of adorable homes like yours, OP, with very narrow driveways and one car garages or carports. Narrow lots as well.
Now what I'm about to propose is not cheap but it's what a lot of folks do around here, since nearly everyone has two cars. I think this has been mentioned already but I'll reiterate.
Keep your single car driveway. Open the garage and make it a drive through carport. Take the driveway out into the backyard. Build a double garage or carport back there with room for one or the other vehicles to back out without having to move the other vehicle.
Some folks around here go ahead and build a garage apartment above the new garage and then either rent it out or put an office or guest room/apt up there.
1) The overall front look of the house is distinctive so you shouldn't do things that will adversely affect that.
2) Just converting the existing garage to a porte-cochere will do nothing to help the steep grade problem. You would have to scoop out a bunch of dirt, so you could lower the height of the driveway where it goes past the house (in other words, the existing height of the garage floor has to come down significantly). The proposed driveway through the proposed porte-cochere would pass within a few inches of the house. If you don't lower it below where the current garage floor is, you won't have done anything to improve the steep grade problem. BUT! When you start digging dirt out from right next to the house, deep enough to make a difference to the slope of the driveway, you will now be affecting the stability of the house's foundation! And, you may need to build a retaining wall all along the driveway where you have dug out to lower it and reduce the grade. Probably you have to build a retaining wall along both sides of the driveway.
3) Depending on the geography where you are, you may have giant rocks just under the surface just where you would have to excavate to reduce the grade of the drive where it passes the house.
4) If you want to put a two car detached garage in the back yard, you have to allow plenty of room for the driveway to flare out. My family has owned a house just like this for over 40 years (one car wide driveway with no way to make it wider where it passes the house, and two car garage in the back yard). It is tricky to get the car on the unaligned side of the garage out because of the S curve you have to make while backing out. You may or may not have enough depth in the lot to put the garage far enough back that you can get that car out without a lot of back and forth.
5) There's nothing wrong with that tree. Leave it alone. Trees along the street add a tremendous amount to the feel of a neighborhood.
6) So, my recommendation would be to come over to the right of the sidewalk that leads to the front door, and pave a pad from the street up into the yard, flat, and big enough for two cars side by side. There will probably need to be some excavation here to get it flat, but it's not next to anything sensitive like the foundation of the house. This parking pad will not affect the street view of your house as much as the other alternatives. If you live in an old neighborhood where there are lots of houses on small narrow lots with one car garages or no garages, you will probably see lots of houses where this has been done, thus you should be able to get approval. Here in New England where there are lots of houses in situations similar to yours, and where you often aren't allowed to park on the street due to snow plowing, the separate parking pad is quite common.
7) I would not use gravel under any circumstances whatsoever. It is not possible to keep it where you want it and you will be picking it up with the lawnmower and flinging it, plus damaging your mower blades, forever. And if you ever decide to eliminate the pad or change it, it's damn near impossible to get rid of the gravel, as you have to pick it up one by one. My parents were enamoured of "rock garden" landscaping and I have been picking up those damn white rocks for 40 years.
1) Your house is a very pretty house so you shouldn't do weird things that damage its appearance.
2) Below grade garages are in my opinion a bad idea because that sloping driveway will fill up with water and flood your garage. You can have all kinds of drains, but sooner or later something's going to go wrong and you will end up with a garage full of water. If it's connected to a basement, you'll get water in there too. I definitely would not recommend it.
I really don't think you'll be able to go to the left of the driveway due to setback provisions. So to the right looks like the only real option. Make it a flat parking pad with a retaining wall and railing separating it from the driveway. Add a set off stairs. That should make it easier to get in and out of your car. The next time, make a two car garage a nonnegotiable requirement.
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