It's nice that you have such a big front yard that you can choose between both options. I think both would work. However, if you put in the circular drive will you have to get rid of one or more of your trees? If that was the case, I personally would put the parking pad nestled between the trees and add a pretty curving walk to the front door.

Could you walk over some distance left of the driveway and take a picture looking back at the house/yard that shows the grade change? And also include a picture of the front yard taken from the street. These all can be slightly overlapping shots while pivoting the camera so you can get wide views.

I think your situation would be best addressed by a comprehensive plan that incorporates parking and landscaping. The long entry walk doesn't seem to serve a purpose as the street doesn't seem wide enough to allow for on-street parking.

I realize your driveway is much longer, but this might spark an idea. This is a recently reconfigured walkway, and newly-poured guest-parking pad. The original walkway that led from the street straight up to the front door was removed, and no trees had to be pulled.

Obviously all I have to go off is the aerial so take it for what it is, but if the grades work out my first instinct would be to tuck a parking pad in between the two trees I see alongside the driveway, and connect that to the front door with a walk. Ignoring the cost factor, a circular drive is a LOT of pavement in the front yard and totally changes the character of the home. I'm not typically a fan. This is the sort of project where a local landscape designer can be a huge help.

Thank you all so much for your suggestions! I tried taking some pictures last night for those who asked for some additional angles. My husband and I have different opinions, so I'm hoping that this feed will help when it comes time to make the decision. Thanks again!!

My vote is for parking pad off the driveway, incorporated into the landscaping. Here are a couple pics I found of a house in our neighborhood that show what I'm talking about. The pics aren't the best, but it looks really, really good in person. This one fits 2 cars.

Neither picture shows the grade involved. We don't need a picture OF the left side, but taken FROM it. In other words, you'd need to walk over toward the left neighbor's house and take a picture looking back at your house ... from enough distance away that it shows the complete bottom and top of the grade and a bit more.

A "heads up" ... depending on your municipality, the vast majority of them do not allow parking, or parking places, in the front yard, while most allow a circular driveway and don't prevent parking in it. Exceptions to straight-up parking might be if the proposed location is behind a building set-back line. If not, usually, a variance (which requires an application, a fee and hearing) is required. (Attorney's, or other professional, fees might be required if you don't feel like you could make a good case speaking on your own behalf at a hearing.) Whether the variance is granted depends on the personalities involved. In a small town where everyone knows everyone and there is not jubilation for imposing regulation, it might be easy. In a large community, there might be a lot of resistance as bureaucrats can be paranoid to death about creating a "precedence" and opening the floodgates for similar requests, Even if there is resistance, in my experience the variance will likely be granted if need is demonstrated (as I think it could be here on account of the grade change) and if the proposed improvement is attractive. They can say all they want that objections are based on safety, but the truth is that they don't want things built that look bad for the next 30 years.

As Rev pointed out, it will cost a lot more for a circular driveway simply on account of the amount of material involved. IMO, if the configuration is well done and the details are nice, it can be a great addition to the home. A main consideration would be if you want to be able to drive to the lower level from the circular drive. This would likely require some reconfiguration of the existing drive. A parking pad off to the side of the drive would be less involved. (But how the grade changes needs to be shown so that the area can be understood.)

I agree with with what Revolutionary Gardens said. I would also add that a circular driveway might require a driveway permit from the DOT. Depending on where you live that may, or may not, be challenging and will likely cost $. Personally, I'd rather put the $ for a permit into the cost of the improvements. How wide is your existing driveway? Do you even need an additional parking space, or will rerouting the sidewalk be enough? If I were visiting someone with a long driveway, I would park near the sidewalk entrance. If guest were to park in your existing driveway, can someone drive past them? You might find just a new landscaping plan rerouting the sidewalk to the driveway, might be all you need. I wouldn't necessarily remove the existing sidewalk. I'd want a sidewalk leading to the street and the driveway.

It's unlikely DOT would be involved at all on a residential city street. The municipality would likely be the controlling body. The drive is not wide enough that a car could park on it and allow another to pass it on their way to the garage.

I would also consider what you want to see out your living room windows when you have company. I'd prefer a plan in which the view out the rooms in the living area aren't just cars.

It's unlikely DOT would be involved at all on a residential city street. The municipality would likely be the controlling body.

What? Someone, whether it is a local County/City DOT, State DOT, or the neighborhood HOA, maintains the roads. That same someone will want to grant or deny permission for a driveway entrance. The complexity of the process can vary greatly depending on geographic location. This can involve anything from a good-ole boy, "yeah, sure, go ahead" to a formal permitting process with engineered drawings to prove you have adequate sight distance and aren't creating drainage or other problems.

I will try to post a better picture of the grade later this afternoon. And again, thank you everyone so far for your input!!

Similar to what I described above, this is what we did for a client with a long driveway who wanted a dedicated guest parking area. Unless you're planning for regular, large parties it's not like you need a ton of real estate to make it work.