I should also add we do plan to work with an architect, but it will be a while before we can begin that process. I would like to have an idea of what is possible so I can weed through my ideas in the meantime.

Since you own the adjacent lot, have you thought about combining the two to easier deal with all of the setback issues and building requirements? A house dealing with all of the many requirements that the lot will have will be an expensive proposition. It might be far more financially sensible to do a teardown of the existing property on the adjacent lot and then just create one larger more conventional home structure on the combined lots.

Or what about approaching the church for an easement to access the garage through the rear of your lot rather than having a drive along side the home? They may not be willing to do that, but if you can put it forward as a security benefit to them to have unpredictable traffic in and out of the space and that you are keeping an eye out for them, they might consider it. Of course, financial incentive to do so always is a good persuader as well.

If none of that isn't possible, then are you allowed to have the drive right on the property line or is there a setback for that as well? If (as I suspect) the 8' setback applies to all sides of the property, then you don't have enough room for a side load garage. Even if you can put the drive right on the line, you barely have room for a side load garage. 24x24 is a bit small if you plan on having two full sized trucks/cars and the typical storage flotsam that goes into garages. Creating a "tunnel" between a fence and your house isn't that inviting of a look, but it does bring up the idea of just creating a "drive through" to the courtyard space for the drive with the second floor home space above it so that you aren't so severely limited in width for the home. TOH did that on a build in one of their local Boston neighborhoods, but that was a long time ago and I can't remember the exact episodes that involved that. I do remember that it involved a historic district and a bunch of prune faced control freaks unhappy about the TV coverage of their meeting.

For your fence issues, I've had clients that have gotten around the "fence zoning" regulations by creating a galvanized "plant trellis" support (NOT using the wire fencing material, but instead grids of galvanized metal) instead of a fence and covering it with various climbing vines and roses. You would need at least a 3' bed for the plant matter, and the "trellis" would need to be at least 1' inside your property line for adequate maintenance.

For research, you might look at the layouts of shotgun houses or double shotgun houses or row houses. Those where the original "urban infill" homes and they deal with long and narrow in some creative ways.

Thanks for your thoughts Hollysprings.

We did look into renovating/adding on to our current house. The house is 85 years old and it would be nearly as much to renovate it (including the price we paid for the house and lot) as it would be to build a new house. We have been doing a lot of work on this house and anticipate we can sell it for nearly the price we paid for the lot and house together (minus the cost of the renovations we did).

We really want a full, finished basement, high ceilings and we don't want to deal with the quirks of an older house, even a renovated one. If we tried to tear this house down, the ARB would come after us with pitchforks. It really is a lovely house, but it just isn't the house for us. Even with all the restrictions, we feel incredibly lucky to have the opportunity to build from scratch in such a great location.

Back to your suggestions, I am almost certain we can get a variance if we need one to put the driveway right on the property line, but I think ground level improvements are permitted anyway. We could also put an easement on the driveway of this house and have a shared driveway or put ours right next to that one if we really wanted to, but the location of that garage means we would lose a good amount of courtyard space so we could back out (I have actually tried this with my car by driving in my yard). I am reluctant to try to share and I loathe backing out onto the street. I can live with it if necessary, but I really don't want to do that for the rest of my life. Right now, my husband parks in the parking lot anyway because our cars won't fit in the 20x20 garage. I could reverse the L, but we can't put a privacy fence between our house and our neighbors. We could have a 4', 50% open wood fence, but even that might be a fight with the city. I am not much for maintaining a lot of plants, though I am hoping to put garden beds along the 8' setback on the south side of the house. We currently have a 4' hedge acting like a fence on the parking lot side and it is a pain to maintain.

I am nearly certain the ARB would not approve any building over the driveway, but we could have a car port there if we really wanted one. I am pretty sure we can fit three bedrooms over the front if it is 26x36. That is as much space as we have for all our bedrooms now and it is more than enough for our two girls, a small guest room and one bath.

I have also thought about putting a gate in the back of the fence. The challenge will be that the church has some kind of agreement with the city that makes the parking lot public during non-church hours, so it won't just be up to the church. We have kicked around the idea of putting an motorized gate and asking the church just to move one parking block so we can go in and out if there isn't a car parked there. We will probably have a gate back there in any case because it will make unloading furniture much easier than dragging it through the front entry of the house.

I doodled a few more plans today and I keep coming back to the 1st floor master as the cause of our layout problem. I guess we are going to have to decide if we are really committed to being on the first floor. It is funny, we have almost everything we need now in an 1800 sq ft house but when we add an extra 700 sq ft, I can't get everything to fit!