Can you? Of course you can. Is it worth it? That’s something only you can answer.

We really would like a two-car garage and my goal is to save 30-40 thousand for this project. Is it more financially feasible to build a 2 car garage in front of this structure and then convert the existing garage and breezeway into addtional living space?

You can do anything if you have enough money.

1. Is it currently wide enough for your purposes? If it’s not, you’d have to completely remove the garage on the right and rebuild.

2. Is that a raised concrete base in the breezeway? If so, its removal and replacement with grade level concrete is going to cost an added amount.

Only you know if the $$ amount is worth it to you. Why do you want/need to extra garage?

That is raised concrete, which is one of the reasons it adds difficulty to the project. We really need the extra space of a 2 car garage, not only to park an additional car in there, but for extra storage for my wife as she is into woodworking.

So, actually, you need a four car garage! (my husband is into woodworking- amazing how much space those tools take up). Honestly, it's probably worth having some contractors come out and give you their ideas plus spit ball on the costs of various options. It may make more sense to tear the whole thing down and replace with a new garage. It might make sense to put a garage in front. It might make sense to push it into the backyard as a tandem garage.

Since it’s raised concrete, and your wife wants woodworking room, I suggest a ‘start over.’ Tear the whole thing off and build what you want. Easier in the long run and maybe you could expand the footprint, either to the right or forward toward the driveway or both.

Have you considered a factory-built garage? I have a family member who went that route, saving tons of money in the process. It was built by an Amish outfit in Eastern PA. They matched the siding, roof pitch, to his main house. It was really a fascinating project to watch (from afar, that is). You’d never be able to tell that it wasn’t site-built.

How big is your lot? Do you have enough room to build the garage perpendicular to the existing garage with the garage doors being basically where your garbage carts are located in your photo?

I'm with @littlebug zone 5 Missouri, tear the whole thing off and start over. Extend the concrete driveway to the right too. Starting over also allows you to easily add all the electrical, lighting/windows, dust extraction and possibly add depth. Looks like you would probably need 1 double door rather than 2 singles.

Garages are cheap, and it would be a really nice feature when selling.

Perfect, thanks for the advice guys!

I wouldn't bother enclosing the breezeway, the roof looks to have been bastardized a lot and is an excuse waiting to happen. Garage infill too much trouble. You are willing to go $30-40K, you could probably demo and do a basic detached 2 car for $20-$30K*.

*in a non-gouging price era