It appears that the " closed in" section was most likely an open front porch. The windows are out of sync as is the pitch of the roof on the left section. I would start by removing that large bush so that you can get a good look at the side of the house.

I would work with an architect before doing any changes. The interior is going to be impacted by the exterior changes.

I would really try to bring a porch back.

The side view-- The front door would be on the far right, or entry under the covered porch? (nice place, by the way!) It comes down to function over form. Drive, parking, kitchen, ease of access and use. It also depends on which direction your home faces and where your location may be. Considering the staining on the siding, my guess is lower door pix is North? Which ever way you choose, it looks like decking is in order. Just be sure to marry the roof lines, the long pitch across the front and followed to the side door, if that is to be the entry. If the budget is open, I would do cedar siding and rock the brick chimney chase & a large deck. good luck!

I’ve flipped redone a few of these hodgepodge added on homes. The addition u call front entrance should be demolished. The old front porch open backup with a center front door and window on each side the coordinate with the 2 on second floor. Then hardboard siding and stone or brick veneer the cinderblocks. Then u have a farmhouse curb appeal. Then you start reworking and restoring the inside.

Lovely home! Unlike some I really like the different roof lines!

With new front entry you mean the door with the two windows next to it? Would look great with a covered porch, perhaps a deck along the side.

When replacing the siding and windows, some windows could be enlarged, to let in more light and soften the look on the outside.

Add some brick facings on the bottom blocks, to go with the chimney.

How is the layout of the plot (street, etc). And could you post a floorplan?

You can always put a ladder up to the porch roof and use your second story entry. Kidding. Looks like a big job. Agree that the driveway and parking determines what door ends up being the front or main entry.

There are two ways of improving an old farmhouse like this: rip off everything that was added onto the original structure and start over with practical rooms that are actually well thought out, or put together a long term plan of how to mitigate what what you can and how to live with the rest. Our farmhouse was built in 1906 and in a perfect world, we'd rip off the kitchen and the upstairs and downstairs bathrooms and start over. Since we're not going to spend 3/4 the value of the home on 3 rooms, we're prioritizing (with the help of a great carpenter/gc) and chipping away at it.

I think you need more help than we can offer get at least a designer and better yet an architect to figure out exactly what is doable with your budget.I agree with 1840 that this is a true farmhouse and you need to decide what you want from it. There are 1000s of answers but you need a pro.Do the house first and then worry about landscaping.

I HAVE A PLAN! Check out my drawing:

Before and After!

Create an Asymmetrical Roof over porch so the original roof line isn't changed (which would be very difficult). Raise roof over porch (right side) to match the upper roof: use metal roofing. Create porch and add windows on both sides of door. Raise interior floor so it is consistent from the East side of house to the West. NO stairs INSIDE, only OUTSIDE on the porch. Add metal casing outside of windows to make the windows pop! All new siding, All new metal roof.

I dunno about that asymmetrical roof--makes it look like someone tilted their head as they drew it... Especially on a farmhouse, kinda odd.

I think your ideas are good but you need to have a budget and what you want to do will require $$$$ I really do think you need some pro help from the start.

My husband is a pro, he is a general contractor. I am trying to come up with a plan for us to build ourselves.

Just a note, if you live in mosquito country, no sense having a big open porch, you'll want something screened in. Your idea of a modest porch for taking off muddy farm boots and maybe setting a spell with a glass of lemonade while you take a break from yardwork seems good. I would not rip off the enclosure for the other former porch, you probably like and need that space.

One you get the entrance sorted, then you might like some foundation plants. I'd go old school with maybe some hydrangeas, small lilac like Ms. Kim or a dwarf variety if you can find them, roses, flowering quince, ostrich ferns. All the old plants you can find growing around the ruins of old farmhouses and their foundations . . . I envy you!