Look at the permits on file at city hall for the remodelling that was done over the last 100 years. Then talk to neighbors who have been there the longest. A look in the attic can tell you if anything up there looks new, too.

Don't tear down the screens on the porch til you have been there a full summer and fall.

You could consult a professional mason about the brick repairs and about removing the top part of the arch on the fence.

Thanks for the suggestions! I've checked for permits from the last few decades, but I'll try to do a historical permit search—that's a great idea. And you're probably right about the screens :-).

A lot of really poorly thought out renos were done here the house looks a bit of a hodge podge to me. If possible those permits will help but probably not a cheap redo

You are talking restoration here rather than renovation. I hope. Start with the local historical society and your local library for property records searches. Maybe a local university if they have archives. Is it located in an historical district? Are there nearby historical districts? Lots of resources to explore while you plan. But, please, please, do not plan on a remuddle!

What a great find! Sounds like you have the eye to bring this home to it's former glory.

I agree with you to remove wooden privacy fence, arched brick and metal gate --they really do not relate to the architecture of your home and add to the "hodgepodge feeling". I would definitely remove the "screened-in" porch. The painted lattice looks cheaply done and not well planned --ditch it. Also, the security door is uninviting and should be removed along with everything else.

Another suggestion, (which I'm not an expert on, so please research the longevity of this idea) is whitewashing the exterior brick. I've seen it done on interior fireplaces. A whitewash will unify the different brick and won't be as harsh of an option as painting the brick, allowing it to maintain it's intended architectural interest.

One last thing that bothers me is the red steps and red accent. It clashes with the red hues of the brick. I would remove the paint all together.

LOVE LOVE LOVE your inspiration photos!

Again, such a great home! Can't wait to see it once you've redeemed it to its architectural roots!

Thanks so much for your thoughts, everybody! To answer your questions:

1. I am definitely planning a restoration and not a remodel/remuddle! The neighborhood is in the early phases of becoming a historic district , but there are tragic renovations being done all over the neighborhood that often involve replacing original windows with vinyl ones (as was done in this home). I wish I knew what they looked like, but this style of house is nowhere to be found in the area. Most of the houses in the neighborhood are craftsman bungalows and queen anne cottages.
2. I haven't been able to find old photos, but I did talk to a longtime neighbor who told me that the arched gate was added in the early 1940s to imitate the style of the ornate Victorian houses in an adjacent neighborhood. So whether to keep it or remove it is a tough call, since it definitely doesn't go with the style of the original house but has been there for over 70 years. If the house were in a historic district, I would actually be mandated to keep in intact for this reason because it's considered a "historically significant addition."
3. I concur—the red paint on the steps and the flesh-colored trim are so gross!
4. Interesting idea about whitewashing the brick! I'm curious as to how it would weather over time, and what kind of upkeep it would need. I'll keep digging for info, but preliminarily it looks like a much better option than painting.
5. Here's a picture of the house from 2008. It already looked so much better then!
   

Wow, it really did look great! Nice to see that only a few minor adjustments will get it that much closer to it's former glory.

(Side note: It really is refreshing hearing you want to restore and not remodel/remuddle!)

K, you and my husband are of the same mind re: the fence! He wants to keep it because even though it's an add-on, it's built so well and shows that someone had a lot of love for the house whenever they added it. I found "1943" on a brick, but who knows. If it stays I think that softening it up with some climber roses is a great idea. Thanks for the feedback re: wood and color schemes too.

nmp19, interesting idea about finding the builder and going from there. I know who subdivided the land and sold the plots, but am not sure otherwise. Hoping that finding the original building permit will give me more info. It's the only house in the neighborhood with a gambrel roof.

Behind that front porch add-on is a really nice Dutch colonial but you'll have to rip off the porch to see it. Right now the house has no character--just a mistaken hodgepodge of things. Having lived in a Dutch colonial for many years, I'm partial to their wide fronts and clean appearances. I don't like the arch but suppose you could keep it but paint it dark. Do NOT paint the house brick.

You can stain brick without the challenges of painted brick (if you are in a deep winter / heavy freeze thaw climate then painting brick is not ideal for thermal properties of brick).

The difference between the site wall / retaining / arch brick and the house brick bother me more than the differences between the foundation brick and house brick - they appear a bit more cohesive. I would try staining the retaining wall browner before trying anything else.

Since you will need a retaining wall, consider tearing out the arch itself and eventually the wrought iron - a green barrier won't need to be so high or gothic looking.

This spring, plant a hedge type evergreen all along the perimeter where the wood fence and edge of retaining wall occurs - a shorter hedge will give as much protection but be less jarring than the wrought iron. Use some of the bricks from the arch to make new craftsman style tops and shorten the corner posts . . that style is also gothic and wrong for the house.

The slanted cedar planking on the front gable needs to be restored to the same as the standard shingles above - that is what is throwing the porch off for me.

As for color, the white white of the windows (though you hope to change them) is throwing me. If the sashes can be painted, then they and the trim should be unified - whether they can or not, a mid-tone olive gray like would be historic, work with the brick and the cedar and the craftsman and the roof. Shifting those will make the largest difference. Try bm Strathmore manor . . https://www.benjaminmoore.com/en-us/color-overview/find-your-color/color/244/strathmore-manor?color=244&source=%2Fen-us%2Fcolor-overview%2Ffind-your-color%2Fcolor%2F1524%2Fnatures-scenery . . against this you can do an eggplant front door or a plum red tone and both will amp up the craftsman factor immediately.

Thanks for saving this beauty - I wish your family great health and happiness here.

Thanks all! Forgive my crude Photoshopping job, but I'm incorporating some of these thoughts as a start. I think the idea of lowering the brick columns on the fence/wall and removing the arch to make them look more craftsman in style is interesting (and then saving the brick to pave the walkway). I may be stuck with the arch for now because my husband wants to keep it, so in the short term disguising it with greenery might be the best thing to do.

If I'm able to find some old photographs or house plans in my archival search, that will make these decisions somewhat easier! Headed to the historical society this weekend to see what I can dig up.

Wonderful! The arch is charming, but your photoshop tells you that it fights the architecture of the porch gable .. love the deeper toned warm gray on the cedar shingles . . .once you take it nearer to the brick tone, you can see what high contrast trim does to bring out her good bones.

If you could provide a better picture and a close up of the brick. I may have more info and possibly a solution

@K.O.H. Construction Corporation - Thanks! Here are some additional photos of the brick. They are from our home inspector (hence the arrows). The first picture is of the house, and the rest are of the wall. As you can see, the wall and the repairs have a more orange-y brick color with white grout (rather than gray). Would love to know your thoughts!

@sunnydrew - I appreciate the research tips! I'll keep you posted on what I find.
@libradesigneye - I'm in the South (Atlanta) so long freezes shouldn't be an issue.

Thanks everybody for the helpful advice. I love the idea of dark or black windows, but the vinyl replacements that are currently there have muntins between the glass so they'd be impossible to paint, even with special vinyl paint.

I'm afraid that means I'll have to wait until I can do a whole-house window replacement (either historical replicas or restoring some original wooden windows thrown into a dumpster by a contractor doing work close by). The window frames up top will have to be built up to accommodate smaller replacement windows that look more to scale, too. In short: The windows seem like they're going to be a major job, but I hate them! And it's a shame, because the vinyl windows that are there don't look to be more than 7 years old. Whatever I end up doing, I'll probably focus only on the front ones for now. I'm also lucky enough to have the original 12-over-12 windows in the library (on one side of the house) intact.

In any case, I think I'm going to begin by removing the red paint from the concrete, cleaning up the yard, and seeing what I can do about those wood planks, which aren't stained or sealed right now. I'll see how far I can get with DIY jobs (we're pretty handy!) and then get quotes for hiring out exterior painting, fence work, window work, etc.

Very helpful @nmp19—thank you!

Susan.This all depends on how far you want to go with this project, The brick in the first pic are different color and can be changed. The reason the joints are white is because the jointed them while the where wet. You need a good mason that has brick that match (they're both out there) and use the proper sand size. Tinted mortar does not last. When we do this type of work we lake sure the brick match, use the appropriate sand , use Brickment ( a gray base mortar) then we rub dirt into the joints and on the brick. So far so good. The brick in front will never completely match because of the texture but as others have said a professional can dye the brick to look very close.