Plants and flowers.

I would consult an architect on this for roof ideas.

What a fascinating home. Is the neighboring property a separate residence? And it appears their steps butt up to your future house?

First things first! Remove the rusty CLF which immediately lowers your property value, even if it were brand new. If the side yard needs fencing then something like a picket fence from the same era as the building would be preferable. I would expand on Brown Dog's suggestion of a brick foundation and include new brick steps that simply lead up to the doorway, spanning that wall and having a decent landing for guests to arrive at your home. Eliminate the triangular ones that look like they could be dangerous and easy to make a miss-step on. I too would avoid roof changes; you have the one unique house in the neighborhood - play it up and make the most of it, including typical signage, as BD suggested. Please let us see the inside too!

Brick steps and large landing

I'm no expert, but that roof looks like it would make an awesome deck!

I can't answer your question, but I'm with others in that I would embrace the history, too. :)

I just LOVE it...lucky you having a non-traditional house..

While you are looking at roofing ideas, you need to work on the hardscape and the commercial vibe. Make sure the existing roof is in good condition. First thing: have the power lines at the pointy corner moved to a less conspicuous location at the other side, away from the street. Power wash the front steps. Kill and remove all the weeds in the sidewalk seams. Change the simple pipe stair railing to something a bit larger. Place colorful pots with flowers and greenery on the left side of each step up from the sidewalk to direct guests to the new handrail. Place a garden bench in the recessed area next to the sidewalk to the right of the railing and add a large pot with flowers at each end of the bench. Have a bright fabric awning hung above the windows above the bench. Change out the chain-link fence for a simple wood fence for privacy.
Your new home is a neighborhood gem many may still remember as the store it was. Make it shine.

Wondering how everyone feels about black shutters on the front windows.
Definitely remove all weeds .....Job #1.

I see there is an access door in the foundation,
which may create a problem where stone facing is concerned. Pots and a bench will warm it up.

If you want to do a new roof to get rid of the flat roof maybe a mono plane roof would work instead of a two plane roof. Probably could do a metal roof at a lower cost on a single plane roof too. Agree, you will need some structure drawings to get done, also approval from some codes in your city/county for building permits. The only fear would be a mono roof looking modern, but might be a nice mix.

https://roofgenius.com/monopitch-roof/

No shutters!! I think it's cute the way it is. Maybe a different more interesting front door painted a unusual color like Robin's egg blue. Or a orange color.

Unless orange is a favorite color....please don’t do......too harsh. Robins egg blue sounds like a pleasing addition.

A roof deck could be great if deemed safe by local codes. You might add glass railing to make it less dangerous and to add some coolness to the building that is more or less invisible.

Greenwich · More Info

LOVE your new home! First things first....go to your local historical society and see if you can find photos of your home from its days as a commercial building. Are you in an historic district with guidelines? There might be $$ incentives available to you if you choose to implement changes that evoke your home’s past. Use early photos to inform your design decisions. I, for one, find your home’s shape the best part of it! Including those cement steps. (Good lighting and an appropriate railing will minimize any risk to your visitors.). I agree with the suggestion to re fence your yard....with a wooden fence. Can’t wait to see your updates! Congratulations on your charming new home!

There is very little about that building that needs to be changed. The roof isn’t one of the things that needs changing. Not unless you really want the expense of rebuilding half the building.

The white foundation is one of those things that needs to change. The building needs grounding with a darker color below. Maybe a deep green or blue to go with the yellow.

The chainlink with razor wire needs changing. If you need a fence for security’s and privacy’s sake, something in a brick with appropriate alarms would look better.

I agree with the others who say to embrace the history. It's unique and interesting as is, which is probably why you bought it.? Spend your money improving the facade, landscaping, fencing and you will really have a gem. Is the yellow the original siding? A vintage looking hanging address plaque could be cool too .

It's better to focus on the transition from the street to front to the yard to the front of the house ...it will do more to make the house feel like a home than anything you could do to change the roofline. What's really important is the sense of arrival. You can add a nice fence, landscaping - plant a nice big tree in front. Celebrate the architecture you already have. It will not only be very satisfying but also better for your wallet.

Lose the storm door. Paint or tile front steps. Pickets or lattice work along the bottom where it’s painted white. Potted plants. Pretty light fixture on the porch. And lose the fence.

On the slab of concrete between the house and public sidewalk could you put a large raised garden box or planter? It could have just some small evergreen shrubs or a mix of herbs and flowers. And if you can't afford to change the fence at first, hide it with some fast growing flowering vines. It looks like you have a start on that with some morning glories. Get an interesting pendant lantern for the porch light. It is a cool house but just needs some plantings to make it look homey.

There are a few houses like this in my neighbourhood. They still look very store like, I don't have any suggestions other than replacing the concrete and adding plants.

I don’t think you have much of a choice BUT to embrace its history. You may even add a little sign that says “Former neighborhood corner store but now a home.” I would start with the less expensive approaches first before you delve into roofing. I think a roof deck is a great idea because it seems you don’t have any outdoor space. You would need to make sure the roof is able to handle the extra weight.

Please update us as you move along in this project, definitely a unique one!

It appears you do have outdoor space...a lovely tree shaded side yard. If you can’t replace the fence..plant climbing roses....fast growing and will give you a bit of privacy from the street.
In the drone shot, there is something at the base of the fence, on the inside....paving stones??????

You would need an architect or at least a good contractor to calculate the weight of a new roof structure added on top of the existing structure. Is the house strong enough, with support in the required spots, to support the new roof? Would the new roof block the sun or the view from the adjacent house?