remove the shutters

better front door & storm door paint a color you love

garage door with a row of windows

walkway to the front door

Landscaping

Conceal the trash/recycle barrels

What jck said.

Plus the ’elephant in the room’ - vehicles parked right up close to the front door. We can’t see what’s to the left to know if there’s room to scoot them over. Or even put the small one in the garage. (I know we love our vehicles, but you asked about making your house attractive so….)

There’s a huge difference in painting garage door and trim, adding stone, changing roof line. Maybe decide on your budget, look at homes in your neighbourhood and on line and even if just deciding to paint, getting lots of ideas will help. For instance, painting siding, new front door, landscaping, etc. A new roof line is a whole different category.

I agree with @jck910. Forget about changing the roof line unless you have money to burn. You should be looking to move before doing that. You also do not want to paint your trim black with that body color, or add stone anywhere. Nor do you need to paint the chimney. Right now it's a no maintenance surface. You need to check the pointing and flashing occasionally, but do you want to be on your roof repainting periodically (or paying someone to do it)? I like the color of exterior currently. If you're tired of it you could change it, but there's nothing wrong with it. Black trim and stone stuck on are today's trends (you've probably seen that on newer homes), but in short order those homes will look dated. Yours looks like it's been well maintained. Make the changes @jck910 suggested and it will be refreshed.

I think we need a lot more info but you could start with the ideas above. I agree changing a roofline is like ppouring money down the toilet.

The pitch of your garage roof is the same as your house roof. Changing the roofline would remove that balance. Your roof has a low pitch, so it is not that noticeable. Sure, you could remove the roof that goes from the garage to the porch, but that would almost certainly require major work and repainting the entire house and for what? A minor difference, given you'd still probably want a roof over the porch and the room next to the garage. Dormers look funny on a roof with a low pitch.

Rather than looking at houses in terms of time "this century", view them in terms of neighborhoods. My bet is that your house is a good fit for your location and neighborhood.

You have a nice classic house. Clean lines and really good proportions. I would not change anything about the structure or architecture of the house.

In my opinion, the biggest impact would be some wonderful landscaping. I'm not the expert on that, but we have some skilled people here who can often photoshop really lovely landscaping and it's incredible what an improvement that can make. Right now you have two little shrubs and a whole lot of grass. Boring. You need beds of flowers and shrubs or small trees to bring in color, texture, and interest.

In terms of the house itself, the color is good and everything looks really solid. If you want to add more pizzaz, a new front door without the storm door might help. You might consider a new garage door with windows as suggested. You could paint the garage door the same color as the body of the house to make it blend in a little more (either the current door or a new door).