Add shutters to the small windows and a large, deep window box to the big window. It's a bit late to plant annuals in the ground in the height of summer, so plan what you want to try for next spring.

I once owned a house like this.... Cute!

Brightly colored front door. Window boxes at all 3 windows. Fix up the stoop a bit. Yep on the herb garden.... Picket fence. More definition to the grass in the foreground: hard to see where the garden starts.

Spend your winter reading up on cottage gardens.... If you're cutting trees, you can use things like stepping stones using rounds of the trunk, etc.

I made window boxes by putting wooden trough planters on brackets. Someone made the brackets for me out of pieces of wood. Not metal.

I have nothing to add, but I just wanted to say that everything tangerine wrote sounds really wonderful!

Following

Does everyone think sticking with black on the roof, and shutters or window boxes?

What about the driveway & walk to the front door? Some type of enclosure for the barrels? Lighter color roof, maybe a medium gray

No to black on the roof unless you love to pay high energy bills.

You can add shutters but also consider climbing roses for your home.

No to a black roof. A medium gray would be nice IMO. Love the suggestions here and Beverly's pix. Perfect house for cottage style.

Wow, Doug...so nice...and so cottage! :-)

@Dig Doug--wow! that's great!

OP--Roof color--I'm not a fan of black. I think grey is more neutral.Some companies have colors that are kind of mix of colors. I'd recommend looking at roofs as you drive around. Here's some random person's advice:

https://www.roofingcalc.com/roof-shingle-colors/

Depending on where you live dark roofs save energy. Dark roofs absorb heat and is a + during the long winter.

I'm not taking the time to draw in cottage garden plants, but subdivide the space to add more variety.

Regardless of what you plant, I'd beef up the stoop, step, landing and walk as that is the beginning of curb appeal.

I am not fond of lining a driveway with plants unless folks have room to step out of a car and onto the drive. Nothing worse than stepping shin deep into wet plants on a rainy evening, and foot traffic in most garden spaces hinders growth. Similarly, plants often splay into the walkway during rain and so unless the front walk is quite wide, lining both sides with plants can make the house approach unappealing in wet weather.

In the long run when there is funding, consider bringing the roof out a bit further and broadening the stoop or adding a patio large enough to sit on if you are likely to use it.

In the short run adding 6’ or deeper beds in front so you have space for some evergreen shrubs for winter interest fronted by flowers or alternating with flowering shrubs will give you both summer and winter interest.

Add a generous landing at the base of the steps and make the path as wide as the steps.

I like the idea of a brightly colored door and gray roof. If you add a window box, don’t add one of the typically tiny ones that are sold in the hardware store because they are so small that the soil dries out too fast and it is extremely difficult to keep them looking decent. Half dead plants aren’t attractive.

if you want an herb garden in the front yard, look up parterre gardens which use a geometric structure to make gardens that may not have a lot of flowers more appealing. Regardless, look up plant size at maturity on a reliable site like the Missouri Botanical Garden’s PlantFinder, not just want the plant tag says which is usually the 5 year size.. You want plants that will stay small enough to not grow above windowsill height.

Just stopping by to add that I had a back doorway very similar to your front doorway. I second the idea of adding one of those old fashioned black metal railings, if you can find them. You will not regret it if you have any icy conditions in your zone.

You can easily enlarge that front bed that has the brick liner. You shouldn't plant things so close to the house anyway. As for herbs, maybe you can get lucky and find a source of some free ones. I have an herb garden, and every year I end up throwing out cuttings and divisions and thinnings, I don't have any more space for any more plants. Find someone like me. Or if not, a lot of herbs are dead easy to grow from seed, like lavender and many of the mints, for example. Depends on what kinds of herbs you like.