I think wider trim on the windows would halp I like the color you have chosen I always like a walkway to a front door from the street so maye start there . As much as I love trees IMO those big ones are really not great for curb appeal so great you removed those .Not sure about your style but maybe window boxes on those upper windows would fix the boxy look a bit. Then go to work on landscaping to have the house a bit more open so more low growth I like the cherry tree for sure but not the rest of the bushes. So first a proper walkway to the front door from the street and a new front door with more glass .

You have some orange in the stones, and your roof is a reddish brown. SW Chelsea Gray or Stamped Concrete read as a sage against the stones. I think that’s pretty, but you may not like the green. Favorite Tan is close to the orange stones, and reminds me of the color of a saddle. Not sure how it would play against your roof, though. Make sure you get tester pots and paint a large board (at least 2’ x 2’, larger is better). Colors seem different when they are larger and outside. Do you have any plans to replace the roof soon? If so, I would choose a lighter color that also works with the stones.

I live in the country and bought a house with a looooooooong dirt and gravel driveway. The house had not been lived in for a while, so in addition to a new roof, I budgeted tens of thousands to re-grade and re-gravel and put newn confines on the driveway (since blacktop would be totally wrong for the neighborhood and the house). Since it was impossible to do that work before winter set in, I ended up living with the old gravel driveway for months. I am never going to spend the money I planned to spend. Instead, my local lawn service tidies up the driveway each spring -- which was actually his advice to me when I first approached him to do the job. He said he would but he warned me it won't last. Just make it part of spring cleaning. I think your porch columns need to be white to show off the charm of the house, and likewise all the front bushes need to be removed or cut practically down to the ground. You definitely want to show off the welcoming openess of the porch. Take away the shutters and re-think the front walk. What is the most used approach to the house and put the walk there, and light it. Doors with oval insets have always been popular on houses like yours. If you like it, keep it. If not, you are not being ahistoric. A lot of these houses were built and sold with an oval inset door on them. Is that your house address over the porch entry steps? If the town allows, put your house number prominently at the end of your driveway instead for safety.

I think staining or painting the red brick only looks like an improvement based on what people saw before. That is to say, if you came upon this house for the first time after all the suggestions for staining or painting had been done, you'd be thinking: How can I change the look of this house? The big black portico overhang is the thing I would most want to change, along with the black roof trim. The house has a design (not saying it is one I like) and I think uncovering the design would be a step in the right direction, rather than constantly applying coats of darker paint. Wondering if any other houses in the neighborhood are like this? Are there photos of the house when it was built? Would love to know what is behind the lattices.