You guys are spectacular!!! I do have a question: The white trim at the windows is the vinyl window itself. Can I just paint these? I hate the white with everything, it contrasts much too much, but it works well inside, because all the trim is white. The white at the door is the storm door, which wouldn't break my heart to paint/replace. ;) I agree that the shingle color on the roof doesn't help, but it's a new roof, so until the next round of hail comes, it is what it is. (Though that may not be long off, I live in Oklahoma.) I LOVE the landscaping and extra winding path. That is happening. I've always wanted to add something over the door, and have contemplated a wood trellis type covering that begins alongside the stone steps at ground level, and comes up over the front door to meet the "long" wall. One thing missing from my photo is guttering that was added. It's not a big deal, but it does match the current mossy/clay trim color. I will probably have to tackle this all piecemeal. (Some day, I'm going to replace that single window that doesn't match the rest. Ugh.) Thank you to all of you, I'm so excited for the potential I'm starting to see. :) This has made me really want to pursue "Tudor-ing" it up! Tudor Cottage, here I come!

If you are open to changing the roof line over the walkway, perhaps you could make the roof over the garage separate. Alter the roof over the garage so the hip corner of it ends at the right corner of the garage. Then build a new roof over the entry sidewalk HIGHER than the garage roof . You could still have it be a shed roof, albeit with sturdier looking posts and supporting angles, but have it begin at a height chosen so that when you add the left slope in front of the upstairs, your left slope will be only a few inches or so beneath the height of the upstairs window trim (bottom trim beneath window sill) . As you reach the front corner with your right-sloping shed roof you can add a small decorative left side slope to the right sloping roof in front of the garage, creating the appearance of a forward facing gable... not unlike this small gable in front of the larger gable: the part of the smaller gable that is in front of the larger gable is decorative rather than actual roof covering any interior space. https://www.pinterest.com/pin/192599321544446995/ You might want to build the new roof starting with the front so you are building both sides of the roof, including the left slope in front of the upstairs, first to be sure you have symmetry. You might even consider a triangle window in the right side of the gable with a black panel (or dark tinted glass with "interior" behind it also painted black) in the same shape on the left side of the gable. https://www.pinterest.nz/pin/545850417335577390/

I found your home’s sibling. :) Ok, it seems like you have some good, definitive ideas. I’m not sure how to help ... I think any of your proposed schemes would look great. I came across this and love the blue: Some others: I could post so many more! Other than a Victorian, this style of house has the most fun, unique, varied, and interesting color palette options. Truly limitless. It sounds like you really love the idea of black paint, though ... what’s your hesitation on that?

Do you need new windows ? What is wrong with the ones you have ? IMO that tudor wanne be trim should go also the shingle type stuff by the window should be the same as the rest of the siding The windows look like they have some sort of pattern in them what is that exactly. I will say I usually love a grayed green for siding with brick this is my fave for that combo.I would do wider trim on the upper windows to match the lower ones Please do not paint any of that brick unless you want to instantly devalue your house .So take a look at this inspo and see if it something you like .