First, my usual disclaimer -- I'm not a designer, just a not-all-that-fussy-about-looks homeowner. You're not going to make this into a cottage, nor do I think you can make it cute. Its basic style just doesn't fall into either category. I'm not a fan of a dark roof for practical reasons -- it increases heat load in the summer (raising your air conditioning costs and/or indoor temperatures), and the roof level heat shortens the life of the roof. In this case, however, it makes the house look MUCH better. So in your place, I'd break my own rule. I think that the problem with the dormers is that they aren't dormers, they're just windows. That's what you get with mansard. I don't see any way to change it either. . The garage is hideous. It looks tacked on, and might well be. It wrecks the line of the house. Ideally you'd somehow move it into the back yard (move or demo and rebuild). You could also extend the mansard roof over the existing garage. But any way you go with it, it's going to be expensive, and you won't get the cost back when you sell. I think if I were in your place, I'd pass on this one.

These shingles have an architectural finish to look like slate. These brown shingles look like wood. This building's mansard roof is covered in metal. I think that would look good on your house in the right color. This one, too. I would replace the shakes that are on the walls of the garage and in the entry with lap siding. The dormer windows with metal and lap siding.

Extend a welcome! Develop a planting bed extending from the front walk across the front of the house along the bow window. Include low shrubs, groundcover, and colorful perennials for year-round interest. Reserve a small area dedicated for flowering annuals for a pop of color (see below). Consider integrating an additional focal point near the entrance. For example, you could draw attention and enhance the arrival experience with a small bubbling fountain or lovely piece of sculpture. Add a bench or chair for a welcoming touch and a spot from which to enjoy your yard. Photo Gallery Layered plantings

Please do not alter all that much on that house. It doesnt need to be modernized. Honor it for the style that it is. It looks nice, and no, to painting the brick. I do agree, that the white is way too stark, and doesnt look good on the house. A darker Cream would be a much better option. Also, you could use some better landscaping. Put your money into painting the trim first, and maybe some new lighting in the front entry, and a colorful pot of flowers on each side of the door. You may want to paint the door a color, so it shows up better as your entryway. Then, get some nicer landscaping. A small tree that flowers in the front yard would be nice.