I think it is cute as all getup;) I might hang a new copper lantern porch light, and throw down a new welcome mat.

From the exterior, there seems to be nothing visually wrong with the bay window element. So my question would be what would changing the bay window do for you on the interior? Are you trying to introduce more natural light into that particular space? Would 3 large and wide double hung windows accomplish that for your?

Regarding the dormer question, you need to weight what adding another dormer would do vs. widening the existing dormer. What is that room behind the small dormer. Which would benefit you more for that space. The existing dormer is nicely centered over the 1st floor windows. I would think that widening the dormer would keep that rhythm intact. Adding a dormer will through the rhythm off.

I would add a stone retaining wall from sidewalk to left corner of house along driveway and fill in with top soil to reduce the slope and then add new stairs and sidewalk to front door ( walkway should be at least 4 feet wide.

Then change landscape shrubs.

Lovely house, I just think landscape and yard changes are all it needs.
Perhaps change exterior light fixtures to update.

Do you have a sense of what construction costs are in the area vs. your budget? I think that the dormer looks a little small on the roof, and usually provide a lot of value to the room that they are in. However, making modifications to the roof come with complication and expense that might not give you a good return on your investment. If the roofing needs to be replaced anyway, then changing the dormer would want to happen before you did that.

Otherwise, I think that maybe a porch and some landscaping could really add a lot of appeal.

I would add wider trim around the bay window and dormer windows, and wider, contrasting corner boards on the front gable (with siding).
On the bay window itself, it might be nice to accent the projection with same-color wood shingles, instead of what looks like aluminum siding (?).
Accentuate the entry by painting the front door an unrelated, contrasting color (red? blue?). It's hard to see the brickwork around the door, but it should be noticeable and attractive... you might want to add this.
It would be very cute to add a second dormer, next to and not far from the one you have.
Finally, enhancing the walkway with landscaping and brickwork would be very beneficial, too.

This house is adorable...the only thing I would change on the outside is the landscaping. All the bushes are too overwhelming.

Hi....I agree with Judy M on the retaining wall, it would help to have a walk from the door to the street separate
of what is going to the driveway, and the retaining wall would level out the slope to make that possible. Large stepping stones with grass in between, less green and more color, possibly hydrangeas and roses lining the walk, a blooming tree as well. I think the house is nice, I'm not crazy about the cream with the brick, and would suggest you paint that BM Swiss Coffee, the shutters color freshened with BM Iron Mountain. I would add a copper roof over the bay window.

Removal of clumpy shrubs, a retaining wall and a new color for the front door would help. The copper roof is a great idea and beautiful azaleas for spring and hydrangeas for summer-fall would top it off.

You need lots of color from the front door to colorful annuals and perennials. The shrubbery is ok if you add color with it.

With some additional trim and another dormer...pardon the quick Photoshoppiness of this...

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