What's unattractive about it? It's not a colonial or a cape, it is what it is. Realistically, all you can change is the paint color and/or the roof color. If that's not enough, you should look for a colonial or a cape.

Landscaping

Love, love your home.

OK I would change the color of your pinkish roof to something more natural in color

However your biggest issues is your LANDSCAPING

None of your shrubs or bushes should cover any of your windows. All those evergreens have to go. See images below for a new look for your home. Perennials

I agree. Play up the landscaping.

Another option is to look at these contemporary Nantucket style homes and do basically no landscaping. Just run the grass to the house and throw out a couple of potted topiaries and you're done

Nothing wrong with the house. Just replace the roof (metal maybe) and pull out the aging and straggly landscaping. Get a professional landscaping plan and DIY or have it done for you. Go with low-maintenance plants to save yourself the worry and trouble.

These are all great ideas - thanks so much!

RappArchitecture, we only have experience with colonials and capes but in no way want to make this into one - we just want it to be more attractive and inviting. The street is full of stately stone mansions and we want this to look just as attractive but within its own style.

BeverlyFLADeziner I was thinking dark shingle or metal roof as well - thank you for the imagery! Do you think changing the trim color from white to dark gray would be a good move?

That said, a friend mentioned the contemporary Nantucket style as well (but we didn't have a name for it) and I have to say I'm intrigued by the possibility! Also, we have a few failing skylights - do you think Dormers (as shown in some of the example photos above) would work in their place? I don't want it to look like we're trying to make it into a cape...

Thanks to all, I can't tell you how much I appreciate your insight!

-L

I would pick a grey roof and paint siding white. Keep the trim and corners same color as the house. Are the windows in good shape? If not, chance them to be black.