Remember a lighter roof gets dirty looking - try an in between value.
I would like to see a garage door with a row or two of windows or a carriage house look; providing depth.
Or a narrow pergola across brick above garage doors to cut down on heaviness of brick
The circular air vents could be replaced with a metal to brighten the front along w matching lights.
Possibly lighten the trim and gutters a little.
A raised flower bed to left of driveway in front of sidewalk would dress things up.
I can't see front door but a lighter color or one with glass insets would brighten up the inside and outside.

There isn't much to update color wise as the entire front is dominated by the brick color. Perhaps try a lighter color for the garage.

Is the new roof cosmetic or a necessity? I think taupe trim would lighten up the look of the house. Maybe a red front door. I agree, that a garage door with some windows will add interest, but still needs to be darker thatn the trim. You want it to be interesting, bnut not draw too much attention to it. The attention needs to go to your front door. Any chnce you could add a portico to the entrance to let people know where the entrance is?

Roof will be a necessity... unfortunate, but thank goodness. Much needed.

Are you leaning towrd one color or another yet?

Finding a good trim color for your house is a tough one. I'm thinking perhaps a medium dark dirty blue/green such as SW Retreat would be worth taking a look at. But also consider a light greyed green such as SW Svelte Sage.
Carolyn Albert-Kincl, ASID

Not really. Only because Im not fond of the brick color. We have played with a few options, but they all lead to a different brick color (painting). I really dont want to paint the brick though.

I would consider going with a lighter shade to brighten up your exterior. Have you considered getting something similar to the grout color for the garage / trim? If not, a greige option might be nice. Sherwin Williams' Paint Color Visualizer tool might help you picture how the color would look on your garage.

Maybe Hammered Silver or Morris Room Grey would be worth looking at for the garage. For the trim, it would help to see a photo with the new roof as that may change the look of the exterior.
I don't know if I would replace the circular vents as they fit the look of the house, but painting them the same color as your trim / garage door wouldn't hurt.

"Keesee and Associates is a Custom Home Design firm in the Orlando Metro."

I'm not sure that a good dose of white paint won't pep up your chocolate house. Maybe shutters too. Be sure they are adequate to look as though they could function. In Tornado Alley, OK they may need to.

nice pics deco! Maybe even a cream instead of white, if you think white is too stark.

I think a white garage door would look nice. White goes with anything, even the color of the brick you have now. If you decide to paint the brick, I think grey or a blue would really pop. Definetly get some nice landscaping going, bright flowers, maybe some under the window flower boxes andyou can re-do the walk way. Good luck with the project, would love to see the 'after' pictures!
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So pretty. Thanks for the pics everyone. We do love white :)
"Sustainable Long Island" walkway---very nice (totally our style)

Please consider a "Cool Roof" to keep your house cooler while saving energy. There are new colors and materials and they look better than ever these days.

White trim looks fabulous on a dark chocolate house. Lots of bright colored flowers in the front beds will lighten it up, too.

The colors in photo posted by decoenthusiate will certainly translate well to your home. Also hop on that landscaping. It is sucking the life out of the house. Use a garden hose to mark a 6' circle just beyond the left end of front wall. Now use the hose to lay out a nice curve. Place left end of hose along front of the circle then make a wide curve going inward first and then outward in front of walkway and curving to 4-6' down the driveway. Tip: gentle curves allow for easy mowing.

A dark green would work, too.