I'm thinkin' a dark roof makes that house look small.
W/ the color choices available today--I'd go very light..even white.

I wouls also take any samples in the construction supply place of the shingles you are thinking of using over to the paint section and
compare that color on a color wheel for matching paint for the house.--also matching color aluminum drip edge which you
may want to be chnging while doing the roof..that's cheap.
A good time to at least paint the facia too.
I'd also consider a few new smaller plants for those flower beds against the house..plants also of colors to compliment and work with the roof.
A roof cost money..a hundred bux more to tie in the rest of the house ow/ the new roof will make that place look new.
Preasure wash the bricks and they may turn a few shades lighter too.
That high up small window to the left..a white window box planter beneath it, hung right from the sill, will even out the proportions immensely.Not to mention a nice bench seat beneath the parlor window.
The last porch post next to drivway has a small bush against it..a four foot tall 'stander' tree would look wonderful there.

Wow thanks for the advice. Yeah I think lighter is better after seeing it on the house. I dunno about white, but for sure a lighter color. Thank you for the other helpful tips on the house. Yeah we have a small house, so I would rather not make it look any smaller then needed. Next year is window year for the house.

Like the place ..it's like a clean slate--too bad ya aint in Fla..I'd come work w/ ya for day.
that place can look like new and cheaply.
Take good care of that Oak tree..it makes the place.
Also..for a fun project you wont regeret--available at any
craft shop--even in that section wal-mart are
kits and paints for making fake stained glass..that big window would look awesome.

This 'id cost about $14 and a saturday.
It's called 'liquid leading'
My window is done with elmer's glue.. I'll take a pic tomorrow.