Remove trees from gutters.

Instead of a picture window replace with 3 double hung. New garage door with a modern style if you really want to change it up.

Izzy Mn - Could you clarify what you mean about removing trees from gutters?

I think you can get a modern flair for you wonderful home by changing out the garage door and the front door to coordinate. Something like the below would work nicely:

Clopay Garage Doors · More Info

^Garage door with windows down the side and there are front door options that mimic this same design like the first one below or coordinate with it like the last pic.

The Cromwell House · More Info

Homes Portfolio · More Info

If you are uncomfortable with windows in the garage door, a solid door works just as well for the modern aesthetic.

Cowart Door - Modern Wood Garage Doors · More Info

Denita - I've been leaning toward a similar idea matching the front door and garage door. Do you think it would be too much if both are the same wood tone?

^Or paint the current screen door a color that blends with the new wood front door.

Gutters clogged with leaves will grow things even trees. Clean them quick or you will find water damage. Our roof repair guy blew ours out this spring and I swear it smelled like something crawl in it and died.
If the garage door is in good shape
just paint it. Choose a color that ties to the brick and use it on front door too. ( Don't fall for painting brick trend.) As much as I love turquoise, that door and rail are too glaring for me. A smoky teal or navy would be a less jarring contrast with your brick. A sage green or rusty red would also look good. I would upgrade the railing and maybe carry it around the rest of the deck. It could be simple black metal panels from HD or Lowe's or a DIY with paverstone post and cedar rails. Low growing ever green shrubs would soften the edges of the deck too.

bcanty13

10 hours ago

Izzy Mn - Could you clarify what you mean about removing trees from gutters?

Maybe I'm mistaken. It really looks like stuff growing out of the gutters but maybe it's the shadows and tree behind house.

Izzy Mn and Kathleen MK - There are no trees or other things living in the gutters, those are just shadows and the tops of trees in the backyard.

Kathleen MK - Totally agree with you about the turquoise door and railing. I like the idea of extending the railing on the front side of the deck and suggestion to plant some low evergreens in the adjacent bed.