Ask the home decorating forum. They're good with this stuff. I'd want to redo the retaining wall with something that brings out the brick or stone or even (faux) railroad ties/landscape timbers and then clean and re-stain the shakes and wood siding and embrace what you have because it's actually pretty nice. I can see taking it to cottage in the woods, but it's just not beachy. I guess you could paint the brick white and the cedar teal and the trim white...

Hello Penny04 (zone 8a), What about a neutral color? It would work well with everything you have and be a bit warmer visually too. This color is Benjamin Moore London Fog 1541. Karen Haggard, CID

With the windows and garage doors I would probably go with the same color for the fascia and gutters. I think white siding would look too stark in the gable ends. Something in the taupe family to bridge the dark trim/windows and the lighter brick would look nice. If you're interested in seeing some virtual finishes on your house check out my web site, Creative Visual Concepts.

Alyssa, it's a very cute house. I'm not a pro but could see the foundation the gray Jerome mentioned or the same color as the siding. Will there be more landscaping that will cover much of it? For me, the only windows suitable for shutters are the smaller ones. The other one in front is much too large. Each shutter should be half the window's width whether functional or decorative. FWIW, this might be helpful when it comes to the shutters. https://www.lifeofanarchitect.com/residential-architecture-101-shutters/