I love the color of your home. If it were my home I would invest my money and effort in the landscape.

https://www.remodelaholic.com/ranch-home-curb-appeal-real-life-rooms/

Your house has a wonderful cottage look, so I would choose a color rather than a neutral (white, gray, beige). I like the existing red paint, but if you want to go lighter, here's a yellow and gray-blue paint for comparison.

click on photo to enlarge

There is a house on my block that is stained Redwood. The father of the current resident built the house in the 50s, so it is been in the family almost 70 years. He used mahogany siding with stain & it looks great to this day.

In my town inhabited by lots of creative-class types your house would be considered to have curb appeal already thanks to its charmingly retro color scheme and cozy ranch architecture. If it aint broke.... Maybe some freshened landscaping would be all the freshening you reallly need?

This is more a question than a statement - is stained and oiled redwood even able to be painted? Redwood is like cedar an oily wood (which is what gives it its weather resistant quality) so it would need special prep work to get paint to adhere. If it was me I would consider whether trading oil stain for paint would lead to more maintenance and more headaches.

Appreciate the feedback! Excellent comments. Still not sure what will be decided since it is more a family group decision...which makes it tougher. I've heard Sand Castle, Cottonwood and Summer House Beige (all Sherwin Williams colors). Tomorrow it could be something else. Depends on which way the wind is blowing.

@Debbie Downer, good question on stain!! We are hiring a painter to do the job and they are aware of what needs to be done. Concerns are valid ones for sure. The older we get the less maintenance we desire to do.

@wiseca9 the images you did help. I tried to do similar ones and they didn't come out as good as yours.

@Jennifer Hogan and @Debbie Downer I am sure whatever gets picked once the house is painted there will be a desire to change some landscaping. That has changed through the years and I am sure it will again. It used to have bushes throughout. They can get out of hand over time.

@mindshift honestly that is what is driving the possible color change. It is one of the, if not the, darkest homes in the neighborhood. It does make it easy to tell people how to find us. The trend today seems to be lighter colors. Many homes have gone to vinyl siding or painted different colors than original when built.

I think ultimately once a color is decided (which it hasn't) and it is painted, it will look nice since it is long overdue. I need to post pictures here when it is all said and done.

I like your house, but I can see why you might want a change. What I see is very prominent, different size windows against the red body and I find it distracting.

I suggest painting your house the exact white of the windows.

My ranch house is white, and the paint store recommended B.M. Soft Gloss for the finish.

Posting this image for inspiration. Love the pergola.

Hard to tell from the photos of your house, you might want to consider having the roof shingles washed.

Here's a couple of photos of your home in white and beige for comparison.

click to enlarge photo