Whats on the roof? Take more and better photos. Landscaping will be the best option.

New roof, paint, landscaping.

Cute postwar cottage…

Looks like the roof will need to come first. A medium gray is a versatile choice. Does the house need new windows, front door and garage door also, or do they just need paint? A lot of different colors will go with a medium gray roof. Are you flipping or are you going to live there?

Transform it into what???

Replace the roof, paint and add landscaping.

Pick colors you will love.

I wouldn't change its fundamental look. New roof and rip out all the plantings and the porch decor, including the railing. If a handrail up to the porch would be helpful, just have one modern rail.

If the hardscape that defines the beds is in excellent shape and attractiive, keep it, but if not, rip it out. Paint the house whatever would be classy for the neighborhood, and then do new landscaping. I would go for all around low and floppy plants that are low-maintenence, drought resistant. I'd probably do low plantings on both sides of the walking path, extending some low greenery into the lawn in a with loose organic edge. Bit woodsy. Let the house float somewhat on low casual greenery. Add a rock here or there if it helps accent the footprint of the house and maybe gives a hint of zen.

I will wait for answers.

I love the green tones and stained wood on this inspiration photo, and think these colors would suit your house very well. These are Benjamine Moore colors.

Some visual to update

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