If you do the wood fence, I would grass up to it on the inside, and landscape the street side and the front foundation. I wouldn't fool with a retaining wall. I'd consider painting your front door red or black too. Can't tell if the shutters are green or black, but I would have them black and door red. Certaiinly need some softening on that left corner--it seems off balance.
Landscape management, design, and installation
Horticulturalist with Specialization in Landscape Management
25 years old 7 years in business ownership