Sounds like one of the newly coined "Woodward 5" communities might be a good fit: Ferndale, Pleasant Ridge, Huntington Woods, Royal Oak, and Berkley. All are in Oakland County but have older, nice housing stock.
Ferndale would be my biased choice of those; you can get downtown via Woodward or I-75. Contrary to Gnome's dire warnings for everything not Birmingham, it's 'urban' and safe. Retail, dining, bars, and other things to do within walking distance from just about every neighborhood.
If you're looking for Detroit options, you might check out houses in the nicer portions of East English Village [[I'd look between East Warren and Mack). You might be pleasantly surprised. There are other more expensive neighborhoods as well and some good condo options in greater downtown, as mentioned earlier.
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