947 Garfield, Oak Park, 312-772-3257, waynebeals.com
If you're the type of home buyer with buckets of money to put down and the means to bid significantly over the asking price for that perfect West Loop loft or Logan Square two-flat, this is the real estate market for you. If you're not that person, be prepared to hustle—and to have an open mind. Real estate agent Wayne Beals might be based in Oak Park, but the man knows every corner of Chicago (and beyond) inside out, and he will patiently explore your housing options in any of them. Traipsing across the city with Beals is like embarking on a live-action history lesson, and examining a home with him is a learning experience even if you think you already know your fair share about vintage fixer-uppers. It helps that he's a native Chicagoan and a former contractor, and has served as a historic-preservation commissioner. But Beals's real gift is his combination of down-to-earth work ethic, sweet-natured calm, and tolerance for a client with Veuve Clicquot tastes on a PBR budget. The only downside to working with Beals is that, once you end up with something you adore, you no longer have an excuse to tour the city with him.
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