Dreading the office after nearly a decade as a civil defense attorney prompted a career pivot for Jennifer Riccolo DeBower that began with a personal renovation project. Converting a local two-flat into a family home alongside her husband sparked a passion for residential real estate. Realizing that building a solid client base in sales required full-time dedication rather than a part-time commitment, she left the law to focus entirely on property advisory.
Now a real estate advisor with @properties Christie’s International Real Estate, DeBower works Chicago’s downtown area and North and West sides — Wicker Park, Bucktown, East Village, Logan Square, Lincoln Park and River North — along with surrounding suburbs. Her clients range from first-time buyers and downsizers to luxury buyers and investors.
Her litigation background provides a distinct advantage, allowing her to analyze transactions from every perspective, spot potential issues early and negotiate terms in writing. This protective approach anchors her referral-driven business, which relies heavily on a network of former legal colleagues, neighbors, long-term friends and repeat clients. She operates solo but leverages a trusted circle of attorneys, lenders, stagers, inspectors and contractors for her clients.
DeBower earned the @properties Road to Rolex award for annual sales exceeding $10 million in 2020 and has been named a Chicago Association of REALTORS® individual top producer each year from 2021 through 2025. RealTrends ranked her in the top 1.5% of agents by volume in 2024 and 2025, and Chicago magazine included her among the top agents in the city in 2023.
Having lived in Chicago since arriving for law school in 2001, DeBower has moved from the Gold Coast through Wicker Park, Bucktown and East Village. Raising children through the public school system, attending local fitness studios and joining neighborhood groups gives her the hyperlocal insight needed to pair clients with areas that fit their lifestyle.
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