2025 Who's Who in Chicagoland Real Estate

Sarah C. Jaffe, Senior Broker

Cross Street Real Estate

Five years ago, Sarah Jaffe was an events manager for a public-policy think tank when the pandemic hit and created the opportunity for a career pivot. After many conversations with loved ones who know her best, she decided to consider a profession in residential real estate. Now well into a flourishing career, she can’t imagine doing anything else.

Jaffe is an expert on the West Side, where she shares an East Village loft with her partner, Sam. She also does a lot of business in the highly sought-after Lincoln Park and Lakeview neighborhoods. Though she admits her work can be exhausting, she truly enjoys what she does. “I love so many things about it,” she says, highlighting “the ability to be a trusted resource for people making arguably the biggest financial decision of their lives … and the opportunity to connect with people from all different walks of life.”

Valued for her responsiveness, expertise and negotiation skills, Jaffe is proud to have nearly doubled her business from 2023 to 2024. She’s a full-time sales leader and partner in Cross Street Real Estate’s Sales Division, which she and three colleagues have grown through their collective effort.

Having experienced significant personal and professional growth in the past five years, Jaffe applies what she has learned to create lasting connections with clients. “My ability to empathize allows me to build deeply personal relationships while remaining professional,” she shares. “Consumers deserve to work with a broker who can understand their specific situations and needs.”

Jaffe is a world traveler with a passion for photography and is currently busy planning her wedding. She is invested in the local community and remains involved with the nonprofit Cara Collective, which helps develop inclusive employment pathways. A vintage-furniture enthusiast, she’s always eager to share vendor recommendations and finds joy in curating home and personal-fashion looks.

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