Jennifer Cummings, Broker Associate

Jameson Sotheby’s International Realty

Jennifer Cummings has established herself as a consummate professional in the Chicago area through her steadfast commitment to her clients and love of real estate. Dedicated to her customers and results driven, Cummings is a broker associate at Jameson Sotheby’s International Realty who works with buyers, sellers and investors of all types, helping them with various kinds of properties, including single-family homes, condominiums, multiunit buildings and more. With 14 years of experience, she specializes in the neighborhoods of Wicker Park, Bucktown, Ukrainian Village and West Town.

Cummings moved to Chicago more than 20 years ago when she relocated from Vancouver, British Columbia, to run the Midwest office of a multinational media company. Now a dual citizen, Cummings got to know Chicago intimately through her job at the time, as well as her own personal real estate ventures, including various property purchases and renovations. Driven by a love of architecture and design, her affection for Chicago’s diverse and beautiful neighborhoods, and her own experiences as a buyer and seller, Cummings took the leap to become a broker. Her years of experience in the fashion and media industries helped her make the transition. “I thought I could use my past professional experiences of building and growing a business and developing strong client relationships and turn them into a new career in real estate,” she says.

Cummings has successfully navigated herself and her clients through various obstacles, including the housing and economic crisis of 2008 and the COVID-19 pandemic. She tries to make the selling and buying process as easy as possible for clients, working hand in hand with them to build and execute the best strategy to achieve their goals. “I’m their advocate every step of the way, no matter what challenges may come,” she says. “Being committed to my clients and doing everything humanly possible throughout the process, no matter what is thrown at me, is probably what I am most proud of.”

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