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Jennifer Cummings, Broker Associate

Jameson Sotheby’s International Realty

Appreciating great architecture and design, Jennifer Cummings became interested in real estate when purchasing and renovating her own investment properties. “In my spare time, I would go to open houses, design centers and The Merchandise Mart to see the latest trends, always dreaming of my next project,” Cummings recalls. “I decided to transfer my past media career experience of building and growing a business and developing strong client relationships into a new life in real estate.” Now with 17 years in the industry, she is a broker associate with Jameson Sotheby’s International Realty.

Specializing in residential real estate, Cummings covers neighborhoods throughout Chicago. “I have lived in more than 16 neighborhoods throughout the city, which gives me a unique perspective,” she shares. Last year was a record year for her due to relationships with loyal past clients and her amazing network. Though last year also brought its challenges, Cummings doubled down on her resilience and problem-solving ability. Known for being hands-on, she spends significant time working with clients to prepare homes for sale—be it through cosmetic or other updates, repairs or staging. This led to her 2022 listings selling in under a month and for nearly 99 percent of their list price, on average. “We have one opportunity to make a great first impression to prospective buyers, so this prep work is paramount,” Cummings says.

With a relationship-based business posture, Cummings relies on repeat business and introductions from past clients for growth. “My goal is to make selling or buying as easy as possible for my clients while also having a little fun along the way,” she says. She is a member of Women Belong, a networking group that supports businesswomen.

Cummings moved to Chicago from Vancouver, Canada, over 20 years ago and is proud to be a dual US-Canadian citizen. An avid fan of British crime dramas, she enjoys knitting, art and fashion, as well as traveling, cooking and curating events using her vintage china and silver collection.

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