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Annie Challenger

Broker Associate

As a life-long resident of the Winnetka, Annie has a comprehensive grasp of the area, the culture, and what makes this place feel like home. She loves the history, the “now” and the diversity of the local real estate. For her, it’s exciting to get a sense of a home’s character because it so often mirrors the residents, which is what intrigues her about real estate. She enjoys the consultative experience of matching individuals, couples, or families with the house of their dreams. Annie has raised six children through the New Trier school system and feeder schools. She would love to help others have the same opportunity for their families and realize the amazing lifestyle the North Shore has to offer.


Annie graduated from the University of Arizona and has travelled the world on Semester at Sea.  As much as she enjoys immersing herself in different cultures, she ultimately wanted to root herself in a great city. After seeing the world, she knew that city was Chicago. She is also an avid “foodie” and is passionate about keeping her finger on the pulse of great local restaurants. She applies the same intensity and energy to her professional life. It’s the love of helping people face challenges and achieving greater things that drives her. She has always worked in a sales-oriented capacity and stays active in the community whether it’s sitting on the PTA or volunteering.  In her spare time, Annie works alongside her husband, as a dog behaviorist. They work with local residents on basic training needs, develop therapy dogs for individuals, and teach dog safety classes in the neighborhood schools.


Annie has always been a top producer in her life’s endeavors. Whether someone is selling or buying a home, she is committed to ensuring a stress-free experience for her clients from beginning to end. It is her goal to provide the best possible outcome in finding a home that fits the needs for whatever stage of life someone is in.

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