The Flanagan Group

The Flanagan Group


30 Green Bay Road
Winnetka, IL 60093

We established The Flanagan Group in 2019 in order to expand our business across the North Shore and Chicago. Our partnership allows our clients to utilize our in-depth and lifelong knowledge of the Chicagoland marketplace, which is matched by our tireless work ethic and attention to every detail. This expertise benefits our clients not only locally, but nationally and globally as well.

Real estate is in our blood. Annie carries on the family tradition of excellence in residential real estate that was started in the 1970's by her mother, a successful real estate broker in the greater Milwaukee area, while Maddie worked alongside her grandmother in Winnetka and the North Shore in the early 90's doing showings and open houses.

Outside of work, we both have our own busy personal lives. Annie is a wife of 25+ years with five active and successful children. She loves to spend quality time with her family, especially attending her kids' sporting events, playing paddle tennis, running, cooking and being an avid philanthropist. Maddie is recently married and enjoying starting her own family in Lincoln Park. She enjoys traveling, trying new restaurants in the city, working out and spending time with her parents and 4 siblings.

The Flanagan Group truly understands the joy and happiness your home can bring – that's why it's our mission to help you find the house that's right for you and sell the home you and your family have cherished!

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