Annie and Maddie Flanagan bring more to the table than your average real estate team. This aunt and niece duo are committed to family first—and determined to make their clients’ buying and selling experience as successful and seamless as possible.
The brokers formed their Winnetka concierge-level @properties team a little over two years ago and haven’t stopped since. Their mission is to consistently provide the highest level of real estate brokerage service for their clients. They have worked hard to create a highly personalized, full-service, boutique experience where their clients are their top priority. Their past professional experience along with their market knowledge, local expertise, innovative marketing, tireless work ethic, and dedication to niche markets are just a few of the things that set them apart.
Both Annie and Maddie grew up on the North Shore and know and love it well. Annie lives in Winnetka where she raised her five children. Prior to being in real estate, Annie worked in insurance and risk management, but real estate is in her blood—her mother has been in the business for forty years. Additionally, her brother is an interior designer and she’s always been drawn to that side of the business.
Maddie grew up in Evanston and currently lives in Lincoln Park. Prior to switching careers to real estate, Maddie worked for a retail clothing company and ran the wholesale part of the business.
“I was ready for a career change,” Maddie says about deciding to go into business with her aunt. “I’ve always been interested in real estate. Growing up on the North Shore, I was intrigued by all the beautiful homes. But also, I was turning thirty and this was something that I felt I could do long-term. Real estate is a career that allows you to have a balance of personal and workplace.”
Annie has worked in the real estate industry for over 14 years and has been with @properties for over two years. Even though she switched companies during the pandemic, she says her business has been stronger than ever. “I couldn’t be happier,” Annie says. She is especially appreciative of the constant support she receives from @properties management along with the technical and marketing support. “There’s always someone available to help and the systems are so much more advanced.”
Annie and Maddie have designed their business so that “one of us is always available,” Annie says. “It’s nice to have a team but more than that, we’re truly a hands-on team. I know that with many real estate teams, there’s usually the main person who may not be around a lot and all the other people are doing a lot of the work. In our case, it’s whoever is available is doing what needs to be taken care of.”
It is obvious that both Annie and Maddie are beyond grateful to be able to work together. When describing Maddie, Annie says, “I love her energy and enthusiasm. I love her positive attitude. But also I just love the fact that if she’s frustrated or something’s not going the way she wants it, she addresses it. I think our open communication makes for a successful team.”
Maddie too says that their partnership is so important to her. “I love that we can be collaborative. I have learned so much. It’s amazing that I can just pick up the phone and call her and ask a question about any sort of situation. There’s always something new presenting itself. Her experience is super valuable because she’s seen a lot of these scenarios before. So just being able to have her help me through different situations that come up is extremely beneficial.”
Their true strength is in their partnership. They both bring important and complementary qualities to the team. “Annie brings a ton of experience and knowledge from being in the business a long time,” Maddie says. “And I bring expertise in social media, marketing, and just bringing in fresh ideas. We have this nice synergy of Annie’s clients that are downsizing and looking to sell and I’m working with buyers who are looking to buy for the first time. So we’re working with lots of different clients, which I think makes us well-rounded.”
Well-rounded along with well-equipped and completely focused on making their clients’ dreams beautiful realities.
The Flanagan Group, 847-881-0200, is located at 30 Green Bay Road, Winnetka. Visit atproperties.com/agents for more information. Call Annie Flanagan at 847-867-9236 or Maddie Flanagan at 312-543-7853.