"I grew up in real estate, and I thought all agents were crazy,” Cindy Windeler, REALTORⓇ and designated managing broker for Keller Williams Premiere Properties, recalls with a laugh. “I never wanted to be a part of it." 

Little did she know it, but Cindy would eventually become one of those “crazy” agents herself. Cindy was born and raised in a household where real estate conversations occurred daily: her mother, Pat Schmidt, was a dedicated agent for forty-three years.

Cindy’s perception of the industry at that time led her to choose a different path. She initially pursued a degree in special education, but after working as a ski instructor in Breckenridge, Colorado, she decided to volunteer for an adapted ski program—a decision that led to a rewarding career in special recreation, where Cindy found her passion in coaching adapted sports.

"I started the wheelchair basketball program at Western DuPage Special Recreation Association and coached many teams all the way to nationals," Cindy says. “One of my proudest achievements was helping to make wheelchair basketball a respected high school sport through our work with the Illinois High School Association’s Adapted Sports Committee.”

Cindy also coached power-wheelchair soccer, wheelchair dance, and many other adapted sports programs for people with physical challenges. She also worked with people with cognitive challenges and seniors.

As much as she loved her work, one day Cindy realized that she wanted to spend more time with her growing family and needed a career with a more flexible schedule. And after a stint with the vision program at the now Salt Creek School District 48, the demanding politics in education became a deterrent. Seeking change, Cindy turned to her roots. 

"I needed something more and I also needed to make more money, so in 2003, I began 'helping my mom' with real estate," Cindy says.

Fortunately for Cindy, she entered the market at an opportune time as many of her friends were buying their first homes. Her initial reluctance gave way to enthusiasm as she discovered a love for helping clients navigate the complexities of buying and selling homes. She obtained her license in 2005. 

“I quickly realized I loved meeting new clients and finding solutions [for them] for homeownership, and that I was able to be a resource to many, just like in my old career,” she explains.

Cindy’s mother, with her many years of experience and wisdom, was Cindy’s guiding force, and Pat’s reputation as a tough cookie who didn't tolerate nonsense, but also a very fair and great agent to work with, remains a source of pride and inspiration for her daughter.

“Unfortunately, my mom was forced to retire in 2018 due to dementia. She was known to be a super smart, hardworking, true professional who also had a little sharp tongue on her. That was funny to me because she’s always been such a nice lady, a true lady!” states Cindy. 

Mother and daughter moved to Keller Williams Premiere Properties together in 2010 and worked under the name PatandCindy. “Best decision we ever made,” adds Cindy. Even today, their dinner and family party conversations always include real estate, and they frequently pull Cindy’s sister, Caryn Prall, a successful businesswoman and REALTORⓇ, into the conversation.

Reflecting on her over-nineteen-year career in real estate and her leadership and mentorship role at her office, which she takes seriously, Cindy emphasizes that continuous learning is a key to success.

“I think about the level of responsibility I have to my team leader, my owners, the investors, and all my agents, and that can be a little stressful at times,” she shares. “I remain open to learning something new every day because success is learning, trying new things, and growing as a person.”

She works hard to help her agents connect as she knows being an agent can be lonely, especially if you are not on a team. Supporting and participating in events like Red Day, a day dedicated to giving back to local organizations, showcases Cindy’s never-ending commitment to service and her community. 

“I am pretty happy. As a REALTOR®, I get to work with awesome clients. I love meeting the executive as much as the first-time homebuyer, and I have no fear of making calls or interviewing for the next transaction,” she says. “As the managing broker, watching and supporting our new and veteran agents grow their businesses is an honor. With this market, I make myself available to teach agents how to find new business and for Sunday night advice calls about multiple-offer situations.” 

Cindy loves adventure and to have fun, especially with her husband, Fred; her two kids, now in their late teens and early twenties, Zoe and Nick; and two dogs. In addition to her immediate family, Cindy has four accomplished sisters, each thriving in their respective careers. With a strong emphasis on independence and self-reliance, Cindy's mother instilled the value of financial autonomy in all her daughters. As Cindy recalls, her mother's motto was, "A man is not a plan!" This guiding principle has clearly influenced Cindy's drive for success and the importance she places on charting her own path.

Cindy is often skiing, ice skating, biking, pickleball—anything outside, anything fast, anything new. She maintains a passion for Special Olympics, and some adapted-sport recreation programs like Buddy Baseball and wheelchair basketball.

Looking ahead, Cindy envisions staying in real estate but remains open to new opportunities. 

"I think I will always be in real estate, but in what capacity, I am not sure,” she says. “Do you ever think to yourself, ‘Where will I be in ten years?’ I think about it all the time, and it excites me.”

As Cindy continues to carve her path, she remains a beacon of inspiration for those around her, embodying the values instilled by her mother and the lessons learned along the way.