A little bit about me...
Charlie Wills is the founder of The Wills Agency, built on a simple belief: real estate is about people first—and property second.
With over 21 years of experience and deep roots in the Madison area, Charlie has built his business around delivering a level of service where clients never feel alone, underprepared, or unsure during one of the biggest decisions of their lives. Whether buying, selling, or investing, his focus is simple—elevate the experience, protect the outcome, and build relationships that last well beyond the transaction.
Charlie’s expertise spans residential and condominium sales, new construction, investment properties, land development, luxury homes, and property management. In December 2024, he launched The Wills Agency to create a more intentional, relationship-driven model—one that prioritizes long-term impact over short-term transactions. In addition to serving clients, he coaches and mentors agents to build sustainable, referral-based businesses rooted in trust and service.
Outside of real estate, Charlie is deeply committed to the community. He serves as Board President of 100 Men of Dane County, an organization focused on elevating children from survival to significance, helping raise over $2.4 million for local youth initiatives. He also supports organizations including Coaches vs. Cancer, Easter Seals, the Tellurian Foundation, and the National W Club.
A longtime Madison resident, Charlie lives with his wife Crystal and their two children, Grant and Charlotte. He is a graduate of the University of Wisconsin School of Business, where he was a four-year basketball letterman, team captain, and part of the 2000 Final Four and 2002 Big Ten Championship teams—experiences that continue to shape his leadership, discipline, and team-first approach today.
With over 21 years of experience and deep roots in the Madison area, Charlie has built his business around delivering a level of service where clients never feel alone, underprepared, or unsure during one of the biggest decisions of their lives. Whether buying, selling, or investing, his focus is simple—elevate the experience, protect the outcome, and build relationships that last well beyond the transaction.
Charlie’s expertise spans residential and condominium sales, new construction, investment properties, land development, luxury homes, and property management. In December 2024, he launched The Wills Agency to create a more intentional, relationship-driven model—one that prioritizes long-term impact over short-term transactions. In addition to serving clients, he coaches and mentors agents to build sustainable, referral-based businesses rooted in trust and service.
Outside of real estate, Charlie is deeply committed to the community. He serves as Board President of 100 Men of Dane County, an organization focused on elevating children from survival to significance, helping raise over $2.4 million for local youth initiatives. He also supports organizations including Coaches vs. Cancer, Easter Seals, the Tellurian Foundation, and the National W Club.
A longtime Madison resident, Charlie lives with his wife Crystal and their two children, Grant and Charlotte. He is a graduate of the University of Wisconsin School of Business, where he was a four-year basketball letterman, team captain, and part of the 2000 Final Four and 2002 Big Ten Championship teams—experiences that continue to shape his leadership, discipline, and team-first approach today.
"Charlie and Jen did a wonderful job and made selling my condo seamless! Charlie helped me buy my condo back in 2021, so when it was time to sell, I knew I could reach back out to him. My schedule during this time was pretty busy with finishing school…
"Worked with Jen Fenster throughout my buying process and let me tell you she’s been a wonderful part of the whole experience. I cannot thank Jen and the Wills Agency for making my first buying experience a joyful and exciting one!"
"It’s hard to capture in words how grateful we are to the Wills Agency! They made our huge transition of selling our home of 14 years and buying a brand new home feel so smooth and quite fun! Charlie and Jen treated us with genuine care and respect, …
"We have utilized Charlie and his team a few times and would highly recommend their expertise and services. I live out-of-state and the sales of our properties required a lot of communication and access to his network of professionals. They knocked it…
