The Wills Agency

The Wills Agency Elevating people. Elevating property. Throughout his career, Charlie has established himself as a top-producing agent and leader in the industry.

A proud resident of Madison for over 25 years, Charlie has dedicated the last 20 years to providing exceptional real estate services. His expertise spans a wide range of markets, including residential, condominium, new construction, investment properties, development, land, property management, and luxury homes. He not only leads a highly successful real estate team but also coaches and mentors ot

hers in the field, sharing his passion and knowledge to elevate their success. Charlie is deeply committed to giving back to his community. He serves as an active board member and board president of 100 Men of Dane County, an organization dedicated to empowering children and fostering their growth from survival to significance. Under his leadership, the organization has raised over $2.2 million in just seven years. Additionally, Charlie supports various causes through his involvement with Coaches vs. Cancer, the National W Club, Easter Seals, the Tellurian Foundation, and other impactful community initiatives. Beyond his professional and philanthropic endeavors, Charlie has pursued his love for sports as a color commentator alongside Brian Butch and Matt Lepay for Learfield Sports and the University of Wisconsin Men’s Basketball team. A graduate of the University of Wisconsin Grainger Business School, Charlie was a four-year basketball letterman, team captain, and an integral member of the 2000 NCAA Final Four Team and the 2002 Big Ten Championship team.

🏡 A LOT is happening around The Wills Agency!We’ve had some exciting movement in the market lately.🎉 Accepted Offers... ...
09/03/2026

🏡 A LOT is happening around The Wills Agency!
We’ve had some exciting movement in the market lately.

🎉 Accepted Offers... We’re celebrating several buyers and sellers who are officially under contract!

👀 Coming Soon... We also have three homes getting ready to hit the market soon. If you’ve been thinking about making a move, this may be a great time to connect.

Comment HOME below and tell us which one caught your eye. We’ll send you more information!

We love being a resource for our community, whether you’re actively buying or selling or simply keeping an eye on the market.

09/02/2026

🏡 Buying a home is about so much more than the pretty pictures you see online.

When you're walking through a potential home, look beyond the finishes and think about the things that really matter:

📍 The lot and location
🏠 The layout and how it functions
🔧 The condition and mechanicals
✨ Updates and improvements
🌳 Curb appeal and how the home has been cared for
📈 Where the neighborhood is headed

A fresh coat of paint is great, but understanding the whole picture is what helps you make a confident decision.

Thinking about buying? We'd love to be a resource. We can walk through a home with you and help you think through the things you may not notice at first glance.

Save this for your next home tour and send it to someone who’s house hunting!

09/02/2026

One question we wish MORE BUYERS asked more often...
How will this neighborhood change over time?

Neighborhoods are always evolving. New developments, businesses, parks and infrastructire can all shape what daily life looks like years down the road.

One benefit of working with a local agent is that they've oftne watched these changes happen firsthand.

Watch until the end to see if Charlie can still knock down a hoop. Think he's got it? 🏀

🎒 Back to school means back to routines… and a new season of fun!With a new school year comes a fresh rhythm, new advent...
09/01/2026

🎒 Back to school means back to routines… and a new season of fun!

With a new school year comes a fresh rhythm, new adventures and plenty of opportunities to make memories together. We put together a few ideas to enjoy the season ahead. 🍂

🏃‍♀️ After School: Let the kids get those wiggles out with a playground adventure or an activity they love. (psst: Have you checked out Firefighters Memorial Park in Middleton? The littles will love it!)
🍦 Explore Madison: Discover a new walking or biking, or grab a sweet treat at a local ice cream shop.
🏈 Make Fall Memories: Head to a UW football game, visit a pumpkin patch, or find a new fall tradition for your family. is a family fav!
🏡 Stay Home: Sometimes the best nights are the simple ones: baking together, ordering pizza, watching a movie, playing a board game and enjoying a night at home.

There are so many great and small ways to make this season special. You don't have to plan something big. It's just about being together. ❤️

We put together this list of ideas to help you find a little inspiration for the weeks ahead.

Share this with a friend, fellow parent, or someone who's new to the Madison area and looking for ways to get out and enjoy the community!
Here’s to a great school year and a beautiful fall. 🍁

🍂 A Very Madison WeekendAugust is wrapping up, summer is winding down and somehow we’re already getting that first littl...
08/31/2026

🍂 A Very Madison Weekend

August is wrapping up, summer is winding down and somehow we’re already getting that first little taste of fall around Madison.

Here’s a peek at what our team was up to this weekend:

🌮 Jen enjoyed lunch on the patio at bartaco with family and friends. Because there are only so many summer patio days left!

🎃 Pumpkin Spice is officially back. And we are nothing if not basic. 😂☕️

🎡 Middleton Good Neighbor Festival brought all the classic fun.

🍝 A new spot at Hilldale: North Italia is coming to Madison.

❤️ Happy anniversary! Charlie & Crystal celebrated 13 years of marriage.

🥬 And a Whole Foods grocery run. Their produce is hard to beat. (Have you had The Sweetest Batch blueberries?!)

This is what we love about Madison. Great food, local traditions, beautiful neighborhoods, good friends, family, and plenty of reasons to get out and explore.

What did you do around Madison this weekend? We’re always looking for our next place to try!

🏡 Your home search just got a whole lot easier.See a house for sale while you're out driving? No need to remember the ad...
08/27/2026

🏡 Your home search just got a whole lot easier.

See a house for sale while you're out driving? No need to remember the address or search for it later.

With our app, you can find your exact location, explore homes for sale around you, save your favorites, share homes with your spouse or family, connect with your Realtor, and even schedule a showing... all in one place.

It’s local real estate information, wherever you are, whenever you need it.

Stop searching harder. Start searching smarter.


📲 Use the link in our bio to download the app and start your search smarter.

Very Madison Weekend ☀️🌽A little bit country, a little bit lake life, a little bit golf and a whole lot of summer fun. ❤...
08/25/2026

Very Madison Weekend ☀️🌽

A little bit country, a little bit lake life, a little bit golf and a whole lot of summer fun. ❤️

This weekend looked like:
🌽 Wisconsin cornfields
🍦 A Dairy Queen Blizzard
🚤 Jet skiing on beautiful Lake Mendota
🍽️ Checking out the new Atico Lounge
🔐 A little friendly competition at an escape room
⛳ The Maple Bluff Country Club Member-Guest golf event
🏌️‍♀️ Topgolf fun
👶 And Sarah’s grandbabies soaking up every bit of that beautiful Wisconsin sunshine

From the cornfields to the lake and everywhere in between, there’s just something about summer in Wisconsin.

This is what a Very Madison Weekend looks like. ❤️

08/19/2026

Moving to Madison, WI? Let us help you feel at home before you even arrive. 🏡

Relocating is more than just finding a house, it’s finding the right community, the right neighborhood and a place where you can build your next chapter.

At The Wills Agency, we specialize in helping relocation clients navigate every step of the process. From virtual home tours and neighborhood insights to connecting you with trusted local resources, our goal is to make your move as smooth and stress-free as possible.

Whether you’re moving for a new job, family, a lifestyle change, or simply because you fell in love with Madison, we’re here to help you make a confident move.

📍Moving to Madison, WI?
🏡 Madison Relocation Experts
🤝 Local guidance. Personalized service. A team that cares.

Have questions about relocating to Madison? Drop them below. We’d love to help!

08/19/2026

A day in the life of helping relocation clients find their next home 🏡✨

Four homes. Four different possibilities. One big goal: finding the right fit.

Every buyer’s journey is different. Some homes check the boxes. Some surprise you. Some help you realize what you truly want (or don’t want) in your next home.

From touring neighborhoods to exploring layouts, finishes and the little details that make a house feel like home... this is the fun part of the home buying process.

Thinking about buying a home in Madison, WI or the surrounding areas? Having the right real estate team by your side can make all the difference. We’ll help you navigate the market and make confident decisions every step of the way.

📍Madison WI Real Estate
🏡 Home Buyer Representation
🔑 Your next chapter starts here

Address

5609 Medical Circle, Suite 202
Madison, WI
53719

Opening Hours

Monday 8am - 5pm
Tuesday 8am - 5pm
Wednesday 8am - 5pm
Thursday 8am - 5pm
Friday 8am - 5pm
Saturday 8am - 5pm

Telephone

+16082208186

Website

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