About Cait Berry

Cait Berry, a real estate agent from the Insiders Realty team, is standing on a sidewalk wearing a beige sweater.

Agent Details

Meet Cait

Team Lead | REALTOR®

hey there

I'm a sixth-generation Madison real estate agent and I'm anything but old school.

I've been keeping it real in Madison, Wisconsin since 1986. I'm a real estate agent, the CEO of my little family, and the future host of an HGTV show (just manifesting that into reality). I am obsessed with social media marketing, impacting my client's lives in the best ways possible, and telling the tales of the wild world of Real Estate!

I specialize in helping awesome people move to, from and around the Madison Area and forging friendships along the way. I LOVE all things home and design - you should see my Pinterest board. A wealth of local neighborhood and community knowledge - I want everyone to love where they live. A total nerd when it comes to numbers - I love myself a good investment. I am equally a 2 and 3 on the Enneagram Personality Test - a helper who cares a great deal about relationships mixed with a high achiever with a contagious zest for life.

Small biz madison

I also am a huge supporter of local businesses and am the founder and operator of a social media community called, Small BIZ Madison over on Instagram. I create content to support local small businesses and bring awareness to around the importance of keeping our small business community thriving. It is also a great place for you to visit if you are interested to learn more about the great restaurants, shops, services and events that Madison has to offer.

Check out small biz madison

My story

i always knew real estate was my path...

Hello! Let’s talk about real estate, but not just any real estate—Madison real estate, which to me, is practically family. I’m not just working in Madison; I’m deeply rooted here, part of a lineage that spans six generations of local real estate professionals. My family has literally helped shape Madison, developing neighborhoods like Shorewood Hills, Sunset Village, Westmorland and Orchard Ridge - just to name a few. It’s safe to say that my love for this city and the helping people find home here runs in my veins.

Growing up, my playground was my dad’s real estate office. I’d flip through the property listing binder before the internet was a thing and tag along to open houses. By seven, I was pretty savvy about the ins and outs of selling homes, thanks to being my dad’s unofficial apprentice. Then, life threw us a curveball when I was ten—my dad was diagnosed with cancer, and we lost him nine months later. With him, our family’s real estate business seemed to pause, but my passion for real estate didn’t.

That tough time taught me resilience and deepened my commitment to continue our family legacy in real estate, blending tradition with a fresh perspective. I understand the emotional and practical sides of buying or selling a home because I’ve lived it for a good majority of my life.

12+ years in business later, I’m here to share that blend of expertise and genuine care with you. Whether you’re looking for your dream home, selling a cherished property, or just curious about what makes Madison’s neighborhoods unique, I’m your go-to. Together, let’s make your real estate experience memorable and successful, with a personal touch that feels like home.

 

The quiz

Sushi, Margaritas, Disney... Time to reveal a few of my obsessions. See anything we have in common?

1. FAVORITE FOOD

ice cream

2. VACATION OF CHOICE

caribbean cruise

3. COCKTAIL ORDER

mocktail

4. FAVORITE CITY TO VISIT

charleston, sc

5. GUILTY PLEASURE

sundara spa

6. FAV. WEEKEND ACTIVITY

brunch

NUMBER OF HOMES I'VE SOLD

300+

YEAR I GOT MY REAL ESTATE LICENSE

2012

BUSINESS THAT COMES FROM PAST CLIENTS OR REFERRALS

100%

TOP RANKING OUT OF 3,000+ AGENTS IN MY MARKET

1%

TOTAL SALES SINCE 2012

$90M+

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Let us use our expertise in the industry, paired with our local insiders knowledge to take all the stress of real estate off your hands, so that you can truly enjoy the process.

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