About Cait Berry

Cait

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.

Cait Berry is a lifelong Madisonian, sixth-generation local, and founder of Insiders Realty—a boutique team helping people buy, sell, and relocate across Dane County with expert guidance and a personal touch. Her family helped shape neighborhoods like Shorewood Hills, Westmorland, and Sunset Village, and today Cait brings that legacy full circle with honest advice, deep local insight, and a straightforward approach that puts her clients at ease.

In 2024, Cait and her team helped more than 50 families move, closing over $25 million in sales. Clients—whether relocating for work, upsizing for their next chapter, or searching for the right school district—appreciate her responsive communication, strategic pricing, and ability to make complex decisions feel clear and manageable.

Her Inside Madison Relocation Guide is a free resource filled with neighborhood insights and lifestyle tips—from school zones and walkability to the best coffee shops, local parks, and hidden gems—designed to help buyers feel like locals from day one. Cait also shares her expertise on YouTube in her series Inside the Home Buying Process and Inside the Home Selling Process, giving buyers and sellers step-by-step guidance before they ever set foot in a home or sign a contract.

Sellers benefit from Cait's thoughtful listing prep, lifestyle-focused marketing, and smart negotiation that consistently delivers strong results. A mom of three and lifelong resident of Madison, Cait sponsors Fetch Wisconsin Rescue and Westmorland Summer Nights, and never misses a Saturday at the Farmers' Market.

 

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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