A Madison-based boutique real estate team helping buyers, sellers, and relocating families across Dane County.
We believe the right plan changes everything. Our team pairs deep Madison roots with a step-by-step process that makes even complicated moves, like buying and selling at the same time, feel manageable. Most of our clients are relocating to Madison, moving up to more space, or juggling a purchase and a sale at once. Each of them gets honest advice, quick communication, and a clear plan from the first conversation to closing day.
Strategy first. Local insight always.
Real estate feels a lot less overwhelming when you can see the whole path. Before you tour a home or list your own, we sit down with you to understand your goals, your timeline, and what a great outcome looks like for your family. Then we build a plan around it and explain each step as we go, so nothing catches you off guard.
Our clients range from families who have owned in Madison for decades to people seeing Dane County for the first time. What they have in common is wanting an agent who will tell them the truth and stay in their corner long after closing.
Cait Berry started in real estate in 2012 and spent most of her career as a solo agent before founding Insiders Realty in 2020. Today, our four agents serve buyers and sellers across Madison and Dane County, and every client still gets the hands-on, boutique service the team was built on.
We start with a plan, not a listing or a showing. Our team lives and works in Madison, and our founder is a sixth-generation Madisonian, so our advice comes from knowing these neighborhoods firsthand. In 2026, our listings sold for 101% of list price on average and went under contract in about 15 days. What that means for you? Our listings sold for 3% more than the average listing to sell in Dane County. Our listings sold in half the time of the other listings in Dane County too.
We guide buyers, sellers, and relocating clients across Madison and Dane County, with a strong focus on helping people navigate transitions thoughtfully, especially when buying and selling at the same time. Our goal is to make each step feel clear and manageable, whether you’re moving across town or across the country.
You'll work directly with one dedicated agent from start to finish, whether that's Cait, Ashlee, Stephanie, or Grace. Behind them, the rest of our team supports your marketing, paperwork, and deadlines, so you get one point of contact with a full team working for you.
We serve buyers and sellers throughout Madison and the surrounding communities, including Middleton, Verona, Waunakee, Sun Prairie, Fitchburg, Monona, McFarland, Oregon, and other Dane County neighborhoods. Because we live and work locally, we’re able to provide insight that goes beyond what you’ll find online.
Guiding clients through a double move is one of our specialties. We help you explore options, understand timing, and build a strategy that reduces pressure - often starting with securing your next home first so decisions feel intentional instead of rushed.
Our clients range from first-time buyers to longtime homeowners planning their next chapter. What they share is a desire for clear communication, honest guidance, and a thoughtful approach to one of life’s biggest decisions. We have sold properties ranging from $90,000 condos in the city to $3,000,000 lake homes.
We are all well-rounded and experienced in working with single-family homes, condos, vacant land, new construction and multi-family properties.
Every listing gets professional photography and a marketing plan built around the home and its neighborhood, shared across our social channels, YouTube, and agent network. For every home, we create cinematic listing videos that show buyers the life that comes with the house.
That conversation starts with understanding your goals and not market pressure. Some clients are ready now, while others begin planning months in advance. Our role is to help you explore your options so you can move forward when the timing feels right for you.
The first step is simply a conversation. We’ll talk through your goals, answer questions, and help you understand what a thoughtful plan might look like - whether you’re buying, selling, or still exploring your options.