Cait Berry

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 dollars 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. 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.