About Maddie Cahill

With over a decade in the real estate industry, Maddie brings a rare blend of operational leadership, strategic marketing, and client-centered service to every facet of her work. As Director of Operations and Community Engagement at First And Main, she plays a pivotal role in shaping the company’s growth, culture, and brand.

Behind the scenes, Maddie helps to drive the systems, structure, and elevated experience that define First And Main. From refining internal processes to launching innovative marketing initiatives, she ensures that every detail is executed with intention and excellence.

At the same time, Maddie is a trusted luxury real estate broker known for her thoughtful approach and deep understanding of the market. She specializes in guiding clients through significant transitions with clarity, discretion, and a refined sense of strategy—delivering results while creating an experience that feels seamless and personal.

A firm believer that real estate is deeply connected to community, Maddie is deeply engrained in First And Main’s philanthropic and local engagement efforts. She has been instrumental in building partnerships, supporting local initiatives, and ensuring that a portion of every transaction gives back—reinforcing the company’s commitment to investing in the places its clients call home.