Debbie Cali

Trusted guidance shaped by experience, driven by care.

With more than 25 years of experience running a successful insurance brokerage in Chicago, Debbie Cali brings a calm, knowledgeable, and client‑first approach to real estate. Her background has shaped her into a trusted advisor—someone who understands how to protect her clients’ interests, navigate complex details, and guide decisions with confidence and care.

After selling her brokerage, Debbie is embracing an exciting new chapter, transitioning from city life to Indiana while bringing her deep expertise into residential real estate. Having owned homes in Harbor Country since 1995—including properties in New Buffalo and Long Beach—Debbie offers firsthand knowledge of the market and a genuine connection to the communities she serves.

For years, Debbie and her family have spent weekends and summers enjoying all that Harbor Country has to offer, from its beautiful beaches to its welcoming neighborhoods. That long‑standing experience, paired with her professional background, allows her to help clients see both the lifestyle and the long‑term value in every property.

As a member of The Dawn McKenna Group, Debbie is passionate about helping buyers and sellers feel informed, supported, and confident at every step of the process. Whether assisting someone with a first home, a second‑home retreat, or a move into their next chapter, Debbie is dedicated to delivering thoughtful guidance and exceptional service throughout Long Beach and the surrounding areas.