Whether guiding a first-time buyer, marketing a luxury listing or navigating a tough negotiation, Debra Dobbs brings the same level of care and intensity to each deal. “This isn’t just a job — it’s a calling,” says the award-winning Realtor with The Dobbs Group at Compass. “I’m grateful every day to do what I love.”

Dobbs entered real estate in 1984 after selling her gelato shop, Baci Gelateria. Michael Pickering, a Baci customer, encouraged her to earn a real estate license and work for him. She began with loft-conversion projects in the West Loop and, with Pickering as a mentor, grew her business from there.

“I’ve lived in Lincoln Park for over 30 years, which has given me an incredible connection to the neighborhood,” Dobbs shares. “But my passion doesn’t stop there. I also serve Lakeview, Gold Coast, Streeterville, Bucktown, Wicker Park, West Town, West Loop, Logan Square and Lincoln Square.”

Closing transactions throughout the city has allowed Dobbs to truly explore and appreciate the diversity of Chicago’s real estate market. “Every neighborhood has its own story, and I’m excited to share those stories with my clients,” she explains. “Chicago’s 77 neighborhoods are like little worlds within a larger world, and I understand them all.”

Constantly learning, exploring and sharing her love for Chicago with clients, Dobbs hosts a real estate podcast to provide listeners with market facts and updates. She’s also active on social media, highlighting neighborhoods, local businesses and her team’s listings.

Dobbs is no stranger to well-deserved accolades. Indeed, Compass Chicagoland inducted her into its Legends Society in 2025, FastExpert named her a 2025 Top Agent and CAR recognized her with a Gold Level 2024 Outstanding Sales Achievement Award.

Nicknamed “The Lioness,” Dobbs strives to be a fierce advocate who’s fully committed to her clients’ best interests and long-term financial success.