While working full time at her sales job, Ann Connolly decided to buy an apartment building and pursue a real estate license for a side career. Her husband was a builder, and after her two sons entered school, Connolly went into real estate full time. A broker with Dream Town Realty, she continues to bring skills from her early years into her business. “I learned how to run meetings, interact with clients, listen to requirements and find solutions,” she explains. “Another important skill is project management, as much of real estate is managing the transaction and moving it forward.”

A Chicago native, Connolly now lives in North Center by Lincoln Square, two of the primary neighborhoods she covers. In the industry for 14 years, she just celebrated her best year with over $15 million in sales and 32 transactions. She also got licensed in Florida and started closing deals there. Described as down-to-earth with excellent follow-up, clients say working with her is similar to spending time with a knowledgeable friend. “It’s important to really listen and understand my clients’ needs in order to find them the perfect home,” she maintains. “I never want to let a client down, so I always go the extra mile, treating each one like a member of my family.”

A supporter of Misericordia Home in Chicago, Connolly was named a top producer by the Chicago Association of Realtors in 2009, 2010, 2012, 2013, 2015-2017 and 2021. “I value family above everything else,” she declares. One of seven children, her father is a retired Chicago fire chief. Her husband, Liam O’Connor, is one of 11 children and immigrated to the city with $100 in his pocket at age 19. He decided to become an American citizen on 9/11.

A proud mother of two grown sons, Connolly was also a state volleyball champion at Mother McAuley High School and competed in the Final Four three times at the University of the Pacific. Ever the competitor, she is currently taking golf lessons to improve her game.