Michael Dickstein, CEO & Co-Founder
Jody Dickstein, Co-Founder
For the team behind The Dickstein Group, a love of North Shore neighborhoods runs in the family. Michael Dickstein grew up in Glencoe and is the son of Jody Dickstein, who spent three decades building her own real estate career in the same town. He didn’t initially set out to follow his mother’s path, spending his early career as a software engineer before burnout pushed him toward a change. He joined his mother’s business, and something clicked. Today, he and his mother lead the team as co-founders, working the Glencoe, Highland Park, Winnetka and Wilmette markets that he has called home nearly his whole life.
Word-of-mouth recommendations and targeted digital systems that connect new buyers to the region fuel the majority of The Dickstein Group’s volume. The team’s hands-on knowledge comes from owning a local development firm that builds and renovates single-family homes, as well as managing a portfolio of multifamily city rentals — giving clients clear, practical insights on renovation costs and true property values. Clients describe the team as straightforward, easy to work with and unafraid of tough negotiations.
The Dickstein Group specializes in luxury and new-construction single-family homes, with a current listing on a $14 million Glencoe lakefront property. The team has been Glencoe’s top producer for five straight years, consistently closing $35 to $50 million in North Shore sales annually. Reflecting on his client approach, Dickstein shares, “I like to have an informal meeting and educate them on the local market, trends I’m seeing and strategies I’ve used to create success.”
In his free time, Dickstein follows his passions for mechanics and exploring nature. He enjoys road trips by car or motorcycle and spends holiday weekends on his boat. His family welcomed twins, Leni and Wesley, this past June — the proudest milestone of his year.
