As a third-generation North Shore native and second-generation REALTOR®, Stephanie (Siegel) Weisman has a deep passion for her community and helping people find their own slice of home within it. Bringing people together is what it’s all about for Stephanie—whether she’s sealing a deal or organizing a charity event, she has an uncanny ability to unite people.

Stephanie’s passion for real estate cultivated during her childhood. It was sparked by her grandmother, who was also a REALTOR®. “We used to drive around to open houses all over the North Shore for fun, and she would buy me Architectural Digest and Better Homes & Gardens like they were teen magazines,” Stephanie recalls.

In addition to her grandmother, Stephanie always looked up to her grandfather. She credits his thoughtful decision-making and emphasis on the importance of family for shaping how she conducts her business today. She recalls the wisdom he passed down from his father whenever he said, “Listen and you might learn something.” She applies it as a mantra today: to truly listen to her clients. To truly listen to what they say and sometimes, more importantly, what they don’t say, so as to truly understand their needs and deliver highly personalized service. 

While Stephanie showed a keen interest in real estate as a child, and even got her license after graduating from the University of Iowa in 2005, she didn’t commit to it as a career until 2020. Avoiding the crash of 2008, she pivoted into luxury hospitality sales where she oversaw and managed several sales teams for high-end hotels throughout Chicago. It was during this time that she learned the importance of client relationships and attention to detail—qualities that make her stand out in real estate today. 

Stephanie spent over a decade living and working in Chicago with her husband, David. It’s where they had their first child, Charlotte, and where the couple grew the most, both professionally and personally. While they enjoyed their time in the city, Stephanie was excited to return home to the North Shore to expand her family, adding their son, Reid; and start the kind of business she always dreamed about: real estate.

“Providing a place of comfort and stability for someone is what makes me passionate about this business. Homes will serve as a place of gathering on the holidays, a place to come together as a family, or even as an investment to help provide additional income. Getting to share in the process of ushering my clients into their next chapters of life is the most rewarding part of my business,” she says. 

As a proud member of the Arrow Home Advisors team with Compass, Stephanie uses her extensive experience in hospitality sales and management to procure a custom buying and selling experience for her clients. She sees every transaction as a step toward building a stable future for herself and family, while helping others achieve their dreams at the same time. For her, success is simple: it’s happiness—finding the balance of the professional and personal while making a difference in the lives of others. 

Stephanie’s passion for making a difference in the lives of others extends to her work as an alumni board member and fundraising chair of Camp Marimeta for Girls. Last year she had the honor of fundraising for Camp for All Kids, too, which provides scholarships to kids from under-resourced communities to experience overnight summer camp. She also just recently hosted a charity game night for Arrow Home Advisors and looks forward to doing more community events with her team. 

When Stephanie isn’t working, she loves taking food-driven travel excursions with David and the kids. They are currently on a quest to find the best pizza. Her guilty pleasures include period-piece dramas like The Great and Bridgerton. When it comes to music, she loves Billy Joel and Elton John. In fact, her very first concert was Elton John at seven years old. A newer obsession of Stephanie’s is the card game Canasta. 

With her roots firmly planted in the North Shore and her heart in creating meaningful connections and homes for her clients, Stephanie represents the ideal blend of professional expertise and personal commitment. Her dedication to family, love for community, and commitment to helping people carve out their own slice of home will continue to make her a beloved figure in the North Shore, further cementing her family’s longstanding legacy in the local community.