ELEVATED BY DESIGN

Charlie Wood and Lauren Mitrick Wood lead The Olive Well Team at Compass, delivering design-forward, strategy-driven representation across Chicago and the North Shore. Known for their polished execution and relationship-first philosophy, they pair data-backed insight with an intuitive understanding of how exceptional homes resonate with discerning buyers.

What trends are shaping the high-end real estate landscape right now?
Wellness and entertainment are major drivers at the high end, with buyers prioritizing in-home gyms, saunas, cold plunges, and golf simulators alongside spaces designed for hosting. Seamless indoor-outdoor living—pools, patios, fire pits, and generous entertaining areas—continues to define today’s luxury market.

How does representing exceptional homes differ from traditional residential sales?
Representing exceptional homes requires a higher level of discretion and a more nuanced approach to showcasing upgrades and craftsmanship. Every decision—from marketing to buyer outreach—is tailored to highlight what truly sets the property apart.

What sets your approach apart when working with high-net-worth clients?
Our clients expect a confident, well-defined strategy, grounded in data, market insight, and experience. Just as important, we value building genuine relationships—bringing ease, humor, and connection to what can otherwise be a high-pressure process.

What’s one standout transaction that reflects your expertise at the high end?
One standout transaction was 180 DeWindt in Winnetka, where our clients navigated a competitive multiple-offer situation with a decisive, well-crafted strategy. The home was a true showstopper, with a comprehensive renovation where no detail was overlooked.

What advice would you give to agents aspiring to work in the luxury space?
Know the inventory inside and out by touring homes, attending open houses, and understanding the data behind them. Just as important, pay attention to the details and show up prepared, polished, and professional, because even something as simple as a clean car reflects respect for the client and the homes you represent.

The Olive Well team is with Compass’s Chicago office, 1643 N Milwaukee Avenue, OliveWell.com, @charliewoodcompass, @lmitrickwood.