Regan Grabill

Regan Grabill is a Chicago real estate broker with Second City Agents, helping buyers, sellers, investors, and those relocating confidently navigate Chicago's ever-changing real estate market. She is known for her personalized approach, strong negotiation skills, creative marketing strategies, and commitment to making every client feel informed and supported throughout the buying or selling process.

Marketing isn't just part of her job—it's her background. Before transitioning into real estate, Regan built a career in marketing, advertising, user experience, and market research after earning degrees in Interactive Media Studies and Entrepreneurship from Miami University (Ohio). Today, she combines that experience with deep market knowledge to give her clients a competitive advantage.

In today's market, getting a home sold takes more than putting it on the MLS. It takes thoughtful pricing, strategic marketing, compelling storytelling, and skilled negotiation. That's where Regan thrives. She creates customized marketing strategies designed to maximize exposure, attract the right buyers, and deliver the strongest possible results.

Since launching her real estate career in 2022, Regan has helped clients buy and sell homes across Chicago—from first homes and luxury condos to investment properties and relocations. She believes every client deserves a strategy tailored to their goals because no two moves are ever the same.

Regan specializes in Chicago's most sought-after neighborhoods, including Fulton Market, West Loop, River North, Gold Coast, Old Town, Lincoln Park, Lakeview, Bucktown, Wicker Park, and West Town. Having lived in several of these neighborhoods herself, she provides firsthand insight into the lifestyle, market trends, and opportunities that help clients make confident decisions.

Above all, Regan believes real estate is about relationships. Her clients appreciate her responsiveness, honesty, attention to detail, and ability to make what can feel like a stressful process both seamless and enjoyable. Whether buying, selling, investing, or relocating, Regan is committed to delivering exceptional service long after closing day.

Outside of real estate, Regan enjoys traveling, playing pickleball, taking classes at Barry's Bootcamp and Ritual Hot Yoga, cooking, and exploring Chicago's incredible restaurant scene with friends and family.