After spending nearly three decades in Chicagoland, Sherry Watkins transitioned from the stage to real estate in possession of a deep knowledge of the area and its neighborhoods. A longtime soprano at Lyric Opera of Chicago, she had already bought and sold several properties of her own when the pandemic prompted a career shift. Recognizing her natural talent for the real estate process and her passion for helping others, she earned her license and began representing clients across downtown Chicago and the surrounding communities.

Watkins is known for her calm presence and adaptability, and she brings empathy, candor and sharp negotiation skills to every transaction. Her approach is tailored and personable, focusing on clear communication and trust building. Whether her clients are first-time buyers, relocating professionals, luxury seekers or downsizing seniors, she meets them where they are and guides them confidently through every step of the journey. She works independently, which enables her to maintain a flexible schedule that benefits her clientele, and her business is driven largely by referrals and the broad network she cultivated during a career in the arts and decades of community involvement.

Watkins is a certified Seniors Real Estate Specialist and a certified Military on the Move and First Responders agent. She is a member of the Professional Women’s Club of Chicago and actively supports the arts through organizations such as Lyric Opera Stage Artists and Gilda’s Club. Her proudest accomplishments include building long-term client relationships and representing buyers in competitive situations, having most recently helped a close friend purchase a home after years of renting.

In her personal time, Watkins enjoys golfing, running, spending time with friends and hosting gatherings with her husband. She adores her two cats, Dewey and Zoe, and can often be found attending live music shows or jumping in for the occasional karaoke song.