The Chicago real estate market attracts professionals from many backgrounds, but few combine performance skills and personal engagement like Sherry Watkins, Real Estate Broker Associate at Baird & Warner. A professional opera singer who moved into real estate during the pandemic, Watkins has found her two careers reinforce each other in practical ways.
Watkins earned her real estate license when the pandemic halted live performances and left entertainers without work. “As a professional singer, I wasn’t working very much,” she says. What began as a necessity has evolved into a successful part-time career, although balancing both roles remains a challenge.
“I’m actually still doing opera. I have a show tonight,” Watkins says, underscoring her ongoing commitment to both fields. “There are certain times a year I’m super busy with the opera and don’t have time for clients. This 2025 was my best year in real estate, but it was basically the first six months of the year that I was super busy, and then the past few months have been opera.”
She also discovered she was not alone in this path. “I’m not the only professional singer who’s a real estate agent. There are others, even in Chicago. I know about five others.”
Watkins draws on more than just stage presence in her real estate practice. “You have to be social, good with people. Confidence is one of those things,” she says. Her experience includes negotiating union contracts for performers, which provided a strong foundation for her real estate negotiations.
These skills shape her approach to client service. “My focus is on people,” Watkins explains. “I tend to represent more buyers than sellers because I like to get to know people and what they’re looking for. I feel like a home is really personal, so the human connection is important to me.”
Her people-first approach is central to her negotiation style. “One of the skills I have with connecting with people is that it also helps me get to know the other side of the negotiation and try to navigate the transaction so that everyone’s happy.”
While many agents rely on market statistics, Watkins prefers to learn neighborhoods through direct experience. “Some real estate agents are very statistic-heavy. I get to know an area by going to restaurants and having cocktails. My approach is very social.”
This method has helped her identify what she sees as overlooked neighborhoods. Living in Printer’s Row, a historic area south of the Loop, Watkins promotes its potential to buyers.
“Printer’s Row is actually one of the oldest, most historic areas in Chicago. It started as an area of buildings for printing newspapers, magazines, and maps in the late 1800s,” she explains. “This neighborhood is full of artists. It’s very diverse and has maintained a serious historic feeling about it.”
She notes that residents tend to stay long-term: “People who come to this neighborhood don’t leave—it kind of sucks you in, and everybody just seems super comfortable here.” For buyers, Printer’s Row offers relative affordability and proximity to downtown.
Watkins addresses current market conditions directly, especially regarding interest rates. She works to correct clients’ expectations shaped by the unusually low rates of the pandemic.
“The interesting thing with young people is that COVID just happened recently, and the interest rates we had during COVID are not normal,” she says. “I think people got this feeling like, ‘Well, I’m only going to buy if the interest rates are like 3% or 3.5%,’ and that’s just not realistic.”
She provides historical context to help clients adjust: “Over history, there used to be interest rates in the twelves. So currently, if you can get an interest rate of 6.5% or 7%, it’s not that bad.”
Rather than advising clients to wait for ideal conditions, Watkins emphasizes individual readiness. “What I tell people is the best time to move is when you’re ready. Life happens, and if you’re ready to make a move, do it.”
On buying versus renting, Watkins is clear in her preference for ownership. “I always encourage someone to buy rather than rent. It’s just a better investment,” she says, especially given Chicago’s rental market.
“Especially in Chicago, rent is really high, and you’re basically paying someone else’s mortgage or someone else’s taxes. So it’s always better to buy if you can, in my opinion.”
She recognizes, however, that renting suits certain needs: those unsure about staying, frequent travelers, or people building credit. Still, she sees renting as temporary: “I always think of renting as a temporary thing for you to build your credit and establish a history of paying your bills on time and all those things that you need to do to qualify for a mortgage.”
Watkins reports that well-priced homes in desirable areas move quickly. “In my neighborhood, places move pretty quickly if they’re priced right, just because this is a desirable place to be,” she says. “If it’s priced right, you should get a buyer within 30 days.”
She also points out Chicago’s pronounced seasonality. “Right now is a slow season. People are getting ready for the holidays, and they just don’t want to deal with something like buying or selling a home right now. But come January, February, and then of course in the spring, there’ll definitely be a lot more inventory out there.”
Watkins responds to negative press about Chicago by highlighting the city’s strengths. “For all the negative press that Chicago gets, the people who are here or know anything about Chicago know that it’s a great place to live,” she says. “It’s still one of the best cities in the world, in my opinion, and most people know that and understand that.”
She acknowledges that big-city crime exists, but keeps perspective: “If you’re in a big city, there’s going to be crime. It’s just a way of life, but I don’t feel unsafe here at all.”
Although Baird & Warner provides the latest technology and AI tools, Watkins relies more on direct interaction. “Personally, I hate technology, so I know that I have to use it, so I do what I have to do,” she admits. “I prefer real intelligence—my own brain.”
This preference shapes her marketing as well. “If I’m selling a home, I will write my own description of the home because I have a creative side to me. That’s another part of being in the entertainment industry—I’m a creative person.”
Watkins is expanding her presence on social media, focusing on local businesses and highlighting her ties to the arts community. Her client base is diverse, including first-time buyers, relocating professionals, and seniors moving to new living arrangements. Her approach centers on building relationships and providing candid advice about market realities.
Her career shows that in real estate, as in opera, authentic performance and genuine connection—whether in a concert hall or a home showing—are essential for lasting success.
For those considering the Chicago market, Watkins offers both professional guidance and the outlook of someone who chose to make the city home, finding value in its neighborhoods and helping clients navigate changing conditions with realistic expectations.
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