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Chicago To Naples

Real estate agent Dawn McKenna expands her Hinsdale success to Chicago and Naples.

For over fifteen years, Coldwell Banker’s Dawn McKenna has made a career out of listening to the wants and needs of her distinguished real estate clients. And indeed, it was one of their growing needs that resulted in a huge move outside the confines of the Hinsdale area for the well-known real estate broker.

“One of my clients came to me and asked me to get my Florida real estate license,” McKenna recalls of the day she began considering expanding her business to warmer climates. “She wanted me to fully represent her family’s transition from Chicagoans to Naples, Florida residents with a place in Chicago. As a homeowner in Naples and Chicago, I saw an opportunity to offer my secret sauce of expertise to both new markets.”

In July of 2017, McKenna launched the Dawn McKenna Group in downtown Chicago, Illinois Naples, Florida. “I was seeing a shift in my clients’ needs,” says McKenna, who is the No. 1 Individual Agent in Illinois among all agencies and the No. 6 Individual agent for Coldwell Banker Worldwide. “Dozens of my clients were downsizing from Hinsdale, buying a smaller condo in Chicago, and moving to Naples, Florida.”

And from that moment on, McKenna says her Chicago and Naples business has flourished. In fact, in less than six months, her team was named the No. 1 Small Team in Naples for Coldwell Banker.

“Naples offers a very laid-back lifestyle which meshes well with my clients,” says McKenna, who is part of the Luxury Alliance Group with Coldwell Banker, which is made up of the number 1 agent from every affluent city in the world. “I’ve owned a home in Naples for almost three years now so I personally love the lifestyle. Professionally, I knew I’d be able to offer a unique Midwestern perspective on the Naples market as a realtor in both Illinois and Florida.”

Yet, all growth comes with its share of growing pains. And yes, McKenna says she has had to learn to adjust to her changing workload.

“The biggest challenge was keeping up with the volume of business we generated from the very beginning, which is an extremely lucky position to be in,” she says. “We’ve been very strategic in our succinct, cohesive marketing and processes and we’re moving full throttle ahead.”

This business philosophy and the ongoing expansion of her business has ultimately helped McKenna’s clients in the long run. “I am able to bring buyers from all around the world and push listings in multiple markets,” she explains. “My clients are also used to the highest quality service if they’ve worked with me before. The expansion has allowed me to offer that quality of service in new markets.”

Are you interested in a possible move to the South, especially during the winter months ahead? Well, McKenna says now might be as good a time as ever to make the move. “In the Naples market, new developments are on the rise,” she says. “Our 22-unit new development listing in Naples, Eight Fifty Central, is already 91 percent reserved—all from clients in the Chicago area—and it hasn’t even hit the market yet!”

Dawn McKenna Group is located at 8 E. Hinsdale Avenue in Hinsdale, 630-546-3763 or [email protected].


We offer the highest level of integrity, expertise, and service. The Dawn McKenna Group is the #1 leading real estate team in the Midwest, Southwest Florida and Park City for Coldwell Banker. With offices in Chicago’s Gold Coast and Lincoln Park, Hinsdale, Lake Forest and Winnetka, Lake Geneva, New Buffalo, and on 5th Avenue in Naples, and Park City, the Dawn McKenna Group agents are ready to serve you everywhere you call home. Whether buying, selling or renting, you can count on our Local Expertise and Global Reach.

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