In Conversation with Dawn McKenna

Dawn McKenna, founder of the Dawn McKenna Group, is one of America’s most successful, creative, and sought-after luxury real estate agents. Her team, based in Chicago and Naples, is composed of area experts who bring exceptional perspective, talent, and insights to some of the country’s top real estate transactions. We chatted with her about everything from the Naples market (and her advice on where to start buying and selling) to her top spots to explore art and fashion locally.

How did you get your start in real estate, and what continues to fuel your passion for it after all these years? I love design and architecture and have been a real estate junkie since I was a little girl riding the CTA with my mother. I became an agent to buy a couch for my new home, but as soon as I sold my first home and saw the happy faces of the buyers and sellers, I was hooked.

 I truly enjoy when a deal comes together because it means happy buyers, happy sellers, and compensation for my efforts. Ever since forming the Dawn McKenna Group, I’ve added the love of seeing my team members experience the same fulfillment. We are all friends and care about each other, so their success is my success.

What drew you to the Naples market? The move to Naples resulted from increasing client demands matching my sense of the market. Over the last 10 years, a lot of my Chicago area clients headed to Southwest Florida for all or part of the year. Many asked for my advice, and I referred them to local agents in the hope that they would be treated the way I treated them. As the volume of requests accelerated and my disappointment with how they were treated increased, I realized I was missing a great opportunity to serve my clients at another crucial stage of their lives. Opening a Naples office was the only practical solution.

Give us some insight on your local Naples team. We have seven full-time agents in our Naples office. All of them are living and breathing the lifestyle we sell in Naples. Most of the team are born and bred Chicagoans who have facilitated the Midwest migration to Naples and understand where many of their clients are coming from and where they are going. Each team member brings unique experiences and qualities to the group. For example, Ardel McKenna was on the Board of Trade in Chicago, played football at Yale, and is an avid golfer. Kathleen Thanas has a golf background and specializes in selling the golf communities in Naples. That’s just two of the team members—each of them have a very unique background. No matter what you are looking for or interested in, we have you covered!

What listing have you had in Naples you’re most proud of, and why? The greatest satisfaction from a listing here in Naples is getting 850 Central. It was instrumental in establishing our group as the go-to for new development in Naples and has created another avenue to expand the DMG’s vision and brand.

Where do you see the Naples real estate market heading in the next five years? Regardless of the national metrics, Naples will continue to be big due to scarcity and demand.

When looking to list or purchase a home, where should one start, and how important is it to utilize the expertise of a real estate agent? The best way to start is to call your local expert. It is extremely important to utilize the expertise of a realtor as selling and purchasing homes requires judgment and experience.

 Honesty and experience up front prevents disappointment later on. For sellers, we price fairly based on sound analytics and don’t pull punches with needed cleanups, staging, and repairs.  For buyers, we combine the clients’ needs, wants, and budget, and set realistic targets. With the right expectations, our clients’ dreams are achieved because they are the product of an experienced professional’s careful planning, vast resources, large network, and excellent execution.

What’s your best advice for a new agent looking to sell real estate in Naples? Establish yourself as a knowledgeable and available expert through research and persistence, and then execute when opportunity presents itself; business and notice will follow.

When you’re off the clock, where can we find you? How do you enjoy the Naples lifestyle? I am an unashamed fashion and art shopaholic who loves wandering shopping malls, boutiques, and galleries. When I have some free time and want to relax, I head to Naples’ Waterside Shops, Saks, Marissa Collections, or the new hottest shop in town. The funny part is that I don’t always buy something. I get just as much enjoyment from looking at the latest fashions and trying them on as I do from buying. At galleries, I take photos, go home, hold the phone up to my walls, and imagine what a piece would look like there. It is a great hobby because there is a powerful, unexpected professional benefit to it.

A core principle underlying my career and the Dawn McKenna Group is the importance and relevance of style, fashion, and art to real estate. Our homes reflect our style and the latest trends. If you want to help your clients achieve their dreams, you need to know what they are looking for, what is exciting to them, and what excites potential buyers. You also need to know how to package and market yourself and your listings in a stylish and creative way. So while I am strolling through shops and department stores, I am doing my homework.

The Dawn McKenna Group is the No. 8 real estate team in the U.S. for Coldwell Banker. With offices in Chicago’s Gold Coast, the prestigious Chicago suburbs of Hinsdale, Lake Forest, and Winnetka, and on Fifth Avenue South in Naples, DMG agents are ready to serve you where they live, work, and play. Find them in The Scout Guide Naples volumes 9 and 10.