Lakehouse life: Luxury agents dig into quirks of second-home market

Deep local knowledge, focus on investment key in vacation home sales

Luxury Agents Explain Second-Home Market in Chicagoland

(Photo Illustration by The Real Deal with Getty)

The allure of lakefront living and beachside retreats is drawing Chicagoland residents to second-home markets across the Midwest and beyond. 

From the serene waters of Wisconsin to the sun-drenched shores of Florida, buyers are seeking more than just property — they’re after a lifestyle escape from the hustle of city life. For real estate agents in these desirable vacation spots, success hinges on a deep understanding of local markets and a commitment to providing tailored guidance, Chicago Agent reported

In areas like Lake Geneva, Harbor Country and Park City, second-home buyers are more about lifestyle than necessity. 

“Selling a second home requires more than just showing properties,” said Dawn McKenna, founder of the Dawn McKenna Group in Chicago. “You need to be deeply familiar with the area and its nuances to truly serve your clients.”

McKenna, who owns properties in several popular second-home markets, believes that being a local resident provides a competitive edge. 

Understanding the details of local lake regulations, or knowing the best places for boating can make a significant difference.

“If you were hiking in the Rockies, you’d want a local guy who lives and breathes the Rockies to guide you. The second-home market is the same thing,” she said.

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Laura Ann Mitrick, a principal broker at COMPASS Michigan, recalled a case where a couple’s lack of understanding about lake types led to a purchase that didn’t meet their needs. A local expert could have prevented the mistake by clarifying the difference between all-sport and no-wake lakes, she said.

Investment potential is another crucial factor in the second-home market. 

“A second home as an investment property allows owners to rent it out and let the property pay for itself,” McKenna said. “You can invest in T-bills, venture funds and buy stocks. But real estate is the only thing you can truly have long-term gains on and actually enjoy in real time.”

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“There’s distractions. You need to hone through those listings and find the ones that will really suit a buyer’s needs and put that in front of them,” said Siavelis, a senior luxury broker with @properties Christie’s International Real Estate in Winnetka and Lake Geneva.

Overall, the emphasis on local expertise and personalized service reflects the broader trend in real estate, where deep market knowledge and hands-on experience are becoming critical for success in the competitive second-home market. 

— Andrew Terrell

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