Water sports in Wisconsin. Fireflies lighting up the Michigan night sky. The sound of waves hitting Florida’s white sand beaches. Lake life and beach escapes are captivating, and they encompass everything good about summer or the luxury of breaking away from blustery Chicagoland winters.

Agents in these second-home markets popular with Chicagoland residents are selling a lifestyle, much like they do when they assist buyers with permanent residences. The difference is a second home is a want, while a permanent residence is a need. There’s no sense of urgency, only desire, and that can be fleeting if agents don’t wow buyers with local knowledge and show them properties to perfectly suit their preferences.
Agents who have achieved success in the second-home market say it requires local expertise, an extensive network and a lot of hands-on experience.

“Anyone in the world can scan listings in another market and take clients on a fun trip to see it,” said Dawn McKenna, founder and principal of The Dawn McKenna Group in Chicago. “You need a deliberately professional process using well-informed, experienced experts who will produce long-term benefits for clients.

“When clients are paired with local experts, there’s not a question they have that they don’t have the answer to or haven’t experienced themselves,” McKenna said. “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.” Last year, McKenna added the No. 1 team in Utah, which has a former Olympic skier among them, to The Dawn McKenna Group.

McKenna owns homes in most of the markets Chicagoans often choose for second homes: Lake Geneva, Wisconsin; Harbor Country, Michigan; Naples, Florida; and Park City, Utah, which makes her a local expert. She also has more than 20 agents across the country on her team, and all of them live full time in the territories they promote.

Living in the market and handling all the details in person gives her team a competitive edge. “Because we sold every house on the block,” McKenna said, “we know the real reason why the home next door sold low — there was an RV parked on cinder blocks behind it.”

While a buyer who grew up with a family lake house may not need to be persuaded to enter the second-home market, the buyer new to it or an investor seeking a return may need some coaxing. “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 a stock. But real estate is the only thing you can truly have long-term gains on and actually enjoy in real time.”

McKenna had a client who was fascinated by the boating lifestyle in Naples, Florida, but wasn’t sure it was for them. So, her team took the couple by boat to every showing and brought them to a yacht dealer to help determine how a boat would fit their lifestyle. They learned about parking a boat on a property, visited boat clubs and talked to a captain to see if they wanted to hire someone or learn how to captain a boat themselves. “It’s all these intrinsic things you need to know to provide somebody with great service and guidance, because it’s very expensive,” McKenna said. “You don’t want anyone to have regrets or make a mistake.”

Laura Ann Mitrick, principal founding broker at COMPASS Michigan, met a couple who did make a mistake, and now they have to list a property they recently purchased. The couple didn’t realize they had purchased a home on a no-wake lake, said Mitrick. “They have kids and cannot take them out water skiing. That is why you need someone who knows those nuances,” she said.

Had the couple originally worked with Mitrick, they would have learned that inland lakes are either all-sport or no-wake lakes. An all-sport lake allows for high-speed boating and various water sports such as water skiing, wakeboarding and Jet Skiing. In contrast, a no-wake lake restricts boats to slow speeds, creating a peaceful environment ideal for activities like kayaking, paddleboarding, fishing and swimming.
By definition, inland lakes are any lakes other than the Great Lakes, Mitrick said. Lake Michigan properties attract residents seeking luxury, expansive views, urban amenities and adventurous water sports — attributes that make them more expensive. “Both types of lakefront properties cater to different lifestyle preferences,” she said. “From Lake Michigan’s dynamic environment to the serene, intimate setting of inland lakes, it’s hard to choose!”

What Chicagoans want in a second home

Chicago-area residents seek a combination of relaxation, recreation and investment potential in second homes, Mitrick said. In recent years, there has been a significant shift toward properties that provide a retreat from the city — lakefront homes, cottages and peaceful settings with outdoor amenities. She has also seen investor interest in 1031 exchanges. That’s when you sell a rental property in Chicago, Mitrick explained, and within a given amount of time can purchase a similar property in another state and offset the tax implications.

Mitrick resides mostly in her family’s lake house on Magician Lake in Southwest Michigan and lives the lifestyle she helps clients find. She understands the nuances of each lake and can answer questions such as: Are short-term rentals allowed? Can you add a pier? Can you swim or do you need insurance? What are the navigation laws on the lake? Is it monitored by the Department of Natural Resources?

Anglers may need a license to fish. Some lakes restrict boat speeds within an hour of sunset. “How would you know that unless somebody told you?” Mitrick said. “There’s lots of little rules, lifestyle tips and hacks you need an expert to help navigate.”

Mitrick attributes her success selling second homes to a comprehensive understanding of each market, having a network of industry partners at the ready and being a lifelong learner. She holds the designations of Resort and Second Home Specialist, Certified Pricing Strategy Specialist and Real Estate Negotiation Specialist.

“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,” she said. Brandie Malay Siavelis said she is the eyes and ears of her clients in Lake Geneva because they live far away and she’s there all the time staying at her own second home. “If something pops up on the market, I’m going to look at it,” said Siavelis, a senior luxury broker with @properties Christie’s International Real Estate in Winnetka and Lake Geneva. She recently toured four homes, filming all of them. She then sent the footage to her client. Desirable homes sell quickly, she said, and this is her way of motivating clients to see them in person.

She also lets clients know it’s a different vibe depending on a home’s location on the lake (walkable to shopping and restaurants, or more remote), and whether it’s a private lakefront property or part of an association. “Some people don’t want to be in an association with other people,” she said. “You have to get along with your neighbors and make decisions together.”

However, she noted prices have become unattainable for properties not affiliated with associations, which makes them attractive. “You feel like it’s your lakefront,” she said of living in an association community. “You get the pier and swim platform. You can put up trampolines and slides if you’d like. There’s usually a park for picnicking, roasting marshmallows and all the fun things to do at the lake without the price tag of a private lakefront.”

However, if somebody plans to Airbnb their property, she warned, not being in an association is a better way to go, Siavelis said. “There’s only a few associations in Lake Geneva that are a little lenient in terms of permitting Airbnb or Vrbo.”

Housekeeping items

Mitrick said it’s important to let buyers know that transactions can differ from state to state. Unlike Chicago, Michigan transactions don’t require an attorney. In addition, providing post-transaction support is crucial for the relationship with your client and for the client to be successful in the second-home market. “They’ll need to connect with local service providers, property managers and know rental options,” Mitrick said. “Be accessible and available.”

“There are so many agents licensed in different states shooting back and forth,” McKenna said. “If you want to sell a second home, you have to live there. My agents are living, breathing, eating all day every day what they’re doing. I think that’s the competitive advantage. You cannot go back and forth with people. It doesn’t work. It’s not good service.”

EXPERT SOURCES

Dawn McKenna
Founder and Principal,
The Dawn McKenna Group

Laura Ann Mitrick
Broker,
COMPASS

Brandie Malay Siavelis
Senior Luxury Broker, @properties
Christie’s International Real Estate