Second Home: A Dream vs. Reality Property-Trading Game


What is an interview but a conversation? What is a conversation but a game?

With that in mind, I’ve invited several friends and acquaintances for a fantasy chat — an imaginary game on an imaginary evening. (The quotes in this story were taken from a series of real, regular interviews, but that’s so … ordinary.)

There is no Park Place or Boardwalk, per se. No dice. No rules. No board to navigate.

Instead I have three decadent (but very game-like) questions:

Do you own a second home?

If so, where is it — and why?

Most importantly, if money were no object and your second home could be anywhere in the world, where would it be?

Later, we’ll invite you to play along (see page 64). But before we start another round, come join our fantasy conversation, won’t you?

Wine is on the table. Ask Joan for a glass; she’d be glad to pass one to you. But at the moment, Mrs. Vesselinovitch is playing the Ritz card.

“I’d probably buy a condo in the Cayman Islands, where our family always goes for spring break with my parents.” Her green eyes flash as she continues, “Ritz Carlton is building on Grand Cayman. Those condos will probably be nice enough.”

Then her husband, Alex, a litigation partner at Katten Muchin Zavis and bass guitarist in the rock band Mea Culpa clears his throat. “I had this quirky idea last spring,” he says. “I realized I already had everything I need or want in life, except maybe a sailboat.” This leads him to the first epiphany of the evening: “Since we don’t have a second home, I must not want one.”

“But dear, where would you have a second home if you had to have one?” Joan asks, peering ever-so-closely at her husband. “And please be reasonable about your family — none of your rock-star-in-southern-France ideas!”

Yes, you sigh. Reasonable.

That’s usually where Fantasy Land ends and The Game of Life begins.

The “dream” second home is like a pre-dinner cocktail, an exotic blend of experience and imagination. Tasty, but less fulfilling, perhaps, than the “real” second-home courses North Shore families ultimately gravitate to.

Consider the story of parlor game participant Liz McEnany of Northfield. She runs E Claire Design while raising three children (with husband, John) but spends every spring break at the Barbados home her parents have owned since 1965. “I love the fact that my children have gone to Barbados since they were born. If we had a second home, I would want it to have a family connection. Therefore, if I have to have a second home, it’s in Barbados.”

“But,” she adds, “because of my business, I work with families who are fixing up second, third and fourth homes, and I see what they demand.” Does she, personally, want to invest that kind of time and money? Not especially. Liz also professes her mission to avoid the “pack and schlep routine” many mothers perform as they transport the “same old stuff between homes.”

John is quick to interject: “I’d like to go to Virginia and own a lot of land, a couple of dogs, a stream and some books,” he says wistfully.

“But we don’t have any family history there!” she cries.

Dream Second Home: 0

Second Home With Childhood Memories and/or Family Ties: 2

Then Wilmette realtor and mother of two Diane Field weighs in to even up the score. “I’m happiest in Colorado,” she says, “and I never went there as a child. I don’t need to see water, either. Some people just connect with the energy and spirit of a place. Santa Fe affects many that way. But for me, it’s the Colorado mountains.”

Diane doesn’t have a second home there at the moment, but she was scouting potential locations when she took her daughter, Alison, a New Trier junior, to look at colleges in Colorado. “I will have another home there soon.”

Until then, perhaps she should follow the example of Liz and John, who have turned their first home into something of a retreat. “We have a pool in the backyard, so there is water. John has done amazing, beautiful work with the landscaping.” Besides, Liz says, why summer away from home when Chicago summers are so fabulous?

This pulls Joan back into the “conversation”: “I really like Chicago summers, too, so we don’t need to leave then.” And the sailboat at Gilson Park? “Actually, I like it,” she says, “as long as he does all the work getting it in and out of the water.” Of course, she’s still holding the Ritz card, still angling for Grand Cayman Place. But that’s what makes our little second-home game so appealing. Even if you don’t own a second home, chances are you dream of one. And sometimes that’s half the fun. It takes strategy — even luck — to maneuver the “where’s,” the “why’s” and the “when’s” of how to make this fantasy come true, Chance cards all tempered by the opoly-esque obstacles of real money and time.

Title deeds. Mortgages. Luxury Tax. House or hotel? Gather your pink and green play dollars and get ready to pass Go.


Winnetkan Kathie Carlson so loved her childhood vacations in her grandparents’ cottage that she and her husband, Phil, bypassed the fantasy life and bought a home on spectacular Grand Island in Lake Superior, near the stunning Pictured Rocks National Park.

The seven-hour drive past scores of other charming vacation spots on Lake Michigan or smaller inland lakes in Michigan and Wisconsin never dampened her enthusiasm for this cherished home. “There are just a million reasons why I love Grand Island,” Kathie gushes. “It’s where my memories are — the fresh air, the stars and wildflowers. The people there really talk to each other.”

“Kathie’s second home is actually in Winnetka. Grand Island has always been her first love,” Phil teases. “It’s been tough on my golf game. They don’t see me at Skokie Country Club as much as I would like.”

Grand Island is 13,000 acres of forest, small lakes and streams that create waterfalls down the colorful cliffs that form the island’s edge. Layers of rock in sunset hues resemble the Grand Canyon but plunge into Lake Superior’s icy, pure water.

Thirteen families own homes on the island, homes that have been passed down through many generations. Indeed, five generations of Kathie’s family have called Grand Island their second hometown.

“There are few secrets here,” she says. “The lifestyle is not fancy — it’s multigenerational. On beautiful days we meet in boats and picnic.”

As each generation becomes parents, they want to share the Grand Island experience with their children.

Score 1 more for childhood connections.


At least one local couple does own that “dream” second home in the south of France, not far from “real” rock star Tina Turner and the Picasso Museum.

Katherine and Julian Harvey of Chicago bought their three-story home, with multiple terraces and ocean views from every room, in 1997. They had been renting a house each summer for the preceding 14 years and vacationing at Cote d’Azur resorts before that.

Katherine’s childhood love of French and Julian’s lifelong inundation in all things French drove their decision. She attended schools in Switzerland and Paris. Julian is a Yale-educated composer and concert pianist.

The Harveys met in Chicago’s Alliance Francaise, where Julian’s mother was president of the Women’s Board. Julian’s music frequently is performed in European Music Festivals.

“We live on the French Riviera,” Katherine explains. “We are actually part of a three-town community. Cap D’Antibes is the glamorous spot, with gated estates and the famous Hotel Du Cap in Roc. Antibes is all twisty and turny, with the museum and charm. Juan les Pins (the Pine Trees) is where the Fitzgeralds (think F. Scott and Zelda) lived and water skiing was invented.”

The Harveys won’t identify which of the three is their second-home town, but they do admit that their home was once owned by author and Nobel Peace Prize winner René Cassin.

Katherine, with her fabulous glasses and chicly cropped hair, loves the pace and quality of life on the French Riviera. Her community is more than 2,500 years old. “It has great sophistication but also great lack of sophistication. One neighbor wears lipstick, and one is a total peasant.”

She enjoys her neighborhood relationships. “If you go into a little shop in Antibes or Cannes, people want you to stop, smile and say bonjour!”

“I have relationships with the men from whom I buy my daily paper, my fish and my other marketing. They tease me and call me La Miss,” she says. “But here, I don’t have those kind of relationships, except maybe with George at Treasure Island.”

The Harveys know at least three other homes in their neighborhood are owned by Americans, but they have yet to meet. Most of their friends there are French or Swedish.

Another factor, besides a love of all things French, that dictated their second-home decision was Julian’s vocation. He needed space for his grand piano and enough distance from neighbors to not be worried that his practicing for several hours each day would bother them.

Imagine the music that must pour out of their house, across the flower-covered walls and rampart and over the azure waters of the Mediterranean Sea. We can’t call it rock star in southern France, per se. Instead it’s the contemporary composer and his tres elegante wife lifestyle.

The story of why Winnetkans Lisa and Duff Peterson have their second home on White Lake in southern Michigan is remarkably similar to Kathie Carlson’s. Duff is the fourth generation of his family to own a home there, and on Lisa’s side, Scandinavian grandparents started her family’s White Lake tradition.

The Petersons met in their 20s at a White Lake campfire and claim they are just one of dozens of “White Lake marriages” in recent history. They now bring their three children, Anna, 11, Andy, 13, and Walker, 16, to the cottage — nestled between seven-mile-long White Lake and Lake Michigan — as often as possible each summer.

The three-hour car commute makes that home easily accessible. Earlier generations were able to use a ferry, the “Carolina,” that connected downtown Chicago and White Lake.

Lisa smiles, “What I have loved about White Lake my whole life is that when I am there I feel safe.” That’s a surprising statement from a beautiful, athletic blonde who exudes confidence and owns a successful business importing Scandinavian home furnishings.

Then she explains, “At White Lake, I always had a group of friends who accepted me and loved me. Now we are all there with our children.”

The Petersons currently love the unscheduled pace of their family life at White Lake.

“We have free time to be together at White Lake,” she says. “We don’t eat until 8 or 9 p.m., and the biggest decision we make each day is whether to go out on the boat or to the beach.”

A richer extended family experience awaits the Petersons at White Lake, too. “Our children get to be with their cousins there. And that’s huge,” she adds.

Mark and Julie Hosfield of Wilmette recently purchased their second home only 90 minutes away, on Lake Beulah in Wisconsin. And again, childhood memories played a big factor in that decision.

Julie’s brothers attended Camp Edwards, a YMCA camp on the lake as they grew up. “I always liked going to pick them up. I thought it was so beautiful. Then our sons, Drew and Gary, went to the same camp.”

The Hosfields originally thought of their second home as a great investment. “The stock market is flat, and real estate in Wisconsin is skyrocketing,” Julie explains. But they already believe that the home’s emotional value will far outweigh its monetary significance.

“The people on the lake are truly beyond friendly, welcoming and interesting,” she says. “Everyone is looking out for each other and proud of their community.”

About 60 percent of the 350 homes that surround the 1,000-acre Lake Beulah are second homes for families from the Chicago area. The community also includes a couple of restaurants and a yacht club that sponsors family-friendly activities.

Teenagers gather in boats in the shallow areas of Lake Beulah, drop anchor and hang out or dive off the 10-foot-high diving board mounted on a raft. That’s important to Julie and Mark because their three children are already teens.

But Lake Beulah beckons to the adults, too. “We have a 96-year-old woman who swims and kayaks every morning. She is my role model!” Julie declares.

Mark, a former Arthur Andersen partner who started his own successful firm, says, “I see my children, grandchildren and great-grandchildren coming back to this home.”

All Things Considered

Taking the leap to second-home ownership is almost as complicated as purchasing a primary residence — sometimes even more so.

Finances, obviously, are the first consideration. But even beyond that, there are other things you must weigh before plunking down the family nest egg. Do you want to find a place around the same lake as your friends or neighbors? (Or find out where their cottages are and avoid that location altogether?)

Here is a short list of “Where” questions to ask yourself (and your family members) as you weigh the options and make the decision that could enhance your lives for generations to come.

1. How far will you go?

Do you want a place that’s a hop, skip and a jump on the Edens away from home? (Read: A place you could escape to every weekend if you so desired.) Or maybe you want some geography between Home No. 1 and Home No. 2 — a seven-hour drive up the other side of the lake, perhaps (or a seven-hour plane ride to the other side of the world). Whatever you decide, be sure to add commuting costs (and time) to your overall cost and maintenance budget.

2. What’s your ideal temperature?

Are you a tropical weather family, content to wile away the hours in the sand and sun? Or do you prefer the pristine joy of winter, cooler climes suitable for skiing, snow sports or just curling up by a fire? Getting an accurate weather read will help you forecast the best location for your second-home retreat.

3. How long will you hold the property?

Emotions aside, real estate should always be viewed as an investment. Ask yourself these questions: Do you want (or need, or hope) to make a profit on the purchase price in the next few years? Or can you afford to own the home indefinitely? Experts say your best bets for short-term profit are within proximity of a major metropolitan area (think Lake Geneva, Saugatuck, Lakeside, Door County). But if you have the luxury to secure a long-term hold, let your heart be your guide. Go to the most beautiful place you can find.

4. Where did you vacation as a child?

Did you love it? More importantly, do you want to pass those joyful memories on to your own children? Heritage and family history have more of an impact on second-home decisions than most marketing people realize. Upscale amenities are wonderful, but nothing can replace the golden glow of happy childhood memories made in a beautiful place.

5. Do particular areas call out to your spirit?

This may be the least tangible of all the factors, but it can often be the most powerful. Think about this: Have you ever been to a place — whether it’s a tiny cottage in Wisconsin or a ski lodge in Colorado — where you just felt “yes”? While most of us don’t have the luxury of acquiring the property of our dreams, if you can find a way to come close (even if it’s very nearby), then the return on your investment will be, as the TV commercial says, priceless.

Now It’s Your Turn: Is your play money color-coordinated? Do you have your playing piece of choice? Submit your Title Deed in our fantasy game by answering the following questions. If we get enough clever responses, we’ll print them, so be sure to include things like your name, where you live, and how we can get in touch with you.

Ready. Set. Pass Go.

Do you (or anyone in your family) have a second home?

If so, where (and why)?

And … (the million dollar question)

If you could have a second home anywhere in the world, where would it be?

Send your responses to or snail mail to: Second Home Game, 3701 W. Lake Ave., Glenview, IL 60026.

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