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From the country road in Waukesha County, you’d never know you were driving by the most expensive home in the five-county metro area. The entrance to the remarkable Swanson residence is marked only by a small, easily missed sign, and from there you take a potholed dirt road that winds through the woods for nearly a mile.

Ultimately, you come upon a statue of a deer that looks almost real and is guarding a small parking lot. Now you can see Oconomowoc Lake stretching out along a 50-acre estate, and you can approach the 13,000-square-foot Twenty Gables mansion. Two 19th century buggies sit on the porch of the white Victorian home, a reminder of the days when the area was known as the “Newport of the West.”

One of the last of the Gilded Age summer “cottages” of Midwestern millionaires, the Swanson home is now surrounded by modern mansions of 18,000 square feet and more. But Twenty Gables still reigns supreme, at least as far as price. Based on assessed value, it’s the most expensive private residence in the five-county metro area.

In searching for magnificent mansions, we used recent sales data and equalized assessment values to find Milwaukee’s most expensive homes. We were surprised by what we found: The explosion in home values has pushed values so high that more than 50 homes are worth $3 million or more, and 20 of them are worth at least $4 million.

That’s rich for Milwaukee, though nothing compared to real estate around the nation: the $70 million oceanfront estate in Florida’s Palm Beach that sold in 2004, Oprah’s $50 million Santa Barbara palace, Chicago’s $20 million mansions or even the Chicago spillover of $9 million estates in Lake Geneva. All of which make Milwaukee’s mansions look like veritable bargains.

No home in the Milwaukee area has ever actually sold for more than $4 million – yet. The highest selling price was on an Oconomowoc Lake home sold privately in 2003 for $3,825,000. But the assessed values in most cases probably understate the likely selling price.

The area’s highest-valued homes are clustered in three small communities – Chenequa and Oconomowoc Lake in Waukesha County and River Hills in Milwaukee County – super residential settings where you’ll find large lots, private drives and exclusive, country club-type settings. But property values for Milwaukee’s Lake Drive mansions are approaching $3 million, too, while pockets of ultra-high-end homes dot the horizon in places you’d expect, such as Elm Grove, Bayside and Mequon, and in some you wouldn’t, such as Oak Creek and the Town of Polk.

The range of home prices in the metro area is quite striking: The top-priced home is $5.6 million in Chenequa but $2.6 million in the City of Milwaukee and a mere $476,900 in South Milwaukee.

At the top is the Village of Oconomowoc Lake, where one-acre lots fetch $1 million and more and the property’s 1,800 feet of shoreline accounts for much of the equalized value of the $5.9 million Swanson home.

But it’s not price alone that makes a home extraordinary. Sometimes it’s the architectural pedigree or historical roots that make for a one-of-a-kind, irreplaceable home, even though it isn’t in the $3 million-plus club. We visited some of those as well.

Among those who own these elite homes, we found CEOs of public companies, heirs to family fortunes, physicians, professional athletes and successful entrepreneurs. Some live in sprawling new estates with swimming pools, home theaters, workout rooms and immense walk-in-closets; others in lovingly restored Victorians and baronial mansions adapted to reflect their owner’s taste.

One thing is certain: Milwaukee’s magnificent mansions are as diverse as the personalities of their owners. That became clear as soon as we began stepping over their thresholds.

The Rich Are Different
Jack Swanson and his wife, Karen, heiress to the Miller Brewing Company fortune, rescued the 1882 Merrick estate on Oconomowoc Lake from demolition in 1964. The newlywed couple were then living modestly in a two-and-a-half-room apartment on Chicago’s Sheridan Road, so they had almost no furniture to put in the massive mansion at first.

Forty years later, that’s no longer a problem. The home is an unusual amalgamation of beautiful oil paintings, bricks from Milwaukee’s historic streets, remnants of long-gone local mansions, Bible study materials and family photos.

Jack Swanson, a Rutgers-educated former accountant and sports buff, has a passion for two things: antiques and Jesus. A sign on the front porch announces that “Jesus Christ Lives in This House.” Swanson vividly recalls the “era of the Jesus People,” when he and his wife took in hoards of homeless hippies (typically known as Jesus freaks) in the 1960s and ’70s. “At that point, we had people sleeping in almost every room of the house,” he recalls.

The couple also raised five children in the home (several of them adopted) and put on a sizeable addition in the 1970s, expanding the home by nearly a third and adding a three-car attached garage. Today, there’s a huge room overlooking the lake dedicated just to Bible study meetings.

Inside the home, a seashell collection greets guests, while bird cages and fish tanks line one side of the dining room. Autographed Brett Favre and Reggie White helmets rest alongside turn-of-the-century medicine bottles, like Dr. Clark Johnson’s Indian Blood Syrup, the original elixir still inside.

At the far end of the house, in the newer wing, is where Jack wrote two books, Out of Oconomowoc and Farewell to Fences, both part memoir, part local lore. Many writers pray for inspiration, but Swanson leaves nothing to chance: He has an altar with a crucifix and stained-glass window across the room from the octagon-shaped alcove where he writes.

Friendly and casual, with a Lincoln-esque silver beard, Swanson improvised as he renovated, buying and bartering historic pieces to fuse together his home’s addition until he felt the home was “an extension” of himself.

With an Italian marble fireplace rescued from Milwaukee’s demolished Plankinton mansion, Twenty Gables at times suggests a museum, but one with a lived-in, charmingly messy humanity. It’s not quite the ambience you’d expect in Milwaukee’s most expensive mansion.

East Side and North Shore
Well before the wealthy were building summer cottages in Oconomowoc, they were building year-round homes not far from Milwaukee’s Downtown. The East Side homes built on Prospect Avenue and Lake Drive have a rich blend of architectural heritage: Tudor, Flemish, French and especially German influences from the city’s 19th and early 20th century immigrants.

Writer and architectural design consultant H. Russell Zimmermann has documented many of these treasures in his books throughout the years, including in his 1976 The Heritage Guidebook and his 1987 Magnificent Milwaukee. Zimmermann is one of the foremost experts on Milwaukee’s historic architecture and has consulted on the restoration of such treasures as the Grain Exchange Room in the Mackie Building.

A number of the mansions Zimmermann has written about have since been razed, turned into museums or office space or broken up into condos. But quite a few still remain in the hands of private owners.

Turnover in ownership can result in an interesting blend of old and new, as in the early 20th century Uihlein mansion on Lake Drive. Built by Herman and Claudia Uihlein, of the Schlitz brewing family, it now sports gold leafing and an Indian influence reflecting the birthplace of its current owner, entrepreneur Kailas Rao.

The Italian Renaissance mansion features the renowned ornamental ironwork of Cyril Colnik and a smooth, buff-colored Bedford limestone exterior. Rao and his wife, Becky, bought it in 1993 for $1.3 million from Peter and Mary Buffett, whose music production company, Independent Sound, was briefly located at the Whitefish Bay home.

Interior designer Jon Schlagenhaft oversaw the renovations, which included the creation of murals depicting the Taj Mahal, a white Bengal tiger and other elements of India’s countryside. And then there’s the 27-seat multimedia theater with nine-speaker surround-sound, the billiards room, wine cellar and grooming area for the Raos’ show dogs. Becky Rao’s Richfield farm, Rao Farms, breeds champion Brittany dogs and Appaloosa horses.

The Raos proudly documented their home’s renovations in the book Restoration of a Masterpiece, which they published in 2003.

Even today, Kailas Rao has to pinch himself to believe the home is his. “You know,” he says, “I didn’t come from old money. I was a professor.”

At $3.3 million, the home is one of the most expensive in the county, with the highest equalized value of any house in Whitefish Bay. Other historic East Side residences don’t quite reach that value but are impressive nonetheless.

Take the Goldberg mansion on Newberry Boulevard in Milwaukee. Real estate investor Jim Wiechmann had his eye on this Queen Anne Victorian for 20 years before he and his wife, Sue, bought it in 1980. But Sue was intimidated by the Gothic, castle-like exterior at first. “For the first year we lived here, I didn’t even come in the front door,” she recalls. “I didn’t feel like I belonged here.”

But she ended up falling in love with the warm, cozy feeling of the 1896 interior, the wooden arches, stained-glass windows and sunny solarium off the dining room. One of the most distinctive features of the home’s exterior is the three-story tower, yet on the inside, it seems to disappear because the Wiechmanns’ grand window treatments and other decorative touches integrate it with the rest of the home.

The woodwork almost glows, a testimonial to 40 years of meticulous care by former owners optician David Wald and his wife, Lenke, who bought lemon oil by the case to give her wood a hand-rubbed luster.

The mansion’s history has its share of intrigue. The man who had the home built never lived there. Attorney Benjamin M. Goldberg was disbarred before its completion for misusing trust fund money. The first residence built on Newberry, the home has some of the same style details as the historic Pabst mansion (2000 W. Wisconsin Ave.), built just a few years earlier. A number of the original chandeliers were melted down to make bullets during World War I, but otherwise, the home is in mint condition.

“We brought it back to its former glory,” says Sue Wiechmann, who grew up in a ranch home and never thought she’d end up in a Victorian mansion. The home’s 2005 assessed value was about $1.4 million.

Just a few blocks away, on Terrace Avenue, live retired business executive Bob Elsner and his wife, Barbara, and their home couldn’t be more different. Their 1916 home was dubbed “the only important residential project by Frank Lloyd Wright in Milwaukee” by Zimmermann in The Heritage Guidebook.

Today, he goes further, calling the Elsners’ home “probably” the best of Wright’s creations in the entire state. That’s high praise, considering other Wisconsin masterpieces like Taliesen East and Wingspread. Jim Draeger, architectural historian at the Wisconsin Historical Society in Madison, agrees, calling it one of the finest examples of the Prairie period.

The Elsners didn’t know much about Wright when they moved from Whitefish Bay to this home in 1955. They were just looking for a bigger place to raise their kids. But they’ve since become experts on the architect, welcoming major Wright scholars and architectural experts from around the world into their

home. They’ve learned to appreciate the complexity of the design and how it creates a sense of quiet that envelopes the house and how Wright played with height and eschewed walls for open spaces. “There’s something about his proportions,” says Barbara Elsner. “It’s like a magic genius.”

In the 1950s, decorators advised the young Mrs. Elsner to paint over the woodwork and knock out a wall in the kitchen, substituting a bay window for the exposed brick wall that lets in carefully placed rectangles of light. “This was a time when beige rugs and white walls were it,” she recalls. But knowing in her gut that the interior aesthetics are just as much a work of art as the outer design, she left these elements intact and gradually furnished the home with a collection of Wright-designed pieces.

The Frederick C. Bogk residence, as it’s known, hasn’t been listed on the market for decades and is irreplaceable, both architecturally and historically, so its current value is all but impossible to estimate. Given that Wright designed every detail, including a wooden built-in radiator cover, the home may be worth more in pieces than as a whole. But as passionately as Mrs. Elsner feels about historic preservation, that’s not likely to happen anytime soon.

The Elsners live just a few blocks away from a proposed condo tower development, and they can feel the neighborhood changing around them. Not so for the residents of ultra-private River Hills, whose five-acre lots and long, winding driveways hide the mansions from view and whose municipal codes seem to prevent change from ever happening. Incorporated in 1930, the village founders outlawed commercial development and decreed that the streets would have no sidewalks, curbs or even lane lines – all in keeping with residents’ desire for “country living.”

But in 2003, Zimmermann got unprecedented inside access when the River Hills Foundation commissioned him to write the first book about the village’s history. In researching River Hills: As It Is and As It Once Was, he studied the architecture, snapped gorgeous full-color photos and chronicled the history of this exclusive community.

For the cover photograph, Zimmermann chose what he refers to as “probably the best and most important home in River Hills,” Jack and Joan Stein’s $3.1 million estate on the Milwaukee River. The slate-roofed 17-room mansion was built in the late 1920s and is now a Milwaukee County landmark.

“We waited a long time for this house,” recalls Joan Stein, whose husband owns Stein Gardens and Gifts. Before buying it in 1986, the couple had lived around the bend in the river and admired it from afar for 15 years.

The grand estate originally belonged to Walter S. Lindsay, a Scotsman who came to Milwaukee in 1911 and made his fortune with the Lindsay-McMillan Oil Company. Lindsay became one of Milwaukee’s elite, serving on the Northwestern Mutual Life board of directors and becoming the first River Hills village president.

A little village of outbuildings forms around the home’s courtyard, but since the Steins do not employ a chauffeur to fetch the car from the coach house (as they speculate the prior owners had), they converted a laundry room into an attached garage.

With a two-story front foyer, paneled library and brick red-hued den, Joan is hard-pressed to choose her favorite place in the home. “I’m crazy about every room,” she says. “I love this house.”

Another of Zimmermann’s River Hills favorites is the home of Donald and Donna Baumgartner, whose 15-acre estate is estimated at $3.3 million. What’s stunning about this one is the landscaping, with extensive walkways, manicured lawns and a stately fountain that serves as a focal point. The Baumgartners even went so far as to create their own ponds and rivers on the land.

“I was jealous that my neighbors were on the river and I wasn’t, so I built my own river,” quips Mr. Baumgartner, founder and chief executive officer of Paper Machinery Corporation. Shelter magazine called the 1929 English Georgian-style house a “fantasia,” highlighting the work of their interior designer, Jon Schlagenhaft (who also redid the Rao home) in a 2002 cover story.

But Zimmermann still likes the landscaping the best.

The Lake Country
As gorgeous as Milwaukee County’s mansions are, Waukesha County’s Lake Country has become the hotbed of prime local real estate. Since the 19th century, when millionaires from Chicago and St. Louis built summer cottages there, the lakeside settings and quiet, country lifestyle have appealed to the area’s wealthy.

Today, the most coveted lakes are Pine, Oconomowoc and Beaver, though real estate on parts of Nagawicka, La Belle and North lakes can also command a pretty penny. Sailing is possible on the larger lakes, and although Pine Lake has no municipal sewer service (and Oconomowoc’s is very limited), their exclusion of all commercial development gives them the edge when it comes to secluded, resort-type living.

It’s no secret that lake home values are sky-high. But exactly what these homes are worth is often hard to pin down. Assessors tend to wait for a critical mass of sales to accumulate before revaluing the homes. For instance, Clark Oil heiress Wendy Gahn-Ackley sold her historic home on Oconomowoc Lake in October 2005 for $3.55 million, while the home still only carried an equalized value of about $2.2 million.

But some have stretched the market too far. A castle-like mansion on Oconomowoc Lake with a $3.4 million equalized value was listed a couple of years ago for close to $6 million before finally being taken off the market because it didn’t sell.

In some communities, the values set by assessors can provoke the ire of the wealthy landowners. In Mequon, for example, several residents who own the highest-assessed properties are suing the city over valuations stemming back to 2002. They even tried (unsuccessfully) to get the Mequon assessor removed from his job, saying his valuations are too high.

No lake has more high-end homes than Oconomowoc Lake, with 19 worth more than $3 million. One of those is a Georgian Colonial built in 1960 for Pabst brewery heiress Elsa Pabst, great-granddaughter of Captain Frederick Pabst. Marie Kasten purchased the home in 2001.

Kasten, whose former husband is Doral Dental co-founder Craig Kasten, grew up on 45th and Hadley streets. Her dad was an airline pilot. “We were working class,” she says. “We used to drive along Lake Drive and fantasize about living in one of the mansions.” Now, with her Oconomowoc Lake home valued at $3.6 million, she is living her fantasy.

Among the renovations Kasten has done are the French ice cream parlor added at the back of the house for kid-friendly summertime treats and a new sound system, which includes a 1,200-movie DVD library and a grand player piano hooked up to play in synch with the flat-screen TV.

The house has 11 bathrooms, 11 fireplaces, a library and three kitchens. “It’s massive,” says Kasten of the 18,000-square-foot, 39-room mansion. The challenge, she explains, is “bringing it down so that each room is friendly.” She and her three daughters go back and forth throughout the year between the lake house and their not-inconsiderable 7,800-square-foot Mequon home, which features a beauty salon complete with pedicure basin on the third floor and a full gym in the basement.

Another elite area is Pine Lake in Chenequa, with 15 homes valued at more than $3 million. Several homes currently on the market give a glimpse into the lifestyle there.

Deborah Marek is asking $4.3 million for the white, 9,500-square-foot Greek Revival home she and her husband built in 1997. The home has a workout room and tanning bed, marble-like columns and a great room with a two-story mirror. Outside, a majestic staircase leads down to the lot’s prime Pine Lake frontage. The assessed (equalized) value is about $3.3 million.

Next door to Marek is another 1997 home, for sale at $4.3 million. The brick home features high-end woodwork, a wine cellar, state-of-the art technology and interior design by Zimmerman Design Group (no relation to Russell Zimmermann, whose firm is called Zimmermann Design Consultants). The 7,500-square-foot home has 360 feet of lake frontage on four acres. Assessed value: nearly $2.9 million.

Another listing on Pine Lake with an assessed value of $2.15 million is on the market for $3.5 million. This is an 1893 summer cottage with a panoramic view of the lake and 900 feet of frontage (about half on the main lake and half on the bay behind the home). The 6,000-square-foot home is an enchanting reminder of the Victorian era.

But it would be hard to find a home that better personified the ideal of Lake Country living than the Queen Anne Victorian summer cottage called Islandale. The home doesn’t just hug the water, it is surrounded by it, on a six-acre island in Lac La Belle. Jutting out from the shore and connected by a narrow causeway, the island has panoramic views of tranquil Oconomowoc, with its church steeples, rooftops and trees. Islandale shares the island with only three other homes, and it’s surrounded on three sides by 900 feet of unobstructed lake frontage.

The 1882 home had fallen into disrepair by the mid-1990s when owner Don Moore first saw it. Unoccupied for 50 years, it “looked worse than dowdy,” he recalls.

But as he calculated all of the time, money and effort it would take to restore the historic home, he saw many elements worth saving: the detailed etching in the woodwork of the spiral three-story staircase, the original hardwood floors made of black walnut and set in a striped pattern, the six fireplaces with carved wood and marble and the door hinges with small brass church steeples on the top and bottom.

Moore’s wife, Connie, knew right away that this was the house for them. “Let’s do it,” she said. It took two years to put in all new electric, plumbing and insulation and to strip the wood and light fixtures of the white paint that coated them. Don Moore credits the dedication of the Milwaukee-area craftsmen who helped do the meticulous work. “This restoration could not have been done in Florida,” he says of his home state. “They just don’t have the craftsmen we have here.”

To keep up their morale, Connie Moore made a scrapbook of the renovation process, including a snapshot of a newly constructed home built in 19th century cottage style, which looked like a pale echo of this real period home after its restoration was completed.

Now the home, originally designed by architect Cass Chapman for Chicago businessman Walter Peck, is an irreplaceable mixture of historic charm and modern convenience. It’s also on the National Register of Historic Landmarks. The Moores’ grandkids play among the sloped ceilings of the third floor and swim in the lake all summer long. From the wraparound porch and strategically placed windows, the family has views of the lake from sunrise to sunset.

The assessed value of Islandale is $1.8 million, with more than half of that in land value. But Moore predicts it could sell for much more. For the retired investment adviser, it’s an island of residential splendor, a masterpiece that feels just like home.

Julie Sensat Waldren is a regular Milwaukee Magazine contributor. Photographed by David Bader.