Hillcroft’s Undivided History

By Anne Morrissy | Photography by Clint Farlinger, John Hagenah, Shanna Wolf

In any given year, a glance at the real estate listings for the Lake Geneva area yields a wide array of impressive, one-of-a-kind homes. But even among the rarefied listings of the area, one recent listing stands out. The agent’s copy reads, “Peace and privacy, grace and character, modern luxury and amenities blend  seamlessly to create a singularly unique offering.” This is a rare case in which it feels like the real estate agent is in fact understating the luxury and grandeur of the home known as Hillcroft, located on 415 feet of lakefront and almost 20 acres of secluded land west of downtown Lake Geneva.

In fact, the beautiful home on this property is not the first one to be known as Hillcroft. When Roger O’Neill and his late wife bought the property in the early 1980s, they razed the existing grand mansion (“unique to another era” in his words) to build the English cottage-inspired summer home of their dreams.

“We had two architects look at [the original Hillcroft] to see if we could salvage it,” O’Neill says. “And they decided it would be better to start over.” From the beginning, O’Neill wanted to focus on comfort. “We wanted it to be a livable house,” he explains. So in addition to its gracious elegance, Hillcroft has a warm, inviting quality to it that O’Neill says is one of his favorite things about living there. He and his wife Darlene have also worked tirelessly in recent years to preserve the history of the property, a history that dates back to the earliest days of Lake Geneva’s emergence as an exclusive resort for wealthy Chicagoans.


The first Chicagoan to spot the property’s potential was the young architect Henry Lord Gay. Gay was still establishing his architectural career when Shelton Sturges, heir to a grain elevator fortune, commissioned him to build Maple Lawn, an imposing Victorian which became the first grand summer home on Geneva Lake when it was completed in the spring of 1871.

Gay liked the area so much that he bought up a sizable tract of land just west of Maple Lawn, and built himself a Swiss chalet-style hunting lodge on the property, which he christened Gay Lynne. Gay’s familiarity with the area led to many more commissions around Geneva Lake as Chicago’s elite families built summer retreats here after the Chicago Fire, and eventually Gay’s portfolio grew to include Ceylon Court, Jerseyhurst and Stone Manor, among many others.

However, as Gay’s architectural career blossomed and he went on to establish Chicago’s Builders’ and Traders’ Exchange, he found he had less time to enjoy hunting. So in 1881 after returning from a trip to Europe, Gay sold the property to his sister and brother-in-law, John Johnston, Jr., and designed a new home for them on the property that incorporated the original hunting lodge as part of its design. Like Gay, Johnston also saw the incredible potential in the real estate around Geneva Lake and bought up more than 500 acres on the west side of Williams Bay prior to the extension of the Chicago & Northwestern train line. In 1893, he donated 53 of those acres to the University of Chicago for the construction of Yerkes Observatory.


In 1902, as Johnston’s health failed, he sold Gay Lynne to a dry goods magnate named Henry C. Lytton. Lytton’s famous Chicago store, nicknamed The Hub, opened in 1887 at the corner of Jackson and State streets, and specialized in mass-produced menswear. (A famous story says that Lytton climbed to the roof of the building and threw brand-new men’s overcoats onto the pedestrian-filled sidewalks below to advertise the opening.)

After purchasing the Lake Geneva property, Lytton added significantly to the existing structure, renaming the property Roselyn Lodge, after his wife. He also installed an elaborate, Italian-style boathouse and promenade to lead to his pier, where he kept his new steam launch. Both Lytton

and his wife adjusted well to country living. As their hobbies expanded, they added more buildings to the property, including a large greenhouse, a horse barn, a dairy barn and a poultry house where they raised prized-winning chickens. A generous employer, Lytton invited employees from his store to Roselyn Lodge for company outings. A write-up in The InterOcean from 1906 recounts that, “The time was passed in automobile rides through the forests and adjacent country, short cruises in Mr. Lytton’s private yacht, rowing on the lake, fishing and other amusements. The day concluded with a dinner prepared principally from the products of Roselyn farm.”

In 1915, Lytton sold the property to Emile K. Boisot, who headed the bond and foreign exchange departments of the First National Bank of Chicago. Little is known of Boisot’s short tenure there, though it is believed that the property acquired the name Hillcroft during this time. Five years later, Boisot sold it to Arthur Leath of Elgin, who owned a chain of furniture stores. Leath’s ownership lasted just seven years before the home was put up for sale again.


In 1911, Hillcroft had gained a famous neighbor. William Wrigley, Jr., founder and president of the William Wrigley, Jr. Company, famous for its chewing gum, owned Green Gables next door. By the time Leath was looking to sell in 1927, Wrigley’s son, Philip K. Wrigley, decided to buy Hillcroft to enjoy with his wife and his growing family. This began a stewardship of the property that would last more than five decades.

According to a Chicago Daily Tribune article from 1940, Philip K. Wrigley and his wife significantly updated, remodeled and rebuilt sections of Hillcroft after purchasing it from Leath. The article indicates that an “attractive double stairway rising from the living room” was one of the few architectural elements that survived from the home’s original Henry Lord Gay design. “The extreme simplicity of its curved white balustrade is as austerely modern as the silver lighting fixtures, and seems, like them, to be an integral part of the architectural design of the room,” the article’s author enthuses.

John Hagenah, a suburban Chicago architect who grew up spending summers at Hillcroft, distinctly remembers the staircase as one of the home’s most dramatic features. “There was this spectacular fireplace with the staircase wrapped around both sides of it,” he recalls. He also reminisces about the formal dining room: “In the old way of doing things, they had a wonderful dining room with a view of the woods and a partial lake view. It was a very traditional home.”

In addition to the formal living and dining room, the home featured living and dining porches: “year-round heated, air conditioned, glazed and screened rooms,” according to the Tribune writer. The story also mentions a “great long game room” that opened from the living room and proved a popular place for the family to congregate over “billiards … and games of every kind,” as well as bookshelves full of books.

The newly expanded and remodeled Hillcroft totaled more than 30 rooms, including sleeping quarters for the help. The Wrigleys also added more outbuildings to the property, including a child’s playhouse and an enormous garage (with space for multiple cars and an upstairs apartment), while maintaining the greenhouse, ice house, horse barn and other structures already present. “The drive down from Snake Road was a beautiful drive down the hill,” Hagenah remembers. “And you’d run around a circle at the bottom and they had built a porte-cochere and expanded a second-floor living space above it.” During this time, according to local newspapers, Hillcroft was the site of debutante balls, wedding receptions, and even something called a “woman’s exchange sale” to benefit Holiday Home Camp.


Following Philip K. Wrigley’s death in the late 1970s, Wrigley’s son reached out to O’Neill to see if he’d like to buy the property, which he did in 1981. This began a lengthy demolition and construction project. “[The new house] took three years to build,” O’Neill remembers. “It was a big job, and we were interested in the end result, not the time it took, so we didn’t rush.”

O’Neill’s favorite room in the new house is the family room, with its salvaged barn wood walls, vaulted ceilings and enormous Wisconsin fieldstone fireplace. “It’s a room that’s very comfortable,” he says. “It’s a put-your-feet-up room, where we can have roaring fires every night.” Like the previous iteration of Hillcroft, the O’Neills also incorporated a glassed-in sunroom into the new design, even repurposing bricks from the old house to create the sun room’s floor. (Other notable items salvaged from the previous Hillcroft include an enormous, vintage clawfoot tub and the impressive 1903 Brunswick pool table from the game room.) The O’Neills loved the house so much that they eventually made it their permanent residence. “The house was built as a family house to be used, not just to look at,” O’Neill says.

In addition to building this new, more livable home on the property, the O’Neills put a lot of energy into restoring the property’s historic outbuildings. “We renovated the carriage house, the gate house, the greenhouse, the ice house, the dollhouse, the gazebo,” he explains. “We wanted them to match the new house.” This attention to detail and serious stewardship are qualities that Hagenah particularly appreciates about O’Neill. “Roger has done a remarkable job with the property,” he says.

However, after more than 30 years in their dream home, the O’Neills have decided to downsize slightly. (“We’re building a house directly across the lake,” O’Neill laughs. “You can see it from the front yard.”) Hillcroft is poised to change hands again, but one thing remains certain: the property won’t be subdivided, a fate that has befallen so many of the original estates around the lake. “It’s one of the last [undivided properties] that will ever be available on the lake,” says O’Neill. And due to an agreement that dates back to the 1981 sale, O’Neill will ensure that it stays that way. “The property is one of the most unique on the lake, and the outbuildings are really special, something that people wouldn’t build today,” he says. “We’ve been very, very lucky to live here.”

Tags from the story
0 replies on “Hillcroft’s Undivided History”