Peak inside Playboy Mansion- Spectacular Gold Coast Homes Showcased in Day School House Tour

A peek inside the former Playboy Mansion, a walk through a historic masterpiece by architect David Adler and a commanding view of Lake Michigan from an East Lake Shore Drive Co-op are among six stunning Gold Coast residences to be showcased in the 16th annual Chicago City Day School 'City Style' House Tour fundraiser on May 2.
Walk back in time to an architectural era of servants' quarters, high-rise terraces, private elevators, paneled living rooms and trap doors. The City Style House Tour offers a rare glimpse of a bygone time of grand lifestyles and entertaining carefully preserved inside some of the most architecturally significant residences in the city.
The tour begins with chilled wine and a lavish buffet in the sparkling formal dining room of the intimate Spiaggia Restaurant where all of the afternoon's destinations are visible from floor-to-ceiling windows overlooking Michigan Ave.
Formerly Hugh Hefner's hanky panky headquarters, the Playboy Mansion now is a stately compound of exquisite condominiums. Few traces remain of Hefnerland, other than the sealed living room trap door to a now vanished swimming pool.
The conversion from party palace to handsome home was no small undertaking. While it may be hard to believe today, the home on this tour once had sizable tree roots poking out of the living room ceiling.
Inside the entrance hall is the home's original stairway. Upstairs, a huge paneled living room is one of the most spectacular spaces in Chicago. The owners painstakingly cleaned and waxed to restore the wood and erase traces of the Playboy past. The room's original trompe líoeil window arches serve to increase the visual depth of the walls and provide a pocket for the curtains.
When architect David Adler built the French Louis XVI home on Astor Street, it was designed as a copy of a favorite Parisian house of steel magnate Joseph T. Ryerson and his wife in 1921. Later it was divided into apartments and stripped of ornamental trim. When John P. Regas bought the property in 1986, it was a neglected eyesore. But Regas, a noted architect and designer, has restored the treasure to its old glory, relying on original blueprints found in the Art Institute. The scope of his undertaking is mind-boggling: a pair of gilders spent over a year and a half applying gold leaf to plaster relief and moldings. Three painting crews worked three years creating detailed trompe líoeil, faux finishes and splendid hues. The home is one of only 18 David Adler residences in existence.
The Drake Hotel serves as another architectural talking point of the tour because its designer, Benjamin Marshall, also built the residence a few doors to the east where another vintage home has been painstakingly renovated. Whereas most lakefront apartments point directly at the water, this apartment offers an uncommon view of the shore and skyline from a living room bay facing north and an enclosed balcony off the master bedroom.
The project on the three-bedroom apartment was completed two years ago by architect Mark Demsky, who faced the daunting task of increasing light without disturbing the clay tile masonry ceilings and designing a useful kitchen around old servantsí quarters and plumbing stacks to create a comfortable great room for the owner's family.
Down the road, a four-story brownstone, built circa 1890, features an original working elevator and is a clever combination of new and old. Built on a wide lot, the home's five-foot wide staircase was a major feature in a renovation completed late last year. At the entrance is a tumbled limestone floor leading to a stunning hand-carved marble fireplace in a soothing living room decorated with Biedermeier couches and armchairs. A leather-tiled powder room with a French deco light fixture gives an updated feel to the vintage home. Birdseye maple cabinets and Greek key mosaic floors make the kitchen a special spot for parties, while its intimate breakfast nook and sliding door leading to a garden make for cozy morning gatherings.
Hours of the self-guided walking tour are 1:00 p.m. to 5:00 p.m. Tickets for the event are $125 in advance and $140 at the door; $100 of the ticket price is tax-deductible. Proceeds benefit educational programs at the Chicago City Day School, 541 W. Hawthorne Place. For more information call 773-818-6006.