On and off and on the market, Vaughn slashed the asking price for the 12,000-square-foot apartment at 159 East Walton Place from $24.7 million in 2011 to $13.9 million today (including another $1 million chop recently).

Vaughn's Chicago triplex is strategically divided with sleeping quarters and a master suite on the lower level (the 35th floor); formal living areas, including a dining room and kitchen with premier appliances on the middle level; and the formal entertainment floor with soaring ceilings on the penthouse’s top floor.

The long-time Windy City resident, who was raised in the Chicago suburb of Buffalo Grove, paid $12 million for the penthouse in 2006. With the listing price seemingly in free-fall, the masterfully-sarcastic star of The Dilemma has his own real life dilemma. Does he stand firm on the price, keep discounting the unit until it sells, or sardonically whine about the predicament (as his film characters would)?

Vaughn's penthouse occupies the top three floors of 159 East Walton Place

Formal living room

Wood-paneling dominates the top penthouse floor.

At least Vaughn can seek free advice from his wife Kyla Weber and mother Sharon “Shea” Vaughn, both experienced former real estate agents. The Break-Up actor broke ties with the previous listing agent in favor of broker Katherine Malkin of Baird & Warner.

Contemporary dining room with view of Lake Michigan outside.

The apartment offers formal and informal entertainment and living spaces.

The home mixes modern living spaces on the middle floor with traditional wood on the top entertaining floor.

Vaughn's penthouse is ideal for entertaining.

Vaughn's Chicago penthouse features two gourmet kitchens with high-end appliances.

Vaughn, famous for his wild partying roles in Swingers, Wedding Crashers and Old School, is trying his best to leave bachelorhood behind. But that requires parting ways with his Chicago bachelor pad, which has a media screening room, wood-paneled billiard and card rooms, two gourmet kitchens, full bar, a den, two offices, and three private terraces overlooking Michigan Avenue’s “Magnificent Mile” shopping district, Oak Street Beach and the Chicago skyline. Coincidentally, the Palmolive building housed the original office of the ultimate bachelor Hugh Hefner and his Playboy empire. With kids in tow, Vaughn’s game nights with the guys were likely replaced with "Peek-a-Boo" and "Patty Cake."

Card table ideal for poker night with the boys.

Games are always on in the triplex's top floor. Here is the billiards room.

Media screening room

With the Palmolive penthouse on the block, Vaughn still owns a River North townhouse in Illinois, which he bought in 2005 for $1.4 million. And while he has cleverly produced and acted in his share of Chicago-based movies in recent years, it appears the father of two is making the full transition from bachelorhood to family man by relocating closer to his office—Hollywood.

Vaughn, who married in 2010, owns several properties in the Chicago area and Los Angeles.

Vince Vaughn and Owen Wilson in "Wedding Crashers"

Family man Vaughn with his wife, daughter, and son (in Mom's tummy)

Vaughn has bought and sold a series of California homes in recent years, perhaps as investments. In February 2014, he purchased a 7,308-square-foot house in Manhattan Beach from former Oakland Raiders and USC football coach Lane Kiffin. In 2013, Vaughn purchased actress Kate Bosworth’s 5,563-square-foot Hollywood Hills home for $2.375 million. In 2012, he bought a five-bedroom, six-bathroom home in La Cañada Flintridge for $3.925 million, which sits on three-quarters of an acre (plenty of outdoor space for his two kids roam free). Vaughn, it seems, is spreading the wealth around, and he’s taking his appearance in the 2001 TV series Going to California to heart. Like his other film in 2001, he’s got it Made.

The comic actor seems content with family life now. As long as he doesn’t go Psycho on us again or cause anymore Domestic Disturbance(s), Vaughn is okay by us. We’d like him to stay old school, continue crashing weddings with Owen Wilson, and keep the laughs coming. If he does, we will be as joyous and enriched as he is. After all, his nickname is “Mr. Sunshine.” Therefore, California is where he must be.

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