List Price: $2.9 million
The Property: This grand old home 75 yards from the Lake Michigan blufftop in Highland Park evokes the early 20th-century age of big North Shore country houses. With its peacock fan of gable beams above a cozy inglenook entry, it would have been a happy place to arrive after a long...

" /> List Price: $2.9 million
The Property: This grand old home 75 yards from the Lake Michigan blufftop in Highland Park evokes the early 20th-century age of big North Shore country houses. With its peacock fan of gable beams above a cozy inglenook entry, it would have been a happy place to arrive after a long...

" /> List Price: $2.9 million
The Property: This grand old home 75 yards from the Lake Michigan blufftop in Highland Park evokes the early 20th-century age of big North Shore country houses. With its peacock fan of gable beams above a cozy inglenook entry, it would have been a happy place to arrive after a long...

" />
List Price: $2.9 million
The Property: This grand old home 75 yards from the Lake Michigan blufftop in Highland Park evokes the early 20th-century age of big North Shore country houses. With its peacock fan of gable beams above a cozy inglenook entry, it would have been a happy place to arrive after a long...

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List Price: $1,850,000
The Property: The colorist behind this "painted lady"—a 120-year-old Queen Anne with 14 different hues of paint accentuating its intricately detailed exterior—is Tracy Hurst, Lake View's painting lady. Hurst, who has lived in the house since 1987 with her husband, Taylor, and their kids, painted the entire exterior herself over three summers in the late 1990s. She did a terrific job, bringing out the...

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List Price: $350,000
The Property: For about five months in 2006, this 11-room house on a cul-de-sac in southwest suburban Homer Glen was home to an aspiring rapper who went by the name Blaxican. The embellishments included gargoyles and security cameras across the front of the roof, a shark tank in the dining room, a recording studio and two baby alligators in the...

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List Price: $1,390,000
The Property: When Kevin Fitzpatrick bought this 12-room hilltop house in St. Charles two years ago, the entire thing was white, inside and out. “It was right out of Raging Bull,” he says...
Plus: A video walk-through with Dennis Read more
List Price: $1,075,000
The Property: Built in 1888 when the mid–South Side was very fashionable, this greystone townhouse was dilapidated and fronted by chain-link fencing in May 2002. That’s when Tim and Lynne Rinkoski, moving from Downers Grove into the city, decided to make it their next restoration project. “It was the best-looking deserted house on...
Plus: a video walk-through with Dennis

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List Price: $2,773,000
The Property: The quintessential center-entry Colonial, this Kenilworth house stood in as the warm family home Steve Martin’s weary, irritable character desperately wanted to reach in time for Thanksgiving dinner in the 1987 movie Planes, Trains & Automobiles. “If I had a big life-sized photo of Steve Martin, I would put it in the window every Thanksgiving,” says Jeanie Schneider, who bought the house in 1996 with her husband, Wes. “Every Halloween, children come to the door and ask...

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List Price: $749,000
The Property: This four-bedroom condo occupies the top (fourth) floor of a nondescript building on busy Pulaski Avenue in Chicago’s Old Irving Park neighborhood. But once the private elevator ascends and the doors open on a Chinese red foyer decorated with beads and vases, the commonplace has clearly been left behind. Off to the left...

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List Price: $1,095,000
The Property: The 16-story Elm Tower, at Elm and Dearborn streets, is a six-year-old building designed to look and feel like the vintage co-ops of the Gold Coast. When he was building it, the developer, Jim Letchinger, told me he had grown up in the neighborhood and wanted to put up something that captured the intimate, urban feeling of the 1920s residential buildings he loved there...

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List Price: $1.149 million
The Property: Behind the dignified 103-year-old façade of this Logan Square greystone stands a contemporary interior by the ultra-stylish Funke Architects. Its most dramatic element is a hanging staircase of steel, glass, and maple. It floats beneath a rooftop pop-up of clerestory windows that let daylight cascade all the way to the basement, creating a far lighter mood than the characteristically dark interior of a historical greystone.

That lightness carries through the three-story structure. The main floor is an airy layout of formal and informal spaces, including a sleek kitchen with...

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