Price: $2.495 million

If I were forced to pick a favorite from architect David Adler’s vast and decadent portfolio of country homes, it would probably be his red tile roof Italianate at Mayflower and Walden Roads in Lake Forest. This double-pronged Old World revival shatters the mold with its five-story observation tower. Medieval—and fairly terrifying—in appearance, the tower makes a lot of sense at this location. The nearly one-acre property is a half-mile from Lake Michigan and the tower inches over trees and neighboring mansions to bring the water into play.

The 1928 house has five bedrooms and five-and-half bathrooms and cobbles together 6,700 square feet of living space. The funny thing is, this wasn’t even the main house in the original scheme for Chicago banker Albert Hamill—it was a complex of garages, servants’ quarters, a “dog trot”, and a greenhouse/work shed. The main house, on Illinois Road, was built earlier by Howard Van Doren Shaw with Adler assisting. The tower was meant as Hamill’s plaything, with a top floor observatory (now a bedroom suite) and the Byzantine Room for the man of the house. But a section of the tower also slept the chauffeur.

“Byzantine” enters the equation via a wraparound mural with dramatic fiery scenes of antiquity. It is original to the space with hairline cracks to show for it. Sellers Eva and Craig Quackenbush elected to let a gradual degradation set in rather than apply a finicky restoration that would inevitably ring false. Compounding such aged opulence are iron lanterns, dark polished tile floors, and a concrete fireplace.

The Quackenbushes’ son lived in the tower’s top observatory level when they purchased the house in 1985. Prior to that, the efficiency had been rented to students of nearby Lake Forest College. Today, as a guest room that’s part of a restored, carpeted tower, there’s central air conditioning and easy access to the roof deck. In summer, the panorama is green with a fleck of blue. In winter, there are clear views of downtown Chicago 30 miles south.

“Hamill was a big fan of Italy,” says co-listing agent Ned Skae of Coldwell Banker. “And in Italy the guy with the tallest tower had the most money.”

Over the course of 29 years, countless improvements and alterations have been made by the owners. Two of the biggies were expansions to living space. In one case, a concrete wall was knocked down between former servants quarters to allow for a library, a secondary bedroom, and the second floor master suite. This also created a contiguous passageway from the tower through the north-south wing on both levels.

The other major expansion came two years ago, with the conversion of a dilapidated greenhouse/work shed to a huge family room with pool table and fireplace. “It was a tough call whether to tear it down or build it up,” says Craig. “The windows and doors are all original and fully restored, and there are no more raccoons floating in the flooded cellar.” It’s a wine cellar now.

Other significant improvements include consolidating three kitchens, one on the second floor, into one delightful, refinished space. The Quackenbushes made two arched cuts into full doorways and tacked on an eat-in conservatory. And, while Adlerian sensibilities always conjure the grand European home with a twist, the sellers’ furnishings are, in many cases, actual European and Middle Eastern artifacts. The living and dining rooms host a 300-year-old sofa, two 400-year-old tables, and a 17th Century carved wood Afghani doorway.

For sleeping, any of the five bedrooms will do. They’re all large and most come with an en suite bathroom. The master is distinguished by the size of its bath and by an attached study/sewing room. The graciousness of the house’s other 13 rooms is plain as day.

The Quackenbushes have kept a home in Paris since 1995 and are moving there permanently. “Thirty years is a long time to be anywhere.”

Price Points: The property is back on the market for $2.495 million after listing for 16 months in 2010-2011. The pricing represents an attempt to bounce partway back from price cuts that saw the ask drop from $2.8 million to $2.295 million. Unique, high-priced homes often take a while to sell, even in an environment like Lake Forest where, at last count, there were 79 listings priced above $2 million.