Filled with sprawling homes boasting upscale, old world-inspired architecture and interior finishes, it’s no surprise that Lake Forest is one of the priciest communities in the Chicago area. Boosting the area's exclusivity is its proximity to Lake Michigan, and hence its collection of homes with private lake frontage. In the last six months alone, at least fifty properties have sold for more than $1 million, sale records show. Asking prices are not far off either — on Redfin, the median listing price over the last 30 days is $925,000.

There is one major caveat when listing a multi-million dollar property in this prestigious suburb: the priciest homes are slow to sell. It’s common to see suburban mega-mansions spend months (or even years) on the market, and Lake Forest is no exception. These estates undoubtedly require buyers with deep pockets and a particular interest in the Arts and Crafts movement, but there are few places in the six-county area where ultra-wealthy home buyers can find true classical mansions with views of Lake Michigan. Here are five in need of new owners.

55 N. Mayflower Road, $15 million

Photo: Coldwell Banker Residential

With its current asking price, this 13,000-square-foot lakefront mansion is the third most expensive listing in the Chicago area at the moment. The listing agent notes that the 118-year-old home was designed by noted estate architect Harrie T. Lindeberg for industrial magnate Clyde Carr. Dubbed "Wyldwoode," the nine-acre property boasts lushly landscaped grounds, an outdoor pool with pool house, and guest quarters. The sprawling estate entered the market three weeks ago.

405 N. Mayflower Road, $8.95 million

Photo: Berkshire Hathaway HomeServices KoenigRubloff

Filled with elaborate ornamentation and fine hand-crafted finishes, this massive 21,000-square-foot mansion epitomizes the ultra-high-end, ultra-exclusive estates preferred by Chicago’s wealthiest families at the turn of the century. Designed by Frederick Wainwright Perkins as a gift from Marshall Field’s exec John G. Shedd to daughter Laura and son-in-law Charles Hodgson Schweppe, the century-old mansion retains much of its original historic character and grandeur. The estate has been on and off the market numerous times over the last decade while also taking several price reductions.

1345 Lake Road, $6.999 million

Photo: Berkshire Hathaway HomeServices KoenigRubloff

This 11,000-square-foot, seven-bedroom mansion on Lake Road is yet another historic Lake Forest estate with a prestigious pedigree. Designed by illustrious Chicago-area architect Howard Van Doren Shaw, the mansion, christened "Stornoway," was built for insurance executive Donald McLennan, as Crain’s Chicago Business reported in March. More recently, the exclusive lakefront estate belonged to Bill Wrigley Jr. of Wm. Wrigley Jr. Company fame.

275 Sussex Lane, $7.9 million

Photo: Berkshire Hathaway HomeServices KoenigRubloff

Spanning two acres of prime Lake Forest property, this opulent 13,000-square-foot, eight-bedroom mansion was designed by architect David Adler for the daughter of Morton Salt founder Joy Morton. Boasting flamboyant luxury finishes, the suburban mansion was intended to reflect the French Provincial style that was popular in the 18th century. Slow to sell, the property has returned to the market several times since it was first listed in June 2010.

395 N. Green Bay Road, $7.5 million

Photo: VHT Studios

This enormous 14,000-square-foot mansion set on 7.5 acres has an equally enormous price tag and a story worthy of tall-tale status. Originally constructed in 1910, the so-called "Two Gables" estate is best known for being the former home of television star Mr. T. In a notorious incident in 1987, the actor, born Laurence Tureaud, removed dozens of mature trees from the Jens Jensen-designed grounds. Mr. T, leery of press, never commented on the incident; however, a New York Times report of the so-call “Lake Forest Chain Saw Massacre” indicates that neighbors suspected that his severe allergies drove him to do the deed.