Price: $925,000

On both banks of the North Branch and North Shore Channel, in Ravenswood Manor and Lincoln Square, homes take on extra grandeur with Spanish colonial influences and clay tile roofs. There’s still a baseline of bungalow, but a critical mass of showier addresses speaks to bigger money (and egos) that also settled here beginning in the 1920s and 30s. Today's featured listing is on the 4900 block of North California Avenue, two blocks east of the fabulous River Park.

Mid 20th Century musical theater and cinema star Betty Hutton, the original “blond bombshell” of Annie, Get Your Gun and The Miracle of Morgan’s Creek, is rumored to have owned this home with her first husband Tim Briskin while briefly nurturing a stage career in Chicago. I can’t confirm this claim, but anecdotal evidence includes the home’s past appearance on tour bus circuits, and the previous owner’s fixation on Hutton and Hutton collectables. The basement bar and Tahitian-themed family room are thought to date to her tenure—they certainly look stuck in the 1940s.

This wasn’t her only stop in Chicago. She apparently lived a short time at an even snazzier house on Uptown’s Hutchinson Street. Hutton’s first marriage didn’t last long and the locus of her career shifted to Los Angeles.

The center of gravity for the current owners has also shifted to a warmer climate. Dan and Angela Latino own a few large bars in Chicago but spend seven months of the year in Naples, Florida. “We still love it here, but when we’re in Chicago we’re mostly working,” says Angela. In other words, they could stand to have something smaller and less labor-intensive than a 4,000-square-foot brick manor.

The Latinos invested roughly $150,000 in improvements since buying in 2007. The linear kitchen got an overhaul and now features expansive cooking and prep space and an eat-in area. There’s central air where there was none; a new master bathroom in place of a closet; and a lot of new paint and trim.

The scale of the house, in desirable Lincoln Square, is absolutely the biggest draw and the reason co-listing agents Colin Hebson and Barbara O’Connor of Dream Town Realty packed Sunday’s open house. But the vintage detailing is not to be missed—everything from stained and frosted glass panels to millwork, light fixtures, and gargoyles. Yep, gargoyles. There’s one staring you down on the front porch.

The other major selling point is the extraordinarily campy basement. One half is a “speakeasy” with vintage bar, built-in benches, and a poker table; the other half is the tropical family room with a tiki hut disguising the furnace and a large cutout of Cleopatra on the window ledge. The Latinos, being in the bar biz, have hosted their share of parties in this alternate reality.

Price Points: The house is on the market for $925,000 after listing on August 11 for $975,000. The Latinos paid $700,000 seven years earlier. The combination of a down market at the time of purchase and the amount spent on upgrades keeps the asking price within reason. At $231 a square foot, the home comes in just under the average price per square foot for the neighborhood. The house is only two stories so stretches out to fill most of the lot. There’s room left for a nice patio and a three-car garage, but only a front yard.