The front yard of the Italianate home rolls down the ridge to Longwood Drive, above, while the backyard stretches more than 250 feet to Lothair Avenue, below. See more photos in the gallery at the bottom of the page. 

List Price: $675,000
The Property: Perched beneath towering oak trees atop a steep ridge, this Italianate house on an enormous parcel of land is within the city limits but feels more like something you would find in a small country town—maybe Galena, where the stair-step terrain stacks older houses as if they were on shelves.

Most likely built in 1874—when its neighborhood, Morgan Park, was developing along the adjacent Chicago, Rock Island and Pacific Railroad—the 13-room house has many of the original features (including tall windows, open porches, and screened sleeping porches) that took advantage of the breezes and views that its lofty placement affords.

With front and back yards that are each more than 150 feet deep—the front yard rolls down the ridge to Longwood Drive, which is about 40 feet lower than the house—this place “feels like your own haven,” says Susan Underwood, who bought it with her partner, Suanne Daves, in 2006. In the summer, she says, “we had a hammock hanging between the trees, or we could sit out on the lawn in Adirondack chairs and we weren’t in the city, we were somewhere else.”

Inside, the house has abundant originals: wood trim and floors, windows, and some chandeliers, all well maintained. The first floor has a more preserved period feel than the second, whose six rooms—once a separate apartment—are now configured as two bedrooms and assorted gathering spaces but could be turned into five or six bedrooms. The rear of the first floor contains a three-room apartment that could also be reworked into the main floor plan or could be left as is for an in-law or an office.

Daves, a pediatric anesthesiologist at the University of Chicago, and Underwood, a nurse at Northwestern Memorial Hospital, are moving to Nashville, where they have taken jobs at Vanderbilt University’s hospitals. “It’s very hard to leave the house,” says Underwood (who does not know whether she’s related to the house’s first owner, Elizabeth Underwood.) “In the summer with the trees in full [leaf], up there on that hill is a lovely, lovely place to be.”

Price Points: The house sits above its neighborhood in another, more figurative way. Chicago’s October 2008 real-estate chart showed an average sale price of $179,467 for the neighborhood, which is in the far southwest corner of the city and characterized by less substantial homes (on far smaller lots) than this one. The @Properties’ market report on the neighborhood says that only two houses have sold for over $500,000 in the neighborhood so far in 2008. That’s not to suggest the house is over-priced, only to point out that is different from most of its neighbors.

Listing Agent: Bernadette Molloy of Molloy & Associates, 773-779-9898;