List Price: $4.975 million
The Property: You could prowl the streets of the Gold Coast for a long time (as I have) and hardly notice this 4,000-square-foot home. Originally built in 1888 as the coach house for two Astor Street houses, this residence now conceals itself behind draping vines and an almost invisible charcoal-colored brick façade.

The home saves all its visual pop for the interior, a dramatic contemporary space whose centerpiece is a 706-square-foot living room. A huge skylight crowns the 24-foot-high ceiling, making up for the lack of windows. Off to one side, a 10-foot overhang creates an intimate subroom. (As with the rest of the house, Bruce Gregga  handled the interior decoration.) A smaller adjoining family room with cherrywood media cabinetry has two sets of French doors that lead to a big rear yard surrounded by a charcoal-colored brick wall. There is a kitchen next to the family room.

The second floor holds three bedrooms. The master bedroom has a terrific view of the yard and leads to a dressing room filled with espresso-dark cabinetry and a master bath with a skylight. One bedroom has a small balcony that hangs above the front doors and overlooks Scott Street; getting to the other takes you across a glass-walled overlook of the living room. The basement contains wine storage, a workout room, and a 570-square-foot entertainment room with sumptuous dark paneling and a bar.

Price Points: Brian and Michelle Flynn bought the house in 1995 and embarked on three years of renovations. County property records are unclear on what the couple paid for the home—which is probably beside the point, given the additional investment they made on the extensive rehab. Their agent, Jane Field, would not disclose their total investment in the property. The Flynns initially listed the property with an asking price of $5.1 million; in late May, they reduced it to $4.975 million.

Listing Agent: Jane Field of Koenig & Strey GMAC, 312-893-3505;