List Price: $3.4 million
The Property: It must have been blind optimism that convinced Tom Tremback back in 1991 that he could turn a fleabag of an apartment building into a loft-style home. Whatever it was, he bought a 100-year-old structure on LaSalle Street that held five decrepit apartments and started renovating. It took ten years of work before he could move in—and a few more before he could call the entire place a home.

Along the way, the building didn’t become a loft but a refined residence filled with elegant finishes. It starts with a two-story living room with a wall of windows on one side and an overlook from the second-floor dining room on the other. That space, with a beamed ceiling, a chandelier, pillars, and artisan-wrought iron handrails, “is the ‘loft’ I ended up with,” says Tremback, a doctor.

Tremback fitted out his new home with nice finishes, including a well-done DiGiulio country-style kitchen and complementary dark wood pilasters in the master bath. But he also included practical things, such as the storage drawers tucked into the kitchen stairs and a dishwasher in the master bath. (Yep, a dishwasher—the first I’ve seen in a master bath, but with a fridge in there already, he can have breakfast in bed and then not bother to haul the dirty dishes downstairs to the kitchen.)

Designed for—and from the looks of it, very good for—entertaining, the home has three connected living rooms on its first floor, dining and kitchen on the second (reached via an elevator if necessary), and a master suite and sitting room on the third. There is also a two-bedroom suite on the English basement level, so while Tremback has the main floors of the home configured as a one-bedroom residence, there are several options for adding more bedrooms. Even the spacious master bath could be divided into two bathrooms; the plumbing for that is in place.

While there are lots of windows on the front of the home (to allow in the warm western sunlight), the primary face of the house is really on the east, which from every level looks over a sumptuous garden and outdoor sitting areas. The garden is so nice that Tremback never followed through on his plan to build a rooftop deck, although there is a balustrade surrounding the rooftop, in case a new owner wants to colonize the space up there and take advantage of the impressive eastern views of North Michigan Avenue.

The view is even good from the staircase. When enclosing outdoor gangways on both sides of the house, Tremback was careful to roof one of the new interior spaces with glass; it perfectly frames a view of the John Hancock Center.

Price Points: Public records do not show what Tremback paid for the property back in 1991, and he would not reveal the amount. It’s safe to say he didn’t pay much: his photos of the building in 1991 show slum-level conditions. In at least one apartment, the plumbing was so derelict that tenants apparently used buckets to empty the bathtub.  

Listing Agents: @Properties’ Chris Mundy (773-490-6813, and Brent Stack (312-493-4725;