For a closer look at the condo, launch the photo gallery »

List Price: $3.3 million
The Property: In Chicago’s toddlin’ times, an era when train travel was the height of elegance, the Ambassador East and Ambassador West hotels were regular stops for movie stars, politicians, and society’s elite. Even Alfred Hitchcock’s 1959 cross-country classic, North by Northwest, included a stop at the Ambassador East.

The tailored sophistication of that era pervades a ninth-floor unit at the former Ambassador West, which was converted to 37 luxury condos in the early 2000s. The living room is a gracious space with dark-stained wood floors, crisp baseboard and crown moldings, a handsome fireplace, and abundant daylight from big south and east-facing windows. The views include Frank Sinatra’s preferred suite at the sister hotel across the street and also long, meandering glimpses of the Gold Coast’s lovely architecture and trees.

The living room anchors the south and more formal end of the 4,000-square-foot condo. Next to it is the dining room, where the designer Thomas Wesley continued the stylish finishes of the living room and topped it with an opulent chandelier. Beyond that is a kitchen that’s filled with fine cabinetry and is large enough to contain an oversized island, a casual dining area, and a home office. Across the hall, an interior bedroom—and the only room that didn’t have windows—had a wall removed so that it gets spillover sunlight from the kitchen. The homeowner, Dr. Enrique Hernandez, uses it as a family room, but it would also make a nice media room.

A zigzag in the long, gallery-style hall marks the transition from the formal south end to the three bedrooms of the north end. Each of the two smaller bedrooms has its own bath, and one has a small balcony. With that room’s west-facing windows, which look onto an internal court of the building, the condo has exposures on all four sides, a rarity.

The master suite has the requisite large bathroom, a walk-in closet, and a sizable bedroom, but its finest feature may be its large north-facing balcony. Because the former hotel was built all the way to the sidewalk while its residential neighbors were all set back, the balcony affords a delightful view up toward Lincoln Park and Lake Michigan. That’s a view that will never go out of style.

Price Points: Hernandez, according to his agent, Nancy Joyce, has purchased a single-family home in the neighborhood. He put this condo on the market in early February. A smaller unit in the building (2,058 square feet and two bedrooms) on a lower floor and with none of the view, sold for $1.125 million in January. That figures out to $546 a square foot; this unit is asking $825 per square foot. But Joyce, who was also the agent on the January sale, says it “was no competition for this [condo], with the upgrades and the views and the style you have up here.”

Listing Agent: Nancy Joyce of Koenig & Strey Real Living; 312-339-4949 or