The Regatta

The Regatta was one of the first towers completed in the Lakeshore East master plan, opening in 2002 when the neighborhood was still largely under construction. The nautical theme runs through the building's design — curved facades, a waterside orientation, and a name that nods to the harbor views.

At 44 floors with 320 units, it's a mid-scale building by Lakeshore East standards. The indoor pool is a genuine amenity. Units are well-proportioned with good lake and harbor views from the upper floors. Being an early-phase building, the finishes are showing their age in some units — buyers should budget for kitchen and bath updates in older units.

The Regatta has a loyal owner-occupant base and a well-established HOA. It's not the newest or flashiest building in the neighborhood, but it's solid, well-located, and competitively priced relative to newer towers.

Waterside Drive puts you on the southern edge of the Lakeshore East residential cluster, with harbor views and easy access to the Riverwalk. The park is a short walk. The Loop is close. It's a quieter address than the Randolph Street buildings, with less street noise and more of a residential feel.