GlenStar Properties bought 311 West Monroe in 2014 in the hopes that it could reposition the building for today's office tenants. Instead, GlenStar and its partner in the building, Prudential Real Estate Advisors, are selling the property to a firm with a proven track record of rehabbing older office assets. Sterling Bay has agreed to buy the 380K SF building for $61M, according to Crain's Chicago Business.

The GlenStar-Prudential JV paid $58M for the building three years ago and announced plans to expand the building's lobby, do a full gut rehab and install energy-efficient glass to give tenants floor-to-ceiling windows.

But GlenStar, which repositioned the Board of Trade building with $30M in improvements, suffered a major loss when its anchor tenant, BMO Harris Bank, left, lowering 311 West Monroe's occupancy rate to 18%.

It is possible that Sterling Bay already has an anchor tenant ready to move into the building, similar to how it lined up Hillshire Brands as a tenant at 400 South Jefferson. But Sterling Bay, which has been on a roll with its land grabs in the North Branch Industrial Corridor and building McDonald's West Loop HQ, now faces the challenge of revitalizing a building that has seen better times.