“The Latin School of Chicago is putting up for sale a quartet of historical homes on Dearborn Street that it bought four years ago, looking at taking a loss of about $2 million on them.

“Latin bought the four buildings on the 1500 block of North Dearborn Street in the spring of 2022 in three separate transactions that totaled a little more than $10.07 million. The asking prices for the four — two are already on the market and two are on their way — is a little over $8.09 million.

“Buying the quartet was part of an overall plan to improve the facilities for Latin’s lower school, junior kindergarten through fourth grade, the letter says, but in subsequent years the lower school building got a multimillion-dollar upgrade. As a result, the letter says, ‘we no longer see the same need for the Dearborn properties as we did in 2022.’

“The pair of greystones at 1505 and 1507 Dearborn, built in the 1880s, contain a combined 15 apartments, as they did prior to Latin’s ownership, with a mix of historical and modern finishes. Lowe and a commercial broker, Joe Smazal of Interra Realty, will represent these two when they hit the market in the near future.

“In 2022, Randall Dunn, who was Latin’s head of school at the time, told Crain’s the school had no specific plan for the row. ‘As an urban school,’ he said at the time, ‘opportunities to acquire properties like these do not come up often, and Latin looks forward to using these properties to continue creating an environment that meets the needs of its students and respects its place in this historic neighborhood.’

“Since the purchases, two successive Latin heads of school have moved on, first Dunn in 2022 and earlier this month, Thomas Hagerman.

“Three years later, in March 2025, Latin’s student newspaper reported the school ‘ha(d) yet to finalize plans for the four properties.’ While the contiguous quartet might offer the school ‘a broad range of options for use,’ the Latin students wrote, ‘concrete plans and action remain elusive.’ (Rodkin, Crain’s Chicago Business, 1/27/26)

For the past number of years, Preservation Chicago has been working with community groups and elected officials to create a new Gold Coast Landmark District. Now is a great time to move forward with the process of formalizing a Designated Chicago Landmark District that would include North Dearborn Parkway and North State Parkway.

Read the full story at Crain’s Chicago Business

• Latin School selling row of residential buildings it bought in 2022, Dennis Rodkin, Crain’s Chicago Business, 1/27/26
• Time is Money: The Fate of Latin’s Dearborn Property Investment Remains Unclear, Mia Kotler and Marin Ralson, ReadTheForum.org, 3/7/25
• Latin School puts Dearborn homes on the block, eyes $2M loss; Elite Chicago private school backed away from expansion plan after years of carrying costs, The Real Deal, 1/27/26
• Latin School buys 4th home on its block; The elite private school has recently spent more than $10 million on neighboring properties, which it says will keep paying property taxes, Dennis Rodkin, Crain’s Chicago Business, 6/2/22
• Latin School buying up historical homes on its block; The elite private school has recently spent nearly $8 million on three addresses in the 1500 block of Dearborn Street and will close on a fourth May 25, Dennis Rodkin, Crain’s Chicago Business, 5/24/22