Latin School Sells Gold Coast Rowhomes at a Loss

The Latin School of Chicago closed the book on a short-lived Gold Coast real estate gamble, finalizing the sale of four historic Dearborn Street properties at a loss of more than $1 million.

The buyer, investor Alan Skidelsky — a tax attorney who described his real estate ventures as a “hobby” — spent nearly $8.9 million, well over the asking price. He plans to gut-renovate the four former Latin School properties in the 1500 block of North Dearborn Parkway to convert them into rentals while preserving their historic facades, Crain’s reported. While he hasn’t yet determined the final unit count, Skidelsky noted he intends to work within existing guidelines rather than advocating for zoning changes.

Skidelsky’s Gold Coast presence will likely grow even larger. In a separate transaction, he is under contract to acquire a fifth adjacent building at 1517 North Dearborn Parkway, which was not owned by the Latin School. Skidelsky won the redstone at a foreclosure auction with a final bid of $2.15 million, the outlet reported. The property, which was last sold in 2001 and had languished in foreclosure since 2009, features a mix of historical and dated modern finishes, and will be folded into Skidelsky’s broader rental redevelopment plan once the sale closes.

Gutted redstones at 1511 and 1515 North Dearborn Parkway were pitched by the Latin School as blank slates, offering developers or trophy-home hunters the flexibility to build single-family mansions or luxury multi-family rentals.

The Latin School in the spring of 2022 scooped up the contiguous portfolio — two income-producing greystones with 15 apartments at 1505 and 1507 North Dearborn, and the two gutted redstone mansions at 1511 and 1515. The school shelled out nearly $10.1 million total for the properties, viewing them as a potential expansion site for classes from junior kindergarten through fourth grades.

However, those ambitions never materialized. Instead, the school opted for a multimillion-dollar upgrade of its existing early elementary building. Faced with mounting carrying costs, and the daunting prospect of years of disruptive construction, leadership reversed course.

In late January, Latin listed the four properties with combined asking prices roughly $8.1 million.

Despite the financial haircut, the school found a silver lining in market demand, with the properties exceeding the listing price by more than 9 percent. Prospective buyers pounced on the Latin School listings almost immediately, with Sidelsky placing the homes under contract by mid-February and closing the transactions this week. Listing agent Jeff Lowe of Compass marketed the redstones and partnered with multifamily brokerage Interra Realty’s Joe Smazal to market the greystones.

Lowe told the publication that 125 tours of the buildings were scheduled in a one-week period and they considered 15 offers. The properties were offered for sale as two pairs or a single four-building package deal, and Skidelsky took the bulk option.

Latin School still owns property on North Dearborn’s 1500 block, including the early elementary school building at 1531 and next door at 1547, a 19th century mansion and its adjacent garden that the school purchased for $12 million from the now-deceased philanthropist Ann Lurie in 2017.

— Sam Lounsberry