The Latin School of Chicago is backing away from its latest real estate gamble on the Gold Coast, quietly putting four historic buildings on the 1500 block of North Dearborn Parkway up for sale. The portfolio includes two occupied greystones and two gutted redstone mansions, with asking prices totaling roughly $8.09 million. School leaders say the move is about paying down debt and avoiding years of noisy, disruptive construction at the Lower School, while neighbors and preservation groups are eyeing what could be a turning point for one of the neighborhood’s marquee blocks.
What’s on the Market
The school has listed 1505, 1507, 1511 and 1515 N. Dearborn Parkway as a package of two income-producing greystones and a pair of gutted redstone mansions, with a combined asking price a little over $8.09 million, as reported by Crain’s Chicago Business. The two redstones at 1511 and 1515 are each listed at $1.6 million, with Compass agent Jeffrey Lowe on the MLS. Public listings for the redstones are available on Redfin, while the greystones are being marketed as active, income-generating properties with leased apartments.
Why Latin Is Selling
The board told families this fall that the Dearborn purchases were originally made to give the Lower School expansion options, but that no workable plan ever came together and that a major construction project would have produced “several years of relocation and disruption for our community,” according to an email reported by the Latin student paper The Forum. The board said the deals were financed with debt, a key factor in deciding to sell the properties rather than push ahead with a disruptive build-out. Board Chair Dara Milner told the paper the transactions “will remove debt from the balance sheet, and there will not be proceeds for the school.”
The Financial Picture
Crain’s Chicago Business reports that Latin paid roughly $10.07 million for the four buildings in 2022 and is now asking about $8.09 million, a spread Crain’s estimates could leave the school roughly $2 million underwater if the properties sell at their listing prices. School officials say any proceeds will go toward paying down the purchase debt rather than funding new operations. Listing activity suggests the school is moving relatively quickly to unwind the holdings after a multiyear stretch of limited renovation and carrying costs, according to Crain’s Chicago Business.
What Buyers Might Do
The two gutted redstones are being pitched as blank slates, with listing language flagging options that range from one grand single-family home to multiple luxury units or high-end rentals. That flexibility is spelled out in the public listings and marketing materials for the properties, which sketch out the kinds of conversions agents say are realistic in this slice of the Gold Coast. Developers and trophy-home hunters are expected to be among the first to kick the tires, and the public listing for 1511 points to the scale of updates and build-outs that would be on the table. Zillow shows the current condition of the building and the marketing pitch.
Neighbors and Next Steps
Nearby residents and preservation advocates say they would prefer to see the historic houses stay largely intact and worry about aggressive gut-and-stack renovations that could erase original character. Current renters in the greystones, meanwhile, are looking for clarity on leases and timelines as the sales process unfolds. The school has not finished a full broker selection for all four parcels, but individual listings and showings are already being scheduled for the redstone pair. Brokers active on the public listings say the Gold Coast market is currently showing solid appetite for historic properties, which could mean a deal lands faster than some neighbors expect. Compass
Background
The Dearborn purchases came on the heels of Latin’s 2017 acquisition of the Lurie Mansion at 1547 N. Dearborn, which the school bought for about $12 million as part of a broader strategy to secure properties near the Lower School. Over time, Latin amassed several properties on the east side of the block between North Avenue and Burton Place, a concentration that drew scrutiny from neighborhood groups and preservationists. With the four buildings now on the market, the next owner will effectively decide whether that stretch of Dearborn stays mostly residential, shifts toward condo conversions, or is refurbished again for institutional use. Chicago Sun-Times