They were built in 1877 a south-side developer named Daniel Crilly who is credited with developing much of Old Town. In 1885. Crilly purchased all of the property between Eugenie and St. Paul from Wells Street to North Park and proceeded to construct his very own planned community, leasing only to young married couples and personalities connected with the arts: writers, actors, musicians, dancers, and painters. He and his son Edgar kept to this plan, for the most part, until the area fell on hard times after World War I.
By the mid-1920s, they had become seedy tenements whose landladies sat on their front stoops barefoot and tossed bones to dogs passing by. They also threw their trash directly into the back yards.
By the late 1920s,the family had to give up pieces of Crilly, a house here, an apartment complex there. Later, they tried to buy them back, but it was too late. Finally, in 1963, they sold off everything they had left: the houses, the apartments, and the stores on Wells Street for just over two million dollars.
Things began to change in the late 30s. In 1937, a young couple named Kappy and Alexander Maley decided to bite the bullet and rent the house at 1716 N. Crilly Court. It took some courage, because they were appalled at what they saw when they first walked inside. The already-small rooms had been chopped in half and had beds in every cubby-hole. Pay phones hung on partitions all over the house. There was only one bathroom, and it was in such terrible condition that it had to be completely redone.
Despite its shabby appearance, the Maleys fell in love with the place, and when Edgar Crilly agreed to tear out the partitions, remove the phones, put in new carpeting, build a second bathroom, and have the entire house painted, they signed a lease--promising to pay $50 per month in rent. Irma O'Toole, daughter of a well-known Old Town saloon keeper, bought the house at 1706 for a whopping $3,000. She and her husband did a complete gut on their place and turned it into an early Old Town showpiece.
The house at 1704, though still a rental, had a nice, cared-for appearance--displaying "clean windows" and polished brass plates and door knockers. Kappy Maley, who by then was becoming seriously invested in the neighborhood, decided to drop by one afternoon and get some decorating tips for her place. She knocked on the door and was courteously received by a handsome woman of a certain age. She walked into a glitzy parlor and found several young ladies all made up and lounging around in their robes, albeit fairly elaborate robes, and looking askance at their visitor. Now this was odd. A few minutes into the conversation, Kappy realized that she had not walked into just an ordinary house. The "older woman" was, in fact, the Madame of a "call house", and the younger women were her "girls".
The tiny row of two-plus story Queen Anne-style houses, fronted by wrought iron fences, tiny gardens, and wooden stairs leading to the main floor entry, makes you think of Victorian England. Crilly Court just oozes charm. Bay windows, iron columns and the engraved names of Crilly's four children above four entrances -- Isabelle, Edgar, Eugene, and Erminie -- distinguish the apartment building facing Crilly Court. There is space for shops on the first floor of the building along Wells Street, and they continue to operate as such.
Now listed in the National Register of Historic Places, the 80-unit complex has survived the ups and downs of the neighborhood.