Advantage is proud to introduce Crilly Court Condominium Association!





Located in Chicago’s historic Old Town Triangle, this 90-unit vintage walk-up condominium association has been managed by Advantage Management since 2008. Originally developed by Daniel Crilly, it was rehabilitated and converted into condominiums by R.P. Fox and Associates. It boasts several spacious floorplans, many of which include outdoor balconies that are commonly used as extensions of the living spaces. The beautiful period designs remain with wooden sash windows, real hardwood floors, and crown moldings, but the property has been updated with modern electrical, plumbing, and HVAC systems.   It is the perfect hybrid of vintage and modern Chicago style tucked away in a charming neighborhood just steps from the some of the city’s finest restaurants, theaters, boutiques and clubs.

The Association consists of two separate properties which were purchased by Daniel Crilly from the City of Chicago in 1885. Both properties were designed by Flanders and Zimmerman. The Wells Building was built in 1888 and the Crilly Building came along later in 1895. The Crilly Building is comprised of four attached apartment buildings that are named after Crilly’s four children: Isabelle, Oliver, Edgar, and Erminnie.   These entrances are noted as some of Chicago’s finest historical architecture. Due to financial difficulties, the Crilly family sold off Daniel’s properties which was believed to have included Crilly Court for a price of only $2,000,000.00. 

In the early 1900s this area was considered to be the “Red-Light District” of Chicago. Between the 1920s and 1970s, it became an area for artsy and progressive types.  Around the block from the famous Second City, it was considered the “Hollywood by the Lake.”  It’s believed some of Second City’s most famous actors once lived on the property – John Candy, Jim Belushi, Gilda Radner, and Bill Murray. It was also the home of Henry Gerber, “the father of the gay movement,” and the sight of the first gay rights organization in the country. Today it is one of the most sought-after properties in the area. New Homeowners flock to Crilly Court because every home has the best of both worlds: a historic neighborhood feel given its aesthetics and central Old Town location and the amenities that one has become accustomed to in the modern day world, such as in-unit washers/dryers, marble baths, and cherry wood kitchens.

Advantage Management has managed Crilly Court for five years. It is a property rich in history and character. The Association and its members are tuned into its legacy and its surrounding urban neighborhood. We are proud to manage a piece of history, and look forward to continuing to serve the needs of the Board of Directors and Homeowners of Crilly Court.