Have you ever wondered how Old Town got its name? Originally established in the 1850s as a German-Catholic community with dairy farms and truck gardens (where produce was transported daily to local markets), the area was sometimes referred to as the “Cabbage Patch” or North Town. The Old Town Triangle Association was formed in 1948 due to residents’ concerns about the community’s “physical deterioration.” A couple of years later, a group of local artists founded the “Old Town Holiday,” a party/fair where they displayed their work along neighborhood fences and tables. The “Old Town” name of this popular annual two-day event, now in its 76th year, has endured, evoking the character and charm of the neighborhood that was almost lost during urban renewal. The triangular area bordered by North Avenue, Clark Street, and the former Ogden Avenue (now a diagonal green space) is now known as the Old Town Triangle District, which was designated a Chicago Landmark by the City Council in September of 1977. This district predates the Great Chicago Fire so the streets and alleys do not adhere to a typical Chicago grid pattern, making it a truly unique place. It’s hard to believe what started out as a small farming settlement is now one of the top 10 most expensive neighborhoods in the city. 

1807 N Orleans St #1S, Chicago, $1,100,000

Photos courtesy of Zillow

Located in the heart of the Old Town Triangle, this 2,300-square-foot, three-bedroom condo with $659 HOAs was originally built in 1889 by German-born architect Theodore Karls for Reinhard Hageman. While the property is contingent, its history and stunning interior still make it worth sharing. What stands out is the spacious front room featuring a gas fireplace and built-in library display, the primary bedroom with an ensuite jacuzzi tub, and the enclosed sunroom off the kitchen that opens onto an outdoor patio. It last sold in 1999 for $550,000.

1706 N Fern Ct, Chicago, $1,750,000

Fern Court is a narrow, alley-like street spanning two mere blocks in the Old Town Triangle. On a corner lot, behind a brick wall setback at the rear of the property, stands this two-bedroom home described in its real estate listing as a “1920s cottage.” According to the Old Town Historic District building catalog, this house was originally built in 1901 for J.A. Licht, with a third floor addition built around 2000. In addition to its postmodern interior, I definitely noticed great details, such as the numerous skylights, interesting staircase, and a painting that covers the television screen. Thanks to its garden wall, you have a private oasis away from the city, featuring a fish pond, a fireplace, and an outdoor kitchen. 

1455 N Sandburg Ter APT 1501B, Chicago, $410,000

You can’t discuss Old Town without mentioning Sandburg Village. Once the western edge of the Gold Coast, many old homes where Puerto Rican immigrants and working-class families once lived were demolished to make way for a 16-acre urban renewal site developed by John Cordwell and Arthur Rubloff for a high-rise development in the 1960s. With southwest views, this split two-bedroom, one-bathroom condo has been completely rehabbed, as you can see by its chef’s kitchen and other updates. The full-amentity building includes $868 monthly HOAs that cover a doorman, on-site manager/engineer, valet service, exercise room, heat, water, cable, and two swimming pools. 

1705 N Crilly Ct APT 2, Chicago, $699,000

According to the AIA Guide to Chicago, real estate developer Daniel F. Crilly purchased the block bounded by North Park Avenue, Wells Street, St. Paul Avenue, and Eugenie Street in 1885 and cut a new street through it. Although he named it after himself (Crilly Court), the four apartment buildings constructed on the street’s east side in 1895 were all named after his children: Isabelle, Oliver, Edgar, and Erminnie. This 1,515-square-foot, two-bedroom, two-bathroom condo now has an open floor plan, a result of a gut rehab nearly 20 years ago. The $633 monthly HOAs include a bike room, water, maintenance, and snow removal. 

1329 N Mohawk St #1, Chicago, $799,000

Last week, I wrote about duplex downs, and here we have another example near the intersection of Clybourn, Larrabee, and Division. The 2,350-square-foot condo with $192 monthly HOAs has two bedrooms on each level, along with three full bathrooms. The downstairs area appears cozy, while the primary walk-in closet is quite impressive. There is a covered balcony adjacent to the kitchen and breakfast nook, but you can also enjoy the outdoors and stunning downtown views from the shared roof deck. It includes one parking space and is within walking distance of “New City” amenities and a Red Line stop.