YoChicago’s hottest neighborhoods of 2006 – Woodlawn

One by one we’ll take a brief look at the state of the eight neighborhoods we spotlighted as Chicago’s hottest back in June of 2006.

Our intrepid reporter wrote this about Woodlawn:

Homebuyers squeezed out of Hyde Park and expensive North Side neighborhoods increasingly have seen Woodlawn’s potential, and more and more developers have been building here, taking advantage of comparatively cheap land prices. At press time, R&B Realty was selling three-bedroom condos priced from the $250s at The Woodlawn, 6531 S. Woodlawn Ave. Handsome but rundown vintage graystone single-families are priced in the $200s.

Well, at this time, Unit 1N at The Woodlawn has been on the market for 83 days at an asking price of $66,333. It sold for $250,000 in January of 2006. Unit 2S closed for $75,000 in January.

It’s not very difficult to find many more illustrations of price deterioration that correspond to the physical deterioration that afflicts many of Woodlawn’s blocks and buildings.

One striking example: a 3-bedroom, 2-bath corporate-owned condo described as being in “very good condition” closed in late April for $10,000. Unit 3# at 1501 E 66th Pl previously sold for $280,000 in December of 2006.

According to Redfin, 103 homes and condos were listed for sale in Woodlawn in April, at a median list price of $129K. There were 14 sales in April at a median sold price of just $24K.

Our reporter, fairly new to Chicago at the time, touted The Woodlawn Organization’s “years improving the neighborhood, spurring housing development, courting retail and instituting anti-gang programs” as a positive for Woodlawn.

Had I been involved in the selection of our 2006 “hottest neighborhoods” I would have suggested that TWO is one of the forces that perpetuate Woodlawn’s blight, and cautioned that many hopes for Woodlawn have been dashed during TWO’s 50-year history.

In the above video I walk Woodlawn with the “Woodlawn Wonder,” a condo owner who blogs at I hate my developer.

You can see more of my walk with Woodlawn Wonder and much more of Woodlawn in the 20 videos on our YouTube playlist.


  • daveydoo 7 years


    Perhaps your drive along 63rd St. some weeks before the Olympic decision would be made by the IOC (fall 2009?) was foreshadowing. I understand that the community has held U of C to the blocks bordering the Midway. If they were ever to reconsider that restriction (negotiated in the late 60’s I believe?) I wonder how they would go about re-negotiating with the university or whether the powers-that- be on campus would even be all that interested.

  • daveydoo,

    Isn’t the University planning expansion to the west rather than south?

  • daveydoo 7 years


    I believe that’s correct. So maybe Woodlawn’s loss is Washington Park’s gain?

  • jim 7 years

    TWO is a racist org who supports any b on b exploitation. It profits from poverty and fights any improvement. Keep the whities out.