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Seller's Proposition: Buy my Condo and I'll Help with Assessments

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Hmm... a 3/3 condo with prime Hyde Park location for $229K? Yeah, something's up. Turns out to be the assessment. At $850/mo, it'll probably approach your mortgage payment. It'd be easy to spin a cautionary tale out of a listing like this, but the seller, no doubt sensing Curbed was on its way, ventured a curious offer in the hopes of making the sale more palatable. S/he will pay half the assessment for the first year after purchase. After which—who knows?—maybe the assessment will shrink on its own accord. There could be a big project on the horizon. It's hard to imagine lawn care and snow removal representing the bulk of such a levy. Anyway, the unit itself spans 2,000 square feet on the ground floor of a well-kept 55-unit building a block from the lake in one direction, and Metra in the other. Two of the bedrooms are quite large, but a Redfin commenter notes the teensyness of the third. The unit is also, apparently, quite dark. Otherwise, it looks very comfortable and certainly has some nice floors and ornate ceilings. It's been on-and-off the market for the better part of a year and last sold in 2001 for $175K. We'd be astonished if it dipped back to that level.
·Listing: 1629 E Hyde Park Blvd #1 [Century 21]