The interesting aspect of the Hyde Park / Kenwood neighborhood is that free standing houses DON'T sell by the square foot price. Before the 1990's, almost 80% of the housing stock in the neighborhood was built before the stock market crash. The lucky thing is that we missed that era of bad architecture (50's-70's) that created some really ugly houses across the city. There has been a surge in new construction since the late 80's, but very little of that has been in detached homes. A house that hasn't been renovated since they put in that great new kitchen and that clever shower in the closet in 1973, will certainly have a different value that one which has been recently updated with new mechanicals and finishes. The great thing about being a buyer in the Kenwood neighborhood is that many of the houses were designed by noted architects in their eras and built by the finest craftsmen. Each house will have its own distinctive features and feel. (I know that house with the hot tub in the bedroom...c'est la vie...). The most convincing thing you can do when negotiating on a house with defects is to do an inspection BEFORE making an offer. Include the inspection report with your offer and document why you are making the offer you are making. This is the best time in the past many years to be a buyer. You have the time and the freedom to be as tough as you'd like.