43 Richmond Hill Road has dropped $200,00, and is now asking $3.775 million. I didn't particularly like this house when it was selling as a spec house back in the day, and I haven't changed my opinion since. But my personal taste isn't particularly relevant; the location is.
Houses on Richmond enjoyed a brief period of popularity ten years ago: this one sold new in 2004 for $4.9 in 2006, for instance, but the street has lost its appeal since then. These sellers paid $3.7 million in 2014, and they are obviously having a hard time recouping their purchase price and subsequent improvements.
And they're not alone out there on the fringe. 25 Richmond, which sold for $7.195 in 2014, is now languishing at $5.999, and 85 Richmond, which sold new in 2006 for $7.1 million, was "improved" by the buyer and put back on the market in 2007 at $8.9 million. Fat chance: it finally fetched $4.825 eight years (!) later. Now those buyers are asking $5.250, a price unchanged for a year, but good luck with that.
The problem with Richmond can probably be found in this description of 43 Richmond Hill as "ideally located near Brunswick School, Sacred Heart, Whitby and Parkway School." That would be the schools located on King Street and (way) upper Lake Avenue. It's accurate enough, but is it a selling point for buyers? Apparently not.