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Depends on where in Highland Park. HP is slowly regentrifying as the artists that used to live in Silverlake and other "hip" areas are moving in as they were priced out of the other places. HP has a fair amount of cool older Craftsman houses that unfortunately ended up as part of the "hood" and saw a fair amount of abuse, along with other crap being tossed up. For those that don't know LA (socal actually, as San Diego is the same way), lots of hills in neighborhoods with canyons and houses tucked everywhere. They are probably on the upslope towards Mt. Washington. Some cool houses there, some crap, and some of the streets are a PITA. I have no doubt the comps even "on the hill" are around $450K. There was a serious correction in that area between '06 and now. It has leveled off but those that bought around '06/'07 are out of luck.
The real question is how much they make, where they work and want to live, and how much rent will be for an "acceptable" place. $5K/mo rent in that area would get you something ridiculously good, and in fact would put you in South Pasadena in a really cool place. In fact I think you'd be hard pressed to find a $5K/mo rent house in HP, and it would be the exception in the neighborhood.
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