I've lived in Diamond Heights for 16 years and love it. For the same square footage, and two car deeded parking, I'd have to pay triple elsewhere in The City. As for the weather affecting the prices here, take a peak at pricing in areas with the same or worse weather: Sea Cliff, St. Francis Wood, Telegraph Hill, etc.
There are micro climates in The City - some sunnier and with less fog in our foggier months - but If I didn't like the weather in San Francisco, I'd probably move - I came here FOR the weather.
We have good public transportation here and easy access to the freeways - as well as a very nice neighborhood shopping center. It's has been less expensive because there were deferred maintenance issues with the larger condo developments - but boy has that changed! If you're asking about the area because you like the views and the pricing, I would highly recommend it. - Wed May 7 2008, 11:09
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