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Boxy Bernal Brothers

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Precariously perched near the peak of Bernal Hill, these simple structures have been in the neighborhood long enough to see at least one San Francisco bubble burst. While the bars on the window tell you things haven’t alway been Instagramable vistas and six-dollar lattes, both homes have been updated to match the Ikea decor that’s sure to fill them. This is your once-in-a-lifetime opportunity to own an entire corner of the most squirrely city in America. Bidding starts at five million.

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Piedmont Pete

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Pete has been lovingly maintained by his upper-middle class family for decades. With subtle castle-like curb appeal and an aesthetically appealing arrangement of windows, rooflines and overhangs, he stands out among his neighbors. While there may be shag carpeting lurking within his plaster walls and perhaps an olive green electric stovetop in his kitchen, most of the leftovers from the 1968 remodel can be quickly erased by an ambitious new owner and a trusty contractor. Bidding starts at 1.25 million. Depending on the fiscal success of your start up, you may want to go ahead and get comfortable with the things you don’t like—there’s a good chance you’ll be living with them for a while.

Stucco Sam

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Delightfully plain, this Piedmont home is perched on a corner lot and surrounded by trees and stray children. My guess is that it was purchased six years ago for $425K and it’s latest tax evaluation was in the one-and-a-half million range (an absolute steal when you consider the school districts!). The rooms are small, the electrical is outdated and the family that lives there has already set their sites on something bigger and newer just a little further up the hill. After all, there’s no space for two new Audis in a single-car garage.

Vera of Vermont Street

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Originally a single-family home, this Oakland retreat offers so much vintage charm it had to be split between two spacious apartments. There’s also a really cute girl living in one of the units and she always says hi when we walk by. This increases my value estimate exponentially. If you wanted to buy the entire building, I’d bring at least a million. Just looking to rent an apartment? I’m guessing $2850 a month, not including utilities.