failed art student

Wendy Winfield

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If you’re not charmed by the brick street out front, then just wait until you see the view of Sutro Tower from the adorable front porch. Located just steps from the bustle of Cortland Avenue, this home has two updated units that still retain their Victorian charm. Live in one and rent the other out? The city’s rental market is almost as absurd as its real estate market, so why not? Not sure if you’re qualified to be a landlord? Don’t worry—anyone can do it! Our very motivated seller will entertain any offer over 1.9 million.

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Spanish Tile Tony

Spanish Sal.jpgWith an oversized one-car garage, plenty of mature trees and a gracefully curved stairway that your movers are gonna hate, this Grand Lake District beauty would probably set you back about a million or more. Like the festive feel? The current owners will throw in the Christmas lights for free.

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.

Bernal Ben

Bernal Ben.jpgBen hasn’t been gentrified yet—even as the Design Within Reach crowd ambushes his fellow, wood-framed neighbors. His eaves are dirty, his first floor siding tagged by teenagers and his porch smells of urine. Although never divided into apartments, this two story Bernal Heights home hasn’t had the maintenance it deserved over the years. Considering his square footage and proximity to “authentic” Mexican food, I’d imagine the starting bid for Ben would be at least two million. And if one of Zuckerberg’s buddies is in the bidding war, the foggy San Francisco sky is the limit.