This photo ran in the November 26, 1992 South County edition of the then Telegram-Tribune but the image looks to be from the late 20s or early 30s. The print also had a penciled note on the back, Trib copy 3/12/57 but I did not find it in the microfilm.
The photo shows dirt roads and few homes. A real estate saleswoman holds a map while a couple gets oriented, or perhaps it is a lesbian couple and a salesman, or a man and his two wives. In any case it is a posed photo showing off the location and the only corner of sidewalk to be seen in the area.
This was likely under county jurisdiction at the time. Pismo Beach incorporated twice. The first time in January 11, 1939, later disincorporating then becoming a city again April 25, 1946.
Is this Wadsworth Ave. at the corner of Bello St.? There is a sturdy brick building on the right that looks like it could be the old elementary school.
The cottage advertised lots for sale in the Pismo Heights No 2. development. Hundreds of lots were available with million dollar views according to one of the billboards.
Another billboard promotes the home builder:
Stop! Look! Listen!
We will sell you modern four room and bath rustic bungalows
Cooper & Brock next door
Any Pismo Beach History buffs have more information?