This street’s etymology is opaque. The most likely inspiration is Pen Mar Park, a Gilded Age resort located on the PENnsylvania/MARyland border. (Get it?) Penmar Avenue was named in 1905 on the Walgrove tract. Two men associated with the tract provide us with Pennsylvania and Maryland connections: R.A. Phillips from Pittsburgh and Wilmot Griffiss from Baltimore. Yet I’m hesitant to credit either for this street name, as the tract’s real owner was Venice real estate agent Louella Sibley, who bought the land from future Santa Monica mayor Thomas Dudley. Neither of them had ties to the East Coast. Perhaps they hoped to compare Venice favorably to Pen Mar Park? If you’re seeking other possible portmanteaux, the “mar” might come from the Spanish word for “sea” or from Mary James, wife of the tract’s surveyor Thomas H. James, but I found nothing and no one who could have provided the “Pen”.