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The Overlook Road Area

On the west side of Los Gatos, a little into the foothills and pulling into Monte Sereno, you'll find Overlook Road and adjoining streets.  This is a very scenic part of town and one of the oldest too.  It was developed beginning in  the late 1800s (starting a little after 1890)  to about 1910 initially.   A hilly place,  there are natural retreats due to bends in the terrain and clusters of trees. It is easy to feel remote.  But it's close-in.

John Steinbeck, the famous novelist known for books such as "East of Eden" and "Cannery Row"  lived near Overlook at 16250 Greenwood Lane (which is now in Monte Sereno and was unincorporated at the time he lived there). His first wife helped design the 800 square foot cottage and they moved in at the height of the depression, about 1935.   Written there, on the front patio of his home and in the living room of the guest cottage, was  “Of Mice and Men”.    Even John Steinbeck experienced setbacks, though.  As he was laboring over this piece,  his puppy was said to have eaten the manuscript and Steinbeck was forced to recreate it from memory!   It seems that he wrote “The Grapes of Wrath” from there too.    For awhile, this spot offered him the solitude and scenery that were conducive to, and critical for, his writing.  

Eventually, Steinbeck's fame made him the victim of uninvited visitors and he felt forced to build a fence to keep unwanted folks out.  As the area continued to develop, Steinbeck became increasingly unhappy until the crowding and the noise made him feel suffocated.  He and his wife then retreated further into the hills, moving to a 47 acre parcel in the Santa Cruz Mountains. Like most folks in Los Gatos, though, he did venture into town at times. He occasionally visit the Lyndon Hotel Bar, where he once reportedly entertained director John Ford and Charlie Chaplain.

As for the home on Greenwood Lane?  The original home has since been expanded. And it is nearly impossible to find - quite on purpose.  The current owners likewise seem to value their privacy.   That might true of most of the people in the Overlook area, who have moved into the small foothills of the valley for just a little more quiet and seclusion than is found in the majority of town.

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RE: The Overlook Road Area

Posted by: kerry martinez
Date: Aug. 23, 2010

Thanks for these notes on this area!

My grandparents lived at 18630 Overlook from 1960 to 1972, They rented a caretakers cottage overgrown with vines from a couple named the Finks.  I went there as a child until grand-dad passed away in 1972.  

I recall my dad honking as we went around the blind corners, as we drove up in our red studebaker wagon. I believe that there was a pony near by.  The Finks house was fancy for the day and had a mignificant view. We kids loved to play in back of the cottage up a slight hill.

Last weekend we took a gander of course, not thinking about the years passed and the fact these houses are likely gone. It was not a road for the faint of heart though several residents breezed by like it was no big deal.We couldnt find the property (someone didnt bring the street #).

I checked out the arial map and see what I think is the property; a quarried stone foundation & an adjacent view lot with a concrete foundation and stone wall on the slope & view side.

Those were the days, when a retired Ford worker on a small income could live on this beautiful hill. It still smells the same with all the wonderful trees :)

RE: The Overlook Road Area

Posted by: Mary Pope-Handy
Date: Aug. 26, 2010

Hi Kerry,

Thanks for sharing your wonderful memories!  What a treasure!


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