1525 Hillside Drive

Lots 61, 62, and 63

“The Dowling House”

Built in 1937

Currently owned by John and Karen Hostetler

Legend of Lots and Addresses
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In 1937, Sydney and Lillian Dowling of Alameda built their summer home in Bracken Brae. They had two children, Syndey Jr. and Elaine. Lillian Dowling was active in the PTA. Sydney Dowling was an architect and ran the S. J. Dowling Company.

The S. J. Dowling Company “Builder of Artistic Homes” was a custom home builder which built hundreds of houses and entire subdivisions of Dowling’s signature Mission Revival, Storybook Ranch, and Monterey Colonial style homes in Oakland, Alameda, and San Leandro.

The Dowling’s were friends with the Charles Smith family and built the house at 535 Burnside Bend for them in 1941. In that same year, Charles and Sydney were involved in a collision with a train. Sydney was driving ‘at a high rate of speed’ when he collided with a Key System train. Sydney was OK, but Charles broke his back. He was in the hospital for months and later sued the Key System for $26,593.

In 1947, Mr. Dowling addressed the club and the directors at the annual meeting. He voiced the opinion of some members that the directors had over-ridden the wishes of the club membership as expressed in the 1946 annual meeting in regard to building the new road between Burnside Bend and Hillside Drive.

He appreciated the fact that it had been done at low cost but it was his opinion that the job was not satisfactory. The president assured the club that the road was being allowed to settle and would be completed later.

Mr Dowling said that he felt that the directors had worked for the best interest of the club as a whole but had overlooked the fact that the majority of the membership was not in favor of the construction of this road.

Mr. Williams (385 Burnside Bend) offered to resign if he had violated the the confidence of the members as he felt the directors had not done wrong. The membership would not accept his resignation but agreed that future directors be obliged to carry out the wishes of the club as expressed at the annual meetings.

The Dowling’s kept the house in the family for 27 years before selling it to A. G. Hutchinson.

The trail of owners as listed in Marion Smeaton’s history of Bracken Brae. The house was built by S. J. Dowling in 1937.
February 16th, 1939 – Santa Cruz Sentinel
After the Bracken Brae Land and Improvement Co. transitioned to the Bracken Brae Country Club. Sidney J. Dowling was one of the first members on the board after incorporation.


April 27th, 1954 – Oakland Tribune
S. J. Dowling is building a house at 1204 Peach Street in Alameda.
1204 Peach Street as it looks today. This was one of Dowling’s signature styles with its distinctive brick work.

The houses in the above article as seen today on Google Maps.
The houses in the above article as seen today on Google Maps.

December 12th, 1937 – Oakland Tribune
4683 Fair Avenue in Alameda with beautiful views of the bay.

April 12th, 1941 – Oakland Tribune
Sidney Dowling’s car is hit by a train. His passenger, Charles E. Smith, was the owner of 535 Burnside Bend.
June 5th, 1941 – Oakland Tribune
Charles Smith’s house in Alameda was built by S. J. Dowling. Smith was the owner of 535 Burnside Bend – also built by S. J. Dowling.

2800 Clay Street in Alameda was the Dowling’s primary address.
An example of an S. J. Dowling house at 4317 Carson Street in Oakland
An example of an S. J. Dowling house at 4446 Davenport Drive in Alameda.
An example of an S. J. Dowling house at 4458 Davenport Drive in Alameda