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Nine Great Commercial Buildings on Leland Avenue

View south down today’s Bayshore Boulevard in the early twentieth century. The Bay Shore Hotel under construction on Leland Avenue with the Spring Valley Water pumphouse building on right. (San Francisco History Center, San Francisco Public Library, AAC-1649.)

by Woody LaBounty

Many might consider Visitacion Valley’s “main street” as Bayshore Boulevard, once known as San Bruno Road and the main pathway between San Francisco and the peninsula. But while Bayshore’s wide lanes have the traffic and the streetcar line, the neighborhood’s commercial heart has historically been Leland Avenue.

Branching off Bayshore to the west, Leland Avenue was created for business. For its first couple of decades the pavement only ran three blocks and its sidewalks were wooden, but by the mid twentieth century that stretch was lined with groceries, butchers, dry goods merchants, barbers, clothing stores, and eateries.

The 1950s creation of the Highway 101 freeway cut-off pushed Bayshore Boulevard into the background for most travelers and Leland Avenue became almost a secret strip known only to locals. The draw of the Greenway and Crosstown Trail has recently brought in urban hikers from outside Visitacion Valley, who have discovered good coffee, tasty sandwiches, and some great small-scale commercial architecture on Leland Avenue. Here are some of my favorite buildings:

Bay Shore Hotel
The former Bay Shore Hotel and Cafe building on the southwest corner of Leland Avenue and Bayshore Boulevard. (Heritage photo.)

The Bay Shore Hotel and Cafe in the early twentieth century. (San Francisco History Center, San Francisco Public Library, AAK-1241.)

Built in the early 20th Century, the Bay Shore Hotel building was a multi-use structure that essentially established and anchored Leland Avenue as Visitacion Valley’s commercial strip, a necessity as developers began hawking home lots on the fields and hillsides. The hotel’s second floor had the rooms, with both rounded and angled bay windows, while. W. A. McGahey operated a corner bar downstairs. Real estate offices, hardware stores, and the Read family’s grocery store used retail spaces along the building’s Leland Avenue side. While now clad with stucco, its former hotel rooms used as apartments, the Bay Shore Hotel building still acts as an anchor of the street and a home to small businesses.

21-29 Leland Avenue
Built in 1946, the block of storefronts at 21-29 Leland are in the Streamline Moderne style. (Heritage photo.)

The upper register of this 1946 Streamline Moderne block of storefronts gets your attention, but I also love the angled entryways on the ground floors. The orange paint of the center storefront is a good start, but can we have a unified color scheme to bring this family closer together? The adjoining building on the west, inserting its rounded corner bay into its neighbor’s roofline, is also charming. Built in the first century of the twentieth century, it is very intact with original transom windows.

37-45 Leland Avenue
37-45 Leland Avenue, constructed in 1933, was home to the local branch library for many years. (Heritage photo.)

Cornice frieze detail of 37-45 Leland Avenue. (Heritage photo.)

For many years, the long commercial building on the corner of Desmond Street housed the local branch library. A new branch was built a couple of blocks farther west in the 2000s. While the form and the decorative frieze along the roofline are intact, we’ve sadly lost some of the tall windows and original entries on the ground floor spaces.

Leland Market
Leland Market, constructed in 1950. (Heritage photo.)

For Modern architecture fans, 65 Leland Avenue is a sweet little example of a midcentury market. An angled hood shelters a span of large windows and a canvas of wall that screams for some illuminated 1950s signage. I’d love to see what the original facade looked like, but who can’t appreciate the hat-tipping penguin?

58 Leland Avenue
58 Leland Avenue, recently used as a Mexican and Central American market. (Heritage photo.)

Tower and finial of 58 Leland Avenue. (Heritage photo.)

This 1941 building has another great Streamline Moderne treatment with a center tower that feels both Mayan Revival and a bit Space Age. Check out the starburst finial—I don’t know that I have ever seen another like it in the city.

93-97 Leland Avenue
The second level of 93-97 Leland Avenue has an interesting overhang on the east elevation. (Heritage photo.)

This 1908 mixed-use building has a permit application to add new housing around and behind it, demolishing two small early cottages at the back of the property, while retaining most of the historic building in front. While a simple building at first glance, an offset second floor extending beyond one side of the mirrored storefronts give this structure some real visual appeal.

186-198 Leland Avenue
Demolition of this unique grouping of vernacular retail buildings would be a significant loss to the neighborhood and city. (Heritage photo.)

This trio of early twentieth century commercial buildings is slated to be demolished. It’s an amazingly intact little row which takes an observer right back to the neighborhood’s earliest days. The corner structure began life as Dougherty’s Grocery and has had murals on its Rutland Street elevation for decades, dating back to when it was a Hawaiian restaurant in the 1980s.

Paddy’s Hawaiian Restaurant at 198 Leland Avenue in the 1980s. (courtesy of Russel Morine)

Visitacion Valley

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