Sherwood Forest, San Francisco: Homes, History & Local Life

Herb Caen, the legendary San Francisco Chronicle columnist, once wrote that he got lost several times trying to find Robinhood Drive for Thanksgiving dinner in Sherwood Forest. The street is real. So is the neighborhood. A three-by-two-block community of approximately 200 homes on the southwest slope of Mount Davidson, Sherwood Forest takes its Robin Hood theme seriously: the streets are named Lansdale, Dalewood, and Robinhood Drive, and the development still sports its original globe streetlights (Western Neighborhoods Project: https://www.outsidelands.org/sherwood-forest.php). Robinhood Drive is the highest residential street in San Francisco. George Moscone lived on Lansdale Avenue before being elected Mayor in 1976, then moved to St. Francis Wood for a more prestigious address. It is that kind of neighborhood: secluded, elevated, known to insiders.

Is Sherwood Forest right for you?

Sherwood Forest is one of San Francisco’s most architecturally distinctive and private residential enclaves. The approximately 200 custom homes, many designed by notable architects including Timothy and Milton Pflueger and Julia Morgan, sit on some of the city’s largest residential lots, with panoramic views of both the Bay and the ocean from different vantage points. The neighborhood has long been nicknamed “Pill Hill” for the doctors and other professionals who have historically concentrated here.

The buyer profile is affluent, often professional, and frequently seeking a significant architectural property rather than a standard SF purchase. Car ownership is essential. Daily life requires driving. This is a neighborhood for buyers who are making a very specific choice: maximum seclusion, maximum lot size, maximum architectural ambition, in a location that does not prioritize walkability or urban texture.

How do you get around in Sherwood Forest?

Sherwood Forest has minimal transit access. The 36 Teresita bus serves the area, connecting to West Portal and the K/L/M Muni metro lines. The nearest practical transit hub is West Portal station, approximately a 10 to 15 minute drive or a challenging walk involving significant elevation change. There is no BART in the neighborhood.

Walk Score: 53. Transit Score: 66. Bike Score: 40. Source: walkscore.com, Sherwood Forest.

The Walk Score of 27 accurately reflects a neighborhood where virtually all daily errands require a car.

Commute to downtown by car runs approximately 20 to 30 minutes via West Portal and the Twin Peaks Tunnel corridor. For two-career households, a car is a necessity, not an option. The 280 and 101 freeway corridors are accessible via St. Francis Wood and West Portal, making Peninsula commutes manageable by car.

The history of Sherwood Forest

The land was part of Adolph Sutro’s vast West of Twin Peaks holdings, planted with eucalyptus, cypress, and pine trees in the late 19th century. After Sutro’s estate went through probate in 1910, real estate agent A.S. Baldwin of Baldwin and Howell acquired portions of the Sutro forest for residential development. Sherwood Forest was developed as a subdivision beginning in the 1930s, with the Robin Hood thematic naming already in place from the original marketing.

The earliest and most architecturally significant homes on Lansdale Avenue and the upper Robinhood Drive sections were designed by Timothy Pflueger, who also designed the Castro Theatre, the Paramount Theatre in Oakland, and the Pacific Telephone Building downtown. Two of Pflueger’s early Sherwood Forest commissions were for doctors, establishing the neighborhood’s “Pill Hill” identity. The radio family “The Edwards” broadcast weekly shows from a dream home at 1 Cresta Vista Drive in 1941, which drew 25,000 visitors on open tour days before Pearl Harbor ended the experiment.

What does the housing look like in Sherwood Forest?

Detached single-family homes are essentially the only housing type in Sherwood Forest. The homes range from 1930s custom residences in Mediterranean, colonial, and early modernist styles to mid-century homes from the 1950s and 1960s designed by prominent architects. Lot sizes are significantly larger than the standard SF lot, with many properties on 5,000 to 10,000-plus square foot lots.

There are no condos, no multi-unit buildings, and essentially no apartments. The thin transaction volume, typically 5 to 10 sales per year, makes any monthly median highly volatile.

Where locals eat, drink, and shop in Sherwood Forest

Sherwood Forest has no neighborhood retail. Daily commercial life runs entirely on adjacent corridors, primarily West Portal Avenue (a short drive west) for the strip dining and small retail mix, and Mount Davidson Park (directly north) for the open space.

The neighborhood is exceptionally quiet and residential, set into the wooded hillside below Mount Davidson. There is no walkable commercial activity within the boundary, and most weekly errands require a car. West Portal Avenue is the most-used corridor for groceries, restaurants, and daily-life retail.

Sherwood Forest Pros:

• Some of the most architecturally significant custom homes in San Francisco, including works by Timothy Pflueger, Julia Morgan, and other notable architects
• Among San Francisco’s largest residential lots, providing genuine yard space and privacy unusual in the city
• Dual ocean and bay views from different parts of the neighborhood, on the highest residential street in The City
• Mount Davidson Park immediately adjacent, providing 38 acres of forested trails without leaving the neighborhood
• One of the most secluded residential enclaves in SF, with minimal through-traffic and a historically stable community

Sherwood Forest Cons:

• Walk Score 27 is one of the lowest in S. This neighborhood is not walkable in any meaningful sense, and car ownership is a daily necessity
• No commercial amenities within the neighborhoo. All shopping, dining, and services require driving
• No BAR. Transit connections require driving or a challenging bus connection to West Portal
• The thin transaction volume makes pricing difficul. Individual comps rather than neighborhood averages are the only reliable guide
• The fog is persistent given the southwest slope exposure

What’s the Sherwood Forest market doing?

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Sherwood Forest is one of San Francisco’s most specific real estate markets. Buyers here are not looking for a neighborhoo. They are looking for a specific kind of property, often with a particular architect’s work or a particular view corridor in mind. When the right property comes up, the buyer pool is small but determined and financially capable. I know this neighborhood and can help you navigate a market where standard comps rarely apply. Contact Luba: https://www.lubasf.com/contact

Sherwood Forest frequently asked questions

What is Sherwood Forest like to live in?

Sherwood Forest is one of San Francisco’s most architecturally distinctive and private residential enclaves. The approximately 200 custom homes, many designed by notable architects including Timothy and Milton Pflueger and Julia Morgan, sit on some of the city’s largest residential lots, with panoramic views of both the Bay and the ocean from different vantage points. The neighborhood has long been nicknamed “Pill Hill” for the doctors and other professionals who have historically concentrated here.

Who is Sherwood Forest right for?

The buyer profile is affluent, often professional, and frequently seeking a significant architectural property rather than a standard SF purchase. Car ownership is essential. Daily life requires driving.

How do you get around Sherwood Forest without a car?

Sherwood Forest has a Walk Score of 53, Transit Score of 66, and Bike Score of 40. Sherwood Forest has minimal transit access. The 36 Teresita bus serves the area, connecting to West Portal and the K/L/M Muni metro lines.

What kind of homes are in Sherwood Forest?

Detached single-family homes are essentially the only housing type in Sherwood Forest. The homes range from 1930s custom residences in Mediterranean, colonial, and early modernist styles to mid-century homes from the 1950s and 1960s designed by prominent architects. Lot sizes are significantly larger than the standard SF lot, with many properties on 5,000 to 10,000-plus square foot lots.

What’s one thing people don’t know about Sherwood Forest?

The land was part of Adolph Sutro’s vast West of Twin Peaks holdings, planted with eucalyptus, cypress, and pine trees in the late 19th century. After Sutro’s estate went through probate in 1910, real estate agent A.S.