Westwood Highlands, San Francisco: Homes, History & Local Life

Westwood Highlands is one of The City’s most precisely built neighborhoods: 283 homes constructed between 1925 and 1929 by the same team that developed Westwood Park next door, using a modular architectural system designed to give every street both unity and diversity. Architect Charles Strothoff designed the housing stock around three interchangeable modules. window, entrance, and garage. that could be configured in multiple arrangements, meaning each house differed from its neighbors while conforming to a coherent overall scheme. The result is a streetscape that reads as intentional rather than accidental, which is more than most San Francisco neighborhoods can say. According to Wikipedia’s Westwood Highlands article, the neighborhood was one of the first residential communities in the United States to agree to a formal set of covenants and restrictions, making it a direct ancestor of the HOA-governed planned communities that spread across American suburbs in the postwar era.

Is Westwood Highlands right for you?

Westwood Highlands is a single-family neighborhood, period. The 283 homes are detached, owner-occupied, and bounded by a ring of arterial streets that keep through-traffic out of the interior.

The neighborhood’s median household income of $116,573 (per Wikipedia) was significantly above the San Francisco median. The buyer profile skews toward families and established professionals who prioritize the physical character of the neighborhood. the curvilinear streets, the period architecture, the low-traffic environment.

How do you get around Westwood Highlands?

Westwood Highlands has good transit access relative to many west-side single-family neighborhoods, primarily because it is close to Ocean Avenue, where the K Ingleside Muni Metro line runs. The K Ingleside stops along Ocean Avenue and provides access to the Twin Peaks Tunnel and downtown San Francisc. From the Ocean Avenue/CCSF Pedestrian Bridge station, riders can reach West Portal in about 5 minutes, Civic Center in about 20 minutes, and Embarcadero in about 25 minutes, per SFMTA. The K runs weekdays from 5 a.m. to midnight and weekends from 5 a.m. to midnight, with 10-minute headways on weekday daytime service.

Walk Score: 69. Transit Score: 67. Bike Score: 51. Source: walkscore.com, Westwood Highlands.

There is no BART station in Westwood Highlands. The nearest BART is at Balboa Park station, reachable via the K Ingleside.

For two-career households: one partner with a downtown destination can commute via the K Ingleside in under 30 minutes. A partner commuting to the South Bay can drive to Balboa Park BART or use the 101 or I-280.

The history of Westwood Highlands

The story of Westwood Highlands begins with the Twin Peaks Tunnel, which opened on February 3, 1918, reducing travel time from the west side of The City to downtown from nearly an hour to 20 minutes, per Wikipedia. Baldwin and Howell, the real estate firm that had already developed Westwood Park, saw an opportunity in the hillside above Monterey Boulevard.

Westwood Park sold lots as empty parcels. Westwood Highlands, which Baldwin and Howell originally called “Woodcrest,” took a different approach: each lot was packaged with a pre-designed house, marketing the development as an “efficient and economical design for a middle-class market.” Charles Strothoff created the modular system. Hans Nelson built the homes. Development ran from 1925 to 1929, producing a complete, planned neighborhood.

The racial covenants, like those in every residence park of the era, became legally unenforceable after the Supreme Court’s 1948 Shelley v. Kraemer ruling and are void.

What does the housing look like in Westwood Highlands?

Detached single-family homes are the only housing type in Westwood Highlands. The 283 homes were built between 1925 and 1929 to Strothoff’s modular system. Spanish Colonial Revival with red clay tile roofs, stucco facades, fluted columns, and barrel bay windows being the dominant signatures. Lot sizes vary with topograph. Steeper gradient lots tend to be smaller with city views.

Attached homes, flats, and multi-unit buildings are absent from the 283-home subdivision.

Where locals eat, drink, and shop in Westwood Highlands

Westwood Highlands has no internal commercial strip. The Ocean Avenue corridor a few blocks south is the primary daily-use spine, with West Portal Avenue as a secondary option a short drive away.

Ocean Avenue holds the broad mix of Cantonese roast meat, Lao and Thai kitchens, retro burgers, Neapolitan pizza, Chinese bakeries, Italian restaurants, banh mi shops, craft beer bars, and the Whole Foods at 1150 Ocean for grocery runs. The corridor has been a working neighborhood spine for decades, with foot traffic primarily from the surrounding hill blocks. Most Westwood Highlands households build their week around Ocean Avenue and the Stonestown Galleria a short drive west.

Westwood Highlands Pros:

• One of SF’s most architecturally coherent neighborhoods: 283 homes built to a unified design system, all from 1925-1929, Spanish Colonial Revival on curvilinear streets
• Exclusively single-family detached housing
• K Ingleside light rail on Ocean Avenue provides a reliable downtown commute in about 20-25 minutes to Civic Center
• Low through-traffic on interior streets
• Adjacent to Mount Davidson Park and Sherwood Forest open space

Westwood Highlands Cons:

• Limited walkable retail within the neighborhood
• No BART in the neighborhood. East Bay and Peninsula commuters need a transfer
• The 1925-1929 housing stock requires maintenance attention common to homes approaching 100 years old
• Very thin resale market: with only 283 homes total, inventory may be zero to two properties in any given month
• Fog and marine layer from the southwest affects this neighborhood in summer

What’s the Westwood Highlands market doing?

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Westwood Highlands is one of the thinnest markets in The City. with 283 total homes, a busy year might see 15 sales. When something comes up it tends to move fast. Reach out to be on my list: luba(at)lubasf(dotted)com

Westwood Highlands frequently asked questions

What is Westwood Highlands like to live in?

Westwood Highlands is a single-family neighborhood, period. The 283 homes are detached, owner-occupied, and bounded by a ring of arterial streets that keep through-traffic out of the interior.

Who is Westwood Highlands right for?

The neighborhood’s median household income of $116,573 (per Wikipedia) was significantly above the San Francisco median. The buyer profile skews toward families and established professionals who prioritize the physical character of the neighborhood. the curvilinear streets, the period architecture, the low-traffic environment.

How do you get around Westwood Highlands without a car?

Westwood Highlands has a Walk Score of 69, Transit Score of 67, and Bike Score of 51. Westwood Highlands has good transit access relative to many west-side single-family neighborhoods, primarily because it is close to Ocean Avenue, where the K Ingleside Muni Metro line runs. The K Ingleside stops along Ocean Avenue and provides access to the Twin Peaks Tunnel and downtown San Francisc.

What kind of homes are in Westwood Highlands?

Detached single-family homes are the only housing type in Westwood Highlands. The 283 homes were built between 1925 and 1929 to Strothoff’s modular system. Spanish Colonial Revival with red clay tile roofs, stucco facades, fluted columns, and barrel bay windows being the dominant signatures.

What’s one thing people don’t know about Westwood Highlands?

The story of Westwood Highlands begins with the Twin Peaks Tunnel, which opened on February 3, 1918, reducing travel time from the west side of The City to downtown from nearly an hour to 20 minutes, per Wikipedia. Baldwin and Howell, the real estate firm that had already developed Westwood Park, saw an opportunity in the hillside above Monterey Boulevard.