Founded in 1924 just south of Sherwood Forest, Westwood Highlands was one of the earliest planned residential communities in the country. This quiet, hilly neighborhood is known for its lovely views, particularly along the Mount Davidson Stairway Walk, which meanders through some beautiful foliage and offers stunning views of West Portal. Because many streets in Westwood Highlands end with “wood” (Brentwood, Hazelwood, Burlwood), the neighborhood is often referred to as simply “the woods.” 

Many of its 283 residences were built in the late 1920s, and the eight wrought-iron signs that outline the neighborhood’s borders give the area an old-town feel. When they’re not reveling in the gorgeous scenery, Westwood Highlands residents head to bustling Ocean Avenue, where everything from a Whole Foods supermarket to hip coffee shops line the streets, or to quaint West Portal Avenue, which is lined with popular shops, restaurants, and bars. Commuters enjoy proximity to the West Portal MUNI station, which offers convenient access to downtown and to other parts of the Bay Area. © 2016 Maryann LoRusso 

Whole Foods on Ocean Avenue is a popular destination for fresh organic food and features a dine-in area.

Whole Foods on Ocean Avenue is a popular destination for fresh organic food and features a dine-in area.

One of the nation’s largest public colleges, City College San Francisco attracts students to the neighborhood.

One of the nation’s largest public colleges, City College San Francisco attracts students to the neighborhood.

 Archbishop Riordan High School is San Francisco’s oldest all-male high school.

 Archbishop Riordan High School is San Francisco’s oldest all-male high school.

Mount Davidson Park is a wooded area at the city’s highest peak that features hilly trails and sweeping urban vistas.

Mount Davidson Park is a wooded area at the city’s highest peak that features hilly trails and sweeping urban vistas.

The West Portal commercial district is a lively area filled with popular restaurants, coffee and wine shops, day spas and fashion boutiques. 

The West Portal commercial district is a lively area filled with popular restaurants, coffee and wine shops, day spas and fashion boutiques. 

Residents flock to neighborhood favorite Fresca for ceviche and other classic Peruvian fare.

Residents flock to neighborhood favorite Fresca for ceviche and other classic Peruvian fare.

Built around the entrance to the Twin Peaks Tunnel, the West Portal MUNI Station runs through the city to the Embarcadero.

Built around the entrance to the Twin Peaks Tunnel, the West Portal MUNI Station runs through the city to the Embarcadero.