Westwood Highlands & Sherwood Forest: San Francisco's Hidden Hillside Neighborhoods
When people think about San Francisco real estate, neighborhoods like Noe Valley, Pacific Heights, or Cole Valley usually come to mind. But tucked away on the city's southwestern hillsides are two of San Francisco's best-kept secrets: Westwood Highlands and Sherwood Forest.
These neighboring communities offer something that's becoming increasingly difficult to find in San Francisco: quiet residential streets, larger homes, scenic views, and a suburban feel while still being within city limits.
Whether you're relocating to San Francisco, searching for a family-friendly neighborhood, or simply exploring where to buy your next home, Westwood Highlands and Sherwood Forest deserve a closer look.
Where Are Westwood Highlands and Sherwood Forest?
Westwood Highlands and Sherwood Forest sit in southwestern San Francisco, just west of Mt. Davidson and adjacent to neighborhoods including West Portal, Miraloma Park, Ingleside Terraces, Monterey Heights, and Forest Hill.
Although they're physically close to many popular neighborhoods, they often fly under the radar—even among longtime San Franciscans.
One reason is their size. Both neighborhoods are relatively small, creating an exclusive residential feel that many buyers appreciate.
For commuters, the location offers convenient access to:
Highway 280
Junipero Serra Boulevard
West Portal Muni Station
Downtown San Francisco
South San Francisco
Silicon Valley
This combination of peaceful living and commuter convenience has become increasingly attractive for professionals who split time between San Francisco and Peninsula employers.
Westwood Highlands: Historic Charm with Stunning Views
Westwood Highlands was developed during the 1920s as one of San Francisco's premier hillside residential communities.
Unlike neighborhoods built on a traditional street grid, Westwood Highlands follows the natural contours of the hills. The winding streets create beautiful sightlines, reduce through traffic, and provide many homes with panoramic city and bay views.
The architecture reflects the era in which the neighborhood was built, with many homes featuring:
Spanish Mediterranean
English Tudor
Colonial Revival
Storybook-inspired architecture
Many properties have retained their original architectural character while being thoughtfully updated with modern kitchens, open living spaces, and contemporary amenities.
Because many homes sit on elevated lots, buyers often enjoy:
Sweeping city views
Bay views
Excellent natural light
Greater privacy than flatter neighborhoods
Sherwood Forest: Larger Homes and a Quiet Residential Feel
Immediately adjacent to Westwood Highlands is Sherwood Forest, one of San Francisco's most exclusive hidden neighborhoods.
Developed primarily after World War II, Sherwood Forest features:
Larger homes
Wider streets
More generous lot sizes
Mature landscaping
Minimal commercial development
Many homes offer significantly more interior space than the typical San Francisco residence, making the neighborhood especially attractive to buyers looking for room to grow.
You'll find homes with:
Four or more bedrooms
Multiple living spaces
Dedicated home offices
Larger garages
Private backyards
Because inventory is limited, homes in Sherwood Forest don't come to market very often. When they do, buyers looking for space within San Francisco frequently pay close attention.
A Neighborhood Built Around Quiet Living
Unlike many San Francisco neighborhoods known for restaurants, nightlife, or heavy foot traffic, Westwood Highlands and Sherwood Forest are almost entirely residential.
That's exactly the appeal.
Residents enjoy:
Quiet streets
Limited traffic
Beautiful landscaping
Well-maintained homes
A slower pace of life
For many homeowners, the neighborhood feels more like a small suburban community than one of America's largest cities.
Access to Nature
One of the biggest advantages of living here is immediate access to outdoor recreation.
Nearby parks include:
Mt. Davidson Park
Stern Grove
Glen Canyon Park
Sigmund Stern Recreation Grove
Lake Merced
Mt. Davidson is particularly popular with local residents. At nearly 930 feet, it's San Francisco's highest natural point and offers peaceful walking trails beneath towering eucalyptus forests along with impressive city views.
Many homeowners appreciate being able to leave their front door and reach hiking trails within minutes.
Schools
Families often consider these neighborhoods because of access to both public and private school options throughout southwest San Francisco.
Nearby schools include several highly regarded public schools as well as respected private institutions located in West Portal, St. Francis Wood, and surrounding neighborhoods.
As with any San Francisco home purchase, buyers should independently verify school assignments and admissions requirements, as attendance boundaries and enrollment policies can change.
Transportation and Commuting
Although these neighborhoods feel tucked away, transportation is one of their strengths.
Residents enjoy relatively easy access to:
Muni Metro via West Portal
Highway 280
BART connections
Downtown San Francisco
South San Francisco biotech campuses
Silicon Valley employers
For many professionals working in biotechnology, healthcare, or technology, this location provides a practical balance between city living and manageable commuting.
What Types of Homes Can You Expect?
Westwood Highlands and Sherwood Forest primarily consist of detached single-family homes.
Compared to many San Francisco neighborhoods, buyers often find:
Larger floor plans
More bedrooms
Attached garages
Larger lots
Better storage
Outdoor entertaining space
Many homes also feature beautiful architectural details that are difficult to replicate today, including original hardwood floors, decorative moldings, vaulted ceilings, and custom craftsmanship.
Who Buys Homes Here?
These neighborhoods tend to attract buyers looking for long-term homes rather than short-term investments.
Common buyers include:
Growing families
Professionals relocating to the Bay Area
Executives seeking more space
Buyers working in biotech and technology
Homeowners wanting a quieter alternative to central San Francisco
Many buyers discover Westwood Highlands or Sherwood Forest only after becoming frustrated with limited inventory in neighborhoods like Noe Valley or Forest Hill.
Once they visit, they're often surprised by how much additional space and privacy they can find.
Real Estate Market
Because these neighborhoods are relatively small, inventory is naturally limited.
It's common for only a handful of homes to come on the market during the course of a year.
That limited supply often creates strong competition when well-maintained properties become available, particularly those with:
Panoramic views
Updated interiors
Larger lots
Flexible floor plans
Outdoor living spaces
For sellers, the scarcity of available homes can work in their favor when pricing and marketing are handled strategically.
Is Westwood Highlands or Sherwood Forest Right for You?
These neighborhoods aren't for everyone.
If you're looking to walk outside your front door and immediately access dozens of restaurants, bars, or shopping districts, other San Francisco neighborhoods may be a better fit.
However, if you're looking for:
Peace and quiet
Larger homes
Scenic views
Excellent privacy
Easy freeway access
Beautiful architecture
Strong long-term desirability
then Westwood Highlands and Sherwood Forest should absolutely be on your list.
They represent a side of San Francisco that many buyers don't realize exists—one that combines the charm of historic residential architecture with the space and tranquility that's increasingly difficult to find within the city.
Thinking About Buying or Selling in Westwood Highlands or Sherwood Forest?
Whether you're relocating to San Francisco, upgrading to a larger home, or preparing to sell, understanding these highly sought-after neighborhoods can make a meaningful difference in your real estate strategy.
As a San Francisco real estate advisor, Nona Ehyaei helps buyers discover neighborhoods that align with their lifestyle, commute, and long-term goals. She also helps homeowners position their properties to attract qualified buyers through strategic pricing, marketing, and local market expertise.
If you'd like to learn more about homes for sale in Westwood Highlands, Sherwood Forest, or other San Francisco neighborhoods, reach out to Nona for personalized guidance and the latest market insights.