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Ask any native of San Francisco where they grew up, and chances are you’ll start hearing about the neighborhoods in District Four: Forest Knolls, West Portal, Diamond Heights, Sunnyside or Monterey Heights, just to name a few. District Four is the residential heart of the city with more single family homes, trees and quiet streets than virtually anywhere else.

At the northern tip of District 4, Forest Knolls sits on the slopes of Mt. Sutro. It’s a steep, foggy neighborhood, but home to plenty of secluded staircases and mid-century homes. It’s a quiet, pleasant neighborhood that offers some amazing views of downtown.

Midtown Terrace sits next door, and it’s home to the largest collection of mid-century homes in the city. The entire neighborhood was built by the Gellert Brothers in the 1950s, and was promoted with ads that promised “unparalleled vistas in all directions!” Most of the homes here begin in the low $800s, and are compact, two-bedroom plans.

Across Portola Avenue, you’ll find Diamond Heights, one of the last areas to be developed in San Francisco. This 300-acre area was once home to San Francisco’s dairies, but was developed in the 1960s under a master plan that incorporated modern, shingled multi-unit buildings and a shopping center (Diamond Heights Village). In fact, there’s only one remaining Victorian in the entire subdistrict (it’s across from the Safeway) — because the owners fought the City over its right to seize and develop the land under eminent domain. Nonetheless, Diamond Heights today offers a plethora of condominiums (priced from the $500s and up for a 1-bedroom), a few single family homes, and easy access to 280 and 101.

Miraloma Park is a planned community of 2,300 homes that were built between 1920-1950. Even though there’s quite a diversity of facades, there are really only seven interior floor plans in the original development, which you’ll often see referred to as “Old Miraloma” in the open home ads. Many feature an atrium with a tunnel entrance. This is a great place to buy a single family home with some history attached — prices start in the mid $700s and top $1 million or more for the fully renovated homes. There’s a strong community here, so much so that there’s even a clubhouse for the Miraloma Park Improvement Club.

Construction in Forest Hill began in 1912, with the promise of creating some of the City’s most exquisite homes in a park-like setting. It’s also one of the least-densely populated neighborhoods in San Francisco, with twisty streets, large Mediterranean-style houses and lots of land.  The 650 homes in Forest Hill belong to a strong community association, which holds regular meetings in a clubhouse designed by noted architect Bernard Maybeck.

Just south is Forest Hill Extension. It was developed in the spirit of Forest Hill, but with smaller homes and lots (but still, lots and lots of trees). One of the city’s most exclusive neighborhoods-within-a-neighborhood is Edgehill (smack in the center of Forest Hill Extension) — with a steep, nearly hidden drive that leads up to a cluster of homes that almost never go on the market. More often than not, they’re traded ahead of the market between friends and family. One of the city’s major developers, the Sangiacomo family, maintains a Kennedy-like compound here.

West Portal is District Four’s retail heart-and-soul, and a great place to live if you appreciate bungalows, great transportation and a little bit of fog. This may be one of the only neighborhoods named after a tunnel — namely, the western terminus of the tunnel that runs from the Union Square to West Portal.  When the tunnel was completed in 1918, it brought a swarm of developers to the area, which previously had been comprised of sand dunes. Homes here are more often than not detached, with traditional front and back yards. You can get going in this area starting in the mid $800s for a fixer, and push a million for a nicely restored two bedroom, two bath home. West Portal is also home to District 4′s best and most vibrant retail strip. And a word to the wise: Even though the Village Grill is a greasy spoon and only takes cash, it makes one of the best waffles around (we suggest getting there early).

St. Francis Wood sits on a 175-acre parcel at the southern foot of Mt. Davidson, and was developed between 1911-1932. It’s probably no surprise that this low-profile, but seriously affluent, neighborhood is home to many of the City’s wealthiest denizens. It’s master-planned community (whose design was influenced by Daniel Burnham, and intentionally tried to mimic Italian Renaissance gardens). St. Francis Wood features some niceties we’d love to see elsewhere in the city, including curvy streets, buried utility lines, scores of trees and two public fountains.  And it contains no retail strip — it’s entirely residential.

Balboa Terrace is just south of St. Francis Wood, and boasts a large selection of single-family “fairytale” style homes. When this neighborhood was built in the 1920s, the Spanish Colonial Revival style was sweeping the city and rustic modular stucco homes went up beside Tudor and English garden cottages. Garages were built at the back of the homes, which makes for a lovely, unified presence on each street. As the 1920s progressed, some large two-story homes were built. This is a great place to find a single family home in the high $900s.

You might not know it, but Ingleside Terrace was once home to San Francisco’s first and only racetrack, and was also the site of California’s first automobile race. You can still take a spin around the turns of the track if you drive around Urbano — but that’s the last you’ll see of the track, which closed after the 1906 earthquake. This community of 750 homes was built between 1910-1913 on the racetrack’s grounds, and it’s often said to be one of the nicest residential “parks” in the city with single family houses, curvy streets and lovely landscaping. And don’t miss the enormous sundial on Urbano at Entrada. Homes here begin in the mid $800s.

Nestled across Ocean is the fascinating hamlet of Mt. Davidson Manor. This neighborhood was developed in 50-acre parcels in the early 1920s. Houses here were intended for working class people, and consequently are smaller (1,200-1,800 sq. ft.). The vast majority are free-standing stucco homes with smaller front and back yards. It’s a livable neighborhood, and prices here start in the mid-$800s.

Head back up the hill to Monterey Heights, and you’ll find yourself in a neighborhood that has a lot in common with St. Francis Wood. It’s a small enclave, but here’s what’s unusual about it: There are lots of two-story homes with two-car garages. The homes are impressive, with big yards and mature landscaping. But it’s also mixed; as you go farther up the hill, you’ll find some 1950-60s architecture we’d rather forget. Homes here can run in the $1.5 million and up range.

It’s a sure bet that lots of people have never heard of Sherwood Forest — one of the smallest neighborhoods in San Francisco with just 200 homes (many of which are rather eccentric ranch homes). Built in the 1930s on the upper, southwestern slopes of Mt. Davidson, you can usually find amazing views of the Pacific in these properties. But there’s a bonus here: the lots are some of the largest in San Francisco. And who wouldn’t want to live on Robinhood Drive, the highest residential street in San Francisco? Prices here begin in the high $800s and move up smartly from there.

Westwood Highlands is a small enclave of about 280 homes — and it’s a great place to look for a first home if you want handcrafted details like plaster walls and old-growth hardwood floors. It’s one of those places that exudes charm, with winding streets, adorable detached houses and neighbors who seem to stay put. Houses here start in the high $900s.

If you love bungalows, then Westwood Park is the neighborhood for you. This community of about 650 homes was designed and built for people of “average means” in about 1915, and most of the streets in the neighborhood are in two concentric ovals. The folks who live here love the unique architecture so much they’re working on making the neighborhood on of the city’s first Residential Character Districts, which would preserve the exteriors of these houses. You can buy a house in Westwood Park for $700,000.

Last but not least, Sunnyside is neighborhood that is home to San Francisco City College as well as the Sunnyside Conservatory, which recently received a $5 million renovation. It’s a substantial neighborhood, with 2,200 single family dwellings. Development began here in the 1890s, so the architecture is more varied than you might expect — a kind of odd assemblage of turn of the century cottages and 1960s duplexes. And although the name is optimistic, Sunnyside usually is fairly foggy. But if you need easy access to the South Bay, you can’t beat Sunnyside. Houses here start in the low $700s.

Useful and Interesting Links about District 4

Forest Knolls Neighborhood Association

Images of Original Ads for Midtown Terrace Neighborhood

Mt. Davidson Organization

Diamond Heights (before it was developed)

Miraloma Park Improvement Club

Miraloma Park History

Wikipedia: Forest Hill

Forest Hill Association

Wikipedia: West Portal

St. Francis Wood History

Balboa Terrace Homes Association

Archive of Ingleside Terrace Photography

Westwood Park History


Chou Chou Bistro
400 Dewey Boulevard

Roti Indian Bistro
53 West Portal Avenue

Fresca West Portal
24 West Portal Avenue

CineArts Movie Theatre
85 West Portal

Tower Burger
729 Portola Drive


Gorgeous. Charming. Fascinating. Old. New. Where else would all the San Francisco natives live?