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San Francisco’s Most Expensive Houses Ranked on the Shoe Index

San Francisco’s Most Expensive Houses Ranked on the Shoe Index


photo: iStock


Thanks to the latest tech expansion, San Francisco has become a boomtown, with prices to match. The median home price in the city is now over a million dollars. Recently, a “fixer-upper” in the Sea Cliff neighborhood was snapped up for a cool $ 11 million, after a reported bidding war.

This onset of pricey popularity is a bit hard to fathom for those familiar with an area that’s often foggy, windy, and cold—and that’s in the summer.

As varied as the weather can be, the topography also presents plenty of challenges. Like London or Manhattan, San Francisco is a walking city. But unlike those other urban hot spots, S.F. has unbelievably steep hills that aren’t easy to navigate in high heels—so save the Louboutins for a door-to-door Lyft ride.

A perk of some of the most expensive single-family homes in the city are the views afforded by their hilly perches. These same hills spell peril for the less sure-footed. In other words, be prepared to trade in your Jimmy Choos for comfy Converse when scaling the peaks here.

For those considering a major real estate investment, we’d also suggest a wise expenditure on footwear to go with the house. Here are the current priciest listings in the City by the Bay, along with our customized Shoe Index.

Address: 2071 Broadway

2701 Broadway

Neighborhood: Pacific Heights

Footwear: rag & bone booties

At an eye-popping $ 39 million, this listing is the city’s priciest home. To live here, you’d have to be at the top of the heap. To get up and down this top hill, we recommend short boots. Luckily, there’s a rag & bone store in the neighborhood ready to outfit you in fashion-forward footwear—for men and women. Sure, they’re expensive, but so is the house.


Address: 3800-3810 Washington St

3800 Washington

Neighborhood: Presidio Heights

Footwear: Golf shoes

This posh property, modeled after the Petit Trianon in Versailles, has a price tag to match: $ 17,995,000. It’s also conveniently close to the Presidio Golf Course & Clubhouse. Lace up a pair of golf spikes, and you’ll be prepared to hit the links.


Address: 990 Fulton St

990 Fulton

Neighborhood: Alamo Square

Footwear: Birkenstocks

Sure, you may be the owner of a multiple-unit “trophy property” with “postcard views” of downtown San Francisco for $ 14,995,000. But the address also comes with—you guessed it—a sharp incline. Go for functional over fancy, and you can stroll the streets, enjoy the picturesque park, and take in the row of famous Victorian “painted ladies” without damaging your instep forever.


Address: 2900 Vallejo St

2900 Vallejo

Neighborhood: Pacific Heights

Footwear: Nikes

The $ 14.5 million home is gorgeous. The views are stunning. But the hill is so, so steep. Be prepared to “just do it” with athletic shoes. Your feet will thank you.


Address: 2698 Pacific Ave.

2698 Pacific

Neighborhood: Pacific Heights

Footwear: Sperry Top-Siders

This Classic Revival–style mansion looks like it was passed down a few generations in great style. Because the home sits on a hill, boat shoes are the preppy and practical solution to the footwear challenge. They’re available in all kinds of cool colors. Gin and tonic optional.


Address: 225 Chestnut St

225 Chestnut

Neighborhood: Telegraph Hill

Footwear: Tevas

The 1980s rubber sandal is back—and it’s more stylish than ever. What better shoe choice for the $ 11.2 million Spanish-style mansion on the market, and on a major hill. The right shoes will make for an enjoyable jaunt to nearby North Beach for dinner.


Address: 2010 Jackson St

2010 Jackson

Neighborhood: Pacific Heights

Footwear: Chanel, Chanel, Chanel

If you’re considering this amazing $ 12.5 million abode, you’re already in head-to-toe Chanel. Enough said.


Address: 1032 Broadway

1032 Broadway

Neighborhood: Russian Hill

Footwear: Riding boots

In Old World Russia, traditional city dwellers donned high boots. Since this $ 12 million stunner sits on Russian Hill, we’ll follow the theme and recommend a flat, tall boot. You’ll look good and feel great while hoofing it on steep inclines.

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