Green Gables Estate: The most expensive house in San Francisco, $135,069,000

Entrepreneur and business magnate Elon Musk is selling his 100-year-old mansion on the San Francisco Peninsula. Listed at $37.5 million, this is the last of his real estate portfolio to be offloaded, in a bid to fund a colony on Mars.

Home to some of the most expensive houses in San Francisco, The Peninsula separates the Bay from the Pacific. At the northern tip is the city, although among locals, The Peninsula excludes that district. At the south lies the top of Santa Clara County.

The exclusive area comprises a large chunk of Silicon Valley, as well as cities such as San Mateo, Redwood, Mountain View, and Menlo Park. The character of each varies, from slices of suburbia to rural hotspots. Architecturally, The Peninsula is rich, with Hillsborough boasting an array of styles.

The cost of living is high, with demand for real estate higher than supply – in part down to the boom of local tech companies and housing not built quickly enough to accommodate.  The Peninsula town of Atherton tops the list of the Bay Area’s most expensive market, with nearby Hillsborough coming in third.

On JamesEdition, the median property price in San Francisco is about $2.7 million (or around $15,000 per square meter), with prices elevating to much higher levels in the upscale Peninsula. Take this immense $135 million historic mansion or Musk’s asset for that matter.

JamesEdition currently has around 100 homes for sale in the prestigious San Francisco Peninsula area, with only 1% modern builds. Let’s take a closer look at our homes for sale there.

Top 10 mansions for sale in the San Francisco Peninsula

10. Seven-bedroom home with a glass sky bridge on an exclusive two-acre plot

Price: $5,995,000

This vacant piece of land is a blank canvas, waiting for development. Perched up high and known as the Island in the Sky, the private lot in one of Hillsborough’s leading estates comes with plans created by modernist Michael Kao of design firm MAK Studio. Think almost 15,000 square feet of interior space, eleven bathrooms, 22-foot grand foyer ceilings, a five-car garage, and a pool. Architectural Design Review Board-approved drawings show the main family house connected by a glass sky bridge to an additional two-story building. Sunlit and with panoramas to the Bay, this offers a super exciting opportunity.

9. Custom-built six-bedroom mansion where contemporary meets old world

Price: $7,388,000

Spread over a plot of 29,155 square feet, this 6,790 detached home in Hillsborough was built in 2010 and features six bedrooms, seven bathrooms, and an array of terraces. At the basement level sits a self-contained apartment – also usable as a billiard room and wine cellar. Designed by Hillsborough architect John Stewart, the three-story property also boasts an office, huge rooms, and verandas looking out to the Mediterranean-style garden with terraced patios and a built-in BBQ. The flat lawn is perfect for a pool, should you wish. This detached residence is a 25-minute drive from the city, and it’s recently had a price drop.

8. French-style estate looking out to Burlingame Country Club

Price: $9,205,000

Picture this: A five-bedroom detached house in Hillsborough covering 6,095 square feet on a plot of 29,621, overlooking the manicured greens of Burlingame golf course. Interested? Drive through gates to the 1947 French-style estate and be greeted by grand-scale sunlit rooms, beautiful grounds with multiple entertaining areas, and a resort-size pool complete with a waterfall and spa. Kids will love the custom-built treehouse; parents will benefit from convenient access to both North and Crocker schools. The spacious residence is a 10-minute drive from scenic 18-hole Crystal Springs and a 30-minute ride from downtown San Francisco.

7. Modern mansion with probably the most scenic views in San Francisco

Price: $10,512,000

This eye-catching grandiose white structure in Hillsborough is set over three acres and could be mistaken for a stylish hotel. Inside, the slick and contemporary multi-level space spans 11,800 square feet across capacious high-ceiling rooms. Boasting sun-drenched views to San Francisco and the Bay out of humongous walls of windows, the detached home offers a master suite with a two-story closet and access to a massive slate sun deck. Enter the residence through the marble foyer before exploring the floor plan featuring a gym, library, and four-car garage. The gated family house is just a five-minute drive from Peninsula Golf & Country Club, too.

6. Professionally landscaped family house with tennis court

Price: $10,261,000

What you have here is a four-bedroom detached home in Lower North Hillsborough, minutes from Burlingame Country Club. Set in a 39,422 square feet estate, the residence itself covers 5,330 square feet, with six bathrooms and ample indoor/outdoor living space. There’s a classic, country vibe to the home that’s a short drive from North and Crocker schools and Burlingame Avenue. Gaze from the wall of windows out to the verdant gardens filled with fruit trees, before heading down the steps to the Primera stone pool. Oh, you’ll also find a water well in the grounds – a unique extra. Alongside the quartet of bedrooms inside, there’s a two-bed guest house with a pair of bathrooms and a fireplace.

5. Eight-bathroom residence with a pair of sweeping staircases

Price: $11,007,000

Constructed in 1990, this six-bedroom detached home in the heart of Hillsborough is found behind gates in a 1.48-acre lot. Covering 9,336 square feet inside, be wowed by the grand foyer and rather lovely stone floors before heading into the formal rooms. Spread over three levels, there’s an eat-in kitchen with a large feature island, plus a walk-in pantry, a playroom, billiard room, gym, sauna, two laundry areas, a wet bar, and a 1,000-bottle wine cellar. Outside on the sprawling lawn surrounded by well-kept flora, enjoy a fire pit and bocce ball court. If you prefer, simply admire the gardens from the balconies or alfresco entertaining patios.

4. Luxury family home with seven bathrooms and a floating staircase

Price: $11,813,000

This luxury five-bedroom Hillsborough residence was built by renowned artistic firm Thorenfeldt Construction and sits in 23,959 square feet. Brought to life inside using imported materials and bespoke amenities, the 5,435 square feet house boasts Italian cabinetry, white oak flooring, high-end Miele appliances, and a three-car garage. Retractable walls in the 50-foot great room reveal a pool and fire pit set in a sculpted garden – the slick modern house typifies outdoor/indoor living. There’s also a stylish pool house spanning 725 square feet, with 14-foot ceilings and a marble bath.

3. Nine-bathroom three-level home with a spa and 21-seater home theater

Price: $12,513,000

Located further south along the peninsula sits this seven-bedroom fairy-tale residence in sought-after Atherton, a 40-minute drive from the heart of San Francisco and a 10-minute ride from Bedwell Bayfront Park. Well-tended gardens spanning the 41,644 square feet plot feature a pool with a swim-up grotto and water slide, plus a play area, putting green, sport court, and seating areas. There’s also a fully-equipped outdoor kitchen. Think 5* luxury as you explore the traditionally yet stylishly decorated 10,345 square feet of interior space. There, you’ll find a fitness center, steam and dry sauna in your very own spa, and a wine cellar with a tasting room. There’s also a garage of 900 square feet for all your vehicle storage needs.

2. Beautifully restored six-bedroom property with an indoor and outdoor pool

Price: $15,858,000

This eight-bathroom modernized home in Hillsborough was built in 1927 and has since been modernized, making it one of our most expensive houses in San Francisco. Designed by George Howard Jr., a member of the first American family to settle in the locality, these days the gated detached family home goes by the name Treehouse. Set over 1.5 acres, the professionally-kept grounds are home to a tennis court, pool, and plenty of seating, while the interior space of 7,160 square feet is classic in style with period detail. There’s a family room with a fireplace, an office, a guest house, and a welcoming lanai. And the kitchen boasts a Wolf stove and a Sub-Zero refrigerator.

1. Green Gables Estate: The most expensive house for sale in San Francisco

Price: $135,069,000

Far and away the priciest San Francisco Peninsula property we have listed, this 32-bedroom whopper of an estate in Woodside is an architectural masterpiece that’s listed on the National Register of Historic Places. Think vast 74-acre grounds with a tennis court, trio of pools, orchards, flower and vegetable gardens, and an impressive main property that’s been standing since 1911.

The extraordinary compound was created by Banker and philanthropist Mortimer Fleishhacker, and is still in the family today. Fleishhacker enlisted the help of Charles Sumner Greene and Henry Mather Greene for design: They conceived the primary residence, surrounded by formal gardens and natural woodlands filled with giant redwoods, spruce, Monterey pines, and eucalyptus. That’s not all: Six additional dwellings dot the sizeable plot.

Alongside these wonderful features and talking points, there are two private roads within the grounds, and wood trails winding their way through – ideal for riding, strolling, and biking. It takes two hours to wander the large acreage. There’s also an on-site reservoir serving the estate’s irrigation needs.

Should you feel the need to leave for green space, Wunderlich County Park is nearby, as are Purisima Creek Redwoods Open Space Preserve and Skeggs Point. And the beaches of Half Moon Bay are just a 25-minute drive away.

Back at the nine-bedroom main house, there’s an elegant yet homely feel. Furnishings were originally chosen by famed New York interior designer Elsie de Wolfe – some still remain today. With clients such as the Duke and Duchess of Windsor and Amy Vanderbilt, her pedigree speaks for itself.

The most expensive house in San Francisco, Green Gables estate is a five-minute drive from Michelin-starred pub The Village and the same journey time from Buck’s of Woodside, a known meeting place for tech entrepreneurs and venture capitalists. The prestigious neighborhood of Woodside is also close to Silicon Valley, a 35-minute drive from downtown, and a quarter of an hour from Palo Alto.

A longstanding gathering site for global dignitaries such as European royalty and senators, the United Nations chose Green Gables for its 20th-anniversary commemoration gala in 1965. A totally private property of this magnitude is a rare find. As a home, it’s an idyllic oasis and a unique investment.

Continue to be inspired by San Francisco mansions


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