Silicon Valley enclaves host priciest Bay Area home sales in 2023

If you wanted to sell a home in the Bay Area this year for more than $20 million, Woodside and Atherton were pretty much the only places you could do it. Outside of a few San Francisco and Marin sales, those two Peninsula towns had a lock on the upper end of the residential market. 

“The Silicon Valley/Peninsula luxury home market has probably been the strongest in the Bay Area in 2023,” said Compass Chief Market Analyst Patrick Carlisle, especially in the circle of cities surrounding Stanford University  including Atherton, Woodside and Palo Alto. 

The number of San Mateo County $5 million-plus sales were down about 12 percent from 2022, according to his data, but that year was one of the market’s strongest ever, especially given the pandemic boom still in play in the first half of last year. Carlisle said via email that he expects the Peninsula’s luxury market to “continue to rebound with the big improvements in economic indicators” in 2024. 

Here are the priciest sales for the Bay Area in 2023.

485 Whiskey Hill Road, Woodside | $44.5 million

The biggest sale of the year and one of the biggest ever in the Bay Area. Former Jetblue Chairman Joel Peterson’s estate on 11 acres in Woodside, originally listed back in 2021 for $49 million, sold in February for just short of $45 million. 

The compound has two main homes, including one designed by Arts and Crafts architect Bernard Maybeck, plus three guest houses, a tennis pavilion, a soccer field, a pool and a barn. The multi-parcel property was purchased by Whiskey Hill LLC, which is linked to cryptocurrency investor Suna Said and husband Scott Maslin, founder of a real estate investment firm called Woodglen Investments, according to the Wall Street Journal.

890 Mountain Home Road, Woodside | $40 million

A Woodside home took the second-place spot, though it tied with an Atherton home that also sold for $40 million this year. 

The Woodside home sold to Warriors owner Joe Lacob who bought it from its developer Rafi Bombad, a source with knowledge of the deal confirmed exclusively to TRD. 

It sits on 3.3 acres across the street from Oracle CEO Larry Ellison’s home. It has an estimated 20,000 square feet of interior space across the estate’s main home and other buildings, including a fitness center with a hair salon, a detached office, a two-bedroom guest house, and a “harvest room” for the fruit of the 150-year-old olive trees planted on the property. 

The original asking price was $110 million, one of the highest ever in the Bay Area. 

233 Park Lane, Atherton | $40M

This newly built Atherton home with six bedrooms and eight bathrooms in more than 14,000 square feet tied for the second-priciest Bay Area sale. It was the biggest in the country’s most expensive zip code.

The seller, West Side Park Place LLC, had designed, built and filled the home with furniture, art and more before deciding to move elsewhere, listing agent Michael Repka told TRD when the property came to the market at nearly $50 million at the start of the year. The home was marketed as fully furnished down to the cutlery and linens and sold in mid-October. The buyers were 233 Pl Holding LLC.

3450 Washington Street | $34.5 million 

The sale of this home, sold by billionaire cloud computer co-founders and married couple Mark Armenante and Young Sohn, is fully covered in TRD’s story on top San Francisco sales for 2023. It was the highest-priced listing in the city when it came to market in September 2022 at $45 million.

100 Why Worry Lane, Woodside | $33.5M

The former Woodside home of Michelle Pfieffer and her writer-producer husband David Kelly, who bought 100 Why Worry Lane for $12 million in 2004 and added an adjoining parcel for $8.6 million in 2008, sold for $33.5 million.

The couple listed the now nearly 9-acre cul-de-sac property for $29.5 million in 2018. It sold the following year for $22 million to Why Worry Properties LLC, which lists Palo Alto-based family office Rosewood Family Advisors as its mailing address in state records. 

The creekside grounds have a 1940 main home with four bedrooms and 4.5 baths with a total of 6,300 square feet, plus a 10-stall barn with paddock and riding arena, three guest suites, an office and a gym across the front courtyard from the primary residence. The buyer was 100 Why Worry Lane LLC, with a mailing address at a UPS mailbox in Downtown San Francisco, according to deed and state records. 

515 Manzanita Way, Woodside | $30 million

The only other Bay Area sale to meet the $30 million threshold was also in Woodside. Located on nearly 3 acres and surrounded by a perimeter of heritage oaks, the original 1968 home had a French Country look, according to listing notes from when it last sold for $4.2 million in 2011. 

The 2011 buyer was a trust in the name of Kelly Anne Skarakis, according to public records, who was formerly married to Christopher Skarakis, one of Google’s first employees and its director of business development from 1999 to 2004. The home underwent a major remodel and addition a few years after she bought the home, according to permit records. 

Skarakis appears to have sold the property in an off-market deal to Manzanita Prestige Worldwide Trust, according to public records, whose trustee is listed as Dilip Patel. He is a New York City-based attorney and partner in Brick and Patel, which specializes in estate planning, tax advice and estate and trust administration, according to the firm’s website. 

Best of the Rest

The biggest sale in Santa Clara County this year was a nearly $20 million deal on a Palo Alto home on two-thirds of an acre in the Crescent Park neighborhood in April. It was built in 1916 but had been completely remodeled, while keeping many period features intact, and has a pool, spa, pool house with media room and a one-bedroom guest house. 

In the East Bay, the biggest listing was the $35 million ask for an estate that cost PeopleSoft founder David Duffield more than $135 million to build. It is still on the market. The biggest sale fell far below that lofty number at just under $13.7 million for a 1996 home with a 2003 remodel on 1.5 acres in Lafayette’s Happy Valley neighborhood. It sold at the end of August.

As usual, Marin’s biggest sales were clustered around the Belvedere waterfront, where a 6,000-square-foot home on Beach Road took the top spot at $23.4 million and sold in December. 

Another notable North Bay sale was at Stinson Beach. A 2009 oceanfront home with about 3,900 square feet sold for $17.5 million. It had been owned in a trust under the name of Kenneth Hao, chairman of Silver Lake Partners, a tech-focused private equity firm, until it sold in late October. 

Nearby, a home that belonged to deceased Sen. Dianne Feinstein sold for $9.1 million in November, the second-biggest sale this year in the waterfront enclave. It was bought by a trust in the names of Peter and April Kelly. Peter Kelly is an investor, a former respiratory services company CEO and a teacher of Entrepreneurial Acquisition and Managing Growing Enterprises classes at Stanford’s Graduate School of Business, according to the university’s website.

A waterfront locale was a key value-booster for Santa Cruz’s biggest sale of the year, a beachfront Aptos home that traded for almost $10 million. The price works out to more than  $4,100 a square foot. The buyer was an affiliate of Driscoll’s berry producers in Oxnard. 

In Napa, a gated vineyard compound with nearly 20 acres in St. Helena took the top spot, selling in April for nearly $18 million. The widow of Pier 39 mastermind and Chevy’s Fresh Mex founder Warren Simmons bought the home in April. No other Wine Country home sale was able to top it for the rest of 2023.

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