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Venture Capitalist Todd Chaffee Puts His $30 Million Island Mansion on the Market

Belvedere, CA – July 16, 2020 –An early Twitter backer, Todd Chaffee spent more than five years creating a unique home on Belvedere Island that incorporates singular views of the San Francisco Bay Area

Just five years after completing his dream home on Belvedere Island just outside of San Francisco, venture capitalist Todd Chaffee is putting the one-of-a-kind property up for sale. He’s listed the 7,500-square-foot house on Belvedere Avenue with Golden Gate Sotheby’s Lydia Sarkissian and William Bullock, with an asking price of $29.5 million. Completed by architectural firm Aidlin Darling in 2015, the sleek, modern abode incorporates natural materials like stone, leather, bronze, and reclaimed oak. Floor-to-ceiling windows frame exquisite views of downtown San Francisco, the Golden Gate Bridge, the hamlets of Sausalito and Mill Valley, along with towering Mount Tamalpais.

Belvedere Showcase home
A spacious living room in the Belvedere, CA home of tech-investor Todd Chaffee
Photo: Matt McCourtney

The house’s formal dining and living spaces are located on the ground floor, along with three bedrooms, a workout room, and an infinity pool and sun deck. The master suite upstairs is “worthy of a five-star resort,” according to the listing. In all, the house includes six bedrooms, six bathrooms, and two offices—one for Chaffee and one for his wife, Kat. Creating indoor-outdoor spaces suitable for entertaining was a prime concern for the couple. Guests can congregate in an interior courtyard or nestle around a fire pit right off the living room. Like the house, the furniture is all custom-made and “comes with the house if someone wants it,” Chaffee said.

Less than one square mile around, Belvedere Island was first developed in the 1890s as a summer getaway for well-to-do San Franciscans, and today it’s one of the wealthiest enclaves in the U.S., with just over 2,000 residents. Architectural styles range from Queen Anne and mission revival to Mediterranean and mid-century modern and beyond, and several properties are listed on the National Register of Historic Places. The area’s tranquil character is preserved by strict construction codes that prevent major alterations to the landscape. There are no stores or restaurants, either—residents hop over to nearby Tiburon for shopping and dining, or to catch the ferry to San Francisco. “The magic of Belvedere Island is that it’s an unbelievable place and a world-class location,” Chaffee told Bloomberg. “The luxury of it is I can pop to the city for meetings, pop up to wine country, or I’m two minutes away from going sailing.”

Belvedere Showcase home
An outdoor seating area in a Marin County, California, home now on the market for nearly $30 million.
Photo: Matt McCourtney

He praised the locale as an “understated, friendly, conscious community.” Chaffee can credit his investment savvy for enabling him to live so large. He’s put money into tech-winners like Netflix, Kayak, Yahoo, and Pandora and was an early investor in Twitter. His company’s $44 million investment in the social media platform ultimately delivered a return of nearly $5 billion, according to Forbes. Though most venture capitalists put down stakes in San Francisco or Silicon Valley, Chaffee has lived in three different houses on Belvedere Island since 2000. This current home sits on nearly 27,000 square feet of meticulous gardens and landscaping, including a courtyard lined with imported olive trees.

There’s also a two-car garage and carport, and a separate 800-square-foot guest house for overnight visitors. Chaffee and his family are decamping for Southern California, but he hasn’t lost his passion for new construction. Their new home in Tahoe will also be built from the ground up. Should he get his asking price, Chaffee should make a tidy profit off of his island paradise: Construction, landscaping and the land itself cost him about $25 million.