Power couple builds up $140M real estate portfolio

Slack’s Stewart Butterfield and Away’s Jen Rubio acquired five trophy homes since January 2021

Slack’s Stewart Butterfield and Away’s Jen Rubio with 3636 Clay Street, San Francisco
Slack’s Stewart Butterfield and Away’s Jen Rubio with 3636 Clay Street, San Francisco (Google Maps, Getty)
Slack’s Stewart Butterfield and Away’s Jen Rubio with 3636 Clay Street, San Francisco (Google Maps, Getty)

They’ve built up two businesses worth over $1 billion, now they’re building up their real estate portfolio.

Silicon Valley power couple Stewart Butterfield, the co-founder of Slack, and Away co-founder Jen Rubio have amassed an impressive array of luxe homes, having spent at least $140 million since 2021, the Wall Street Journal reported.

Butterfield and Rubio, who married in 2020 and share two children, have purchased five homes — located in three states — between January 2021 and August 2022, the outlet reported.

The couple in January 2021 first bought a 20,000-acre New Mexico ranch from fashion designer Tom Ford for an estimated $40 million, much lower than the $75 million original listing in 2016.

In addition to a main house, two private guest houses and a horse facility, the ranch includes the Silverado Movie Town built in the 1980s for the 1984 film “Silverado” starring Kevin Costner. The movie town has since featured in “Thor” and “All the Pretty Horses,” according to the Journal.

“There are a lot of fabulous ranches in New Mexico, but this is the crown jewel,” listing agent Kevin Bobolsky told the outlet.

Compass’ Clayton Orrigo and Sotheby’s International Realty’s Neil Lyon represented the buyer.

Rubio and Butterfield then purchased from David Walentas an 11-bedroom mansion at 199 Coopers Neck Lane in Southampton, New York, for $32.2 million.

Bespoke Real Estate and Brown Harris Stevens’ Christopher Burnside marketed the property, and Sotheby’s International Realty’s Harald Grant represented the buyers.

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Walentas purchased the 17,000-square-foot, century-old home with his late wife, Jane, in 2019 for $11.6 million. Walentas set about fixing up the property and selling it, dedicating extra time to the 17,000-square-foot project after handing day-to-day operations of the development firm to his son, Jed.

The home includes 11 bedrooms, 12 bathrooms and two powder rooms. There are two gated driveways and an all-weather tennis court has reportedly been proposed for the property. The estate is close to Cooper’s Beach in Southampton.

The couple has also purchased two properties in New York City: 36-foot-wide, 8,000-square-foot West Village townhouse for $27.27 million in August 2021; and a Tribeca townhouse with the city’s only private skybridge for $20 million in August 2022, according to the Journal.

Orrigo, the Compass agent, told the Journal at the time of the purchase that the Tribeca townhouse would serve as programming space for the couple’s foundation.

​​It was first listed for $50 million in 2016 before the asking price was reduced to $35 million in 2019. The three-story, 25-foot-wide townhouse at 9 Jay Street connects to a 2,300-square-foot condo unit at 67 Hudson Street, which was included in the sale.

Butterfield and Rubio in January 2021 also bought a 5-acre estate in the Five Trees neighborhood in Aspen, Colorado, for $25 million, the Journal reported.

The 10,600-square-foot home has six bedrooms, a three-car garage, a 500-bottle wine cellar and a tasting room.

The couple has also sold some properties in the past two years, including their 8,000-square-foot Presidio Heights Victorian for just under $19.2 million in October 2022.

They listed 3636 Clay Street for $19.8 million with Sotheby’s International Realty agent Neil Bassi.  They also sold a Tribeca townhouse for $8.4 million in 2021, the Journal reported.

— Ted Glanzer