2140 Jefferson St. (Photo courtesy of Venture Sotheby's Int'l Realty)

2140 Jefferson St., San Francisco (Photo courtesy of Venture Sotheby’s Int’l Realty)

A lot happens in a year, and as the New Year gets closer many individuals start to reflect on everything they’ve accomplished. If you’ve ever sold a home, you know that this endeavor can take a lot more time and effort than it seemed like it would in the beginning, and when escrow finally closes it seems like you’ve cleared an obstacle course of inspections, paperwork, and fees.

The upside is that real estate transactions aren’t easy for anyone, even celebrities and billionaires. In fact, considering the amounts of money many of them may have first spent on their homes, and the fees they’ll need to pay to sell them, it may be more difficult for the well known

Here’s a look at 4 of the homes sold in the Bay Area by well-known celebrities and entrepreneurs alike, each with their own sets of difficulties:

Robin Williams (Actor/Comedian) Villa Sorriso, Napa – $18, 100,000

Villa Sorriso (Image courtesy of Coldwell Banker Previews International)

Villa Sorriso (Image courtesy of Coldwell Banker Previews International)

 

Robin Williams had Villa Sorriso (Villa of Smiles) built in the early 2000s, but after a divorce began to put a strain on his finances, he put it on the market in 2012 at $35 million.

Living room. (Image courtesy of Coldwell Banker Previews International)

Living room. (Image courtesy of Coldwell Banker Previews International)

 

The main residence alone is over 20,000 square feet on 653 acres. When he was unable to find a buyer, he took it off the market and then relisted it months later for $29.9 million.

 Infinity pool overlooking the Mayacamas Mountains. (Image courtesy of Coldwell Banker Previews International)

Infinity pool overlooking the Mayacamas Mountains. (Image courtesy of Coldwell Banker Previews International)

 

After his untimely passing in 2014, the estate passed to his three children. Still without a buyer, they initially lowered the price to $25.9 million, and a few months later to $22.9 million. I’m surprised that it hadn’t sold after the initial price drop, knowing what an iconic figure Williams was in both comedy and acting.

Vineyards. (Image courtesy of Coldwell Banker Previews International)

Vineyards. (Image courtesy of Coldwell Banker Previews International)

 

Villa Sorriso included 18.4 acres of vineyards producing Cabernet Sauvignon, Merlot and Cabernet Franc wines with existing contracts with Robert Craig Winery and Rombauer Vineyards. It’s no surprise then that the home finally sold to French winemakers Alfred Tesseron and his niece Melanie Tesseron for a 2016 price of $18.1 million.

Colin Kaepernick (SF 49er)4903 Eastbourne Ct, San Jose – $2,895,000

Driveway/Exterior of home. (Photo courtesy of Intero Real Estate Services)

Driveway/Exterior of home.

 

Colin Kaepernick had some interesting times in 2016. He went from team darling to a somewhat more controversial figure this past season. Love him or hate him, this home is now pending sale, though the MLS won’t show the figure. That was a quick sale; though $2.8M is about the standard price for homes in the Silvercreek area of San Jose.

Tiled entry with fish tank. (Photo courtesy of Intero Real Estate Services)

Tiled entry with fish tank. (Photo courtesy of Intero Real Estate Services)

 

Though he’d only lived in this sprawling estate for two years, records show that he invested over $300,000 in renovations. The in-wall fish tank is my favorite.

Second living room. (Photo courtesy of Intero Real Estate Services)

Second living room. (Photo courtesy of Intero Real Estate Services)

 

Since he recently purchased a condo in New York for a million more than he paid for this home – at a fraction of the size – will he miss this slate-gray man-cave entertainment room?

Pool with fountain. (Photo courtesy of Intero Real Estate Services)

Pool with fountain. (Photo courtesy of Intero Real Estate Services)

 

My feeling is that he’ll miss this pool more than the room, especially during a hot New York summer. Kaepernick is scheduled to make $14.9 million in salary and bonuses next season, though with his New York purchase CSN is betting he’ll opt-out to become a free agent.

Peter Thiel (PayPal founder) – 2140 Jefferson St, San Francisco – $8,000,000

2140 Jefferson St. (Photo courtesy of Venture Sotheby's Int'l Realty)

2140 Jefferson St. (Photo courtesy of Venture Sotheby’s Int’l Realty)

 

Another home that’s having a heck of a time attracting buyers is Peter Thiel’s house in San Francisco. This surprises me only because of the stunning views it has of the Palace of Fine Arts as well as the Golden Gate Bridge. In addition, for a 4+ story house in the Marina district, this is a steal.

Rooftop lounge. (Photo courtesy of Venture Sotheby's Int'l Realty)

Rooftop lounge. (Photo courtesy of Venture Sotheby’s Int’l Realty)

 

Thiel originally listed this house back in May for $9,025,000. Less than a year later it’s already been reduced by a million. I can’t imagine many homes in the city would provide such a bucolic view of an iconic landmark like the Palace of Fine Arts.

Dining room. (Photo courtesy of Venture Sotheby's Int'l Realty)

Dining room. (Photo courtesy of Venture Sotheby’s Int’l Realty)

 

Built in the 1940s, this house still has the original architectural elements from that time such as the arched walkways and crown molding.

Bedroom. (Photo courtesy of Venture Sotheby's Int'l Realty)

Bedroom. (Photo courtesy of Venture Sotheby’s Int’l Realty)

 

The home has 5 bedrooms and 6 bathrooms, and is well maintained throughout, though I don’t get the feeling that it’s been truly lived in for quite a while. I imagine that Mr. Thiel would have to travel often, and with co-founders of the company like Elon Musk and Ken Howery, this is more than likely not his only house.

Kyle Vogt (Tech entrepreneur) – 2250 Vallejo Street, San Francisco – $21,800,000 

Exterior of home. (Photo courtesy of OpenHouse Realty, Inc.)

Exterior of home. (Photo courtesy of OpenHouse Realty, Inc.)

 

I know, it’s hard to feel bad for people who are having ‘problems’ selling a house when the numbers hit the multi-millions. To round it out, here’s a house that’s recently been purchased in San Francisco to the tune of $21.8 million – which makes it the most expensive home sold in the area to date. Kyle Voght may not be a household name, but he’s made a fortune selling two different start-ups. How very Silicon Valley.

Living room. (Photo courtesy of OpenHouse Realty, Inc.)

Living room. (Photo courtesy of OpenHouse Realty, Inc.)

 

Speaking of the Silicon Valley and the movers and shakers living there, Mr. Voght may have chosen this particular home for the neighborhood; his new neighbors will include Larry Ellison, the Gettys, and David Sacks.

Upstairs living room. (Photo courtesy of OpenHouse Realty, Inc.)

Upstairs living room. (Photo courtesy of OpenHouse Realty, Inc.)

 

This living room is upstairs and provides a stunning panoramic view of the city outside. This house has 7 bedrooms and 7 bathrooms, so he’ll have no issues making room for overnight guests.

Wet bar. (Photo courtesy of OpenHouse Realty, Inc.)

Wet bar. (Photo courtesy of OpenHouse Realty, Inc.)

 

Speaking of overnight guests, Voght bought this home from the founders of Blue Bottle coffee; so I’m sure he’s well-stocked with both regular and decaf after dropping that amount of money on real estate.