1. Bing Crosby’s Iconic Hillsborough Estate Sells for $25 Million

After just under three months on the market, one of Hillsborough’s most iconic properties has officially sold. The French chateau-style estate at 1200 Jackling Drive, once home to legendary crooner Bing Crosby, closed on June 12 for a whopping $25 million—making it one of the top five most expensive home sales in Hillsborough history. Originally listed at $40 million following the passing of Crosby’s second wife, the 5-acre estate still made headlines with its impressive closing price. In fact, it’s the largest sale in Hillsborough since the Western White House sold for $23 million in October.

Built in the 1920s for the Howard family—best known for owning racehorse Seabiscuit—the property has long been tied to Bay Area lore. While it was once rumored that Seabiscuit was buried on the grounds, historians have since confirmed the horse was laid to rest at Ridgewood Ranch near Ukiah.

Bing Crosby and his family purchased the estate in 1965 and poured their personal style into it. The legendary entertainer even brought in antique furnishings and wood paneling from the collection of William Randolph Hearst, a close friend, adding a layer of old Hollywood glamour to an already storied residence.

Spanning 13,635 square feet, the 11-bedroom mansion is filled with standout features—from a cozy smoking room with a built-in bar to a formal dining space highlighted by a Venetian glass chandelier. Other unique touches include hand-painted wallpaper, carved woodwork, and an abundance of vintage details that speak to the estate’s grandeur and character.

Even with a price reduction from its original listing, the sale of 1200 Jackling Drive signals strong continued demand for high-end, historically significant real estate in the Bay Area. Legacy homes like this are rare, especially in sought-after enclaves like Hillsborough—known for its privacy, prestige, and timeless architecture. View the Estate Here!

2. Nob Hill to Chinatown Sees 51% Home Price Surge — SF Market Signals a Shift

In a surprising real estate twist, San Francisco’s 94108 ZIP code — which covers Nob Hill, Chinatown, Union Square, and parts of the Tenderloin — saw home prices skyrocket by 50.7% year-over-year, jumping from $962K in May 2024 to $1.45M in May 2025, according to Realtor.com.

Analysts say this dramatic spike is fueled by renewed buyer interest in once-overlooked districts that offer relatively “affordable” options by San Francisco standards. Demand is rising in areas where prices dipped significantly in recent years, and it’s sparking competition.

What’s behind the shift? Improvements in city life may be playing a role — from a reported 22-year low in car break-ins to a decrease in tent encampments, San Francisco is slowly regaining buyer confidence. Other nearby ZIPs like 94109 (Polk Gulch, Russian Hill) are also heating up, with professionals prioritizing walkability and urban proximity without returning fully to in-office life.

📌 While the city’s ultra-luxury ZIP codes are cooling, mid-priced neighborhoods are seeing the biggest growth — a sign of shifting priorities among today’s San Francisco homebuyers. Read more here!

3. Roar & Pour Wine Festival @ SF Zoo 🍷🦓

• Jun 27 at 5:00PM - 7:30PM
• San Francisco Zoo
• Upper Great Highway
  San Francisco
  94132
• $125.00

Wine and animals? What more does a person need! Head over to the SF zoo this weekend and experience a wild wine festival. Get your tickets here!

Stay in the know! Visit AMSI Living for all the Buzz in The Bay.