Bing Crosby Estate Listed For $29 Million In Hillsborough

Bing Crosby’s legendary French chateau-style estate in Northern California just hit the market again — this time asking $29 million. The new owner is already looking to flip it after picking it up last year for $25 million, a deal that was already a steep discount from its original $40 million ask.

The property had spent nearly six decades off the market before that sale, dating back to when Crosby and his wife, former actress Kathryn Crosby, quietly bought it in the 1960s for $175,000 as a surprise for their growing family.

Property Highlights

Price: $29 million
Location: Lower North Hillsborough, CA
Size: 10,980 square feet
Bedrooms: 10
Bathrooms: 9
Notable Features: Designed by renowned architects John Bakewell Jr. and Ernest Weihe, antique furnishings from William Randolph Hearst’s collection, hand-carved wooden staircase banister, Georgian paneling from a 17th-century English manor, dining room walls decorated by artist Al Proom

The Legendary Bing Crosby Estate

The estate was originally built in 1929 by renowned architect John Bakewell Jr., the same mind behind San Francisco City Hall. Decades later, in 1965, it became home to Bing Crosby and his wife, Kathryn, who lived there until her passing in 2024.

As highlighted in a segment from ABC7 News Bay Area, listing agent Jennifer Gilson walks through the property, pointing out preserved treasures like Crosby’s iconic hat collection and the grand piano from High Society still sitting proudly in the living room.

For an even deeper look into the home’s history, a 1998 clip features Kathryn Crosby guiding viewers through her favorite spaces.

In the video, she shares personal memories and details the major renovation and restoration work she undertook to preserve the estate’s charm while updating it for modern living. It’s a rare glimpse into how the Crosby legacy shaped and protected the home’s timeless character.

Our Favorite Spots

In a house as legendary as Bing Crosby himself, there are many standout spots that are hard to look away from. Here are a few of our favorite spaces that truly capture the spirit of the home.

A Grand Entrance

The entrance to Bing Crosby’s Bay Area estate is a grand yet inviting introduction to the home, framed by striking red doors that open to a sophisticated entry hall.

Inside, gray paneled walls, gilded sconces, and an opulent crystal chandelier set a refined tone, while an elegant blue and cream area rug adds a touch of warmth.

The space flows seamlessly into the front hall, where parquet flooring, unique furnishings, and classic European-inspired details lead guests toward sweeping views of the estate’s lush grounds.

Formal Living Room For Christmas Gatherings

The formal living room of the estate is a grand display of French-inspired elegance. Framed by intricate moldings and gilded accents, the space is anchored by a marble fireplace topped with a Baroque-style painting.

Chess Room

The chess room offers a cozy setting for a game with a friend or family member, wrapped in rich wood paneling that enhances its intimate ambiance. A black marble fireplace, positioned beneath a portrait of Bing Crosby, adds warmth and character to the space.

Study

The classic office features intricately carved wood paneling, a commanding fireplace, and floor-to-ceiling bookshelves filled with literary treasures, providing a distinguished setting for deep focus.

Backyard in The Bay

The backyard of Bing Crosby’s Bay Area estate is an expanse of green lawns, mature trees, and winding garden paths.

The historic brick facade of the home overlooks the rolling greenery, with multiple terraces and balconies offering picturesque views of the landscaped grounds.

A covered loggia and slate stone patio extend the living space outdoors, setting the stage for elegant entertaining or quiet relaxation amid the estate’s lush surroundings.

Full Estate Tour

See more of the regal interiors inside the Bing Crosby Estate in the Instagram post from Pricey Pads, which offers a full look at the library, dining room, and several of the elegant bedrooms.

The details, from rich, elegant moldings to vintage chandeliers, capture the timeless sophistication that defined Crosby’s personal style.

Sometimes pictures just don’t do the estate justice, but in the video tour from Jennifer Gilson, the Crosby family’s legacy comes to life. As you walk through the halls, the charm, history, and intimate details of the home reveal a clearer picture of how they truly lived.

What are The New Owners’ Plans?

While the estate ultimately sold for $15 million less than its original asking price, the listing agent told KPIX that the home needs a bit of TLC. The buyer, seeing its potential and legacy, purchased it with plans to renovate, make it more family-friendly, and eventually resell it.

Final Thoughts

At $29 million, Bing Crosby’s Bay Area estate has now opened another window into the private life of one of Hollywood’s most iconic figures.

For decades, he and Kathryn raised their three children there, entertained guests, and took in sweeping views of the San Francisco Bay. The home stayed in the family through Bing’s passing in 1977 and well beyond, until Kathryn’s death in 2023 finally brought it to market for the first time in 60 years.

After a fresh remodel, it’s now looking for a new owner.