The Bing Crosby Estate

Located at 1200 Jackling Drive, Hillsborough, California, the Bing Crosby Estate is a historic French chateau-style residence built in 1929 (per tax records). The estate spans approximately 13,635 square feet of finished space (per floorplan artist) and 18,535 square feet in total, including finished and unfinished areas.

It is situated on a 5.36-acre lot, divided across four parcels:

• APN: 027-341-030 – 21,751 sq. ft. (0.5 acres)
• APN: 027-330-490 – 36,912 sq. ft. (0.85 acres)
• APN: 027-330-500 – 11,639 sq. ft. (0.27 acres)
• APN: 027-341-070 – 162,971 sq. ft. (3.74 acres, house parcel)
• Total: 233,273 sq. ft. (3.74 acres)

The Bing Crosby Estate, located in Hillsborough’s prestigious Lower North area within the Fagan Estates neighborhood, is an architectural masterpiece designed in the French Renaissance Revival style by the renowned firm of John Bakewell Jr. and Ernest Weihe. The estate was commissioned by sportsman and racehorse enthusiast Lindsay C. Howard and completed in 1929. Lindsay and his wife, Anita (née Zabala) Howard, resided in the home until their divorce in 1938, after which he sold the property to his father, Charles E. Howard.

Charles Howard, an auto magnate and owner of the legendary racehorse Seabiscuit, lived at the estate with his wife Marcella until his passing in 1950. In 1954, Marcella sold the estate to Kermit L. Williams, who, in 1961, transferred ownership to auto dealer Joseph W. Cochran III and his wife, Joan. After four years, the Cochrans sold 1200 Jackling Drive to famed singer and actor Bing Crosby and his wife, Kathryn. Following Bing’s death in 1977, Kathryn remained at the estate until 2024.

Architectural Features

The design of the home bears a striking resemblance to Champ Soleil in Newport, Rhode Island, which itself was inspired by La Lanterne, an 18th-century hunting lodge at Versailles.

The home boasts 11 bedrooms, 10 full bathrooms, and 5 half bathrooms. The first-floor living areas include an entry hall, smoking room, library, living room, and dining room—some of the most impressive spaces in the house. These rooms feature exquisite finishes such as hardwood parquet floors, lath and plaster walls, extensive wood paneling, and built-in cabinetry. Chandeliers and ornamental light fixtures enhance the grandeur, while Rococo plasterwork and marble mantels, particularly in the living room, emphasize the home’s French Renaissance character.

The stair hall and entry hall stand out with their unpainted oak balustrades, plaster wall paneling, and elegant wood flooring. The library, paneled in redwood, features a striking black marble fireplace mantel.

The Crosbys made significant updates to the home. Kathryn, alongside Bing’s musical director John Scott Trotter, incorporated antiques from William Randolph Hearst’s collection, adding elements such as a wooden staircase banister, “linen fold” paneling, and custom furnishings.

Bing Crosby’s Ownership

Bing Crosby, a longtime friend of Lindsay Howard, was familiar with the property through their shared passion for horse racing. Crosby, an emerging singer at the time, partnered with Howard in the Bing-Lin Stables venture. When the estate became available in 1964, Joseph Cochran III approached Crosby about purchasing it. Although Kathryn was initially hesitant, she fell in love with the home’s 14-foot ceilings, French architectural details, and secluded setting.

By July 1965, the Crosbys had moved in with their children, Harry Lillis Jr., Nathaniel, and Mary Frances. Seeking a quieter lifestyle away from Hollywood, Bing and Kathryn found solace in Hillsborough, where they could provide their children with a normal upbringing. The family worshiped at Our Lady of Angels Catholic Church in Burlingame, and Bing, an avid golfer, often played at the Burlingame Country Club. The Crosbys were well known in the community and enjoyed a relatively private life.

Historical Significance

1200 Jackling Drive remains a landmark of 20th-century luxury and history. The estate embodies the opulent architectural style of the late 1920s and serves as a testament to its notable owners, from Lindsay Howard and his association with Seabiscuit to Bing Crosby, one of Hillsborough’s most iconic residents. Today, the estate stands as a symbol of elegance, history, and cultural significance in the region.