1. $125 Million | 27560 Pacific Coast Highway | Malibu  

Occupying a waterfront bluff with breathtaking views of the Pacific Ocean, this three-acre compound is one of the largest residential parcels in Malibu. Once owned by country music crooner Kenny Rogers—who installed a small train that goes to the beach below—the estate comprises a four-bedroom main home, three-bedroom guest house, and a guardhouse. The current owner, entrepreneur Diana Jenkins, is parting with the property after 15 years.

This home is listed with Chris Cortazzo of Compass.

2. $119 Million | 1011 North Beverly Drive | Beverly Hills 

The 18-bedroom Beverly House sits on three and a half manicured acres in the heart of Beverly Hills, protected behind wrought-iron gates. Designed by architect Gordon Kaufmann in 1926 for banker Milton Getz, the sprawling Mediterranean-style house was later purchased by publishing titan William Randolph Hearst and Hollywood star Marion Davies. At the request of the couple, herringbone parquet floors and a fireplace were removed from Hearst Castle and installed at the palatial abode, which has also made cameos in The Godfather and The Bodyguard. 

This home is listed with Mauricio Umansky of The Agency.

3. $115 Million | 2000 South Ocean Boulevard | Lantana, Florida 

Nearly five years since listing for $195 million, this 15-acre Palm Beach County compound has shaved roughly $80 million off its asking price. Dating to the 1940s, the manse was once home to style icon Gloria Guinness, a muse of writer Truman Capote. Now in the possession of the Ziff publishing family, the beachfront estate comprises a 12-bedroom manor home, seven-bedroom guest house, and a pair of cottages plus separate staff quarters. Notably, the spread comes with 1,200 feet of dune-lined beach with 1,300 feet of frontage on Lake Worth.

This home is listed with Cristina Condon of Sotheby’s.

4. $115 Million | 27930 Pacific Coast Highway | Malibu 

In the late 1990s, broadcasting billionaire David Saperstein commissioned this 10,600-square-foot residence known as Mar de Amor, or Sea of Love. Now he’s unloading the two-and-half-acre complex, which overlooks the Pacific and comes with access to the exclusive Paradise Cove beach. In addition to 12 bedrooms, the opulent dwelling includes a pair of treehouses, a 20-seat movie theater, lighted tennis court, and an 18-foot-tall crystal chandelier in the entryway.

This home is listed with Drew Mandile of Sotheby’s.

5. $100 Million | 31118 Broad Beach Road | Malibu 

Hollywood star Pierce Brosnan had already played James Bond in a trio of films when he and his wife, Keely, purchased a midcentury-modern ranch house in Malibu some 20 years ago. But after 2002’s Die Another Day grossed $431 million at the global box office, the Irish actor found himself with a hefty bonus that prompted the pair to create their dream home on the three-acre lot, which boasts 120 feet of ocean frontage on Broad Beach. The resulting 12,500-square-foot home, dubbed “Orchid House,” features a peaked roof clad in green clay tiles that were glazed to match the exact shade of the lush mountains in the distance.

This home is listed with Chris Cortazzo of Compass.

6. $99 Million | 908 Bel Air Road | Bel-Air, California

Built by Los Angeles plastic surgeon Raj Kanodia, this striking 34,000-square-foot home features nine bedrooms and 20 baths and is located just a stone’s throw from famed Sunset Boulevard. The mammoth estate was most recently listed as a rental seeking $1.5 million a month, making it the country’s most expensive residential lease. Perched on a hilltop and equipped with a 90-foot-long infinity pool, the house boasts spellbinding views that stretch all the way to the Channel Islands’ Santa Catalina.

The home is listed with Williams Williams Estates Group.

7. $98.5 Million | 16401 Calle Feliz | Rancho Santa Fe, California 

Encompassing 77 acres in northern San Diego County, the Covenant estate is comprised of seven parcels that include multiple dwellings, a pair of horse barns, arenas, pastures, trails, a tennis court, and a massive lake teeming with bass. The 15,000-square-foot Spanish-style main home is complemented by a two-bedroom guest house with a game room, gym, and bowling alley.

This home is listed with Patricia Kramer of Sotheby’s.

8. $90 Million | 432 Park Avenue | New York City 

Crafted by Uruguayan architect Rafael Viñoly, 432 Park Avenue caused quite the stir when it was completed in 2015, its slender silhouette soaring 1,396 feet above so-called Billionaire’s Row in midtown Manhattan. This five-bedroom unit—the most expensive in New York—occupies the building’s entire 82nd floor and clocks in at 8,000 square feet. The panoramic vistas, which include the entirety of Central Park, are the biggest selling point.

This home is listed with Ryan Stenta of Douglas Elliman. 

9. $88 Million | 9 East 71st Street | New York City 

Manhattan’s most expensive townhouse is this 28,000-square-foot Upper East Side behemoth, known as the Herbert N. Straus mansion. Built in 1930, the neoclassical residence is seven stories tall and sits on a lot that is over 100 feet deep. Original elements include 15-foot-tall oak entry doors, imported French-limestone carvings, and ornamental iron works—and it was most recently renovated by legendary designer Alberto Pinto. The structure, however, has a checkered recent past: It was the last home of disgraced financier Jeffrey Epstein and is being sold by his estate.

This home is listed with Adam Modlin of the Modlin Group.