$85 Million Italian ‘Villa’ in California With 3,500-Bottle Wine Cellar Pops to the Top of the Most Expensive Homes List

A 12,305-square-foot, Italian-inspired legacy compound in Portola Valley, CA, just hit the market for an eye-watering $85 million, making it this week’s most expensive listing.

The 12-acre Silicon Valley property known as Villa del Prato is subdivided into three separate plots with each structure occupying its own address.

The enormous estate boasts a 12,305-square-foot mansion, a 6,500-square-foot entertainment building, and a 2,000-square-foot pool house with guest accommodations.

And for those with a taste for fine wines (and with very deep pockets), the 3,500-bottle cellar will no doubt prove a prime selling point.

Other unique amenities include “hospital-grade” HEPA filters for clean air, commercial “skyscraper-quality” materials for a secure exterior, and a video surveillance system.

Other eye-popping abodes this week include a Palm Beach, FL, estate that the sellers are trying to more than double their investment on; a Greenwich Village townhouse fresh off a three-year renovation; and a 538-acre Texas ranch with an airplane hangar.

10. 2990 Broadway St, San Francisco, CA

Price: $32,000,000

Outer Broadway neighborhood: Offering panoramic views from the Golden Gate Bridge to Alcatraz, this 10,180-square-foot mansion on Billionaire Row is said to be owned by the family of the late philanthropists Fritz and Lucy Jewett.

The four-story Presidio residence originally hit the market last year for $38 million as San Francisco‘s most expensive listing and has once again commanded the top spot. Luxurious details inside the four-bedroom estate include a two-story foyer with a grand curved staircase, a full-service bar, a solarium, two fireplaces, and a seven-car garage.

The last house on Outer Broadway designed by architect Sandy Walker was custom built in 1987 for the Jewett family and has “dazzled heads of state, royalty, and the city’s high society.”

9. 1140 Calle Vista Dr, Beverly Hills, CA 

Price: $32,000,000

Ready-to-build estate: This 1.12-acre elevated lot offers a “once-in-a-lifetime opportunity to create a grand estate” with views of the Beverly Hills skyline, Pacific Ocean, and downtown Los Angeles.

Approved plans are said to be in place to construct a 13,600-square-foot estate, and site work has already begun. The proposed five-bedroom estate with three-phase power features a “world-class” wellness center with a sauna and an indoor pool, a home theater, fitness center, and private lounges.

The three-story residence will also have an in-ground pool and spa.

8. Park City, UT

Price: $32,000,000

The Colony enclave: Built in 2019, this ski-in, ski-out mountain mansion designed by architect Rick Otto sits on 7.46 acres of wooded privacy.

Located in the exclusive private Colony community, the six-bedroom contemporary with an oxygenation system boasts wood floors, copper accents, a custom floating staircase, designer lighting, and oversized windows that capture the mountain views. The 14,850-square-foot interior also offers two private offices, a home gym, a separate yoga/Pilates studio, a home theater, a bunk room, and several family rooms.

Private terraces overlook the in-ground pool with spa.

7. 239 Emerald Ln, Palm Beach, FL

Price: $33,000,000

Newly renovated: Just three years ago, a Chicago-based real estate chief flipped this six-bedroom residence for $6.2 million more than his purchase price less than a year prior.

The 7,496-square-foot estate was said to be purchased by Buck House Limited, a Cayman Islands company that is now looking to more than double their investment. Built in 1950, the redesigned residence has just completed an “extraordinary” two-year renovation.

Highlights include a custom English oak front door, a 40-foot loggia with an outdoor fireplace, a media room, fitness center, and garage apartment.

6. 34 W 12th St, New York, NY

Price: $35,000,000

Greenwich Village townhouse: This former multifamily property, said to be owned by Snir David and Moshe Levy, was purchased in 2022 for $8.4 million and recently underwent a three-year renovation transforming it into a luxurious, single-family residence.

The six-story estate boasts a private elevator, mosaic marble tiling, Spanish white-oak floors, and wood-paneled walls. A grand living room has a custom-built wet bar and access to a private terrace overlooking a bi-level landscaped garden with an outdoor kitchen. The primary suite with walnut walk-in closets spans the fourth floor.

Other lavish amenities include a rooftop terrace and a recreational level with a fitness center and wine cellar.

5. 5055 Wayside Dr, Wimberley, TX

Price: $39,900,000

4-S Ranch: This 538-acre ranch boasts five residences, an airplane hangar, a private 3,300-foot runway, frontage along the Blanco River, and two creeks running through the property.

The legacy compound, “with strategically placed dams to enhance water retention,” nestled in the Texas Hill Country also has guest and “ranch-hand” quarters. Half of the land is said to be “manicured,” while the rest of the acreage “remains in its natural state preserved for hunters and nature enthusiasts.”

Other opulent amenities include grand entertainment spaces, an outdoor kitchen, commercial catering facilities, a fully equipped workout room, a professional stage, sports courts, and a soccer field.

4. 4230 Cresta Ave, Santa Barbara, CA

Price: $40,000,000

Hope Ranch villa: This 4.8-acre, coastal Mediterranean estate last traded hands in 2018 for $13.6 million.

Built in 2012, the four-bedroom residence features a wine cellar, first-floor primary suite, an ocean-facing living room, and a dining room with access to the pool area, pool house, and outdoor kitchen.

The manicured property also has fountains, a six-car garage, a one-bedroom guesthouse, and private beach access.

3. 1220 Sunset Plaza Dr, Los Angeles, CA 

Price: $50,000,000

Casa Bella: This 11,412-square-foot Mexican Colonial estate is said to be owned by Televisa chairman Emilio Azcarraga Jean, who tried selling it back in 2023 for $60 million.

The six-bedroom mansion off the Sunset Strip features exposed wood beams, hand-carved stonework, and Mexican tile. There is also a “voluminous” library, a wine cellar, and a spectacular 3,800-square-foot primary suite with sitting areas and spa-inspired bathrooms.

The 2.3-acre property also has an in-ground pool, an orange grove, a 2,000-square-foot guesthouse, and parking for more than 20 cars.

2. 9006 Thrasher Ave, Los Angeles, CA

Price: $72,500,000

Brand-new build: This seven-bedroom contemporary in the prestigious Bird Streets is also available to rent for $130,000 a month.

The “ultimate view estate” offers “jetliner vistas” spanning Century City to the Pacific Ocean. Inside the 13,400-square-foot residence are a custom-built bar, billiard room, glass wine display, media room, home theater, and a wellness retreat with a spa and massage room. There is also a lower-level guest suite and two staff quarters.

Lounging terraces with outdoor fireplace overlook the zero-edge pool and spa.

1. 20 Meadow Ln, Portola Valley, CA

Price: $85,000,000

Villa del Prato: This 12-acre estate boasts a 12,305-square-foot primary residence, a 2,000-square-foot pool house, and a stunning 6,500-square-foot entertainment pavilion.

The five-bedroom Italian-inspired villa was built in 2021 and designed by Andrew Skurman and Suzanne Tucker. Four en suite bedrooms are situated in the main home along with radiant floors, Italian stone columns, an elevator, and a 3,500-bottle wine cave. There is also a family room with a “raised stage” and a primary retreat with 900-square-foot, Chanel-inspired dressing suite that doubles as a safe room.

Loggias overlook the pool and pool house with guest accommodations. The three-plot compound also boasts three separate addresses and five garages.