Elegant, Tuscan-Style, Country Estate

Elegant, Tuscan-style, country estate expertly designed with unparalleled attention to detail. Stunning architectural elements imported from Italy add texture and a sense of history. The layout of the property takes full advantage of the natural beauty of the setting. Built for entertaining with its spacious guest accommodations and expansive grounds, this one-of-a-kind estate feels blissfully remote, but is close to all that living in the Bay Area has to offer.

3-Car Garage & Gym: 1 Half Bath | 1,496 square feet
OFFERED AT: $23,000,000

Tour the Property


Construction: R.J. Dailey Construction
Architect: Arnn Gordon Greineder
Interior Design: Wheeler Design Group
Lighting Design: David Wilds Patton Lighting Design
Decorative Painting: Evans & Brown
Landscape Design: Ron Herman Landscape Architect
Architectural Elements, New & Reclaimed: COORItalia

Completed in 2006, Woodside Italian Villa was carefully designed and built to look like a rambling country estate that had been built over the course of many years.  To take full advantage of the natural beauty of the setting, which includes majestic redwoods, a meandering stream and sunny meadows, almost every room was designed to open to or look outdoors.  The beautiful final result was a main home that appears to be two separate structures – one made of stone and the other clad in stucco connected by an entry hall.


More than Seven
Landscaped Acres



Dreyfus Group, Golden Gate Sotheby's International



Recreation and
Entertaining Options

• 25 shipping containers of materials were hand-selected and shipped back to Woodside for use on the home and property.

• Stone walls on the inside and outside the home are a mixture of Wyoming Valley gold and a blend of stones from Wyoming and Montana.

• Roof is covered in 300-year-old hand-selected terracotta tiles imported from Italy.

• Kitchen is outfitted with two Miele dishwashers, built-in Miele coffee maker, ice maker, trash compactor, Thermador double ovens, warming drawer, and built-in microwave.

• Flooring of the octagonal breakfast room is a custom terracotta & black slate pattern with exterior thresholds San Pietro-honed travertine.

• 750-bottle wine room features an Evans and Brown mural painted on the wall.

• Acoustically-treated music room’s carved wood ceiling is from a Venetian villa circa 1490. It was salvaged from the master suite of the original Cliff May ranch house that once stood on the property.

• Both guest bedrooms were designed as luxury suites.  Each with sitting area and full bath.

• Master bedroom lounge area showcases a gas fireplace, leaded glass windows and Venetian plaster tray ceiling.

• AMX home automation with touchscreens to control systems with ease.

• Private terrace off the master suite.

• Master bath includes separate his and her water closets and two walk-in closets.

• Guest house with a full bath and bedroom and a kitchen with Subzero refrigerator, Viking stove (4 burners and a grill), Viking hood, Miele dishwasher and a double sink.

• Gate keeper’s house offers a full kitchen, bath, separate living area and separate parking area behind the cottage.

• Three-car garage with built-in storage.

• Separate gym features natural light and opens out to a private garden view.

• Loggia, located off the kitchen of the main residence, has heated radiant floors, outdoor kitchen, stone fireplace and built-in speakers.

• Landscaping includes native plants, expansive lawns, professionally-designed lighting and many options for recreation and entertaining including a spa, tennis court, bocce ball court, vegetable/cutting garden and a dining area in yard’s redwood grove.

• 60’x15.5’ salt water swimming pool is heated and features a shower descent water feature.

Site Plan & Floor Plan

The Neighborhood

The Hidden Valley neighborhood flourishes in verdant beauty with breathtaking vistas, scores of vineyards, walking trails, and wildlife. This peaceful pocket of land stretches over acres of natural landscaping providing an secure and private setting for the quaint community which consists of less than one hundred houses.

Woodside, CA

Woodside residents value secluded outdoor living while enjoying a strong sense of community. Separated from the ocean by the Santa Cruz Mountains, towering redwoods dominate its western hills, with oaks and eucalyptus in the lower areas. Residents value its privacy, access to nature, large parcels of land and diverse architecture.

This town of just over 5,000 enjoys a rural lifestyle with local trails, horse properties, open space preserves, an artists’ colony and summer jazz at the beautiful Filoli Garden. Popular cycling routes draw cyclists in droves on the weekends along Cañada Road, Old La Honda Road, Kings Mountain Road, Skyline Boulevard and Highway 84. Woodside is also home to several open space preserves, including Purisima Open Space, Huddart County Park, the Phleger Estate and Skeggs Point.

The small business district includes Roberts Market, a hardware and horse tack store, and a few restaurants, including the iconic Buck’s of Woodside, where many venture capital deals have been inked. Woodside is home to a mix of Silicon Valley movers and shakers – CEOs and venture capitalists, as well as famed musicians and artists.

Hidden Valley

The Hidden Valley neighborhood is contained within the original 150-acre Hidden Valley Farm that was in unincorporated Portola Valley. Hidden Valley Farm was owned by the Roth family who had previously owned Why Worry Farm and then Filoli. The Roth’s kept horses on the property but in the late 1950’s they approached the Kelley brothers and their Portola Valley development company about purchasing the farm. The Kelley’s were already involved in the build out of the 500 home Ladera neighborhood. Nevertheless, they purchased the farm and decided rather than create the 100 allowed lots the county would allow on the farm, they would limit the development to 29 larger lots, an unusual decision at that time when land was being carved up for mass development. Subsequently, a dispute developed between the county and the developer over the width of the roads and creating access into the Westridge neighborhood to make a cohesive road system. The developer wanted to opt for more country lanes than large roads. Unable to resolve the dispute the Kelley’s went to the newly formed town of Woodside and managed to get Hidden Valley annexed into the town.

Today the Kelley’s vision remains. Hidden Valley has the feel of country roads leading to the end of the line. There is no throughway for cars so anyone coming in and out is either your neighbor or lost. 30 Trail sits at the end of the lane, adjacent to the creek which separates it from the Portola Valley neighborhood of Westridge and backing to Stanford’s Jasper Ridge Preserve.

Silicon Valley

Silicon Valley is a leading hub for high-tech innovation and development. Historically, it produced technological wonders by companies that defined the high technology industry, beginning with semiconductor businesses and research groups. These companies, anchored by Stanford University, formed an ecosystem in which later innovators could thrive: Hewlett-Packard, Apple, Yahoo, Google, Facebook, and many more. Thousands of start-up companies currently call Silicon Valley home.

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