211 Winding Way,
Woodside
A rare offering on one of Woodside’s most prestigious streets, this extraordinary estate showcases architectural excellence, vineyard beauty, and a luminous natural setting. Spanning over almost 4.4 acres with an optional adjacent 3-acre parcel also available, the grounds have been thoughtfully opened to invite abundant sunlight, enhancing both the ambiance and the usability of the land.
Designed by Ugo Sap and built by Van Acker Construction, the main residence is defined by dramatic scale, elegant curved forms, and exceptional materials. An elevator connects the two levels, which include six en suite bedrooms including a showstopping primary suite with terrace and spa bath beneath a retractable skylight.
Outdoor living is equally impressive, featuring a thriving Pinot Noir vineyard, olive orchard, and multiple destinations for entertaining. A spacious poolside guest house includes a bedroom, full kitchen, sauna, and bath, while a separate structure with bath and kitchenette is ideal for a fitness center or executive office plus there is a building with temperature-controlled wine storage. A truly world-class property with access to acclaimed Woodside School.
At a Glance
- Premier street in central Woodside just off the Mountain Home Road corridor
- Architecture by Atelier Ugo Sap, San Francisco; built by Van Acker Construction
- Two levels with elevator
- 6 bedrooms, each with en suite bath, plus 2 half-baths
- 1-bedroom, 1-bath pool/guest house with full kitchen
- Separate building with kitchenette and bath, perfect for office, gym, or additional guest house
- Additional building with temperature-controlled wine storage
- Approximately 11,650 total square feet
- Approximately 4.4 acres with Pinot Noir vineyard
- Option to purchase adjacent 3-acre lot with Pinot Noir vineyard for a total of 7.4 acres
- Acclaimed Woodside Elementary School (K-8) and nearby private schools
Offered at $25,000,000
With adjacent lot for $35,000,000
Details of the Home
Entrance
Rustic wood and bamboo style automatic gate with natural stone pillars; a serene lily pond, interconnected waterways, and stone paths lead to the front door, all bordered by dogwood trees, horsetail reeds, and tufted grasses; massive glass and iron doors enter the home
Foyer
Venetian plaster walls and floors in French antique limestone or walnut extend throughout; a central gallery, lined with three sets of double glass doors to the rear terrace, showcases a floating solid limestone staircase in a window-lined turret
Living Room
Grand formal venue with signature curved wall of windows, masonry fireplace with antique mantelpiece and multiple glass doors to the rear terrace
Dining Room, Butler’s Pantry & Wine Cellar
Glass drum chandelier and front wall of glass with doors to the gardens; adjacent butler’s pantry with Sub-Zero beverage cooler, icemaker, and 3 full-height concealed wine coolers plus temperature- and humidity-controlled cigar cabinet
Library
Walnut-paneling and custom cabinetry on all sides with custom inset lighting, and integrated antique marble fireplace from France
Kitchen
Tremendous space finished with custom wood cabinetry topped in granite; island, peninsula counter seating, built-in desk center, and breakfast area
Appliances
Viking 8-burner gas cooktop with double griddle; Viking French door oven and second oven; 2 Miele dishwashers; KitchenAid compactor and microwave; 2 Thermador warming drawers; Sub-Zero refrigerator and separate freezer; 2 Sub-Zero refrigerator drawers; additional Sub-Zero refrigerator in walk-in pantry
Family Room
Fully open to the kitchen with fireplace, media cabinetry, surround sound, and front terrace access
Main-Level Bedroom Suites
Two main-level bedrooms, each with walk-in closet, glass doors to the grounds, and en suite bath (one with shower and one with tub and overhead shower) finished in limestone from France
Primary Bedroom Suite
Upstairs with double door entrance, private balcony, entire wall of cabinetry with fireplace, and 2 customized walk-in closets; bath with retractable skylight, limestone from France, dual-sink vanity, steam shower, tub, private commode room, heated floors, and private balcony
Upstairs Bedroom Suites
Three additional bedrooms, one with fireplace and each with en suite bath (two with shower and one with tub and overhead shower) finished in limestone from France
Pool/Guest House
Rustic-designed vintage pool house with timbered all-wood ceiling, antique rock walls, and updated engineered wood floors; central recreation room with antique stone fireplace; separate kitchen with electric range, dishwasher, and refrigerator; large bedroom with outside entrance; bath with curbless shower; cedar-lined sauna
Detached Office/Gym
Large detached flexible use building with retractable glass doors, kitchenette with refrigerator and microwave, separate storage room lined entirely with cabinetry and file drawers, bath with shower, and keyless rear entry
Other Features
- Elevator
- Formal powder room plus half-bath off the kitchen
- Upstairs laundry room with sink, washer, and dryer
- Attached 3-car garage with EV charging
- Central vacuum; security and surveillance; multi-zone HVAC; programmable lighting; audio throughout home and grounds
- Commercial-grade water chiller HVAC cooling system
- High-quality slate tile roof
The Grounds
- Free-form, dark-bottom pool accented with stone boulders
- Pinot Noir vineyard with tucked away gazebo
- Olive orchard yielding high-quality olive oil
- Spacious rear terrace
- Tufted grass lawns and crushed stone paths throughout the property
- Additional building with temperature-controlled wine storage
- Garden storage building and potting shed by the vineyard
- Multi-room all-glass greenhouse
- Multiple raised vegetable beds
- Optional adjacent 3-acre lot with Pinot Noir vineyard