Architectural Excellence in an Extraordinary Setting

211 Winding Way

Woodside

Home on 4.399 acres - $38,000,000
Adjacent 3 acres - $15,000,000

The allure of nature seamlessly intertwines with architectural brilliance at this vineyard estate on one of Woodside’s most esteemed streets. The property spans over 4.399 acres (with the possibility of purchasing the adjacent lot of 3 acres, with second Pinot Noir vineyard and 11 raised and irrigated vegetable beds, for a total of 7.4 level acres). The entrance sets the tone of what lies within with an organic setting that begins with a serene lily pond and interconnected waterways. Crushed stone walkways lead to a living wall of flourishing dogwood trees and horsetail reeds arriving at massive glass and iron doors. Inside, renowned architect Ugo Sap has masterfully created a residence that embraces the essence of its location. The detail work is undeniable and built by Van Acker Construction with curved walls of glass, fine oak millwork and moldings, Venetian plaster walls, and floors in limestone or walnut all lend an air of sophistication that harmonizes with the surroundings. The interiors are bright and light, and spaces flow effortlessly off a central gallery showcasing a floating solid limestone staircase. An elevator provides alternate transport to the upper level.

The grand formal living room and formal dining room are serviced by a walk-through station ideal for caterers with concealed wine cellar storage and all the necessary elements for hosting events. A manorial fireplace with antique mantelpiece enhances the ambiance in the living room, while multiple glass doors in both rooms provide access to front or rear terraces. The kitchen is truly exceptional, boasting a suite of high-end appliances, many in duplicate, to effortlessly accommodate large gatherings. For more intimate everyday living, the family room extends off to one side of the kitchen and is wired for surround sound media enjoyment. Awaiting après-dinner enjoyment or as a cozy retreat with a book, the paneled library is warmed by a fireplace with antique marble mantelpiece.

Personal accommodations comprise six bedroom suites, all thoughtfully arranged for privacy and catering to various lifestyle needs. Two bedrooms are conveniently located on the main level, while four are situated upstairs, including a sumptuous primary suite with fireplace, extensive built-ins, and private terrace. The limestone bath, featuring an operable seamless glass retractable skylight, provides a breathtaking view of the vineyard and offers an oversized steam shower, a soothing tub, and heated floors and private balcony. Every bathroom showcases limestone finishes, accentuating their individual organic designs and signature curved cabinetry.

For extended family or guest quarters, a secluded space awaits poolside. This rustic-designed vintage building seamlessly blends into the surroundings, serving equally well for entertainment purposes or personal accommodations. This space includes a full bath with exquisite sauna and a fully equipped kitchen. Completing the living space on the estate grounds is a detached office/gym/additional guest quarters, equipped with retractable glass doors, a kitchenette, full bath, and extensive file storage room.

Tying it all together are remarkable grounds with Pinot Noir vineyard beneath a canopy of lush foliage yet bathed in abundant natural light. A gently flowing waterway meanders alongside a picturesque path leading to a tucked-away gazebo beside the vineyard. This enchanting setting offers an idyllic space for wine tasting or enjoying a picnic in the midst of nature's beauty. Architectural excellence in an extraordinary setting – the best of Woodside living.