Exceptional Scale, Far-Reaching Views, and European Luxury
211 Winding Way, Woodside
307 OLIVE HILL LANE | WOODSIDE
At A Glance
- Exceptional estate home with new retreat, new second pool, and new landscaping, all of impeccable quality
- Approximately 3.08 acres with western hill views and Cabernet vineyard
- 2 bedrooms and 2 baths in the new retreat with full kitchen
- 6 bedrooms, office, and 5 baths in the main residence
- Approximately 10,000 total square feet (buyer to confirm)
- Main-level primary bedroom suite and adjacent office, plus five lower-level bedrooms and three baths
- Fully renovated state-of-the-art theatre with 9.2.4 surround sound
- Temperature-controlled, customized wine cellar
- Detached fitness center and basketball half-courtÂ
- Two detached 2-car garages with EV charging
- Newly added large pool and spa, all saltwater, plus original oval pool and spa
- 310-vine Cabernet vineyard, bountiful orchard, vegetable beds, and heritage olive trees
- Acclaimed Woodside Elementary School (K-8)
This exceptional property spans more than 3 acres with sweeping western hill views and 9,880 square feet of total living space. The main home was completely rebuilt in 2000, and in 2025, an entirely new guest house and entertainment complex was added to the estate. The classically styled main residence features nearly every room opening to the views and includes a state-of-the-art theatre and temperature-controlled wine cellar. The newly completed guest house showcases authentic European detail with roof tiles handmade in Provence and Genoise eaves, complemented by modern seismic construction and smart home technology. A new saltwater pool and spa, nearly 60 feet in length, is surrounded by an expansive terrace with sound system, outdoor kitchen, pizza oven, and easy catering access.
The south-facing grounds are equally impressive, with a 310-vine Cabernet vineyard, heritage olive trees and oaks, a parterre rose garden, bountiful orchard, and raised vegetable beds. Reflecting timeless European elegance and exceptional craftsmanship, the estate is remarkably private, with far-reaching views enhancing the entire setting – and all midway between Silicon Valley and San Francisco.
