$25,000,000
211 Winding WY
Woodside, CA, 94062
A rare offering on one of Central Woodsides most prestigious streets, just off Mountain Home Road, this extraordinary estate showcases architectural excellence, vineyard beauty, & a luminous natural setting. Spanning 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 show stopping primary suite with terrace and spa bath beneath a retractable skylight. A special hemlock wood cabinetry with custom inset lighting. 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 a building which has temperature controlled wine storage. A truly world-class property with access to acclaimed Woodside School.
Property Details
Price:
$25,000,000
MLS #:
ML82012031
Status:
Active
Beds:
6
Baths:
8
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
699notdefined
Listed Date:
Jan 4, 2026
Finished Sq Ft:
7,930
Lot Size:
191,612 sqft / 4.40 acres (approx)
Year Built:
1997
Schools
School District:
Other
Interior
Appliances
DW, FZ, MW, RF, GS, DO, HOD, VEF, WOD
Bathrooms
6 Full Bathrooms, 2 Half Bathrooms
Cooling
CA
Flooring
STON, WOOD
Heating
CF
Laundry Features
DINC, WINC
Exterior
Construction Materials
STC
Parking Spots
3
Roof
TARGRV, SHK, SLT
Financial
Get Out There, A Simply Outgoing Approach to Life. James Outland Jr. is one of those rare people who simply has an outgoing approach to life. No matter the activity… from dune buggy riding to skydiving to motorcycling to riding the local Pismo Beach waves… James Outland Jr. approaches life with a “just get out there and do it” kind of attitude. A zest for Life. James’ zest for life is obviously apparent in his many exciting hobbies. In his spare time, he loves riding dune buggies or hi…
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Map
Current real estate data for Single Family in Woodside as of Feb 13, 2026
15
Single Family Listed
52
Avg DOM
1,366
Avg $ / SqFt
$6,188,497
Avg List Price
Community
- Address211 Winding WY Woodside CA
- CityWoodside
- CountySan Mateo
- Zip Code94062
Similar Listings Nearby
Property Summary
- 211 Winding WY Woodside CA is a Single Family for sale in Woodside, CA, 94062. It is listed for $25,000,000 and features 6 beds, 8 baths, and has approximately 7,930 square feet of living space, and was originally constructed in 1997. The current price per square foot is $3,153. The average price per square foot for Single Family listings in Woodside is $1,366. The average listing price for Single Family in Woodside is $6,188,497. To schedule a showing of MLS#ml82012031 at 211 Winding WY in Woodside, CA, contact your James Outland agent at 8057482262.
Courtesy of Compass. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the California Regional Multiple Listing Service. Detailed information about real estate listings held by brokerage firms other than James Outland include the name of the listing broker. Neither the listing company nor James Outland shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. California Regional Multiple Listing Service. All rights reserved. 211 Winding WY
Woodside, CA


































