$34,995,000
307 Olive Hill LN
Woodside, CA, 94062
One of Woodside’s premier estates, encompassing nearly 10,000 square feet across all structures, this property offers exceptional scale, quality, and lifestyle, highlighted by a classically styled main residence and a brand-new guest house crafted with authentic European detail. The main home is luxuriously appointed across two levels, with nearly every room opening to the outdoors. A state-of-the-art theatre and a temperature-controlled wine cellar are just two of many standout features. The newly completed guest house pairs handmade roof tiles and Genoise eaves inspired by the South of France with state-of-the-art smart home technology. Designed for entertaining, the guest house opens to a new saltwater pool and spa and expansive limestone terrace with a full outdoor kitchen and easy catering access. A 310-vine Cabernet vineyard anchors the south-facing gardens, while heritage olive trees and oaks, a fragrant parterre rose garden, bountiful orchard, and raised vegetable beds enhance the estates agrarian beauty. The result is a property where timeless elegance and refined European living are masterfully expressed in an extraordinary private setting of more than 3 acres with western hill views. Main Residence 6,485 | Guest House 1,505 | Garage One 560 | Garage Two 520 | Gym 560
Property Details
Price:
$34,995,000
MLS #:
ML82038776
Status:
Active
Beds:
6
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
699notdefined
Listed Date:
Apr 23, 2026
Finished Sq Ft:
6,485
Lot Size:
134,164 sqft / 3.08 acres (approx)
Year Built:
1977
Schools
School District:
Other
Elementary School:
Other
High School:
Woodside
Interior
Appliances
DW, GD, MW, RF, GS, VEF
Bathrooms
5 Full Bathrooms
Cooling
CA
Flooring
STON, WOOD
Heating
CF
Exterior
Architectural Style
MED
Common Walls
NCW
Garage Spaces
4
Parking Spots
4
Parking Total
4
Patio And Porch Features
DK
Roof
TLE
Spa Features
HT, IG
View
HI, MT
Window Features
SK
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 May 25, 2026
29
Single Family Listed
59
Avg DOM
1,779
Avg $ / SqFt
$8,176,621
Avg List Price
Community
- Address307 Olive Hill LN Woodside CA
- CityWoodside
- CountySan Mateo
- Zip Code94062
Similar Listings Nearby
Property Summary
- 307 Olive Hill LN Woodside CA is a Single Family for sale in Woodside, CA, 94062. It is listed for $34,995,000 and features 6 beds, 5 baths, and has approximately 6,485 square feet of living space, and was originally constructed in 1977. The current price per square foot is $5,396. The average price per square foot for Single Family listings in Woodside is $1,779. The average listing price for Single Family in Woodside is $8,176,621. To schedule a showing of MLS#ml82038776 at 307 Olive Hill LN 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. 307 Olive Hill LN
Woodside, CA






















