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Jenn Smart

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307 Olive Hill Ln , Woodside, CA 94062
$29,995,000
Est. Payment: $66,655.56/mo
8 Bed
7 Bath
6485 Sqft
3.08 Acres
Status: active | Days on site: 21
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ML5014372 - ML5079959
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House Description

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 theater and temperature-controlled wine cellar. The newly completed guest house showcases authentic European detail with roof tiles handmade in Provence and Genoise eaves, complemented with modern 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.

Highlights

Listed by Brent & Mary Gull... , 650-888-0860 Compass , (650) 462-1111. CRMLS/Multi-Regional MLS mls logo

Property Type

Residential

Lot/Acreage
3.08

Year Built

1977

County

San Mateo

Area

699 - Not Defined

School District

Other

Listing ID

ML82065658

Questions about this listing?

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Interior Features

Bedrooms and Bathrooms
  • ▪ Bedrooms:8
  • ▪ Bathrooms:7
  • ▪ Full Bathrooms:7
Appliances:Dishwasher, Gas Cooktop, Disposal, Microwave, Refrigerator, Vented Exhaust Fan
Air Cond:Central Air
Fireplaces:Family Room,Gas Starter,Living Room,Outside
Floor:Stone,Wood
Other:
  • ▪ Additional:Breakfast Bar, Wine Cellar, Walk-In Closet(s)
Water:Public

Exterior Features

Lot:No Land Lease
Garage Capacity:4
Zoning:R1003A
Roof:Tile
Others:
  • ▪ Additional:Has ADU
Parking Features:Guest,Off Street
Principal Interest
$66,656
Taxes
$19,122

Home Price

$29,995,000

Loan Details

30 yrs
0%

Down Payment

20%
$5,999,000
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$66,655.56

Principal

Taxes

Principal Taxes HOA Total
Monthly $66,655.56 $19,121.81 $0.00 $85,777.37
Yearly $799,866.67 $229,461.75 $0.00 $1,029,328.42
Total $23,996,000.00 $6,883,852.50 $0.00 $30,879,852.50
Lender profile image
So-Crates Johnson
Dust, Wind, Dude
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Market insight data is pulled from the same city as the listing being viewed (Woodside, CA).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

Based on information from California Regional Multiple Listing Service, Inc. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. All properties are subject to prior sale, change or withdrawal.

IDX service by Blueroof 360

Data last updated: 2026-11-14T19:39:52.000Z

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