414 Pinehill Rd

$9,500,000
Price
5
Beds
8,350 Sq. Ft.
$1,138 / Sq. Ft.
8,350
Sq. Ft.
$1,138
per Sq. Ft.

Description

Welcome to Villa De Pinehill an exceptional Mediterranean masterpiece nestled on nearly two acres of enchanting, Italian-inspired gardens. Spanning three stories, this estate is a harmonious blend of timeless elegance and modern sophistication. Inside, exquisite craftsmanship is on full display with custom woodwork, premium natural stone, and globally sourced materials that infuse each space with old-world charm and refined luxury. A grand entrance sets the tone for the expansive interiors, featuring...Welcome to Villa De Pinehill an exceptional Mediterranean masterpiece nestled on nearly two acres of enchanting, Italian-inspired gardens. Spanning three stories, this estate is a harmonious blend of timeless elegance and modern sophistication. Inside, exquisite craftsmanship is on full display with custom woodwork, premium natural stone, and globally sourced materials that infuse each space with old-world charm and refined luxury. A grand entrance sets the tone for the expansive interiors, featuring soaring ceilings, generously scaled rooms, and a chefs kitchen with a large island that flows seamlessly to the outdoor lawn and detached guest house. The lower level is designed for entertaining, complete with a wine room, full bar, and flexible bonus space. Multiple balconies and terraces overlook the gated, resort-like grounds. Additional amenities include radiant heating, a security system, an outdoor kitchen, three fireplaces, and a hot tub. A private one-bedroom guest house, with its own eat-in kitchen offers an ideal retreat for guests all set within a coveted enclave of equally stunning estates. Main house 7710sqft + guest house 640 sqft
  1. Listed by Phil Chen • DRE #01715177 • Brokerage DRE #02101181 • Christie's International Real Estate Sereno • 415-271-1920

Property Details for 414 Pinehill Road

MLS City Name
Hillsborough
Building Type
Detached
Style
Custom, Mediterranean, Other
Garage Spaces
3
View
Hills, Mountains, Forest / Woods, Neighborhood, Garden / Greenbelt
Cross Street
Pullman Road
LISTING UPDATED: 10/30/2025 10:32 AM

Property Details for 414 Pinehill Road

StatusPending ( Do Not Show )
MLS #ML82012753
Days on Compass78
Taxes-
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle-Family Homes / Detached
Year Built2014
Lot Size2.05 AC / 89,333 SF
CountySan Mateo County

Location

Listing Courtesy of Christie's International Real Estate Sereno, Phil Chen, DRE #01715177
Add your commute

Building Information for 414 Pinehill Road

Stories3Year Built2014Building Size-Lot Size2.05 AC / 89,333 SF

Payment Calculator

$57,015 per month

30 year fixed, 6.28% Interest

Principal and Interest

$46,943

Property Taxes

$10,072

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 414 Pinehill Road

Features
Room Information
  • Additional Rooms: Recreation Room, Wine Cellar / Storage
  • Bathroom: Granite, Stall Shower, Shower and Tub, Tile, Full on Ground Floor, Half on Ground Floor, Oversized Tub, Primary - Oversized Tub, Dual Flush Toilet, Primary - Stall Shower(s)
  • Bedrooms: 5.0
  • Dining Room: Formal Dining Room
  • Family Room: Separate Family Room
  • Kitchen: Dishwasher, Microwave, Oven - Double, Refrigerator, Oven Range - Built-In, Gas
  • Number of Full Bathrooms: 4
  • Number of Half Bathrooms: 2
Features
  • Amenities: Walk-in Closet, Wet Bar, High Ceiling
  • Energy Features: Low Flow Shower, Low Flow Toilet, Thermostat Controller, Double Pane Windows
  • Fireplace: Yes
  • Fireplaces: Living Room, Outside
  • Fireplaces Min: 3
  • Flooring: Stone, Tile, Hardwood
  • Laundry: Washer / Dryer
  • Living SqFt: 8350
  • Pool: No
  • Security Features: Fire System - Sprinkler, Secured Garage / Parking, Security Fence
Utilities
  • Cooling: Central AC
  • Heating: Central Forced Air
  • Sewer Septic: Sewer - Public
  • Utilities: Public Utilities
  • Water: Public
Garage
  • Garage and Parking: Attached Garage
  • Garage Max: 3
  • Garage Min: 3
Property Details
Homeowners Association
  • HOA Exists: 0
  • HOA Fee: 0
Property Details
  • Exterior: Double Pane Windows, Stone
  • Property Condition: Built / Remodeled Green, Other
  • Area Text: Carolands Etc.
  • Roof: Tile
  • Stories: Three or More Stories
  • Subclass: Single Family Home
  • Year Built Source: Assessor
  • Street Number: 414
  • Street Name: Pinehill
  • Street Suffix: Road
  • Area ID: 446
Second Unit Information
  • Second Unit Description: 1 bed + kitchen
Lot / Property Details
Building Information
  • Number Of Stories: 3
  • Structure SqFt: 8350
  • Structure SqFt Source: Other
  • Age: 11
Development Information
  • Construction Status: Completed
  • Construction Type: Stone, Wood Frame, Stucco
  • Zoning Detail: R1002A
Location Information
  • City Limits: Yes
  • Incorporated: No
  • Parcel Number: 030-084-130
  • County Name: San Mateo
  • City Name: Hillsborough
  • City Postal ID: 23
  • Postal Code: 94010
  • Elementary School: 679
  • Elementary School District: 925
  • Middle School Text: Crocker Middle
  • High School District Text: San Mateo Union High
  • High School Text: San Mateo Union High
Lot Information
  • Current Rent: $0
  • Fencing: Gate, Fenced
  • Foundation: Concrete Perimeter and Slab
  • Horse Property: No
  • Lot Acres: 2.05
  • Lot Description: Views, Grade - Hillside, Grade - Mostly Level
  • Lot Size Area Maximum Units: Square Feet
  • Lot Size Area Minimum Units: Square Feet
  • Lot Size Source: Assessor
  • Soil: Unknown
  • Yard Grounds: Outdoor Fireplace, Outdoor Kitchen

Property History for 414 Pinehill Road

DateEvent & SourcePriceAppreciation
Oct 28, 2025

Pending

MLSListings #ML82012753

Oct 28, 2025

Pending

EBRD #ML82012753

Aug 11, 2025

Listed (Active)

MLSListings #ML82012753

$9,500,000
Aug 11, 2025

Listed (Active)

EBRD #ML82012753

$9,500,000
Apr 20, 2025

Expired

EBRD #ML81962295

Apr 19, 2025

Expired

MLSListings #ML81962295

$9,500,000
Dec 3, 2024

Temporarily Off Market

EBRD #ML81962295

Dec 3, 2024

Temporarily Off Market

MLSListings #ML81962295

$9,500,000
Nov 1, 2024

Price Change

EBRD #ML81962295

$9,500,000
Sep 12, 2024

Price Change

EBRD #ML81962295

$10,900,000
Sep 12, 2024

Price Change

MLSListings #ML81962295

$10,900,000
Sep 12, 2024

Price Change

EBRD #ML81962295

$9,090,000
Sep 12, 2024

Price Change

MLSListings #ML81962295

$9,090,000
Apr 20, 2024

Listed (Active)

EBRD #ML81962295

$11,300,000
Apr 19, 2024

Listed (Active)

MLSListings #ML81962295

$11,300,000
Nov 26, 2018

Sold (Public Record)

Public Record #636778841

$9,400,000

+12.8% / yr

Oct 31, 2018

Expired

EBRD #ML81693047

Oct 30, 2018

Expired

MLSListings #ML81693047

$9,850,000
Feb 19, 2018

Listed (Active)

EBRD #ML81693047

$10,500,000
Feb 19, 2018

Listed (Active)

MLSListings #ML81693047

$10,500,000
Jan 1, 2018

Expired

EBRD #ML81680747

Dec 31, 2017

Expired

MLSListings #ML81680747

$10,500,000
Oct 7, 2017

Listed (Active)

EBRD #ML81680747

$10,500,000
Oct 6, 2017

Listed (Active)

MLSListings #ML81680747

$10,500,000
Jul 31, 2011

Withdrawn

RESFAR #81117499

Jul 7, 2011

Withdrawn

MLSListings #ML81117499

Jul 7, 2011

Withdrawn

EBRD #ML81117499

Apr 21, 2011

Listed (Active)

MLSListings #ML81117499

$2,698,000
Apr 21, 2011

Listed (Active)

EBRD #ML81117499

$2,698,000
Apr 21, 2011

Listed (Active)

RESFAR #81117499

$2,698,000
Oct 25, 2010

Expired

EBRD #ML81020318

Oct 24, 2010

Expired

MLSListings #ML81020318

$3,150,000
Apr 24, 2010

Listed (Active)

EBRD #ML81020318

$3,250,000
Apr 24, 2010

Listed (Active)

MLSListings #ML81020318

$3,250,000
Mar 15, 2006

Sold (Public Record)

Public Record #192634976

$2,025,000
Mar 15, 2006

Sold

MLSListings #ML80554432

$2,025,000
Mar 15, 2006

Sold

RESFAR #80554432

$2,025,000
Mar 15, 2006

Sold

EBRD #ML80554432

$2,025,000
Feb 23, 2006

Pending

RESFAR #80554432

Feb 23, 2006

Pending

EBRD #ML80554432

Feb 23, 2006

Pending

MLSListings #ML80554432

Sep 16, 2005

Price Change

RESFAR #80554432

$2,195,000
Sep 16, 2005

Listed (Active)

RESFAR #80554432

$2,050,000
Sep 16, 2005

Listed (Active)

EBRD #ML80554432

$2,195,000
Sep 16, 2005

Listed (Active)

MLSListings #ML80554432

$2,195,000
DateEvent & SourcePrice
10/28/2025

Pending

MLSListings #ML82012753

10/28/2025

Pending

EBRD #ML82012753

08/11/2025

Listed (Active)

MLSListings #ML82012753

$9,500,000
08/11/2025

Listed (Active)

EBRD #ML82012753

$9,500,000
04/20/2025

Expired

EBRD #ML81962295

04/19/2025

Expired

MLSListings #ML81962295

$9,500,000
12/03/2024

Temporarily Off Market

EBRD #ML81962295

12/03/2024

Temporarily Off Market

MLSListings #ML81962295

$9,500,000
11/01/2024

Price Change

EBRD #ML81962295

$9,500,000
09/12/2024

Price Change

EBRD #ML81962295

$10,900,000
09/12/2024

Price Change

MLSListings #ML81962295

$10,900,000
09/12/2024

Price Change

EBRD #ML81962295

$9,090,000
09/12/2024

Price Change

MLSListings #ML81962295

$9,090,000
04/20/2024

Listed (Active)

EBRD #ML81962295

$11,300,000
04/19/2024

Listed (Active)

MLSListings #ML81962295

$11,300,000
11/26/2018

Sold (Public Record)

Public Record #636778841

$9,400,000

+12.8% / yr

10/31/2018

Expired

EBRD #ML81693047

10/30/2018

Expired

MLSListings #ML81693047

$9,850,000
02/19/2018

Listed (Active)

EBRD #ML81693047

$10,500,000
02/19/2018

Listed (Active)

MLSListings #ML81693047

$10,500,000
01/01/2018

Expired

EBRD #ML81680747

12/31/2017

Expired

MLSListings #ML81680747

$10,500,000
10/07/2017

Listed (Active)

EBRD #ML81680747

$10,500,000
10/06/2017

Listed (Active)

MLSListings #ML81680747

$10,500,000
07/31/2011

Withdrawn

RESFAR #81117499

07/07/2011

Withdrawn

MLSListings #ML81117499

07/07/2011

Withdrawn

EBRD #ML81117499

04/21/2011

Listed (Active)

MLSListings #ML81117499

$2,698,000
04/21/2011

Listed (Active)

EBRD #ML81117499

$2,698,000
04/21/2011

Listed (Active)

RESFAR #81117499

$2,698,000
10/25/2010

Expired

EBRD #ML81020318

10/24/2010

Expired

MLSListings #ML81020318

$3,150,000
04/24/2010

Listed (Active)

EBRD #ML81020318

$3,250,000
04/24/2010

Listed (Active)

MLSListings #ML81020318

$3,250,000
03/15/2006

Sold (Public Record)

Public Record #192634976

$2,025,000
03/15/2006

Sold

MLSListings #ML80554432

$2,025,000
03/15/2006

Sold

RESFAR #80554432

$2,025,000
03/15/2006

Sold

EBRD #ML80554432

$2,025,000
02/23/2006

Pending

RESFAR #80554432

02/23/2006

Pending

EBRD #ML80554432

02/23/2006

Pending

MLSListings #ML80554432

09/16/2005

Price Change

RESFAR #80554432

$2,195,000
09/16/2005

Listed (Active)

RESFAR #80554432

$2,050,000
09/16/2005

Listed (Active)

EBRD #ML80554432

$2,195,000
09/16/2005

Listed (Active)

MLSListings #ML80554432

$2,195,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 414 Pinehill Road

Taxable ValueLand$4,015,865Additions$6,470,007Total$10,485,872
Tax Record2024$120,862 ($10,072 / month)
Home Facts
Beds4Total Finished SqFt5,551 SqFtAbove Grade Finished SqFt5,551 SqFtStories2Lot Size89,333 SqFtStyleSingle Family ResidenceYear Built2014ZoningR1002ACountySAN MATEOAPN030-084-130Fireplace TypeHas Fireplace

Schools near 414 Pinehill Road

This home is within San Mateo Union High School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Charter - 9 to 12
Rating
School
Distance
North Hillsborough School
PublicK to 5

Crocker Middle School
Public6 to 8

Burlingame High School
Public9 to 12

Design Tech High
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Christie's International Real Estate Sereno, Phil Chen, DRE #01715177

Based on information from one of the following Multiple Listing Services: San Francisco Association of Realtors, the MLSListings MLS, the BAREIS MLS, the EBRD MLS, Shasta Association of REALTORS® Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by San Francisco Association of Realtors, the MLSListings MLS, the BAREIS MLS, the EBRD MLS, Shasta Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.