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3 Beds
4 Baths
3,865 sqft

$4,598,000

20585 Whispering Oaks Drive, San Jose CA, 95120

Price per sqft$1,189.65
Built in1986
Property size3,865 sqft
Property typeResidential
test courtesy

Overview

Active

Listed Jul 3, 2025

Updated Apr 10

Build for the future on this private 2.1-acre hilltop estate with county-approved surveys and environmental clearance for expansion. This English-inspired custom home offers 3 bedrooms plus an office, optional 4th/guest bedroom, 2 full and 2 half baths, and is surrounded by leveled land ideal for a separate guest house, perfect for multi-generational living. The residence features a dramatic spiral staircase, marble flooring, leaded glass, crystal chandeliers, and 3 marble fireplaces. Entertain in formal living and dining rooms, a spacious family room with coffered ceilings, hidden theater screen, wet bar, and a chef’s kitchen with mahogany cabinetry, granite counters, and high-end appliances. The upstairs primary suite includes a fireplace, sitting area, and private balcony, joined by two additional bedrooms with views. Outdoors, enjoy multi-level terraces, a lush grassy yard, custom solar-heated pool, and mature landscaping with unobstructed 360 degree views. The property’s north and south ends provide ample flat land for expansion, horses, vineyards, or orchards, with a 3-car garage and generous guest parking. Top-rated schools: Williams, Bret Harte, and Leland High.

$30,591/mo

Est. mortgage payment based on a $4,598,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
OC25134772

Interior Features

Bedrooms
3
Bathrooms
4

Exterior Features

Lot Size
2.1 Acres

Other Property Details

Pool
Yes
55+/Senior Community
No
MLS provider logo

Broker Reciprocity Courtesy of Homs Real Estate, Sweenie Khachi

Riff Rifferson - Full Name

- Phone Number

[email protected] - Email

- Brokerage Name

78108 - MLS License Number

 

Data last updated 6:56 AM UTC, 4/10/2026

 

Based on information from California Regional Multiple Listing Service, Inc. as of 4/10/2026. 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.

 

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