20585 Whispering Oaks Drive
San Jose, CA, 95120
$4,888,000
4 Beds
4 Baths
3,865 SqFt
2.1 Acres
Add
Welcome to the ultimate lifestyle of serenity and privacy. Perched atop a private 2.1-acre hilltop, with a escalating private driveway, wrought iron fencing, mature eucalyptus trees and fruit trees, breathtaking long distance sunrise and sunset views, this custom English-inspired estate blends timeless craftsmanship and breathtaking 360 degree views from every window and terrace. The 4-bed, 2 full, 2 half bath home, features a dramatic spiral staircase with hand-forged iron railing upon entry, rich marble flooring throughout the main level, elegant details including leaded glass, crystal chandeliers, and three marble fireplaces, and spacious areas with privacy from every room. The formal living and dining rooms provide classic entertaining space, while a downstairs room allows for a private office or an optional guest bedroom flexibility. The expansive family room impresses with coffered ceilings, hidden automatic theatre screen and surround sound speakers, a custom walk-around wet bar great for entertaining and parties, and one of three classical fireplaces. A chef’s dream kitchen features mahogany cabinetry, granite countertops, high-end updated appliances and 6 burner stovetop, a large island with sink, and a sunny spacious breakfast nook with plenty of dining storage. Second story with endless view features the luxurious large primary suite with a sitting area and a cozy fireplace, joined by two well-sized guest bedrooms and balconies. Recent upgrades include thermal windows, upstairs carpet, kitchen appliances, and fresh interior/exterior paint. Step outside to enjoy multi-level front and back terraces, an enormous patio gazebo with an outdoor kitchen area, a newly plastered custom pool with a solar heating system, a lush grassy yard with stone finishes, all surrounded by mature trees and endless unobstructed meditative views. Lot includes a full acre of county-approved building and land surveys with environmental clearance to expand the main house to total 8 bedrooms or a second ADU or JADU dwelling sized at 1,700 sqft. Land for horses, vineyards, or orchards, with a 3-car garage and ample parking for entertaining and guests. This one-of-a-kind property offers the ultimate privacy and luxury lifestyle all within minutes from the local amenities of Almaden Valley.

Property Details

Price:
$4,888,000
MLS #:
OC25134772
Status:
Active
Beds:
4
Baths:
4
Address:
20585 Whispering Oaks Drive
Type:
Single Family
Subtype:
Single Family Residence
City:
San Jose
Listed Date:
Jun 16, 2025
State:
CA
Finished Sq Ft:
3,865
ZIP:
95120
Lot Size:
91,536 sqft / 2.10 acres (approx)
Year Built:
1986
Ask a Question

See this Listing

Send
  

Mortgage Calculator

 

Schools

School District:
Santa Clara Unified
Elementary School:
Graystone
Middle School:
Bret Harte
High School:
Leland

Interior

Appliances
6 Burner Stove, Dishwasher, Double Oven, Electric Oven, Electric Cooktop, Gas Oven
Cooling
Central Air
Fireplace Features
Family Room, Living Room, Primary Bedroom
Flooring
Carpet, Stone
Heating
Electric, Forced Air
Interior Features
Balcony, Bar, Built-in Features, Cathedral Ceiling(s), Granite Counters, High Ceilings, Recessed Lighting, Stone Counters, Storage, Wet Bar

Exterior

Community Features
Foothills, Mountainous
Exterior Features
Barbecue Private, Lighting
Garage Spaces
3.00
Lot Features
2-5 Units/ Acre, Lawn
Parking Features
Paved, Driveway Up Slope From Street, Garage – Three Door, Garage Door Opener, Guest
Parking Spots
3.00
Pool Features
Private, Solar Heat
Roof
Stone
Security Features
Fire Sprinkler System, Security System, Smoke Detector(s)
Sewer
Septic Type Unknown
Stories Total
2
View
Canyon, Panoramic, Pool, Trees/ Woods
Water Source
Public

Financial

Association Fee
0.00

Map

Community

Similar Listings Nearby

20585 Whispering Oaks Drive
San Jose, CA