Experience unmatched privacy and 360 degree views from this English-inspired custom estate on 2.1 acres atop a hilltop and buildble leveled land for an ADU. The 4 bed, 2 full plus 2 half bath home features a dramatic spiral staircase, marble flooring, leaded glass, crystal chandeliers, and 3 marble fireplaces. Classic entertaining spaces in both formal living and dining rooms, a spacious family room with coffered ceilings, hidden theater screen, custom wet bar, and chef’s kitchen with mahogany cabinetry, granite counters, and high-end appliances. Upstairs includes a the primary suite with fireplace and sitting area, plus two guest bedrooms with balconies. Enjoy outdoor multi-level terraces, a lush grassy yard with stone finishes, a custom solar-heated pool, all surrounded by mature trees and endless unobstructed meditative views. Property includes county-approved surveys and environmental clearance for expansion, potential for an 8 bedroom addition to main house or a separate private 1,700 sq ft ADU/JADU in a private area near the top of the road. Land surrounds both the north and sound ends of the property for expansion. Plenty of space for horses, vineyards, or orchards, plus a 3-car garage and ample guest parking. Top schools include Williams, Bret Harte and Leland High.
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
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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
- Address20585 Whispering Oaks Drive San Jose CA
- CitySan Jose
- CountySanta Clara
- Zip Code95120
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20585 Whispering Oaks Drive
San Jose, CA
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