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 1,700 sq ft ADU/JADU, 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.
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
Bathrooms
2 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Flooring
Carpet, Stone
Heating
Electric, Forced Air
Laundry Features
Individual Room
Exterior
Architectural Style
Tudor
Community Features
Foothills, Mountainous
Exterior Features
Barbecue Private, Lighting
Parking Features
Paved, Driveway Up Slope From Street, Garage – Three Door, Garage Door Opener, Guest
Parking Spots
3.00
Roof
Stone
Security Features
Fire Sprinkler System, Security System, Smoke Detector(s)
Financial
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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