20585 Whispering Oaks Drive, San Jose, CA

$4,598,000

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3

Beds

4

Baths

3,865

Square feet

2.10

Acres

About 20585 Whispering Oaks Drive

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.

Features of 20585 Whispering Oaks Drive

MLS® # CROC25134772
Price $4,598,000
Bedrooms 3
Bathrooms 4.00
Full Baths 2
Half Baths 2
Square Footage 3,865
Acres 2.10
Year Built 1986
Type Residential
Sub-Type Single Family Residence
Style Tudor
Status Active

Community Information

Address 20585 Whispering Oaks Drive
City San Jose
County Santa Clara
State CA
Zip Code 95120

Amenities

Utilities Other Water/Sewer
Parking Spaces 3
Parking Attached, Other, Guest
# of Garages 3
View Canyon, Panoramic, Trees/Woods, Other
Is Waterfront No
Has Pool Yes
Pool Solar Heat

Interior

Interior Features Family Room, Storage
Appliances Dishwasher, Double Oven, Electric Range
Heating Electric, Forced Air
Cooling Central Air
Fireplace No
Fireplaces Family Room, Living Room
# of Stories 2
Stories Two Story

Exterior

Exterior Features Lighting, Other
Lot Description Other

Additional Information

Date Listed July 3rd, 2025
Zoning RR-S
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

AgentSweenie Khachi
OfficeHoms Real Estate

Listing Map

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