20585 Whispering Oaks Dr, San Jose, CA 95120
$4,888,000 Mortgage Calculator Active Single Family Residence
Property Details
About this Property
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.
MLS Listing Information
MLS #
CROC25134772
MLS Source
California Regional MLS
Days on Site
51
Interior Features
Bedrooms
Ground Floor Bedroom, Primary Suite/Retreat
Kitchen
Other
Appliances
Dishwasher, Other, Oven - Double, Oven - Electric, Oven - Gas
Dining Room
Dining Area in Living Room, In Kitchen
Family Room
Other, Separate Family Room
Fireplace
Family Room, Living Room, Primary Bedroom
Laundry
In Laundry Room
Cooling
Central Forced Air
Heating
Electric, Forced Air
Exterior Features
Roof
Rock
Pool
Heated - Solar, Pool - Yes
Style
Tudor
Parking, School, and Other Information
Garage/Parking
Garage, Gate/Door Opener, Guest / Visitor Parking, Other, Garage: 3 Car(s)
Elementary District
Santa Clara Unified
High School District
Santa Clara Unified
HOA Fee
$0
Zoning
RR-SR
Neighborhood: Around This Home
Neighborhood: Local Demographics
Market Trends Charts
Nearby Homes for Sale
20585 Whispering Oaks Dr is a Single Family Residence in San Jose, CA 95120. This 3,865 square foot property sits on a 2.101 Acres Lot and features 4 bedrooms & 2 full and 2 partial bathrooms. It is currently priced at $4,888,000 and was built in 1986. This address can also be written as 20585 Whispering Oaks Dr, San Jose, CA 95120.
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This listing information is up-to-date as of August 21, 2025. For the most current information, please contact Sweenie Khachi, (949) 339-7775
