20585 Whispering Oaks Drive, San Jose, California 95120, San Jose, - bed, bath

home-pic
ACTIVE$4,598,000
20585 Whispering Oaks Drive, San Jose, California 95120
4Beds
4Baths
3,865Sqft
91,536Lot
Year Built
1986
Close
-
List price
$4.6M
Original List price
$4.89M
Price/Sqft
-
HOA
-
Days on market
-
Sold On
-
MLS number
OC25134772
Home ConditionFair
Features
Excellent View: Canyon, Panoramic, Pool, Trees/Woods
Deck
Pool
Spa
Patio
ViewCanyon, Panoramic, Pool, Trees/Woods

About this home

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.

Price History

Date
Event
Price
08/27/25
Price Change
$4,598,000-5.9%
07/03/25
Listing
$4,888,000
Neighborhood Comparison

 SubjectAverage HomeNeighbourhood Ranking (81 Listings)
Beds44
50%
Baths43
85%
Square foot3,8652,228
95%
Lot Size91,5368,721
98%
Price$4.6M$2.28M
98%
Price per square foot$1,190$1,020
80%
Built year19869865987
85%
HOA
Days on market125160
38%
Condition Rating
Fair

Built in 1986, this property is well-maintained but shows signs of an older renovation style. The kitchen features mahogany cabinetry and granite counters, but the black appliances and fluorescent lighting are dated. Bathrooms also exhibit older finishes and fixtures. While functional and clean, the overall aesthetic and specific components like kitchen appliances and lighting suggest a renovation that occurred 15-30 years ago, requiring minor updates to meet current market expectations.
Pros & Cons

Pros

Development Potential & Large Acreage: The private 2.1-acre hilltop estate offers county-approved surveys and environmental clearance for significant expansion, including ample flat land for a separate guest house, horses, vineyards, or orchards, catering to diverse future development needs.
Unobstructed 360-Degree Views: Positioned on a hilltop, the property boasts rare and unobstructed 360-degree panoramic views, enhancing its exclusivity and aesthetic appeal.
Luxury Custom Finishes & Amenities: The home features high-end custom details such as a dramatic spiral staircase, marble flooring, leaded glass, crystal chandeliers, three marble fireplaces, a chef’s kitchen with mahogany cabinetry and high-end appliances, a hidden theater screen, wet bar, and a custom solar-heated pool.
Top-Rated School District: Located within the highly desirable Santa Clara Unified School District, with access to top-rated schools like Williams, Bret Harte, and Leland High, making it attractive to families.
Multi-Generational Living & Flexible Space: The property is ideal for multi-generational living with leveled land suitable for a separate guest house, and a flexible interior layout including 3 bedrooms plus an office and an optional 4th/guest bedroom.

Cons

Potential for Dated Aesthetics: Built in 1986 with an 'English-inspired' design featuring leaded glass, crystal chandeliers, and extensive marble, the aesthetic may be considered dated by some modern luxury buyers, potentially requiring significant updates.
High Maintenance Requirements: The expansive 2.1-acre lot, multi-level terraces, mature landscaping, and custom solar-heated pool imply substantial ongoing maintenance costs and time commitment for a homeowner.
Limited Buyer Pool: The high list price of $4.598 million, even after a reduction from $4.888 million, targets a very niche market, potentially extending the time on market and limiting the pool of prospective buyers.

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