- 3 Beds
- 4 Baths
- 3,865 Sqft
- 2.1 Acres
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.
Essential Information
- MLS® #OC25134772
- Price$4,598,000
- Bedrooms3
- Bathrooms4.00
- Full Baths2
- Half Baths2
- Square Footage3,865
- Acres2.10
- Year Built1986
- TypeResidential
- Sub-TypeSingle Family Residence
- StyleTudor
- StatusActive
Community Information
- Address20585 Whispering Oaks Drive
- CitySan Jose
- CountySanta Clara
- Zip Code95120
Amenities
- Parking Spaces3
- # of Garages3
- Has PoolYes
- PoolPrivate, Solar Heat
Parking
Garage, Garage Door Opener, Door-Multi, Driveway Up Slope From Street, Guest, Paved
Garages
Garage, Garage Door Opener, Door-Multi, Driveway Up Slope From Street, Guest, Paved
View
Panoramic, Trees/Woods, Canyon, Pool
Interior
- InteriorCarpet, Stone
- HeatingForced Air, Electric
- CoolingCentral Air
- FireplaceYes
- # of Stories2
- StoriesTwo, Multi/Split
Interior Features
Wet Bar, Built-in Features, Cathedral Ceiling(s), Eat-in Kitchen, Granite Counters, High Ceilings, Recessed Lighting, Storage, Bar, Bedroom on Main Level, Entrance Foyer, Primary Suite, Walk-In Closet(s), Balcony, Stone Counters
Appliances
SixBurnerStove, Double Oven, Dishwasher, Electric Cooktop, Electric Oven, Gas Oven
Fireplaces
Family Room, Living Room, Primary Bedroom
Exterior
- Exterior FeaturesBarbecue, Lighting
- Lot DescriptionLawn, TwoToFiveUnitsAcre
- RoofStone
School Information
- DistrictSanta Clara Unified
- ElementaryGraystone
- MiddleBret Harte
- HighLeland
Additional Information
- Date ListedJune 16th, 2025
- Days on Market86
- ZoningRR-SR
Listing Details
- AgentSweenie Khachi
- OfficeHoms Real Estate
Price Change History for 20585 Whispering Oaks Drive, San Jose, (MLS® #OC25134772)
| Date | Details | Change |
|---|---|---|
| Price Reduced from $4,888,000 to $4,598,000 |
Sweenie Khachi, Homs Real Estate.
Based on information from California Regional Multiple Listing Service, Inc. as of September 27th, 2025 at 8:50am PDT. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.