20585 Whispering Oaks Dr San Jose, CA 95120
Property details
About 20585 Whispering Oaks Dr
Experience unmatched privacy and 360 degree views from this English-inspired custom estate on 2.1 acres atop a hilltop and buildble leveled land for an ADU. The 4 bed, 2 full plus 2 half bath home features a dramatic spiral staircase, marble flooring, leaded glass, crystal chandeliers, and 3 marble fireplaces. Classic entertaining spaces in both formal living and dining rooms, a spacious family room with coffered ceilings, hidden theater screen, custom wet bar, and chef’s kitchen with mahogany cabinetry, granite counters, and high-end appliances. Upstairs includes a the primary suite with fireplace and sitting area, plus two guest bedrooms with balconies. Enjoy outdoor multi-level terraces, a lush grassy yard with stone finishes, a custom solar-heated pool, all surrounded by mature trees and endless unobstructed meditative views. Property includes county-approved surveys and environmental clearance for expansion, potential for an 8 bedroom addition to main house or a separate private 1,700 sq ft ADU/JADU in a private area near the top of the road. Land surrounds both the north and sound ends of the property for expansion. Plenty of space for horses, vineyards, or orchards, plus a 3-car garage and ample guest parking. Top schools include Williams, Bret Harte and Leland High.
Highlights
Virtual tour
Summary
- Partial Bathrooms: 2
- Full Bathrooms: 2
- Appliances: Stove, Double Oven, Dishwasher, Electric Cooktop, Electric Oven, Gas Oven
- Flooring Type: Carpet, Stone
- Interior: Wet Bar, Built-in Features, Balcony, Cathedral Ceiling(s), Eat-in Kitchen, Granite Counters, High Ceilings, Stone Counters, Recessed Lighting, Storage, Bar, Bedroom on Main Level, Entrance Foyer, Primary Suite, Walk-In Closet(s)
- Fireplace: Family Room, Living Room, Primary Bedroom
- Total Bedroom Count: 4
- Garage Space: 3 spaces
- Attached Garage: Yes
- Private Pool: Yes
- Parking: Door-Multi, Driveway Up Slope From Street, Garage, Garage Door Opener, Guest, Paved
- View: Canyon, Panoramic, Pool, Trees/Woods
- Exterior: Barbecue, Lighting
- Architectural Style: Tudor
- Heating: Electric, Forced Air
- Cooling: Central Air
- List Price: $4,888,000
- Price/SqFt: $1,264
- HOA Amount: $0
- Annual Tax Amount: $13,760
- Tax Year: 2024
- Lot: Lawn
- Directions: Off McKean Rd south from Almaden Expressway / Harry Road
- Year Built: 1986
- Stories: 2
- Living Area: 3,865 SqFt
- Lot Size: 2.1014 Acres
- MLS Number: OC25134772
- MLS Name: CRMLS
- Office Name: Homs Real Estate
- Office Phone: (949) 339-7775
- Listing Agent: Sweenie Khachi
Based on information from California Regional Multiple Listing Service, Inc. and /or other sources. All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. The data contained herein is copyrighted by CRMLS and is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited.
The information being provided by California Regional Multiple Listing Service, Inc. (“CRMLS”) 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. Any information relating to a property referenced on this web site comes from CRMLS. Properties may or may not be listed by the office/agent presenting the information. Real estate listings held by brokerage firms other than this broker are marked with the Internet Data Exchange logo and detailed information about them includes the names of the listing brokers and listing agents. MLS search engine provided by IHR Technology Services. This data is updated every 2 hours. Some properties appearing for sale on this display may subsequently have sold and may no longer be available.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 7/30/2025, 9:45:30 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
| Date | Event | Price |
|---|---|---|
| Nov 22, 1996 | Home Sold | $750,000 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2024 | $1,197,556 | $13,760 |
| 2023 | $1,174,076 | $13,547 |
| 2022 | $1,151,056 | $13,499 |
| 2021 | $1,128,488 | $13,208 |
| 2020 | $1,116,918 | $13,010 |
| 2019 | $1,095,018 | $12,687 |
| 2018 | $1,073,548 | $12,687 |
| 2017 | $1,052,499 | $12,590 |
History based on county public records data.
Nearby schools
8
Graystone Elementary School
Public District KG-5
1.6 mi
•6982 Shearwater Dr
9
Williams Elementary School
Public District KG-5
2.1 mi
•1150 Rajkovich Way
6
Taylor Elementary School
Public District KG-6
2.3 mi
•410 Sautner Dr
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $89,015. The most common annual income of people living in San Jose, CA is between $35k-100k. The most common type of family is married, no kids. The most common level of education of people living in this area is post secondary degree.
How much money do the neighbors make?
What level of education do the neighbors have?
What types of families live nearby?
Are the neighbors home owners or renters?
How old are people in this area?
What do the neighbors do for fun?
Skiing/snowboarding
PGA/LPGA
College Football
Where do the neighbors shop?
BJs Wholesale Club
Stein Mart
Express/Express For Men
Where do the neighbors go to eat?
Panera
Cracker Barrel
Bob Evans
What do the neighbors drive?
Infiniti
Lexus
Lincoln
What do the neighbors listen to?
Adult Hits
Oldies
News/Talk/Information
Frequently asked questions
About 20585 Whispering Oaks Dr
The listing price of 20585 Whispering Oaks Dr property is $4,888,000.
The property 20585 Whispering Oaks Dr is a house located in San Jose, California, 95120.
Active Listing: 20585 Whispering Oaks Dr is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 20585 Whispering Oaks Dr are: Graystone Elementary School (GreatSchools Rating 8/10), Williams Elementary School (GreatSchools Rating 9/10), Taylor Elementary School (GreatSchools Rating 6/10), Bret Harte Middle School (GreatSchools Rating 8/10), Bernal Intermediate School (GreatSchools Rating 6/10), Discovery Charter II (GreatSchools Rating 5/10), Leland High School (GreatSchools Rating 9/10), Phoenix High School (GreatSchools Rating 2/10), Santa Teresa High School (GreatSchools Rating 8/10).
According to the records, the last property tax for 2024 is $13,760 (source: MLS/based on county public records data).
The last sale was on November 22, 1996 for $750,000 (source: MLS/tax record).
The property at 20585 Whispering Oaks Dr has 4 bedrooms and 2 full and 2 half bathrooms.
The property 20585 Whispering Oaks Dr is 3,865 SqFt (source: MLS/tax record).
The year of construction for 20585 Whispering Oaks Dr is 1986.
This home is located at 20585 Whispering Oaks Dr in San Jose, CA and zip code 95120 in the Whispering Oaks neighborhood. This 3,865 square foot home, which was built in 1986, sits on a 2.10 acre lot. Features: 4 bedrooms, 4 bathrooms. It has been listed on Rocket Homes since July 3, 2025 and is currently priced at $4,888,000.
In June 2025 in San Jose, CA there were 7.8% less homes for sale than in May.