$4,487,000

14990 Winchester Boulevard, Los Gatos, CA 95030

4 beds |
5 baths |
3,201 sqft

Single-Family Home
Built in 1946
0.82acre lot
3 car garage
$1,402/sqft
Listed 14 days ago

Property Description

Hidden along a quiet stretch of Winchester Boulevard, this LG property is accessed via a long private drive surrounded by mature trees & landscaping, creating a peaceful, secluded setting. Motor court, 3-car garage & inviting outdoor areas give the property a private feel. Inside, a striking black entry door opens to wood floors, vaulted ceilings & expansive windows that fill the home with natural light. 2 living areas include a lounge with a built-in media center & a second space with a gas-log fireplace and built-in shelving. The kitchen features a green Marinace granite island with a Thermador cooktop, dual sinks, ample cabinetry, a walk-in pantry & high-end appliances including Thermador double ovens, a GE Monogram refrigerator & a Bosch dishwasher. A breakfast area overlooks the gardens, and the dining room opens to the backyard for indoor-outdoor living. 2 main-level bedrooms share a full bath. Upstairs, the primary suite offers vaulted ceilings, a Juliet balcony with views of the LG Hills & a bath with soaking tub, glass shower, dual vanity, and walk-in closet. The permitted detached cottage includes a living area, kitchenette, bedroom & updated bath. Outdoor spaces w/ gardens and paths. Solar w/ Tesla battery storage and dual HVAC complete this property near downtown LG.

Listing Status:: Active
Date Added:: March 19, 2026
Data Last Updated:: April 2, 2026 at 6:06AM
Listing Office:: Golden Gate Sotheby's International Realty : 408-358-2800
Listing Agent:: Amy McCafferty : 408-387-3227
MLS ID:: ML82038974

General: Family RoomFormal Dining RoomBreakfast NookPantry
Appliances: DishwasherDouble OvenGas RangeOven
Flooring: HardwoodTile
A/C: Ceiling Fan(s)
Heating: Zoned
Fireplace: Family RoomGas StarterFireplaceFireplaces: 1
Eco/Green Feature: Solar

General: Back Yard

Roofing: Shingle
General: 2

School District: Los Gatos-Saratoga Joint Union High
County: Santa Clara

Zoning: R12042430124
Fencing: Fenced

This listing courtesy of Amy McCafferty , Golden Gate Sotheby's International Realty

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

Ready to Start a VA Loan?

Get Started

NMLS #1907 ^†

Get Prequalified »

Interest rates used in the VA mortgage calculator are shown for illustrative purposes only. Your rate may differ based on a variety of factors, including your credit score and the current market conditions. To get your personalized interest rate, start your quote online.

Location

Schools Nearby

Daves Avenue Elementary School

17770 Daves Ave, Monte Sereno, CA, 95030

Grades KG-5

0.99 miles away

Raymond J. Fisher Middle School

19195 Fisher Ave, Los Gatos, CA, 95032

Grades 6-8

1.16 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.