14990 Winchester

Los Gatos Los Gatos, CA, 95030
For Sale $4,487,000
  • 4beds
  • 3,201sqft
  • 35,837sf lot
Listing agent:
Amy McCafferty
Golden Gate Sotheby's International Realty
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. In addition, the permitted detached cottage includes a living area, kitchenette, bedroom & updated bath. For the main house, 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 2nd space with a gas-log fireplace and built-in shelving. The kitchen features a 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. Breakfast area overlooks the gardens, and 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. Outdoor spaces w/ gardens and paths. Solar w/ Tesla battery storage and dual HVAC complete this property near downtown LG.

Now it's your turn

Interested in this property or one like it? Reach out today!

14990 Winchester is a Residential Single Family Residence property located in Los Gatos, California, featuring a 35,837 sqft lot, 3,201 sqft, 4 bedrooms, MLS #ML82038974.
Based on information from one of the following Multiple Listing Services: MLSListings and/or MLSL. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by MLSListings Inc and/or OpenStreetMap and is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. All data, including all measurements and calculations of area, is obtained from various sources, is approximate, and has not been, and will not be, verified by broker or MLS. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. All information should be independently reviewed and verified for accuracy. No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of such measurements.

Data last modified: 2026-04-06 21:29:41