14990 Winchester BL Los Gatos CA 95030 MLS #ML82038974

14990 Winchester BL
Los Gatos, CA, 95030
$4,487,000
4 Beds
5 Baths
3,201 SqFt
0.82 Acres
$4,487,000
14990 Winchester BL
Los Gatos, CA, 95030
MLS #ML82038974 image #0
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.

Property Details

Price:
$4,487,000
MLS #:
ML82038974
Status:
Active
Beds:
4
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
699notdefined
Listed Date:
Mar 19, 2026
Finished Sq Ft:
3,201
Lot Size:
35,837 sqft / 0.82 acres (approx)
Year Built:
1946
699 – Not Defined699notdefinedOtherDaves AvenueRaymond J. FisherLos Gatos

Schools

School District:
Other
Elementary School:
Daves Avenue
Middle School:
Raymond J. Fisher
High School:
Los Gatos

Interior

Appliances
DW, GD, RF, GS, DO, VEF
Bathrooms
3 Full Bathrooms, 2 Half Bathrooms
Cooling
WW
Flooring
TILE, WOOD, CARP

Exterior

Common Walls
NCW
Construction Materials
STC
Direction Faces
E
Fencing
CH, WD
Garage Spaces
3
Parking Spots
3
Parking Total
3
Patio And Porch Features
DK
Roof
CMP

Financial

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Get Out There, A Simply Outgoing Approach to Life. James Outland Jr. is one of those rare people who simply has an outgoing approach to life. No matter the activity… from dune buggy riding to skydiving to motorcycling to riding the local Pismo Beach waves… James Outland Jr. approaches life with a “just get out there and do it” kind of attitude. A zest for Life. James’ zest for life is obviously apparent in his many exciting hobbies. In his spare time, he loves riding dune buggies or hi…

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Map

Current real estate data for Single Family in Los Gatos as of Apr 07, 2026
132
Single Family Listed
69
Avg DOM
1,136
Avg $ / SqFt
$3,200,826
Avg List Price

Community

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Property Summary

    14990 Winchester BL Los Gatos CA is a Single Family for sale in Los Gatos, CA, 95030. It is listed for $4,487,000 and features 4 beds, 5 baths, and has approximately 3,201 square feet of living space, and was originally constructed in 1946. The current price per square foot is $1,402. The average price per square foot for Single Family listings in Los Gatos is $1,136. The average listing price for Single Family in Los Gatos is $3,200,826. To schedule a showing of MLS#ml82038974 at 14990 Winchester BL in Los Gatos, CA, contact your James Outland agent at 8057482262.
14990 Winchester BL
Los Gatos, CA
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