14990 Winchester Blvd, Los Gatos, CA 95030 - Photo 1

1/1

$4,000,000

Sold
Closed
Single Family
4 Beds
3 Full Baths
2 Partial Baths
3,201 Sq. Ft.
3 Car Garage

1/1

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. 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.

Full Property Details

Full Property Details for 14990 Winchester Blvd

General

Sold For: $4,000,000
Status: Closed
Type: Single Family
Source: RE_Infolink
MLS ID: ML82038974
Added to Site: 101 day(s) ago

Interior

Rooms/Areas: Bonus / Hobby Room, Laundry Room
Interior Features: Vaulted Ceiling , Walk-In Closet
Fireplace(s): Family Room, Gas Starter
Flooring: Carpet, Hardwood, Tile

Rooms

Bathrooms

Total Bathrooms: 5
Full Bathrooms: 3
Half Bathrooms: 2
Bathroom Features: Full on Ground Floor, Half on Ground Floor, Primary - Stall Shower(s), 2 Stall Showers or More, Tile, Tub , Updated Bath

Bedrooms

Total Bedrooms: 4
Bedroom Features: Ground-Floor Bedroom, More than One Bedroom on Ground Floor, Primary Suite / Retreat, Walk-In Closet

Other Rooms

Family Room: Separate Family Room
Kitchen: Gas Cooktop, Granite Countertop, Dishwasher, Exhaust Fan, Garbage Disposal, Island, Built-In Oven, Double Oven, Pantry, Refrigerator
Laundry: In Utility Room

Additional Information

Extras: Not Applicable

Parking

Garage Spaces: 3
Parking Features: Detached Garage

Location

Area: Los Gatos/Monte Sereno
County: Santa Clara
Cross Streets: Lark

Heating & Cooling

Cooling Type: Ceiling Fan, Multi-Zone, Window / Wall Unit
Heating Type: Heating (2 Zones or More)

Utilities

Sewer: Public Sewer
Water: Public
Utility Description: Public Utilities

Structural Information

Construction: Detached, Stucco
Foundation: Concrete Perimeter and Slab
Roof: Composition
Square Feet: 3,201
Year Built: 1946

Lot Features

Lot Size (Acres): 0.8227
Minimum Lot Size: 35837
Lot Size (Sq. Ft.): 35,837
Grounds/Landscape: Back Yard, Balcony / Patio, Deck , Fenced
Zoning: R120
Fencing (Description): Chain Link, Wood

Green Features

Energy Efficient: Solar Power

Listed by Golden Gate Sotheby's International Realty, Amy McCafferty
Sold by Ggsir, Eric McCafferty

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Listing agent

— 14990 Winchester Blvd —

Amy McCafferty

Golden Gate Sotheby's International Realty

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Schools

Schools serving 14990 Winchester Blvd

School Districts:Los Gatos Union Elementary School District, Los Gatos-Saratoga Joint Union School District

Name	Grades	Distance
Daves Avenue Elementary School 17770 Daves Ave., Los Gatos, CA 95030	K-5	1 mi
Raymond J. Fisher Middle School 19195 Fisher Avenue, Los Gatos, CA 95032	6-8	1.2 mi
Los Gatos High School 20 High School Court, Los Gatos, CA 95030	9-12	2 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 14990 Winchester Blvd

Date

Details

Price

Change

Source

5/19/2026

Sold

$4,000,000

-10.85%

MLS

3/19/2026

Listed

$4,487,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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2
Beds
2
Total Baths
1,202
Sq. Ft.

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Updated 3 days ago

1
Bed
1
Total Bath
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Sq. Ft.

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4
Beds
3
Total Baths
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Sq. Ft.

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Beds
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Total Baths
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14990 Winchester Blvd, Los Gatos, CA 95030 (MLS# ML82038974) is a Single Family property that was sold at $4,000,000 on May 19, 2026. Want to learn more about 14990 Winchester Blvd? Do you have questions about finding other Single Family real estate for sale in Los Gatos Mountains? You can browse all Los Gatos Mountains real estate or contact a Coldwell Banker agent to request more information.

14990 Winchester Blvd Los Gatos, CA 95030