14990 Winchester Boulevard, Los Gatos, CA 95030

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14990 Winchester Boulevard, Los Gatos, CA 95030

(Active)

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Listed by: Amy McCafferty - Golden Gate Sotheby's International Realty

Active

est.$4,487,000/month.

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4 beds. 3 baths. 3,201 Sqft.

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Today (2:00 PM - 4:00 PM)

Fabulous property surrounded by mature trees w/ views in great Los Gatos location plus spacious ADU & 3 car garage. 2 main flr bedrooms, spacious living areas. Close to dwntwn LG, Country Club, Vasona & Oak Meadow Parks! Easy access to 880/85.

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Mortgage Broker

Ray Avanzino
Polaris Capital Partners
Ray@polariscappartners.com
(650) 576-6531
NMLS# 288504
Company NMLS# 01391664

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or Call Now: (650) 576-6531

14990 Winchester Boulevard, Los Gatos, CA 95030

$4,487,000

Active

est.$4,487,000/month.

Start My Approval

4 beds 4 baths 3,201 Sq.ft.

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Property details for 14990 Winchester Boulevard, Los Gatos, CA 95030

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, and high-end appliances including Thermador double ovens, a GE Monogram refrigerator, and 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. Detached cottage includes a living area, kitchenette, bedroom & updated bath. Outdoor spaces w/ gardens and paths. Solar with Tesla battery storage and dual HVAC complete this property near downtown LG.

Broker details: Golden Gate Sotheby's International Realty

Listed by: Amy McCafferty

Property Description

MLS Information

Listing: ML82038974
Listing Last Modified: 2026-03-22

Property Details

Standard Status: Active
MLS Status: Active
Built in: 1946

Geographic Data

County: Santa Clara

Features

Interior Features

Flooring: Carpet, Hardwood, Tile
Bedrooms: 4
Full baths: 4
Half baths: 2
Living area: 3201
Interior Features: Vaulted Ceiling(s), Pantry, Walk-In Closet(s), Kitchen Island
Fireplaces: 1