14990 Winchester Boulevard

• Sun Mar 22, 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.

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.

Days on Market

3 days

Current Status

Active

Original Price

$4,487,000

List Price

$4,487,000

On Market Date

Mar 19, 2026

Property Type

Single Family Home

Area

16 - Los Gatos/Monte Sereno

Zip Code

95030

MLS ID

ML82038974

APN

424-30-124

Year Built

1946

Stories in Building

2

Possession

Unavailable

Data Source

MLSL

Origin MLS System

MLSListings, Inc.

Bed

4

Bath

5 (3/2)

Full on Ground Floor, Half on Ground Floor, Primary - Stall Shower(s), Stall Shower - 2+, Tile, Tub, Updated Bath

Parking

3

Detached Garage

SQ FT

3,201

SQ FT Source

Unavailable

Lot SQ FT

35,837.0

Lot Acres

0.822704 Acres

Kitchen

Cooktop - Gas, Countertop - Granite, Dishwasher, Exhaust Fan, Garbage Disposal, Island, Oven - Built-In, Oven - Double, Pantry, Refrigerator

Cooling

Ceiling Fan, Multi-Zone, Window / Wall Unit

Dining Room

Breakfast Nook, Formal Dining Room

Disclosures

NHDS Report

Family Room

Separate Family Room

Flooring

Carpet, Hardwood, Tile

Foundation

Concrete Perimeter and Slab

Fire Place

Family Room, Gas Starter

Heating

Heating - 2+ Zones

Laundry

In Utility Room

Fee

Unavailable

MLS and other Information regarding properties for sale as shown in Theo have been obtained from various sources such as sellers, public records, agents and other third parties. This information may relate to the condition of the property, permitted or unpermitted uses, zoning, square footage, lot size/acreage or other matters affecting value or desirability. Unless otherwise indicated in writing, neither brokers, agents nor Theo have verified, or will verify, such information. If any such information is important to buyer in determining whether to buy, the price to pay or intended use of the property, buyer is urged to conduct their own investigation with qualified professionals, satisfy themselves with respect to that information, and to rely solely on the results of that investigation.

School data provided by GreatSchools. School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly.