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Shawn Bengtson

Office Broker - DRE 01236964

  • Office 760-805-7199
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14990 Winchester Boulevard, Los Gatos – $4,487,000

  • 4 Beds
  • 5 Baths
  • 3,201 Sqft
  • .82 Acres
  • 4 Beds
  • 5 Baths
  • 3,201 Sqft
  • .82 Acres

14990 Winchester Boulevard

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.

Essential Information

  • MLS® #ML82038974
  • Price$4,487,000
  • Bedrooms4
  • Bathrooms5.00
  • Full Baths3
  • Half Baths2
  • Square Footage3,201
  • Acres0.82
  • Year Built1946
  • TypeResidential
  • Sub-TypeSingle Family Residence
  • StatusActive

Community Information

  • Address14990 Winchester Boulevard
  • Area699 - Not Defined
  • CityLos Gatos
  • CountySanta Clara
  • Zip Code95030

Amenities

  • Parking Spaces3
  • # of Garages3

Interior

  • InteriorCarpet, Tile, Wood
  • CoolingWall/Window Unit(s)
  • FireplaceYes
  • FireplacesFamily Room, Gas Starter
  • # of Stories2

Interior Features

Breakfast Area, Walk-In Closet(s)

Appliances

Double Oven, Dishwasher, Gas Cooktop, Disposal, Refrigerator, Vented Exhaust Fan

Exterior

  • ExteriorStucco
  • RoofComposition
  • ConstructionStucco

School Information

  • DistrictOther
  • ElementaryDaves Avenue
  • MiddleRaymond J. Fisher
  • HighLos Gatos

Additional Information

  • Date ListedMarch 19th, 2026
  • Days on Market3
  • ZoningR120

Listing Details

  • AgentAmy Mccafferty

Office

Golden Gate Sotheby's International Realty

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Amy Mccafferty, Golden Gate Sotheby's International Realty.

Based on information from California Regional Multiple Listing Service, Inc. as of March 22nd, 2026 at 7:56am PDT. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.