$4,487,000 - 14990 Winchester Boulevard, Los Gatos

  • 4Beds
  • 5Baths
  • 3,201SQ. Feet
  • 0.82Acres

Los Gatos Home For Sale

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.

Sales Agent

Sam Smith
  • Sam Smith
  • San Clemente Realtor ®
  • Phone: 949-204-5110
  • Cell: 949-204-5110
  • Contact Agent Now

Amenities

  • Parking Spaces3
  • # of Garages3

School Information

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

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
  • Listing AgentAmy Mccafferty
  • Listing OfficeGolden Gate Sotheby's International Realty

Exterior

  • ExteriorStucco
  • RoofComposition
  • ConstructionStucco

Additional Information

  • Date ListedMarch 19th, 2026
  • Days on Market23
  • ZoningR120
  • Short SaleN
  • RE / Bank OwnedN

Community Information

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

Interior

  • InteriorCarpet, Tile, Wood
  • Interior FeaturesBreakfast Area, Walk-In Closet(s)
  • AppliancesDouble Oven, Dishwasher, Gas Cooktop, Disposal, Refrigerator, Vented Exhaust Fan
  • CoolingWall/Window Unit(s)
  • FireplaceYes
  • FireplacesFamily Room, Gas Starter
  • # of Stories2

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  • City:
    Los Gatos
  • Price Range:
    $300,000 - $21,998,888
  • Current Listings:
    173
  • HOA Dues:
    $182
  • Average Price per Square Foot:
    $1,112

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Based on information from California Regional Multiple Listing Service, Inc. as of April 11th, 2026 at 9:11pm 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.