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$4,487,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2 Partial Baths
  • 3,201 Sq. Ft.
  • 3 Car Garage
  • Updated 1 day ago

Next open house:

Open House: 2:00 PM - 4:00 PM

Saturday 3/21 2:00 PM - 4:00 PM

14990 Winchester Blvd,Los Gatos, CA 95030

14990 Winchester BlvdLos GatosCA95030

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Join us at 14990 Winchester Blvd on:

  • Open House: 2:00 PM - 4:00 PM

    Sunday 3/22 2:00 PM - 4:00 PM

    14990 Winchester Blvd,Los Gatos, CA 95030
    14990 Winchester BlvdLos GatosCA95030
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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. A 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. Two 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. Two main-level bedrooms share a full bath. Upstairs, the primary suite offers vaulted ceilings, a Juliet balcony, and a bath with soaking tub, glass shower, dual vanity, and walk-in closet. A detached cottage includes a living area, kitchenette, bedroom, and updated bath. Outdoor spaces offer gardens and paths. Solar with Tesla battery storage and dual HVAC complete this offering near downtown Los Gatos.

Full Property Details for 14990 Winchester Blvd

General

  • Price: $4,487,000
  • Status: Active
  • Type: Single Family
  • Source: RE_Infolink
  • MLS ID: ML82038974
  • Updated: 3/19/2026
  • Added to Site: 1 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

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Listing agent

— 14990 Winchester Blvd —

  • Amy McCafferty

    Golden Gate Sotheby's International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 14990 Winchester Blvd

School Districts:Los Gatos Union Elementary School District, Los Gatos-Saratoga Joint Union School District
NameGradesDistance
Daves Avenue Elementary School
17770 Daves Ave., Los Gatos, CA 95030
K-51 mi
Raymond J. Fisher Middle School
19195 Fisher Avenue, Los Gatos, CA 95032
6-81.2 mi
Los Gatos High School
20 High School Court, Los Gatos, CA 95030
9-122 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/19/2026
Listed
$4,487,000
52.1%
MLS
4/13/2020
Sold
$2,950,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 14990 Winchester Blvd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$38,204
4%
$3,226,251
2%
2024
$36,825
2%
$3,162,992
2%
2023
$36,209
1%
$3,100,974
2%
2022
$35,961
2%
$3,040,172
2%
2021
$35,406
171%
$2,980,562
184%
2020
$13,086
2%
$1,047,752
2%
2019
$12,852
4%
$1,027,209
2%
2018
$12,377
—
$1,007,069
2%
2017
$12,384
—
$987,324
2%
2016
$12,337
1%
$967,966
2%
2015
$12,247
2%
$953,427
2%
2014
$12,051
2%
$934,752
—
2013
$11,809
—
$930,529
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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

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14990 Winchester Blvd, Los Gatos, CA 95030 (MLS# ML82038974) is a Single Family property with 4 bedrooms, 3 full bathrooms and 2 partial bathrooms. 14990 Winchester Blvd is currently listed for $4,487,000 and was received on March 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.

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