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16244 Kennedy Road, Los Gatos, CA 95032

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For Sale

$5,500,000

5 beds • 3 baths • 3,645 sqft

Estimated Payment

$      /mo. †

APR for 30 years

Change Loan Terms

  • Single Family Detached
    Property type

  • $1,508.92
    Price per square foot

  • Over 50 Years Old
    Age

  • Fireplace
    Fireplace

Explore this Property

Offered for sale for the first time is 16244 Kennedy Road, a stunning custom-built 5 bedroom, 3 bath residence nestled in one of Los Gatos' most desirable settings. The inviting entry opens to a spacious living room with vaulted ceilings, lovely center fireplace, setting the tone for the home's blend of comfort and elegance. A beautiful formal dining room with French doors flows seamlessly to a elegant brick patio, perfect for dining and entertaining. The expansive kitchen features a central island, skylight, and generous eating area, while the adjacent family room is highlighted by a striking adobe-style fireplace. The main level also offers a versatile office/bedroom, workout room, and a full bath. Upstairs, the primary suite boasts a private balcony, walk-in closet, and a large bath. Three additional bedrooms, one with direct access to a large balcony, and another full bath complete the upper level. The grounds are truly exceptional, featuring a sparkling pool, sprawling lawn, orchard with room for a tennis court, and a massive deck ideal for entertaining. This remarkable property combines timeless design with extraordinary outdoor living. Minutes to vibrant downtown Los Gatos shops and restaurants, hiking, biking, top-rated schools, and transportation.
MLS# 425078109

Courtesy Of Compass

(415) 660-9955

Open Houses

October

4

Saturday

In Person

Saturday, October 4, 2025

2:00PM - 4:00PM

October

5

Sunday

In Person

Sunday, October 5, 2025

2:00PM - 4:00PM

Property Features

  • Age
    Over 50 Years Old
  • Amenities
    Patio, Wet Bar, Garden
  • Appliances
    Cooktop, Cooktop - Gas, Dishwasher, Garbage Disposer, Microwave, Range, Trash Compactor, Washer
  • Architecture Style
    Other
  • Exterior Type
    Adobe, Stucco
  • Fireplace
    Fireplace
  • Floor Covering
    Carpet, Tile, Wood
  • Lot Size
    0.94 Acres
  • Roof Type
    Tile
  • View Type
    Hills

Map and Directions

Directions to 16244 Kennedy Road, Los Gatos, CA 95032

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Copyright © 2025 San Francisco Association of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data powered by Attom Data Solutions. Copyright© 2025. Information deemed reliable but not guaranteed.

This information is provided for general informational purposes only and should not be relied on in making any home-buying decisions. School information does not guarantee enrollment. Contact a local real estate professional or the school district(s) for current information on schools. This information is not intended for use in determining a person's eligibility to attend a school or to use or benefit from other city, town or local services.

† Based on a 30-year fixed rate of 3.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.