16244 Kennedy Rd

• Sun Oct 5, 2:00 pm - 4:00 pm

  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 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. Close to downtown shops, restaurants, hiking, biking, top-rated schools.

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.

Days on Market

3 days

Current Status

Active

Original Price

$5,500,000

List Price

$5,500,000

On Market Date

Oct 2, 2025

Property Type

Single Family Residence

District

900016 - Los Gatos/Monte Sereno

Zip Code

95032

MLS ID

425078109

APN

532-18-013

Year Built

1970

Stories in Building

2

Possession

Close Of Escrow

Data Source

SFAR

Origin MLS System

Bed

5

Bath

3

Parking

5

Attached, Enclosed, Garage Door Opener, Garage Facing Side, Interior Access, Uncovered Parking Spaces 2+

SQ FT

3,645

SQ FT Source

Unavailable

Lot SQ FT

40,800.0

Lot Acres

0.9366 Acres

Pool Info

Built-In, Pool Sweep

Kitchen

Breakfast Area, Island, Pantry Closet, Skylight(s), Tile Counter

Cooling

Ceiling Fan(s), Central

Dining Room

Formal Area

Exterior Details

Balcony

Family Room

Deck Attached

Living Room

Cathedral/Vaulted

Flooring

Carpet, Stone, Tile, Wood

Fire Place

Den, Gas Starter, Living Room

Heating

Central

Laundry

Hookups Only, Inside Room, Sink

Upper Level

Bedroom(s), Full Bath(s), Primary Bedroom

Main Level

Bedroom(s), Dining Room, Family Room, Full Bath(s), Garage, Kitchen, Living Room, Street Entrance

Views

Garden/Greenbelt, Hills

Possession

Close Of Escrow

Architectural Style

Mediterranean, Spanish

Special Listing Conditions

None

Fee

$0

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.