23185 Old Santa Cruz Highway

Fully remodeled and expanded in early 2000s with modern systems and design, set on nearly 8 private acres just minutes from downtown Los Gatos, this rare multi-structure estate offers an exceptional combination of scale, flexibility, privacy, and long-term value. The property includes a 4,427+/- SF main residence plus a separate ground-floor studio with attached bath not included in the reported square footage, creating additional flexibility for guest quarters, office, gym, media room, or creative space. A detached studio/flex building and separate cottage further expand the possibilities for multigenerational living, retreat use, or future income potential. Surrounded by mature redwoods and natural beauty, the home features soaring ceilings, exposed Douglas fir beams, hardwood floors, expansive windows, and multiple indoor-outdoor living spaces designed to embrace the setting. The land itself is a defining feature with usable areas, meandering paths and gardens, peaceful clearings, and exceptional privacy while remaining approximately 10 minutes to downtown Los Gatos and moments to Hwy 17. Served by sought-after Los Gatos High and Loma Prieta schools. A compelling opportunity for buyers seeking space, versatility, and lifestyle in one of the regions most desirable settings.

Days on Market

84 days

Current Status

Contingent

Sold Price

Original Price

$3,248,000

List Price

$2,498,000

On Market Date

Apr 8, 2026

Contract Date

Jun 10, 2026

Close Date

Jul 6, 2026

Property Type

Single Family Home

Area

Zip Code

95033

MLS ID

ML82042183

APN

096-081-20-000

Year Built

1969

Stories in Building

2

Possession

Unavailable

COE

Jul 6, 2026

Data Source

MLSL

Origin MLS System

MLSListings, Inc.

Bed

5

Bath

5 (4/1)

Shower over Tub - 1, Tub, Primary - Stall Shower(s), Stall Shower - 2+, Primary - Tub with Jets, Tubs - 2+

Parking

2

Attached Garage, Detached Garage, Gate / Door Opener, Guest / Visitor Parking, Room for Oversized Vehicle

SQ FT

4,427

SQ FT Source

Unavailable

Lot SQ FT

345,518.0

Lot Acres

7.932002 Acres

Kitchen

220 Volt Outlet, Dishwasher, Garbage Disposal, Hookups - Gas, Oven - Self Cleaning, Pantry, Oven Range - Built-In, Refrigerator, Trash Compactor

Cooling

Central AC

Dining Room

Breakfast Bar, Formal Dining Room

Disclosures

Natural Hazard Disclosure

Family Room

Separate Family Room

Flooring

Tile, Carpet, Hardwood

Foundation

Concrete Perimeter

Fire Place

Family Room, Living Room, Wood Burning, Wood Stove

Heating

Gas, Heating - 2+ Zones, Propane, Central Forced Air - Gas

Laundry

Inside

Views

Forest / Woods, Greenbelt, Mountains

Architectural Style

Contemporary

Fee

Unavailable

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.