23185 Old Santa Cruz Highway, Los Gatos, California 95033, Los Gatos, 95033 - 5 bed, 5 bath

23185 Old Santa Cruz Highway, Los Gatos, California 95033 home-pic-0

23185 Old Santa Cruz Highway

Los Gatos, California 95033

ACTIVE
CONDITION: GOOD
5Beds
5Baths
4,427Sq Ft
345,518Lot Size

Property Price

LIST PRICE$2,890,000

SUMMARY

Analysis of 23185 Old Santa Cruz Highway, Los Gatos, California 95033 is currently available with a list price of $2,890,000. The property maintains a Good Condition Rating (78/100), reflecting solid structural condition with well-maintained systems. The property presents an attractive opportunity for buyers seeking a move-in ready home. Located in a high-demand neighborhood within the Los Gatos Unified School District, this asset is categorized as a low-risk, high-reward acquisition suitable for both Buy-and-Hold Investors and Owner-Occupants willing to undertake light renovation work.

Condition Analysis

OVERALL CONDITION SCORE

Good
TeardownExcellent

Property is move-in ready.

The main residence is move-in ready and features high-end finishes, including a spacious modern kitchen with premium appliances, custom woodwork, and updated bathrooms. While the original structure dates to 1969, the interior has been significantly updated and well-maintained. The 'good' score reflects the high quality of the primary living spaces, though it is not 'excellent' as the secondary cottage requires interior finishing and the property age necessitates ongoing maintenance.

PROSSTRENGTHS & OPPORTUNITIES

  • High Available Lot Utilization

    The property has a large lot size, which is more than 4 times of its living area. lot size in square feet = 345518, living area = 4427.

  • Multi-Unit Income Potential

    The estate functions as a versatile compound with a main residence, a rented detached studio, and a separate one-bedroom cottage, offering significant potential for rental income or multi-generational living.

  • Expansive Private Acreage

    Set on nearly 8 private acres of redwood forest, the property provides a rare level of seclusion and natural beauty while remaining just 10 minutes from downtown Los Gatos and major tech employers.

CONSRISKS & DEFICIENCIES

  • Unfinished Secondary Structure

    The 800 SF separate cottage requires interior finishes, which will necessitate additional capital investment and construction management from the buyer before it is habitable.

  • Property Age and Maintenance

    Built in 1969 and situated in a dense forest setting, the property may require significant ongoing maintenance related to fire safety, vegetation management, and aging infrastructure.

About 23185 Old Santa Cruz Highway

Incredible Value! Set on nearly 8 private acres just 10 minutes from downtown Los Gatos, this distinctive executive estate offers rare space, flexibility, and income potential in a redwood setting. The 4,427± SF main home is complemented by a detached studio with adjacent flex/gym space and a separate one-bedroom cottage with own address...creating a versatile compound ideal for modern living. The main residence features high end finishes, a spacious kitchen, exposed beams, custom woodwork, abundant natural light, and seamless indoor-outdoor living with multiple courtyards, decks, and forest views. Outdoor amenities include a private hot tub pergola and a forest fire pit, creating a peaceful, wellness-oriented environment. The detached 600± SF studio is currently rented and offers flexibility for work, guests, or income. The adjacent gym/flex area provides the potential to reconfigure or expand into a one-bedroom layout over time. A separate 800± SF one-bedroom cottage with a new roof, ready for interior finishes and with its own address has previously been rented and is well suited for multigenerational living or additional income. Enjoy privacy and natural beauty just minutes from Los Gatos and Netflix, with access to Loma Prieta Elementary and Los Gatos schools.

Property Details

Public Facts

Property Type
Single Family Residence
Year Built
1969
Lot Size
345,518 Sq. Ft.

Interior

Total Bedrooms
5
Total Bathrooms
5 (5 Full, 0 Half)

Exterior & Parking

No exterior & parking available.

Utilities & Misc

HOA Fee
$0 / Month

Neighborhood Insights

Sensitive Facilities

No sensitive facilities data found.

Neighborhood Comparison

FeatureSubjectAverage HomeNeighborhood Ranking (50 Listings)
Beds5.03.0
86%
Baths5.03.0
90%
Square foot4,4272,037
93%
Lot Size345,51893,654
86%
Price$2.89M$1.25M
86%
Price per sq ft$653$633
55%
Built year19691978
28%
HOA$0$0
50%
Days on market25198
3%

Pricing History

Listed for Sale

Mar 3, 2026

$2,890,000

$3,248,000

-11% Price Drop

Initial Listing

Price Change

Feb 10, 2026

$3,248,000

Initial Listing

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