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
Property Price
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
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
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 5.0 | 3.0 | 86% |
| Baths | 5.0 | 3.0 | 90% |
| Square foot | 4,427 | 2,037 | 93% |
| Lot Size | 345,518 | 93,654 | 86% |
| Price | $2.89M | $1.25M | 86% |
| Price per sq ft | $653 | $633 | 55% |
| Built year | 1969 | 1978 | 28% |
| HOA | $0 | $0 | 50% |
| Days on market | 25 | 198 | 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




































