19960 Skyline Boulevard, Los Gatos, California 95033, Los Gatos, 95033 - 4 bed, 4 bath

19960 Skyline Boulevard
Los Gatos, California 95033
Property Price
SUMMARY
Analysis of 19960 Skyline Boulevard, Los Gatos, California 95033 is currently available with a list price of $3,149,000. The property maintains a Excellent Condition Rating (95/100), indicating excellent structural integrity and modern finishes throughout. This turnkey property requires minimal updates and is ready for immediate occupancy. 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 new construction or fully renovated.
Although originally built in 1983, the property has undergone extensive high-end renovations that meet modern luxury standards. The chef's kitchen is equipped with professional Thermador appliances, dual dishwashers, and custom cabinetry, while the primary suite features a recently updated spa-inspired bathroom. The inclusion of vaulted ceilings, refined finishes, and a well-maintained secondary guest house indicates the property is in top-tier condition with no deferred 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 = 165528, living area = 3717.
- Dual-Residence Versatility
The estate includes a substantial 1,260 sqft, 3-bedroom guest house with its own garage and private driveway, providing excellent potential for multi-generational living or rental income.
- Architectural Design and Views
The main residence features soaring vaulted ceilings and walls of glass that frame breathtaking valley and city light views, complemented by a high-end chef's kitchen with Thermador appliances.
CONSRISKS & DEFICIENCIES
- Market Pricing Volatility
A significant price reduction of $450,000 shortly after the initial listing suggests the property may have faced challenges with its original valuation in the current market.
- Mountain Maintenance Requirements
Built in 1983 and situated on nearly 4 acres of mountain terrain, the property likely requires more intensive ongoing maintenance and land management than a typical suburban lot.
About 19960 Skyline Boulevard
Absolutely stunning Skyline Blvd. estate featuring two residences & sweeping valley views. Perfectly positioned just 10 minutes to the Bear Creek overpass, this exceptional property offers the rare combination of serene mountain living with effortless valley access. The main house showcases soaring vaulted ceilings, open-beam architecture, & walls of glass that frame breathtaking vistas. Designed with uncompromising quality, the interior features a dramatic stone fireplace, refined finishes, & a chefs kitchen appointed with a professional Thermador range, dual dishwashers, wine refrigeration, custom cabinetry, & a discreetly integrated television. The primary suite is a private sanctuary with valley views, a spa-inspired bath, & its own patio. The main level is completed by two generously sized bedrooms, a full bath, & powder room. Upstairs, an additional bedroom with views, full bath, family room, & media room create flexible living & entertaining spaces. Every bedroom includes a spacious walk-in closet. Enhancing the versatility is a separate 3-bedroom, 1.5-bath guest house of approx. 1,260 square feet, complete with its own garage & private driveway, ideal for extended family, guests, or income potential. Award-winning Los Gatos schools further elevate this rare offering.
Property Details
Public Facts
- Property Type
- Single Family Residence
- Year Built
- 1983
- Lot Size
- 165,528 Sq. Ft.
Interior
- Total Bedrooms
- 4
- Total Bathrooms
- 4 (4 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 | 4.0 | 3.0 | 69% |
| Baths | 4.0 | 3.0 | 90% |
| Square foot | 3,717 | 2,037 | 83% |
| Lot Size | 165,528 | 93,654 | 69% |
| Price | $3.15M | $1.25M | 86% |
| Price per sq ft | $847 | $633 | 86% |
| Built year | 1983 | 1978 | 76% |
| HOA | $0 | $0 | 50% |
| Days on market | 12 | 198 | 3% |
Pricing History
Listed for Sale
Feb 24, 2026
$3,149,000
Initial Listing
Price Change
Feb 23, 2026
$3,599,000
Initial Listing
Sold
Apr 29, 1998
$754,500
Public Record









































































