19975 Skyline Boulevard, Los Gatos, California 95033, Los Gatos, 95033 - 5 bed, 5 bath
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Los Gatos, California 95033
Analysis of 19975 Skyline Boulevard, Los Gatos, California 95033 is currently available with a list price of $3,149,000. The property maintains a Fair Condition Rating (50/100), suggesting the property is in acceptable condition with potential for value enhancement through selective updates and improvements. 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.
Property is moderate renovation needed.
Built in 2001, the property is 23+ years old, placing it in the 'Fair' category based on age. While the estate is meticulously maintained and move-in ready, the kitchen and interior finishes—including the cherry-toned cabinetry, granite countertops, and carpeted living areas—are dated and original to the construction, suggesting a need for cosmetic updates to meet modern luxury standards.
The property has a large lot size, which is more than 4 times of its living area. lot size in square feet = 3746160, living area = 4740.
Set on a massive 86-acre lot, this estate offers unparalleled privacy, private trails, and open meadows, a rare find that provides a true sanctuary within the Santa Cruz Mountains.
The home features soaring ceilings and expansive walls of glass specifically designed to capture breathtaking panoramic views of Monterey Bay and the surrounding mountain landscape.
Located high on Skyline Boulevard, the property requires a lengthy and winding drive to reach downtown Los Gatos and major Silicon Valley employment hubs.
Managing 86 acres of mountain terrain, including private trails and sculpted gardens, requires significant ongoing investment in landscaping, road upkeep, and wildfire mitigation.
An extraordinary architectural estate set on 86 +/- acres in the Santa Cruz Mountains, just minutes from downtown Los Gatos. Designed to capture sweeping panoramic views of Monterey Bay, the home features soaring ceilings, expansive walls of glass, and refined sight-lines that seamlessly integrate the indoors with the surrounding landscape. Rich hardwood floors and curated finishes define the interiors, offering five spacious bedrooms, three full baths, and two half baths. The primary suite is a private retreat with a fireplace, spa-caliber bath, and a generous walk-in closet. Built with exceptional craftsmanship and uncompromising attention to detail, this meticulously maintained home reflects enduring quality throughout. The grounds offer sculpted landscapes, rose gardens, open meadows, and private trails, complete with recreational amenities, creating a rare balance of luxury, scale, and mountain serenity. Served by award-winning Los Gatos Schools.
No exterior & parking available.
No sensitive facilities data found.
| Feature | Subject | Average Home |
|---|---|---|
| Beds | 5.0 | 4.0 |
| Baths | 5.0 | 3.0 |
| Square foot | 4,740 | 2,262 |
| Lot Size | 3,746,160 | 11,200 |
| Price | $3.15M | $2.86M |
| Price per sq ft | $664 | $1.3K |
| Built year | 2001 | 1964 |
| HOA | $0 | $175 |
| Days on market | 130 | 39 |
Jul 21, 2026
$3,149,000
$3,349,000
-6% Price Drop
Initial Listing
May 2, 2026
$3,349,000
$3,499,000
-4% Price Drop
Initial Listing
Mar 14, 2026
$3,499,000
Initial Listing
Sep 2, 2020
$2,325,000
Public Record
Jun 4, 2002
$1,625,000
Public Record
Jan 11, 2001
$275,000
Public Record
Jun 5, 1997
$233,500
Public Record