18516 Skyline Boulevard Los Gatos, CA $ 5,000,000
18516 Skyline Boulevard
$ 5,000,000
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18516 Skyline Boulevard

Los Gatos, CA, 95033
$ 5,000,000
Bedrooms2 Baths2.0 Sq 2,424

Monthly Estimate*

$ 30,786

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Single Family Home for sale in Los Gatos, CA

for $5,000,000 with 2 bedrooms and 2 full baths. This 2,424 square foot home was built in 1951 on a lot size of 19.9954.

Set across approximately 30.9 gently rolling acres at approximately 2,400 feet in elevation within the prestigious Santa Cruz Mountains AVA, Ascona Vineyards is a distinguished wine country estate that seamlessly blends agricultural functionality with timeless architectural elegance. Sweeping vineyard and countryside views frame approximately 16 acres of organically farmed vines planted with a curated collection of premium grape varietals, presenting a rare opportunity for boutique wine production, lifestyle ownership, or long-term legacy investment. At the heart of the estate, the Tuscany Revival farmhouse designed by renowned Santa Barbara architect Thomas Bollay evokes the warmth and character of a refined European vineyard retreat. Thoughtfully positioned to capture the surrounding natural beauty and tranquil setting, the residence features luxurious finishes, inviting living spaces, and an effortless connection to the landscape. Designed for both private enjoyment and commercial vineyard operations, the property is fully fenced and extensively improved with a professionally designed winery facility, utility and storage buildings, and infrastructure supporting ongoing production and future expansion.

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Single Family Active

Price

$ 5,000,000

Bedrooms

2

Full Bath

2

Property Type

Single Family

Taxes

$ 0

Style

Detached

Lot Size

19.9954

Year Built

1951

Town/City

Los Gatos

County/Region

Santa Clara

MLS | Web ID

ML82050479

Features
General
Living Area 2424
Heating Forced Air
Cooling Central Air
Roof Tile
Zoning HS-S
Garage Spaces 1
Year Built 1951
Stories Count 1
Levels One Story
Property Subtype Detached
County Santa Clara
Property Type Residential
HOA false
Garage Y/N true
Full Baths 2
Status Active
City Los Gatos
High School District Los Gatos-Saratoga Joint Union High
MLS Area Listing
Lot Size Square Feet 871000
Standard Status Active
Elementary School District Lakeside Joint School District
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Interior
Interior Amenities Formal Dining Room
Fireplace Features Wood Burning
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Total Bedrooms 2
Total Baths 2
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Exterior
Parking Features Parking Lot
Lot Features Horses Possible
Lot Size Area 19.9954
Foundation Details Slab
Building Area Total 2424
Lot Size Acres 19.9954
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* Excluded Features
List By
Billy Caruso

Listing Agent

Kw Bay Area Estates

Broker

billycrealty@gmail.com

Email

Affordability Calculator

$30,786
Per Month
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Monthly Principal & Interest
$30,786
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Monthly Home Insurance
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
6/10/2026$5,000,000 Listed Price

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18516 Skyline Boulevard, Los Gatos, CA, 95033 is a Single Family Home for sale at $5,000,000 with 2,424 sqft and a lot size of 19.9954. 18516 Skyline Boulevard has 2 bedrooms, 2.0 baths, and was built in 1951. The property's zip code is 95033 which is in Los Gatos, CA