18516 Skyline Boulevard , Los Gatos, CA 95033
$5,000,000
Est. Payment: $26,703.50/mo
2 Bed
2 Bath
2424 Sqft
Status: Pending | Days on site: 14
Get Pre-Qualified
ML89184 - ML5103219,ML5079234
By proceeding and clicking the sign up button, you consent to receive calls and texts (SMS/MMS) including marketing and promotional communications, from Chris Heller, its affiliates, and agents or vendors acting on their behalf. These communications may be delivered using an automatic telephone dialing system or by using an artificial or prerecorded voice. Message and data rates may apply. To opt out of text messages, reply STOP. Your consent is not required as a condition of any purchase. By continuing, you also agree to our Terms of Use and Privacy Policy.

House Description

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. **Accepting BackUp offers** At the heart of the estate, the Tuscany Revival farmhouse 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.

Highlights

Listed by Billy Caruso , 408-304-4872 and Danielle Davenport , 408-888-7794 KW Bay Area Estates , (408) 560-9000. CRMLS/Multi-Regional MLS mls logo

Property Type

Farm/Ranch

Lot/Acreage
20

Year Built

1951

County

Santa Clara

Area

699 - Not Defined

School District

Other

Listing ID

ML82050479

Questions about this listing?

Contact Agent

Interior Features

Bedrooms and Bathrooms
  • Bedrooms:2
  • Bathrooms:2
  • Full Bathrooms:2
Air Cond:Central Air
Fireplaces:Wood Burning
Water:Agricultural Well,Well

Exterior Features

Lot:No Land Lease
Garage Capacity:1
Zoning:HS-SR
Roof:Tile
Sewer:Septic Tank
Principal Interest
$26,703
Taxes
$3,188

Home Price

$5,000,000

Loan Details

30 yrs
7.034%

Down Payment

20%
$1,000,000
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$26,703.50

Principal

Taxes

Principal Taxes HOA Total
Monthly $26,703.50 $3,187.50 $0.00 $29,891.00
Yearly $320,441.99 $38,250.00 $0.00 $358,691.99
Total $9,613,259.83 $1,147,500.00 $0.00 $10,760,759.83

Today's Rates

30 Year

7.03%

20 Year

7.02%

15 Year

6.38%

Never Miss a Property

Be the first to know when a property hits the market.

Current Listings

Last 30 Days
N/A
Sep 2026

Average Price

All Price Ranges
N/A
Sep 2026

Average Days on Market

All Price Ranges
N/A
Sep 2026
Market insight data is pulled from the same city as the listing being viewed (Los Gatos, CA).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

Based on information from California Regional Multiple Listing Service, Inc. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. All properties are subject to prior sale, change or withdrawal.

IDX service by Blueroof 360

Data last updated: 2026-09-23T05:04:10.000Z

© 2026 CRMLS/Multi-Regional MLS

MLS Logo - CRMLS/Multi-Regional MLS