18516 Skyline BoulevardLos Gatos, CA 95033

Single Family · 2 Beds · 2 Full Baths · 2,424 Sq. ft. | 20.00 Acres
$5,000,000 Active

18516 Skyline Boulevard Overview

Time on Site:
19 days
Visits:
0

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 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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18516 Skyline Boulevard Facts & Features

  • Type Single Family
  • Sq. ft. 2,424
  • Price/Sq.ft. $2,063
  • Lot 20.00 Acres

Details

General

Association/HOA

  • Association: No

School Information

  • School District: Other

Building Information

  • New Construction: No
  • Year Built: 1951

Location/Region

  • County Or Parish: Santa Clara
  • MLS Area Major: 699 - Not Defined
  • Postal City: LOS GATOS

General Information

  • Parcel Number: 54420005
  • Property Sub Type: Farm
  • Property Type: Residential
  • Special Listing Conditions: Standard
  • Zoning: HS-SR

Interior

Parking Information

  • Garage Spaces: 1.0
  • Garage: Yes

Beds/Baths

  • Bathrooms Full: 2
  • Bathrooms Total: 2
  • Bedrooms Total: 2

General Information

  • Fireplace Features: Wood Burning
  • Fireplace: Yes
  • Foundation Details: Slab
  • Living Area: 2424.0
  • Living Area Source: Assessor
  • Stories Total: 1

Exterior

Parking Information

  • Parking Total: 1.0

Lot Information

  • Lot Size Acres: 19.9954
  • Lot Size Area: 871000.0
  • Lot Size Source: Assessor
  • Lot Size Square Feet: 871000.0
  • Lot Size Units: Square Feet
  • Water Source: Agricultural Well,Well

Waterfront/View

  • View: No

Building Exterior/Construction

  • Attached Garage: No
  • Property Attached: No
  • Roof: Tile

General Information

  • Sewer: Septic Tank

18516 Skyline Boulevard Neighborhood

Community

95033 (Los Gatos) Demographics

47
Median Age
107
Population Density (per sq. mile)
72%
College Educated
$168,723
Estimated Median Income
3,020
Estimated Total Home Owners
757
Estimated Total Renters
80% / 20%
Estimated Owner / Renter Divide
3
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

18516 Skyline Boulevard Monthly Cost

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

18516 Skyline Boulevard Market Data

Based on the last 30 days in this zip code

$2,120,319
Average List Price
$778
Average Price per Square Foot
9
Properties Sold
119
Average Days on Market
237
Properties for Sale
Calculations provided by Reliance Network

18516 Skyline Boulevard History

Date Event Value Agent
6/24/2026Source: bridgeMLS Status Change
Pending
6/24/2026Source: MLSListings Status Change
Contingent
6/10/2026Source: CRMLS Added to Database
June 10, 2026
6/10/2026Source: bridgeMLS Added to Database
June 10, 2026
6/10/2026Source: MLSListings Added to Database
June 10, 2026
Listing provided courtesy of KW Bay Area EstatesBilly Caruso- MLS# ML82050479MLS ProviderContact Information: (408) 560-9000