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Under contract
  • $5,000,000

    18516 Skyline Blvd, Los Gatos, CA 95033

    2beds
    2,424sqft
    : 
    $34,207/mo
    Get pre-qualified
    Farm, Residential
    Built in 1951
    20 Acres Lot
    $-- Zestimate®
    $2,063/sqft
    $-- HOA

    What's special

    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.
    50 days
    |
    77
    |
    4
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    Zillow last checked:

    Listing updated:

    Listed by:

    Billy Caruso 02224726 408-304-4872,

    KW Bay Area Estates 408-560-9000,

    Danielle Davenport 00954910 408-888-7794,

    KW Bay Area Estates

    Source: MLSListings Inc,MLS#: ML82050479MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 2
      • Full bathrooms: 2
      Dining room
      • Features: FormalDiningRoom
      Family room
      • Features: KitchenFamilyRoomCombo
      Heating
      • Forced Air
      Cooling
      • Central Air
      Features
      • Fireplace features: Wood Burning
      Interior area
      • Total structure area: 2,424
      • Total interior livable area: 2,424 sqft

      Property

      Parking
      • Total spaces: 1
      • Parking features: Parking Area
      • Garage spaces: 1
      Features
      • Stories: 1
      Lot
      • Size: 20 Acres
      Details
      • Parcel number: 54420005
      • Zoning: HS-SR
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Farm, Residential
      Materials
      • Foundation: Slab
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 1951

      Utilities & green energy

      • Gas: PropaneOnSite
      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Propane

      Community & HOA

      Location
      • Region: Los Gatos

      Financial & listing details

      • Price per square foot: $2,063/sqft
      • Tax assessed value: $981,901
      • Annual tax amount: $11,711
      • Date on market: 6/10/2026
      • Listing agreement: ExclusiveRightToSell

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/24/2026Contingent$5,000,000$2,063/sqft
        Source: MLSListings Inc #ML82050479 Report a problem
        6/10/2026Listed for sale$5,000,000+2%$2,063/sqft
        Source: MLSListings Inc #ML82050479 Report a problem
        7/24/2015Listing removed$4,899,999$2,021/sqft
        Source: Intero Real Estate Services #81453856 Report a problem
        3/1/2015Listed for sale$4,899,999-12.5%$2,021/sqft
        Source: Intero Real Estate Services Report a problem
        1/3/2015Listing removed$5,600,000$2,310/sqft
        Source: Artisan Sotheby's International Realty #06132014 Report a problem
        6/14/2014Listed for sale$5,600,000+700%$2,310/sqft
        Source: Artisan Sotheby's International Realty #06132014 Report a problem
        7/31/1995Sold$700,000$289/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$11,711 -1.1%$981,901 -0.8%
        2024$11,843 -1.2%$989,490 -1.6%
        2023$11,989 -2.7%$1,005,344 +0.4%
        2022$12,317 +23.9%$1,001,137 +27.1%
        2021$9,940 +4.4%$787,639 +3.7%
        2020$9,518 $759,493 +2%
        2019$9,518 +2.7%$744,602 +2%
        2018$9,266 $730,003 +2%
        2017$9,266 +0.2%$715,690 +2%
        2016$9,244 +8.3%$701,658 +1.5%
        2015$8,533 +1.8%$691,120 +2%
        2014$8,385 $677,583 +0.5%
        2013-- $674,522 +2%
        2012-- $661,297 +2%
        2011-- $648,332 +0.8%
        2010-- $643,488 -0.2%
        2009-- $645,018 +2%
        2008-- $632,371 +2%
        2007-- $619,973 +2%
        2006-- $607,818 +2%
        2005-- $595,901 +2%
        2004-- $584,217 +1.9%
        2003-- $573,510 +2%
        2002-- $562,266 +2%
        2001-- $551,242
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 95033

        Getting around

        0 / 100
        Car-Dependent
        3 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • District: LakesideJointSchoolDistrict

        Source: MLSListings Inc. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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