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5401 Greenside DriveSan Jose, CA 95127

Single Family · 4 Beds · 4 Full Baths · 2,524 Sq. ft. | 0.39 Acres
$2,499,900 Active

5401 Greenside Drive Overview

Time on Site:
60 days
Visits:
0

Rare offering in the prestigious Hillcrest community. Iconic 1930s Spanish estate exudes timeless elegance & elevated California living. Perfectly positioned along the 16th hole of the San Jose Country Club. Property delivers unmatched resort-style living. Rich in architectural significance. Home showcases original artist hand-painted grand living room wood beams, walls & ceilings. Meticulously maintained hardwood floors, antique fixtures & statement fireplace adorned with rare, locally hand crafted 100-yr-old tile also featured in bathrooms. Chefs kitchen beautifully appointed with custom cabinetry & marble countertops, while a main-level bedroom highlights custom bespoke moldings. Upstairs, refined living continues with 2 guest beds, spacious primary suite with dual closets & multiple balconies including a stunning terrace overlooking the fairway. Set on an expansive 17,136 sq ft lot, the grounds are designed for grand entertaining. Featuring mature fruit trees, garden beds, pizza oven, BBQ area, basketball court, multiple lounge spaces, room for a pool & direct golf cart access. Detached 2-car garage with adjacent ADU offers ultimate flexibility. Oversized driveway, RV/boat parking & EV chargers. Moments to SJCC, Alum Rock Park & more!

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5401 Greenside Drive Facts & Features

  • Type Single Family
  • Sq. ft. 2,524
  • Price/Sq.ft. $990
  • Lot 0.39 Acres

Details

General

Association/HOA

  • Association: No

School Information

  • School District: Other

Building Information

  • New Construction: No
  • Year Built: 1936

Location/Region

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

General Information

  • Parcel Number: 59935018
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Special Listing Conditions: Standard
  • Zoning: R1-20

Interior

Parking Information

  • Garage Spaces: 2.0
  • Garage: Yes

Beds/Baths

  • Bathrooms Full: 4
  • Bathrooms Total: 4
  • Bedrooms Total: 4

General Information

  • Basement: Yes
  • Common Walls: No Common Walls
  • Fireplace Features: Gas Starter
  • Fireplace: Yes
  • Flooring: Tile,Wood
  • Interior Features: Utility Room,Workshop
  • Living Area: 2524.0
  • Living Area Source: Other
  • Stories Total: 2

Exterior

Parking Information

  • Parking Features: Electric Vehicle Charging Station(s),Golf Cart Garage,Workshop in Garage
  • Parking Total: 2.0

Lot Information

  • Lot Features: Level
  • Lot Size Acres: 0.3934
  • Lot Size Area: 17136.0
  • Lot Size Source: Assessor
  • Lot Size Square Feet: 17136.0
  • Lot Size Units: Square Feet
  • Water Source: Public

Waterfront/View

    Building Exterior/Construction

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

    General Information

    • Sewer: Public Sewer

    5401 Greenside Drive Neighborhood

    Community

    95127 (SAN JOSE) Demographics

    37
    Median Age
    4,864
    Population Density (per sq. mile)
    32%
    College Educated
    $104,518
    Estimated Median Income
    10,542
    Estimated Total Home Owners
    5,245
    Estimated Total Renters
    67% / 33%
    Estimated Owner / Renter Divide
    4
    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.

    5401 Greenside Drive Monthly Cost

    $
    $ %
    %
    $
    $
    * 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.

    5401 Greenside Drive Market Data

    Based on the last 30 days in this zip code

    $1,243,580
    Average List Price
    $750
    Average Price per Square Foot
    17
    Properties Sold
    84
    Average Days on Market
    192
    Properties for Sale
    Calculations provided by Reliance Network

    5401 Greenside Drive History

    Date Event Value Agent
    6/24/2026Source: bridgeMLS Status Change
    Pending
    6/24/2026Source: MLSListings Status Change
    Pending (Do Not Show)
    4/30/2026Source: bridgeMLS Added to Database
    April 30, 2026
    4/30/2026Source: CRMLS Added to Database
    April 30, 2026
    4/22/2026Source: MLSListings Added to Database
    April 22, 2026
    Listing provided courtesy of Infinite Real EstateLizzeth Flores- MLS# ML82044086MLS ProviderContact Information: 408-272-1031