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$2,499,900

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 2,524 Sq. Ft.
  • 2 Car Garage
  • Updated 6 days ago

Next open house:

Open House: 1:00 PM - 4:00 PM

Saturday 5/9 1:00 PM - 4:00 PM

5401 Greenside Dr,San Jose, CA 95127

5401 Greenside DrSan JoseCA95127

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Join us at 5401 Greenside Dr on:

  • Open House: 1:00 PM - 4:00 PM

    Sunday 5/10 1:00 PM - 4:00 PM

    5401 Greenside Dr,San Jose, CA 95127
    5401 Greenside DrSan JoseCA95127
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See This Home
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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 custome 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!

Full Property Details for 5401 Greenside Dr

General

  • Price: $2,499,900
  • Status: Active
  • Type: Single Family
  • Source: RE_Infolink
  • MLS ID: ML82044086
  • Updated: 5/1/2026
  • Added to Site: 7 day(s) ago

Interior

  • Rooms/Areas: Finished Basement, Bonus / Hobby Room, Den / Study / Office, Laundry Room, Mud Room, Office Area, Recreation Room, Storage, Utility Room, Workshop
  • Interior Features: High Ceiling
  • Fireplace(s): Gas Starter
  • Flooring: Hardwood, Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Family Room: Kitchen / Family Room Combo
  • Kitchen: Marble Countertop, Island, Built-In Oven, Pantry
  • Laundry: In Utility Room

Additional Information

  • Extras: Not Applicable

Parking

  • Garage Spaces: 2
  • Parking Features: Detached Garage, Electric Car Hookup, Golf Cart, Room for Oversized Vehicle, Tandem Parking, Workshop in Garage

Location

  • Area: Berryessa
  • County: Santa Clara
  • Cross Streets: Crest Drive

Heating & Cooling

  • Cooling Type: Central AC, Whole House / Attic Fan
  • Heating Type: Central Air (Forced Air)

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Public Utilities

Structural Information

  • Construction: Detached
  • Foundation: Crawlspace
  • Roof: Tile
  • Square Feet: 2,524
  • Year Built: 1936

Lot Features

  • Property View: Golf Course
  • Minimum Lot Size: 17136
  • Lot Size (Sq. Ft.): 17,136
  • Zoning: R1-20
  • Lot Description: Level, Views

Listed by Infinite Real Estate, Lizzeth Flores and Infinite Real Estate, Eduardo Huerta

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Listing agents

— 5401 Greenside Dr —

  • Lizzeth Flores

    Infinite Real Estate

  • Eduardo Huerta

    Infinite Real Estate

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5401 Greenside Dr

School Districts:East Side Union High School District, Alum Rock Union Elementary School District
NameGradesDistance
Linda Vista Elementary School
100 Kirk Avenue, San Jose, CA 95127
K-50.6 mi
William Sheppard Middle School
480 Rough and Ready Road, San Jose, CA 95133
6-81.4 mi
James Lick High School
57 North White Road, San Jose, CA 95127
9-122.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5401 Greenside Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/30/2026
Listed
$2,499,900
459.26%
MLS
5/23/1996
Sold
$447,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5401 Greenside Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,628
2%
$742,562
2%
2024
$10,404
2%
$728,003
2%
2023
$10,197
3%
$713,730
2%
2022
$9,937
3%
$699,736
2%
2021
$9,608
1%
$686,017
1%
2020
$9,475
3%
$678,984
2%
2019
$9,231
1%
$665,672
2%
2018
$9,182
-1%
$652,621
2%
2017
$9,241
6%
$639,826
2%
2016
$8,722
—
$627,281
2%
2015
$8,738
2%
$617,859
2%
2014
$8,528
1%
$605,757
—
2013
$8,456
—
$603,020
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Infinite Real Estate, Lizzeth Flores and Infinite Real Estate, Eduardo Huerta

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5401 Greenside Dr, San Jose, CA 95127 (MLS# ML82044086) is a Single Family property with 4 bedrooms and 4 full bathrooms. 5401 Greenside Dr is currently listed for $2,499,900 and was received on April 30, 2026. Want to learn more about 5401 Greenside Dr? Do you have questions about finding other Single Family real estate for sale in San Jose? You can browse all San Jose real estate or contact a Coldwell Banker agent to request more information.

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