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5401 Greenside Drive, 
San Jose, CA 95127

$2,499,900

4

Beds

4

Baths

2,524

Sq Ft

Single Family

Active

Listed by

Lizzeth Flores

, 

Eduardo Huerta

Infinite Real Estate

408-272-1031

Last updated:

May 24, 2026, 04:33 PM

MLS#

ML82044086

Source:

CRMLS

About This Home

5401 Greenside Drive

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!

Home Facts

Single Family

4 Baths

4 Bedrooms

Built in 1936

Price Summary

2,499,900

$990 per Sq. Ft.

MLS #:

ML82044086

Last Updated:

May 24, 2026, 04:33 PM

Added:

24 day(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

4

Interior

Living Area:

2,524 Sq. Ft.

Structure

Structure

Building Area:

2,524 Sq. Ft.

Year Built:

1936

Lot

Lot Size (Sq. Ft):

17,136

Finances & Disclosures

Finances

Price:

$2,499,900

Price per Sq. Ft:

$990 per Sq. Ft.

Source:CRMLS
The information being provided by California Regional MLS (Southern California) is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the California Regional MLS (Southern California). Coldwell Banker Gay Dales, Inc., Realtors is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Gay Dales, Inc., Realtors, a broker participant of California Regional MLS (Southern California). This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by California Regional MLS (Southern California) and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright 2021 California Regional MLS (Southern California). All rights reserved.

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Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.