$2,499,900

beds

baths

2,524

square ft

5401 Greenside Drive

San Jose, California 95127

Active / MLS #82044086 / Single Family / San Jose

Listing information updated 6/8/2026 at 6:08am

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!

Full Features

Basement:

Finished

Beds Above Grade:

Cooling System:

CentralForcedAir, WholeHouseFan

Heating System:

Central Forced Air

Appliances:

Oven Built In

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

90 Years

Roof Type:

Tile

Parking Type:

Detached, Electric Car Hookup, Golf Cart, Roomfor Oversized Vehicle, Tandem Parking

Parking Spaces:

Garage:

Garage - 2 Car(s)

Square Feet:

2,524

Lot Size:

17136 SquareFeet

Internal Features:

High Ceiling

Taxes & Assessments

Tax Amount:

N/A

Tax Year:

N/A

Location

Zip Code:

95127

City:

San Jose

County:

Santa Clara

Schools

School District(s):

Alum Rock Union Elementary, East Side Union High

Elementary School:

N/A

Middle School:

N/A

High School:

N/A

Basement:

Finished

Beds Above Grade:

Cooling System:

CentralForcedAir, WholeHouseFan

Heating System:

Central Forced Air

Appliances:

Oven Built In

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

90 Years

Roof Type:

Tile

Parking Type:

Detached, Electric Car Hookup, Golf Cart, Roomfor Oversized Vehicle, Tandem Parking

Parking Spaces:

Garage:

Garage - 2 Car(s)

Square Feet:

2,524

Lot Size:

17136 SquareFeet

Internal Features:

High Ceiling

Tax Amount:

N/A

Tax Year:

N/A

Zip Code:

95127

City:

San Jose

County:

Santa Clara

School District(s):

Alum Rock Union Elementary, East Side Union High

Elementary School:

N/A

Middle School:

N/A

High School:

N/A

Listing Agent: Lizzeth Flores

Listing Office: Infinite Real Estate

Disclaimer: The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListings MLS system. Real estate listings held by brokerage firms other than Christie’s International Real Estate Sereno are marked with the Internet Data Exchange icon (a stylized house inside a circle) and detailed information about them includes the names of the listing brokers and listing agents. Based on information from the MLSListings MLS as of 6/8/2026 at 6:08am (date the MLS data was obtained). All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy.