$2,499,900

5401 Greenside Drive, San Jose, CA 95127

4 beds |
4 baths |
2,524 sqft

Single-Family Home
Built in 1936
0.39acre lot
2 car garage
$990/sqft
Listed 20 hours ago

Property Description

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 bespoke moldings by Sr. Designer Stephanie Croce of JP Weaver Co. 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!

Listing Status:: Active
Date Added:: April 30, 2026
Data Last Updated:: May 1, 2026 at 12:17AM
Listing Office:: Infinite Real Estate : 408-272-1031
Listing Agent:: Lizzeth Flores : 408-649-1886
MLS ID:: ML82044086

General: Utility RoomWorkshop
Flooring: TileWood
A/C: Central AirWhole House Fan
Heating: Central
Fireplace: Gas StarterFireplace

Parking: Electric Vehicle Charging Station(s)Golf Cart GarageWorkshop in GarageParking spaces: 2

Roofing: Tile
General: 2

Originating MLS: CRMLS_MLSL
School District: Other
County: Santa Clara

Zoning: R1-2059935018
View: Golf CourseView

Water: Public
Sewer: Public Sewer

Source: CRMLS_MLSL

This listing courtesy of Lizzeth Flores , Infinite Real Estate

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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