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!
Property Details
Price:
$2,499,900
MLS #:
ML82044086
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
699notdefined
Listed Date:
Apr 30, 2026
Finished Sq Ft:
2,524
Lot Size:
17,136 sqft / 0.39 acres (approx)
Year Built:
1936
See this Listing
Schools
School District:
Other
Interior
Bathrooms
4 Full Bathrooms
Cooling
CA, WHF
Flooring
TILE, WOOD
Heating
CF
Exterior
Common Walls
NCW
Garage Spaces
2
Parking Spots
2
Parking Total
2
Roof
TLE
View
GC
Financial
Map
Community
- Address5401 Greenside DR San Jose CA
- CitySan Jose
- CountySanta Clara
- Zip Code95127
Subdivisions in San Jose
Market Summary
Current real estate data for Single Family in San Jose as of May 06, 2026
1,529
Single Family Listed
51
Avg DOM
919
Avg $ / SqFt
$1,620,008
Avg List Price
Property Summary
- 5401 Greenside DR San Jose CA is a Single Family for sale in San Jose, CA, 95127. It is listed for $2,499,900 and features 4 beds, 4 baths, and has approximately 2,524 square feet of living space, and was originally constructed in 1936. The current price per square foot is $990. The average price per square foot for Single Family listings in San Jose is $919. The average listing price for Single Family in San Jose is $1,620,008.
Similar Listings Nearby
Courtesy of Infinite Real Estate. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the California Regional Multiple Listing Service. Detailed information about real estate listings held by brokerage firms other than include the name of the listing broker. Neither the listing company nor shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. California Regional Multiple Listing Service. All rights reserved.5401 Greenside DR
San Jose, CA