5401 Greenside Drive, SAN JOSE, CA 95127 (MLS # ML82044086)
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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!
| LAST UPDATED | 4/30/2026 | YEAR BUILT | 1936 |
|---|---|---|---|
| GARAGE SPACES | 2.0 | COUNTY | Santa Clara |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| ADDITIONAL DETAILS | |
| AIR | Attic Fan, Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| BASEMENT | Crawl Space, Finished, Yes |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Central, Forced Air |
| INTERIOR | Eat-in Kitchen, High Ceilings, Kitchen Island, Pantry |
| LOT | 0 |
| LOT DESCRIPTION | Level, Views |
| LOT DIMENSIONS | 17136.00 |
| PARKING | Workshop in Garage, Detached, Electric Vehicle Charging Station(s), Golf Cart Garage, Oversized, Tandem |
| POOL DESCRIPTION | None |
| SEWER | Public Sewer |
| STORIES | 2 |
| VIEW | Yes |
| VIEW DESCRIPTION | Golf Course |
| WATER | Public |
| ZONING | R1-20 |
The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the MLSListings™ MLS system. All real estate listings in the MLSListings MLS system are marked with the MLSListings 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 MLSListings MLS as of 5/7/26 1:24 AM PDT. 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. Properties may or may not be listed by the office/agent presenting the information.
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This IDX solution is (c) Diverse Solutions 2026.
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