5401 Greenside Drive, San Jose, California 95127, San Jose, 95127 - 4 bed, 4 bath
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San Jose, California 95127
This Iconic 1930s Spanish Estate is a High-Potential Investment Opportunity, listed at $2,499,900—positioned well above the $2,106,016 Fair Market Value. While priced at a premium, the property offers a Condition Rating of 3, featuring a Chef's Kitchen, Detached ADU, and Golf Course Views. The expansive 17,136 sq ft lot provides significant utility for grand entertaining. Despite lower-rated local schools, the architectural significance and resort-style amenities make this a unique acquisition for Luxury Homeowners or Discerning Investors seeking a trophy property with long-term appreciation potential.
Comparables within 1 miles sold in recently
| Address | Sold Price | Beds | Baths | Sq Ft | $/Sqft | Distance |
|---|---|---|---|---|---|---|
★ 5401 Greenside Drive Subject | $2,499,900* List Price | 4 | 4 | 2,524 | $834 | - |
A 282 Bayview Avenue Sold | $2,101,000 | 4 | 3 | 2,464 | $853 | 0.4 mi |
B 309 Crest Drive Sold | $2,250,000 | 4 | 3 | 3,201 | $703 | 0.2 mi |
* Subject property listed price vs sold prices of comps.
Property is move-in ready.
Despite the 1936 build date, the property is meticulously maintained with significant updates including a chef's kitchen with marble countertops and custom cabinetry. The presence of EV chargers and a detached ADU indicates updated systems and functional modern living, while the historic architectural elements like hand-painted beams and hardwood floors are in move-in ready condition.
The property has a large lot size, which is more than 4 times of its living area. lot size in square feet = 17136, living area = 2524.
This iconic 1930s Spanish estate features rare hand-painted wood beams, 100-year-old handcrafted tiles, and antique fixtures, offering a level of historical charm and craftsmanship that is difficult to replicate in modern builds.
Perfectly positioned along the 16th hole of the San Jose Country Club, the property offers stunning fairway views, direct golf cart access, and an expansive 17,136 sq ft lot designed for resort-style entertaining.
Living area discrepancy between mls listing and other public or private record. mls listing living area = 2524, other record living area = 2468. Bedroom count discrepancy between mls listing and other public or private record. mls listing bedroom count = 4, other record bedroom count = 3.
The assigned public middle and high schools carry lower ratings (3/10 and 4/10), which may be a concern for families prioritizing high-performance public education.
Built in 1936, the home's age and specialized architectural details, such as original hand-painted surfaces and antique fixtures, may necessitate higher-than-average maintenance costs and specialized care compared to newer constructions.
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!
No exterior & parking available.
Grades K-5 • 0.7 mi
Grades 6-8 • 1.1 mi
Grades 9-12 • 1.3 mi
No sensitive facilities data found.
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 4.0 | 3.0 | 66% |
| Baths | 4.0 | 2.0 | 94% |
| Square foot | 2,524 | 1,324 | 91% |
| Lot Size | 17,136 | 6,588 | 92% |
| Price | $2.50M | $1.15M | 98% |
| Price per sq ft | $990 | $780 | 80% |
| Built year | 1936 | 1955 | 9% |
| HOA | $0 | $0 | 50% |
| Days on market | 37 | 113 | 3% |
Apr 30, 2026
$2,499,900
Initial Listing
May 23, 1996
$447,000
Public Record