21075 Greenleaf Drive, Cupertino, California 95014, Cupertino, 95014 - 8 bed, 5 bath
Loading property details...
Cupertino, California 95014
Analysis of 21075 Greenleaf Drive, Cupertino, California 95014 is currently available with a list price of $3,880,000. The property maintains a Fair Condition Rating (50/100), suggesting the property is in acceptable condition with potential for value enhancement through selective updates and improvements. Located in a high-demand neighborhood within the Cupertino Unified School District, this asset is categorized as a low-risk, high-reward acquisition suitable for both Buy-and-Hold Investors and Owner-Occupants willing to undertake light renovation work.
Property is moderate renovation needed.
Originally built in 1950, the property shows signs of a major renovation likely performed 20-25 years ago. While the home is well-maintained and move-in ready, it features dated elements such as parquet wood flooring, older wall-mounted heaters alongside newer mini-splits, and basic oak cabinetry with white appliances in the ADU. The kitchen and systems are functional but dated, fitting the criteria for a property needing minor updates to meet modern luxury standards.
High School: Monta Vista High School (10/10).
The property features a rare, fully detached 3-bedroom, 2-bathroom ADU, providing exceptional flexibility for significant rental income or multi-generational living.
Zoned for top-tier Cupertino schools, including Monta Vista High (10/10), Lawson Middle, and Garden Gate Elementary, ensuring long-term property value and appeal to families.
Living area discrepancy between mls listing and other public or private record. mls listing living area = 4132, other record living area = 3268. Bedroom count discrepancy between mls listing and other public or private record. mls listing bedroom count = 8, other record bedroom count = 5.
Originally constructed in 1950, the property may require more intensive maintenance or infrastructure updates compared to newer builds in the surrounding area.
The 8-bedroom total layout across two units is highly specialized, which may limit the buyer pool to specific large families or investors rather than traditional single-family buyers.
Stunning property in the most desirable Cupertino location! Main house offers 5B3B with 3,268 sqt, plus a fully detached 3B2B ADU with 864 sqt, for a total of 4,132 sqt living space on an expansive 10,626 sqt lot! Bright, open interior with breathtaking grand high ceilings and multiple living areas including formal living, family room, and dining, with abundant natural light, and elegant architectural details. Functional layout with 3 bedrooms on the first floor, ideal for multi-generational living or flexible use. Huge master bedroom suite on upper level, plus a bonus room perfect for office or gym! Large, private backyard with mature landscaping and gazebo great for entertaining or everyday enjoyment. Detached ADU provides exceptional versatility: perfect for rental income or extended family living, adding significant long-term value! Top Cupertino schools: Monta Vista High, Lawson Middle and Garden Gate Elementary. Easy access to Highways 85 and 280, Apple Park, Google, Meta, Nvidia and so many more! Close proximity to Target, Whole Foods, Memorial Park, YMCA, Main Street Cupertino and all the daily conveniences needed! Generous space, a large lot, a detached ADU, top-rated schools, a prime location, and outstanding long-term potential all in one!
No exterior & parking available.
Grades K-5 • 0.2 mi
Grades 6-8 • 0.9 mi
Grades 9-12 • 1.3 mi
No sensitive facilities data found.
| Feature | Subject | Average Home |
|---|---|---|
| Beds | 8.0 | 4.0 |
| Baths | 5.0 | 3.0 |
| Square foot | 4,132 | 2,288 |
| Lot Size | 10,626 | 6,830 |
| Price | $3.88M | $3.54M |
| Price per sq ft | $939 | $1.6K |
| Built year | 1950 | 1958 |
| HOA | $0 | $0 |
| Days on market | 13 | 31 |
Jul 9, 2026
$3,880,000
Initial Listing
Apr 17, 2015
$2,200,000
Public Record