21685 Olive Avenue, Cupertino, California 95014, Cupertino, 95014 - 3 bed, 1 bath
21685 Olive Avenue
Cupertino, California 95014
Property Price
SUMMARY
Analysis of 21685 Olive Avenue, Cupertino, California 95014 reveals a Fairly Priced Property with a current list price of $2,198,000 aligned with the estimated $2,170,243 Fair Market Value. This represents a stable investment opportunity at market rate. 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.
Estimated Market Value
Condition Analysis
OVERALL CONDITION SCORE
Property is moderate renovation needed.
Built in 1944, this home is well-maintained but reflects its age with outdated features. While the hardwood floors are in good condition and the interior is clean, the kitchen and single bathroom are dated, featuring older white appliances and basic cabinetry. The property lacks recent major renovations to its core systems and layout, fitting the criteria for a functional but aged home maintained through regular upkeep.
PROSSTRENGTHS & OPPORTUNITIES
- Great Schools
Middle School: John F. Kennedy Middle School (9/10). High School: Monta Vista High School (10/10).
- Elite School District
The property is zoned for top-tier, award-winning schools including Monta Vista High (Rating 10) and JFK Middle, all located within a half-mile, which significantly bolsters long-term investment value.
- Expansion and ADU Potential
The deep lot and open backyard layout provide a rare and valuable opportunity for future home expansions or the construction of an Accessory Dwelling Unit (ADU) in a high-demand area.
CONSRISKS & DEFICIENCIES
- Restrictive Interior Layout
At just 1,015 square feet with only one bathroom serving three bedrooms, the current living space is undersized and may require a significant reconfiguration to meet modern family needs.
- Aging Infrastructure
Built in 1944, the home's vintage construction may necessitate costly updates to core systems like electrical, plumbing, and insulation to align with contemporary building standards.
About 21685 Olive Avenue
Move in and enjoy this well maintained single-story home on a deep lot and quiet street with Abraham Lincoln Elementary, John F. Kennedy Middle and Monta Vista High. All 3 bedrooms are spacious. Inviting casual dining and living room off the kitchen. Desirable single-story layout. Gleaming floors. Oversized driveway. Large, gorgeous trees near property boundary perimeter. Peaceful & low maintenance backyard. Wonderfully open backyard for future home expansions or ADU. Easy access to Blackberry Farm, Mcclellan Ranch Preserve, all 3 spectacular Cupertino schools and shops. Neighborhood roads to many technology company campuses. Spectacular commute location with easy access to Highways 280 & 85. Award-winning Cupertino schools: Monta Vista High, John F. Kennedy Middle & Abraham Lincoln Elementary.
Property Details
Public Facts
- Property Type
- Single Family Residence
- Year Built
- 1944
- Lot Size
- 5,335 Sq. Ft.
Interior
- Total Bedrooms
- 3
- Total Bathrooms
- 1 (1 Full, 0 Half)
Exterior & Parking
No exterior & parking available.
Utilities & Misc
- HOA Fee
- $0 / Month
Neighborhood Insights
Cupertino Unified Schools
Abraham Lincoln Elementary School
Grades K-5 • 0.3 mi
Stevens Creek Elementary School
Grades K-5 • 0.8 mi
John F. Kennedy Middle School
Grades 6-8 • 0.5 mi
Sensitive Facilities
No sensitive facilities data found.
Neighborhood Comparison
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 3.0 | 4.0 | 40% |
| Baths | 1.0 | 3.0 | 7% |
| Square foot | 1,015 | 2,110 | 2% |
| Lot Size | 5,335 | 7,490 | 13% |
| Price | $2.20M | $3.39M | 4% |
| Price per sq ft | $2.2K | $1.5K | 87% |
| Built year | 1944 | 1968 | 4% |
| HOA | $0 | $0 | 50% |
| Days on market | 198 | 137 | 80% |
Pricing History
Listed for Sale
Feb 23, 2026
$2,198,000
$2,298,000
-4% Price Drop
Initial Listing
Price Change
Jan 23, 2026
$2,298,000
$2,398,000
-4% Price Drop
Initial Listing
Price Change
Nov 21, 2025
$2,398,000
$2,498,000
-4% Price Drop
Initial Listing
Price Change
Oct 11, 2025
$2,498,000
$2,588,000
-3% Price Drop
Initial Listing
Price Change
Aug 21, 2025
$2,588,000
Initial Listing