21685 Olive Avenue, Cupertino, California 95014, Cupertino, 95014 - 3 bed, 1 bath
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Cupertino, California 95014
This Strategic Value-Add Residence is listed at $2,198,000, positioned near its $2,140,532 Fair Market Value. Despite a Dated Condition Rating, the property offers immense upside through its ADU and Expansion Potential on a deep 5,335 sqft lot. Its primary value driver is the Elite School District, providing access to Monta Vista High (10/10), Kennedy Middle (9/10), and Lincoln Elementary (8/10). Located in a prime Silicon Valley pocket with easy highway access, this home represents a stable long-term asset. It is an ideal match for Owner-Occupants prioritizing education or Value-Add Investors targeting high-demand Cupertino land.
Comparables within 1 miles sold in recently
| Address | Sold Price | Beds | Baths | Sq Ft | $/Sqft | Distance |
|---|---|---|---|---|---|---|
★ 21685 Olive Avenue Subject | $2,198,000* List Price | 3 | 1 | 1,015 | $2,109 | - |
A 10178 Orange Avenue Active | $2,588,000 List Price | 4 | 3 | 1,367 | $1,893 | 0.1 mi |
* Subject property listed price vs sold prices of comps.
Property is moderate renovation needed.
Built in 1944, this home is well-maintained but significantly dated. While the floors have been refreshed, the kitchen and bathroom feature cabinetry and fixtures that appear to be 20-30+ years old. The presence of a wall heater indicates older mechanical systems, and the property requires modernization to meet current market standards.
Middle School: John F. Kennedy Middle School (9/10). High School: Monta Vista High School (10/10).
The property is zoned for top-tier Cupertino schools, including Monta Vista High (10/10) and John F. Kennedy Middle (9/10), which are premier drivers for property value and long-term appreciation.
The deep lot and open backyard layout provide an excellent footprint for future home expansions or the addition of an ADU, offering significant value-add potential for the buyer.
At just 1,015 square feet with only one bathroom, the current living space is undersized for the price point and may require immediate renovation to meet modern family needs.
The property has undergone five price reductions totaling nearly $400,000 since its original listing, indicating a struggle to find market equilibrium despite the desirable neighborhood.
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.
No exterior & parking available.
Grades K-5 • 0.3 mi
Grades K-5 • 0.8 mi
Grades 6-8 • 0.5 mi
No sensitive facilities data found.
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 3.0 | 4.0 | 38% |
| Baths | 1.0 | 3.0 | 9% |
| Square foot | 1,015 | 2,177 | 2% |
| Lot Size | 5,335 | 7,500 | 11% |
| Price | $2.20M | $3.40M | 4% |
| Price per sq ft | $2.2K | $1.5K | 85% |
| Built year | 1944 | 1969 | 5% |
| HOA | $0 | $0 | 50% |
| Days on market | 244 | 99 | 93% |
Feb 23, 2026
$2,198,000
$2,298,000
-4% Price Drop
Initial Listing
Jan 23, 2026
$2,298,000
$2,398,000
-4% Price Drop
Initial Listing
Nov 21, 2025
$2,398,000
$2,498,000
-4% Price Drop
Initial Listing
Oct 11, 2025
$2,498,000
$2,588,000
-3% Price Drop
Initial Listing
Aug 21, 2025
$2,588,000
Initial Listing