Oak Valley Homes for Sale | Cupertino CA
Oak Valley is a residential neighborhood in western Cupertino near Homestead Road and the foothills, with a median sold price of $2,430,000, a median of 10 days on market, and a median sold price of $1,246 per square foot. Detached single-family sales span from 3-bedroom homes near $2,200,000 to 5-bedroom homes near $3,500,000. Oak Valley offers the most accessible price-per-square-foot entry point into western Cupertino's 95014 market, below Monta Vista ($1,572), Seven Springs ($1,516), and Rancho Rinconada ($1,760).
Oak Valley Cupertino
Oak Valley Market Data
- Median sold price: $2,430,000
- 3-bedroom median: $2,200,000 (3 sales)
- 4-bedroom median: $3,401,750 (3 sales)
- 5-bedroom median: $3,500,000 (2 sales)
- Median price per square foot: $1,246
- Median home size: approximately 1,883 square feet
- Median days on market: 10 days
- Detached single-family sale range: $1,000,000 – $3,750,000
- All property types sale range: $1,000,000 – $5,300,000
A note on how to read these figures. Oak Valley includes both detached single-family homes and attached units — 22330 Homestead Road is a multi-unit property that appears in the data at lower price points. Because attached units and smaller original homes pull the overall median below the bedroom-level medians, the $2,430,000 figure reflects the full mix of property types rather than the typical detached family home, which trades higher. Transaction volume is also low, so individual sales move these numbers more than they would in a larger neighborhood. Active listings currently range from $960,000 to $3,999,000.
The $1,246 median price per square foot is the lowest among western Cupertino neighborhoods in this analysis, which is the neighborhood's central advantage for buyers who want a foothill-adjacent western Cupertino location.
Where Is Oak Valley?
Oak Valley is located in western Cupertino near Homestead Road, with homes concentrated on streets including Homestead Road, Caroline Drive, Wallace Drive, Madera Drive, Hibiscus Drive, Lucky Oak Street, Mann Drive, and Barranca Drive. The neighborhood sits near the western edge of 95014, close to the Cupertino-Los Altos Hills boundary, with access to Stevens Creek Boulevard, Foothill Expressway, Interstate 280, and Highway 85.
Buyers comparing western Cupertino neighborhoods often evaluate Oak Valley alongside Monta Vista, Seven Springs, and Rancho Rinconada.
Why Buyers Choose Oak Valley
Oak Valley offers the most accessible price-per-square-foot entry point into western Cupertino’s 95014 market. Buyers who want a foothill-adjacent location and access to Cupertino Union and Fremont Union school districts without paying the premium attached to Monta Vista or Seven Springs consistently find Oak Valley worth evaluating. The neighborhood’s location near Homestead Road provides convenient access to Apple Park, De Anza Boulevard, and the broader Cupertino employment and retail corridor.
The trade-off is home size. At a median near 1,883 square feet, Oak Valley homes are smaller than Monta Vista (2,435 square feet), Seven Springs (2,256 square feet), and Rancho Rinconada (2,152 square feet). Buyers get a lower rate per square foot but less square footage, so those needing substantial interior space should weigh expansion potential and lot size carefully when comparing individual properties.
Homes and Architecture
Oak Valley homes span a range of sizes and configurations. The market includes compact 2 and 3-bedroom properties in the 1,200–1,600 square foot range on Homestead Road, Caroline Drive, and Wallace Drive, mid-size 4-bedroom homes around 1,400–2,400 square feet, and larger 4 and 5-bedroom properties exceeding 2,800 square feet on Mann Drive and Barranca Drive. The largest recent sale was a 4-bedroom home at 4,032 square feet on Barranca Drive. Most homes were built during Cupertino’s mid-century growth period and range from original ranch-style properties to remodeled and expanded residences.
Schools Serving Oak Valley
Oak Valley is served by Cupertino Union School District for elementary and middle school and Fremont Union High School District for high school. The neighborhood’s western Cupertino location commonly associates addresses with Monta Vista High School and Lincoln Elementary, though school assignments vary by individual parcel. Buyers should always verify current school assignments directly with the appropriate district before making an offer or relying on listing information.
For context on schools across the broader 95014 market, visit the 95014 Real Estate & Development Guide.
Commute Access and Apple Park Proximity
Oak Valley’s location near Homestead Road provides direct access to Apple Park, De Anza Boulevard, Foothill Expressway, and Highway 85. For Apple employees and other technology professionals working in western Cupertino and Sunnyvale, Oak Valley offers a practical combination of residential character and commute convenience. The neighborhood connects easily to employers throughout Cupertino, Sunnyvale, Mountain View, and Santa Clara.
Oak Valley vs. Other Western Cupertino Neighborhoods
Among western Cupertino 95014 neighborhoods, Oak Valley has the lowest median sold price ($2,430,000) and lowest price per square foot ($1,246) — offering meaningful savings relative to Monta Vista ($3,790,000 median, $1,572/sqft), Seven Springs ($3,399,000 median, $1,516/sqft), and Rancho Rinconada ($3,475,000 median, $1,760/sqft). The tradeoffs are smaller homes, lower transaction volume, and less established neighborhood identity than Monta Vista. Buyers who prioritize western Cupertino location and school access at the lowest available price point should evaluate Oak Valley carefully before assuming Monta Vista or Seven Springs is the only option.
Frequently Asked Questions — Oak Valley Real Estate
What is the median home price in Oak Valley?
The median sold price in Oak Valley is $2,430,000 across all property types. 3-bedroom homes have a median near $2,200,000, 4-bedroom homes near $3,401,750, and 5-bedroom homes near $3,500,000. Detached single-family sales range from $1,000,000 to $3,750,000 depending on size, condition, and location. Oak Valley has a smaller transaction volume than neighboring 95014 neighborhoods, so individual sales influence these figures more than they would elsewhere.
How fast do homes sell in Oak Valley?
Oak Valley homes sell in a median of 10 days, consistent with the broader western Cupertino market. Well-priced homes in strong school locations can move faster. Some larger or more specialized properties have taken longer, with a few sales in the 33–36 day range.
What schools serve Oak Valley?
Oak Valley is served by Cupertino Union School District for elementary and middle school and Fremont Union High School District for high school. Many addresses are associated with Monta Vista High School and Lincoln Elementary, though assignments vary by parcel. Buyers should verify current school assignments directly with the appropriate district.
How does Oak Valley compare to Monta Vista?
Oak Valley has a lower median sold price at $2,430,000 vs. Monta Vista at $3,790,000, and a lower price per square foot at $1,246 vs. $1,572. Homes are also smaller, with a median near 1,883 square feet against Monta Vista’s 2,435. Both neighborhoods are in western Cupertino with similar school district access. Monta Vista has a stronger neighborhood identity and higher transaction volume, while Oak Valley offers a more accessible entry price.
Why is Oak Valley’s median price lower than its bedroom-level medians?
Oak Valley includes both detached single-family homes and attached units, and the overall median reflects that full mix. Attached units and smaller original homes trade at lower price points, pulling the overall median below what a typical detached 4-bedroom home sells for. Buyers should compare against the relevant bedroom-level figure rather than the overall median.
Where exactly is Oak Valley in Cupertino?
Oak Valley is in western Cupertino near Homestead Road, with homes on Caroline Drive, Wallace Drive, Madera Drive, Hibiscus Drive, Lucky Oak Street, Mann Drive, and Barranca Drive. It sits near the Cupertino-Los Altos Hills boundary with access to Foothill Expressway, Highway 85, and Interstate 280.
Related Cupertino Real Estate Guides
- Cupertino Real Estate Guide
- 95014 Real Estate & Development Guide
- Monta Vista Real Estate Guide
- Seven Springs Real Estate Guide
- Rancho Rinconada Real Estate Guide
- Homestead Villa Real Estate Guide
- Jollyman Real Estate Guide
- Garden Gate Real Estate Guide
- Homes Near Lynbrook High School
- Cupertino Condos & Townhomes Near Apple Park
- Cupertino Development Videos
Work With a Local Oak Valley Real Estate Expert
Oak Valley’s 10-day median market time means preparation matters. Buyers need financing confirmed, school boundaries verified, and a clear read on recent comparable sales — particularly important in a neighborhood with lower transaction volume where each comparable carries more weight. Sellers need to position an Oak Valley home against a market where buyers are simultaneously evaluating Monta Vista, Seven Springs, and Rancho Rinconada.
Bruce Wagg is a Cupertino and Bay Area real estate agent with Keller Williams Elevate, DRE #01760054, working with buyers and sellers throughout Oak Valley and the wider 95014 market. Call or text (669) 202-7777. Learn more about Bruce Wagg.