Blog > The Most Expensive Streets in Cupertino: Five Years of House Sales, Street by Street
The Most Expensive Streets in Cupertino: Five Years of House Sales, Street by Street
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Neighborhood averages hide a lot: two streets a few blocks apart can sell hundreds of thousands of dollars apart. To see where house prices are highest in Cupertino, street by street, we took the 1,055 single-family houses that sold through the MLS from October 1, 2021 to October 21, 2026, removed duplicate listings of the same sale, and grouped them by street. 36 streets had at least 6 house sales in those five years, enough for a median. Across Cupertino, the median house sold for $3.19M, or $1,607 per square foot.
The short answer
- Highest median sale price: N Stelling Rd ($3.88M, 7 sales), Linda Vista Dr ($3.65M, 11 sales) and Regnart Rd ($3.6M, 9 sales).
- Highest price per square foot: Alderbrook Ln ($2,123, 7 sales) and Clifford Dr ($2,113, 6 sales).
- Most house sales: Gascoigne Dr, with 14 in five years.
- Lowest median among the ranked streets: Sterling Blvd ($2.05M) and Johnson Ave ($2.25M).
Next steps in Cupertino
- What’s my Cupertino home worth? Request an estimate, and ask us for the recent sales on your street.
- See Cupertino homes for sale, then use Save Search to get new listings by email.
- Book a strategy call with a Property Nerd.
The 15 highest-priced streets
Ranked by median sale price. Typical lot is the median lot size in the sold houses’ listings.
| street | neighborhood | sales | median price | $ / sq ft | typical lot |
|---|---|---|---|---|---|
| 1. N Stelling Rd | Garden Gate | 7 | $3.88M | $1,339 | 9,380 sq ft |
| 2. Linda Vista Dr | Linda Vista & Deep Cliff | 11 | $3.65M | $1,619 | 8,400 sq ft |
| 3. Regnart Rd | several neighborhoods | 9 | $3.6M | $1,187 | 2 acres |
| 4. Wunderlich Dr | Rancho Rinconada | 8 | $3.59M | $1,703 | 5,390 sq ft |
| 5. Columbus Ave | Linda Vista & Deep Cliff | 6 | $3.5M | $1,678 | 7,600 sq ft |
| 6. Barnhart Ave | Rancho Rinconada | 10 | $3.48M | $1,551 | 5,370 sq ft |
| 7. Stafford Dr | — | 8 | $3.46M | $1,615 | 7,390 sq ft |
| 8. Bonny Dr | Jollyman | 6 | $3.45M | $1,896 | 7,830 sq ft |
| 9. Jamestown Dr | — | 7 | $3.41M | $1,503 | 6,120 sq ft |
| 10. Scenic Blvd | — | 9 | $3.4M | $1,369 | 9,040 sq ft |
| 11. S Stelling Rd | several neighborhoods | 13 | $3.2M | $1,626 | 7,840 sq ft |
| 12. Minette Dr | Rancho Rinconada | 9 | $3.2M | $1,522 | 5,910 sq ft |
| 13. San Juan Rd | Inspiration Heights | 6 | $3.15M | $1,537 | 12,580 sq ft |
| 14. Dempster Ave | — | 6 | $3.14M | $1,566 | 7,490 sq ft |
| 15. Johansen Dr | Rancho Rinconada | 6 | $3.1M | $1,676 | 5,780 sq ft |
Highest price per square foot
Price per square foot evens out house size, so smaller houses on sought-after streets rise here.
| street | neighborhood | sales | $ / sq ft | typical size | median price |
|---|---|---|---|---|---|
| 1. Alderbrook Ln | — | 7 | $2,123 | 1,219 sq ft | $2.62M |
| 2. Clifford Dr | — | 6 | $2,113 | 1,164 sq ft | $2.89M |
| 3. S Tantau Ave | Rancho Rinconada | 14 | $2,003 | 1,432 sq ft | $2.64M |
| 4. Kirwin Ln | Jollyman | 8 | $1,943 | 1,388 sq ft | $2.92M |
| 5. Bonny Dr | Jollyman | 6 | $1,896 | 1,780 sq ft | $3.45M |
| 6. La Mar Dr | — | 6 | $1,885 | 1,600 sq ft | $3.06M |
| 7. Farallone Dr | — | 10 | $1,854 | 1,514 sq ft | $3.08M |
| 8. Kentwood Ave | Jollyman | 6 | $1,830 | 1,158 sq ft | $2.27M |
| 9. S Blaney Ave | — | 7 | $1,790 | 1,564 sq ft | $2.8M |
| 10. E Estates Dr | several neighborhoods | 11 | $1,774 | 1,662 sq ft | $2.87M |
The busiest streets
The streets with the most house sales in five years. Long streets that run through several neighborhoods naturally rise here.
| street | neighborhood | sales | median price | $ / sq ft |
|---|---|---|---|---|
| 1. Gascoigne Dr | Rancho Rinconada | 14 | $2.74M | $1,471 |
| 2. S Tantau Ave | Rancho Rinconada | 14 | $2.64M | $2,003 |
| 3. S Stelling Rd | several neighborhoods | 13 | $3.2M | $1,626 |
| 4. Linda Vista Dr | Linda Vista & Deep Cliff | 11 | $3.65M | $1,619 |
| 5. E Estates Dr | several neighborhoods | 11 | $2.87M | $1,774 |
| 6. Johnson Ave | Rancho Rinconada | 11 | $2.25M | $1,525 |
| 7. Barnhart Ave | Rancho Rinconada | 10 | $3.48M | $1,551 |
| 8. Farallone Dr | — | 10 | $3.08M | $1,854 |
| 9. Regnart Rd | several neighborhoods | 9 | $3.6M | $1,187 |
| 10. Scenic Blvd | — | 9 | $3.4M | $1,369 |
Where houses sold for less
The ranked streets with the lowest median sale prices. Lower medians often mean smaller houses or lots, so check the price per square foot too.
| street | neighborhood | sales | median price | $ / sq ft | typical size |
|---|---|---|---|---|---|
| 1. Sterling Blvd | Rancho Rinconada | 9 | $2.05M | $1,699 | 1,153 sq ft |
| 2. Johnson Ave | Rancho Rinconada | 11 | $2.25M | $1,525 | 2,058 sq ft |
| 3. Kentwood Ave | Jollyman | 6 | $2.27M | $1,830 | 1,158 sq ft |
| 4. Brookgrove Ln | Fairgrove | 7 | $2.53M | $1,766 | 1,432 sq ft |
| 5. Alderbrook Ln | — | 7 | $2.62M | $2,123 | 1,219 sq ft |
| 6. S Tantau Ave | Rancho Rinconada | 14 | $2.64M | $2,003 | 1,432 sq ft |
| 7. November Dr | — | 7 | $2.73M | $1,652 | 1,659 sq ft |
| 8. Gascoigne Dr | Rancho Rinconada | 14 | $2.74M | $1,471 | 2,077 sq ft |
| 9. Tilson Ave | Rancho Rinconada | 7 | $2.75M | $1,597 | 1,920 sq ft |
| 10. S Blaney Ave | — | 7 | $2.8M | $1,790 | 1,564 sq ft |
How we counted
- Sales: single-family houses that closed through the MLS from October 1, 2021 to October 21, 2026. Condos, townhomes, mobile homes and land are left out. Sales that never reached the MLS aren’t included.
- Duplicates: the same sale reported by two MLS feeds is counted once.
- Streets: names are standardized (Avenue and Ave are the same street). A street needs at least 6 house sales to be ranked, so short cul-de-sacs with only a few sales don’t appear.
- Neighborhoods: each street is placed in one of our neighborhood guides by the center of its sales; streets whose sales spread over more than about 1.2 km are marked as crossing several neighborhoods, and a dash means the street sits outside our guide outlines.
- Medians, not averages, so one unusual sale moves a street less. Small samples still swing, and a street’s median reflects which houses happened to sell.
- Lot size and square footage come from the listings, which can differ from county records. Price per square foot leaves out the few listings whose size is far out of line with the city (under 30% or over three times the city’s median price per square foot), which are usually typos.
Keep going: the neighborhood ranking by price per square foot compares whole neighborhoods, the price per square foot map plots every recent sale, and the Cupertino city guide links every neighborhood guide. For one specific house, ask us for the comparable sales on its own street.
Selling? Start with selling a home in Cupertino: how we’d price, prepare and launch your sale, and the homes we’ve listed and sold in Cupertino.
The Cupertino data series: housing market by the numbers · neighborhoods ranked by price per sq ft · where homes sell over asking · ten years of prices by neighborhood · condos and townhomes · house prices by bedrooms · houses under $3.5M · houses at $4.5M and up · the best month to sell · houses by neighborhood · our sales map
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