The Most Expensive Streets in Sunnyvale: Five Years of House Sales, Street by Street

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 Sunnyvale, street by street, we took the 2,501 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. 120 streets had at least 6 house sales in those five years, enough for a median. Across Sunnyvale, the median house sold for $2.5M, or $1,468 per square foot.

The short answer

• Highest median sale price: Helena Dr ($3.32M, 6 sales), Lewiston Dr ($3.3M, 9 sales) and Samedra St ($3.29M, 7 sales).
• Highest price per square foot: Lewiston Dr ($2,034, 9 sales) and Heatherstone Way ($1,939, 6 sales).
• Most house sales: S Mary Ave, with 29 in five years.
• Lowest median among the ranked streets: Birch Ave ($1.3M) and Blazingwood Dr ($1.4M).

The 25 highest-priced streets

Ranked by median sale price. Typical lot is the median lot size in the sold houses’ listings.

Highest price per square foot

Price per square foot evens out house size, so smaller houses on sought-after streets rise here.

The busiest streets

The streets with the most house sales in five years. Long streets that run through several neighborhoods naturally rise here.

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.

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.

Keep going: the neighborhood ranking by price per square foot compares whole neighborhoods, the recent sales page shows what sold lately, and the 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 Sunnyvale: how we’d price, prepare and launch your sale, and the homes we’ve listed and sold in Sunnyvale.

The Sunnyvale 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 $2.5M · houses at $3.5M and up · the best month to sell · houses by neighborhood · flood zones by neighborhood · our sales map

We’re the Boyenga Team at Compass. We represent buyers and sellers in Santa Clara County, bay-side San Mateo County and San Francisco. Commissions are negotiable, and we offer bundled services, so ask us what’s included. Call (408) 373-1660 or (650) 383-8606.