The Most Expensive Streets in Woodside & Portola Valley: 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 Woodside & Portola Valley, street by street, we took the 656 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. 26 streets had at least 6 house sales in those five years, enough for a median. Across Woodside, the median house sold for $4.05M, or $1,341 per square foot; in Portola Valley, $4M, or $1,466 per square foot.

The short answer

• Highest median sale price: Westridge Dr in Portola Valley ($8M, 17 sales), Woodside Rd in Woodside ($6.5M, 9 sales) and Eleanor Dr in Woodside ($6.5M, 9 sales).
• Highest price per square foot: Woodside Rd in Woodside ($2,289, 9 sales) and Westridge Dr in Portola Valley ($1,875, 17 sales).
• Most house sales: La Mesa Dr in Portola Valley, with 24 in five years.
• Lowest median among the ranked streets: La Honda Rd in Woodside ($1.66M) and Blakewood Way in Woodside ($2.08M).

The 15 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. 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 Woodside city guide and the Portola Valley city guide link every neighborhood guide. For one specific house, ask us for the comparable sales on its own street.

Selling? Start with selling a home in Woodside or Portola Valley: how we’d price, prepare and launch your sale, and the homes we’ve listed and sold nearby.

More on Woodside and Portola Valley: home prices by neighborhood, five years of house sales (with Atherton) · lots by neighborhood (all three towns)

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.