Blog > Woodside vs. Portola Valley: Home Prices, Sizes and the City Line (2026)
Woodside vs. Portola Valley: Home Prices, Sizes and the City Line (2026)
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Woodside and Portola Valley sit about 3 miles apart, center to center, both in San Mateo County. Here’s how they compare on what houses, condos and townhomes sold for in the 12 months to October 27, 2026, and on the things that change at the city line: trains, electricity and transfer tax.
The short answer
- Houses: the median sale was $4.06M in Woodside and $4.03M in Portola Valley, so typical houses cost about the same in both.
- Per square foot: $1,412 in Woodside and $1,424 in Portola Valley; the median house was 3,210 sq ft in Woodside and 3,320 sq ft in Portola Valley, on a 1.18-acre lot versus a 1-acre lot.
- Competition: 29% of Woodside houses sold over asking, against 35% in Portola Valley.
- Condos and townhomes: Woodside and Portola Valley had fewer than 10 sales each, so this comparison is about houses.
- At the city line: they match on trains, electricity and transfer tax.
See it live
- Open Woodside vs. Portola Valley in the City Match-Up: homes for sale now and the last 90 days of sales, side by side.
- Talk to a Property Nerd about the streets that fit in either city.
Houses, side by side
Houses (MLS property type “single family home”) sold in the 12 months to October 27, 2026. The last three rows count listings whose description says so, so they undercount.
| Woodside | Portola Valley | |
|---|---|---|
| Sales | 76 | 71 |
| Median price | $4.06M | $4.03M |
| Median per sq ft | $1,412 | $1,424 |
| Median size | 3,210 sq ft | 3,320 sq ft |
| Median lot | 1.18 acres | 1 acre |
| Median bedrooms | 4 | 4 |
| Sold over asking | 29% | 35% |
| Median sale vs. asking | 1.7% under | 1.4% under |
| Sold for $2 million or less | 7% | 8% |
| Listing says single-story | 9% | 14% |
| Listing mentions a pool | 38% | 28% |
| Listing mentions an ADU or in-law unit | 29% | 13% |
At the city line
Some costs and services follow the city, not the mailing address.
| Woodside | Portola Valley | |
|---|---|---|
| County | San Mateo County | San Mateo County |
| Caltrain | none | none |
| BART | none | none |
| VTA light rail | no | no |
| Electricity | WestLight Energy, delivered by PG&E | WestLight Energy, delivered by PG&E |
| Transfer tax on a $2 million sale | $2,200 | $2,200 |
| Eichler tracts | none on our index | 1 tract on our Eichler index |
Electricity is the default provider for most homes; some addresses differ. Transfer tax is the county tax plus any city tax, by the rates on our calculators page; who pays it is set in the contract. School district lines don’t follow city lines, so check the district’s own boundary lookup for any address.
How we counted
Closed sales reported to the MLS and read through the IDX feeds that power our home search, with repeat records removed (same MLS number and sale date). A sale is placed by the city in its MLS address, so a few homes in unincorporated pockets count under the nearby city. Medians follow the mix of homes, and cities are averages: blocks within each can differ a lot. Past sales aren’t a forecast or the value of any one home.
Go deeper
- Woodside: Woodside city guide, Woodside neighborhoods compared and Woodside home types by the numbers.
- Portola Valley: Portola Valley city guide, Portola Valley neighborhoods compared and Portola Valley home types by the numbers.
- More comparisons: Portola Valley vs. Los Altos Hills and Woodside vs. Atherton.
Weighing the two?
We’ll compare the homes and streets you’re actually considering, on both sides of the line, and set up a search that catches new listings the day they hit. Call (408) 373-1660 or (650) 383-8606, or book a strategy call. Commissions are negotiable, and we offer bundled services, so ask us what’s included.