Skyline Woodside, CA
Homes along the Skyline ridge above Woodside, with redwoods, views and a rural feel.
Living in Skyline
The Skyline area covers homes along the Skyline Boulevard ridge above Woodside, among redwoods and open space. Homes are scattered on large, often wooded lots, many with sweeping views. It's the most affordable part of the Woodside market, with a 12-month median around $2.24M, and one of the slower-moving: homes took a median of about 6 weeks to sell in 2025 at about 95% of asking.
Parking & walkability: Homes have driveways and off-street parking on large, often wooded lots, and the roads are rural. It's a driving area: Woodside's Town Center and Highway 280 are a 15 to 20 minute drive down the hill, and open space preserves and trails are all around.
What homes in Skyline are doing
Single-family homes in Skyline sold for a median of about $1.53M in 2015–16 and $1.94M in 2024–25, a 27% increase, behind Woodside as a whole (+56%). In 2025, homes here sold slowly (median 44 days on market) and usually below asking (95.2% of list price on average). So far in 2026 (16 sales through September), the median is $2.36M.
Median single-family price, 2015–2026
* 2026 covers January through September. Hollow dots mark years with fewer than 3 single-family sales; treat those medians as rough. 223 single-family sales since 2015.
| Year | Sales | Median price | $/sq ft | Days on market | Sale-to-list |
|---|---|---|---|---|---|
| 2026 (Jan–Sep) | 16 | $2.36M | $741 | 66 | 97.7% |
| 2025 | 17 | $1.76M | $810 | 44 | 95.2% |
| 2024 | 15 | $2.15M | $941 | 36 | 100.0% |
| 2023 | 15 | $2.19M | $787 | 32 | 97.1% |
| 2022 | 10 | $1.95M | $975 | 18 | 97.4% |
| 2021 | 29 | $1.55M | $838 | 18 | 100.0% |
| 2020 | 18 | $1.67M | $743 | 27 | 96.7% |
| 2019 | 19 | $1.7M | $727 | 30 | 96.8% |
| 2018 | 14 | $1.44M | $715 | 53 | 97.9% |
| 2017 | 30 | $1.66M | $697 | 51 | 99.7% |
| 2016 | 20 | $1.4M | $721 | 55 | 95.0% |
| 2015 | 20 | $1.65M | $581 | 20 | 98.0% |
Skyline on the map
Borders are built lot by lot from the county's property lines and where homes have been listed (MLS neighborhood codes), and stay inside official city limits (dashed), so a home or two along an edge may differ from official MLS lines.
Other Woodside neighborhoods
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Source: MLSListings, Inc. closed sales, 2015–September 2026, summarized by Drew Lehr. Neighborhood figures combine the MLS area(s) that make up Skyline; where there are several, yearly figures are sales-weighted. Information deemed reliable but not guaranteed.