Skywood Woodside, CA
Wooded hillside homes near Sky Londa and La Honda Road, above Woodside.
Living in Skywood
Skywood is a wooded hillside area near Sky Londa, the crossroads of Skyline Boulevard and La Honda Road; maps from as early as 1909 show the name, a blend of the two roads. The crossroads' first building was a small store serving the logging community, which became the well-known Alice's Restaurant in the 1960s. Homes here are single-family houses on large, often forested lots, with a 12-month median around $2.39M, and they take longer to sell than on the valley floor, a median of about 2 to 3 months recently.
Parking & walkability: Homes have driveways and off-street parking, and the roads are rural and winding. It's a driving area, with Skyline Boulevard, open space preserves and trails close by, and Woodside's Town Center and Highway 280 about 15 minutes away.
What homes in Skywood are doing
Single-family homes in Skywood sold for a median of about $2.13M in 2015–16 and $2.95M in 2024–25, a 39% increase, behind Woodside as a whole (+56%). In 2025, homes here sold slowly (median 93 days on market) and usually below asking (97.6% of list price on average). So far in 2026 (6 sales through September), the median is $2.55M.
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. 81 single-family sales since 2015.
| Year | Sales | Median price | $/sq ft | Days on market | Sale-to-list |
|---|---|---|---|---|---|
| 2026 (Jan–Sep) | 6 | $2.55M | $1,128 | 60 | 97.9% |
| 2025 | 8 | $3.12M | $1,122 | 93 | 97.6% |
| 2024 | 3 | $2.5M | $758 | 70 | 100.0% |
| 2023 | 4 | $2.3M | $976 | 16 | 96.4% |
| 2022 | 4 | $3.08M | $997 | 42 | 98.9% |
| 2021 | 16 | $2.61M | $889 | 16 | 100.0% |
| 2020 | 9 | $2.7M | $1,083 | 19 | 97.7% |
| 2019 | 7 | $1.85M | $819 | 42 | 95.4% |
| 2018 | 6 | $2.83M | $817 | 47 | 92.3% |
| 2017 | 3 | $3.02M | $740 | 17 | 101.2% |
| 2016 | 5 | $2.5M | $681 | 46 | 99.1% |
| 2015 | 10 | $1.95M | $704 | 35 | 100.0% |
Skywood 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 Skywood; where there are several, yearly figures are sales-weighted. Information deemed reliable but not guaranteed.