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portola valley neighborhood guide · property nerds® at compass
Woodside Highlands & Hayfields, Portola Valley Homes for sale, recent sales and a Property Nerd’s guide
A 1920s summer-cottage subdivision of small hillside lots off Portola Road, plus the acre-plus Hayfields lots above it and the 1931 Portola Redwoods street across the road. Despite the name, it is in Portola Valley.
Woodside Highlands & Hayfields by the numbers
woodside highlands & hayfields by the numbers · live from the mls
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Calculated in your browser from MLS data for Woodside Highlands & Hayfields (approximate outline traced from the boundary streets). Sales are single-family homes, townhomes and condos.
homes in woodside highlands & hayfields · live from the mls
Homes for sale, for rent and recently sold in Woodside Highlands & Hayfields
Every active listing, rental and closed sale in Woodside Highlands & Hayfields from the MLS, updated automatically, with a map of the neighborhood outline.
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Listings come from MLSListings and other MLSs through IDX and show their listing brokerage; confirm details with the listing agent. The map outline is the neighborhood boundary used by our listing search (Woodside Highlands & Hayfields (approximate outline traced from the boundary streets)); it may not match every local definition.
the story
How Woodside Highlands & Hayfields came to be
From the 1860s to 1919 this hillside was ranch land. A Town archive account describes a holding of more than 300 acres used for grazing, hay and firewood; in 1879 the farm reported 800 bushels of barley and 600 of oats. In 1919, 205 acres were sold and split into two country estates that shared an entrance at today's Santa Maria Avenue. Water was a constant problem, and the estates hauled it in every summer. One estate's 17-room house, on what is now Tynan Way, burned in 1923 before anyone moved in.
By the mid-1920s that estate had been sold for subdivision. It was first marketed as Coombsville, after its subdividers, and soon renamed Woodside Highlands; the Town archive's timeline records 179 lots in 1926. Buyers were mostly after summer cottages. The account counts 20 houses by 1925, another 25 by the end of 1930 and ten more in the following decade, and a 2001 oral history in the archive recalls water hauled in barrels and early water lines made from old water heaters laid under the roads. Across Portola Road, Portola Redwoods (Wyndham Drive) followed in 1931 with 46 lots.
The other estate's land was divided in stages. Its Portola Road frontage was subdivided in the 1940s, and in 1975 a group of buyers purchased 78 acres for a modern subdivision, Hayfields, which the archive dates to 1978. The Larry Lane Trail was built through the property in 1979. Despite the Woodside name, all of it is inside the Town of Portola Valley; the Woodside town line runs just to the north.
streets and homes
The streets and the houses
Santa Maria Avenue is the spine. It leaves Portola Road at the north end and winds south, with Russell Avenue, Tynan Way, LeRoy, Louise Lane and Trinity Lane branching off. Wayside Road leaves Portola Road a few hundred yards farther south and runs southwest to a dead end. The roads are narrow and follow the slope, a layout that dates from the 1920s cottage era rather than from car-scale planning.
Lots are small for Portola Valley. County parcel maps put the typical Woodside Highlands lot at about a third of an acre, with many under a quarter acre, especially on Russell Avenue, and some parcels of an acre or more on Wayside Road. About 37 parcels inside the outline are vacant, most of them under half an acre. A 2001 account in the Town archive says many owners hold a second, vacant lot, often because drainage made it hard to build.
Hayfields Road climbs from Portola Road at the north end to 11 homes on lots of about 1.1 to 2.6 acres, a 1970s subdivision on a 1920s hillside. Wyndham Drive, the 1931 Portola Redwoods street, is a short street on the east side of Portola Road with 29 homes on lots of about a quarter to a third of an acre. Town archive maps list Ann Road and Catherine Court as Portola Redwoods streets too, but neither appears on current county or street maps.
streets in woodside highlands & hayfields
- Santa Maria Avenue
- Russell Avenue
- Tynan Way
- Wayside Road
- LeRoy Avenue
- Louise Lane
- Trinity Lane
- Hayfields Road
- Wyndham Drive
- Portola Road
parks and places
Parks, shops and landmarks near Woodside Highlands & Hayfields
- landmark
Portola Valley Town Center
Town Hall and the Portola Valley branch of the San Mateo County Library are on Portola Road about half a mile straight-line to the southeast.
- trail
Larry Lane Trail
A Town trail built in 1979 through the Hayfields property. The archive account suggests hiking it in spring, when old plantings of daffodils come up near the top.
- park
Windy Hill Open Space Preserve
Midpen's 1,414-acre preserve has its lower parking area on Portola Road and trails up to Skyline Boulevard, including the 1.6-mile Sausal Pond Loop. Dogs, bikes and horses are allowed on designated trails only.
- shopping
Alpine and Portola corner
Roberts Market (4420 Alpine Road) and Portola Valley Hardware are about 1.9 miles straight-line down Portola Road.
- shopping
Ladera shopping center
The center at 3130 Alpine Road in unincorporated Ladera, with a grocery and small shops, is about 2.8 miles straight-line.
schools and commute
School districts and getting around
School districts
Woodside Highlands, Hayfields and Wyndham Drive are in the Portola Valley School District and the Sequoia Union High School District (Census school-district maps, checked lot by lot), not the Woodside district the name suggests. The district's Ormondale School (TK/K-3) is about 1.1 miles straight-line to the southeast, and Corte Madera School (grades 4-8, 4575 Alpine Road) about 1.8 miles. Attendance boundaries can change, so check the exact address with each district.
Portola Valley School District guide · Sequoia Union guide · Silicon Valley school districts
Getting around
- On street maps, every road here connects to the rest of town only through Portola Road: Santa Maria Avenue, Wayside Road, Hayfields Road and Wyndham Drive all end there.
- I-280: the Sand Hill Road interchange is about 2.7 miles straight-line and the Alpine Road interchange about 2.8 miles.
- Caltrain: Menlo Park and Palo Alto stations are each about 5.8 miles straight-line.
- Transit is thin: the Sequoia Union High School District lists SamTrans school-day routes 86 (to Menlo-Atherton High) and 87 (to Woodside High) for Portola Valley. Check SamTrans for current routes.
- On foot: the Town Center is about half a mile straight-line, and the Larry Lane Trail starts on the hillside above.
nerd notes
Buying or selling in Woodside Highlands & Hayfields: what we check
Buying here
- Sewer or septic: on county district maps, all but two of the homes here sit outside the West Bay Sanitary District boundary. Ask whether the house is on septic, get the county septic permit and pumping records, and have the system inspected. On a small lot, check where a replacement field could go.
- Slope and soils: county maps put about 66 of the 166 home parcels inside the state's Alquist-Priolo Earthquake Fault Zone and about 70 in mapped landslide zones, and the Town archive records a house on Tynan Way that sank in 1967. Read the natural hazard disclosure and budget for a geotechnical report before planning work.
- Lot lines: many owners hold a second, vacant lot. Confirm with the title report which parcels convey, whether adjacent lots have been merged, and what the Town allows on each before you count on building.
- Roads: these are narrow 1920s lanes. Ask whether your street is Town-maintained or private with a road maintenance agreement, and check parking and turnaround space for the specific house.
- Older houses: cottage-era framing, foundations, wiring and drainage may predate permits. Pull the Town permit history and check the State Fire Marshal's current fire hazard severity zone map for the address.
Selling here
- Have septic records and a recent inspection ready; it is the first question buyers ask about this side of Portola Road.
- Spell out exactly what is for sale, including any second lot, with the APNs in the listing documents.
- Gather permits for past additions and any drainage, retaining-wall or foundation work; documentation matters more on a slope.
- Put slope, access and parking in the disclosures and listing materials; on these lanes they are the practical questions.
nerd noteCommissions are always negotiable, and we offer bundled services, so ask us what's included.
faq
Woodside Highlands & Hayfields questions, answered
Is Woodside Highlands in Woodside?
No. It is inside the Town of Portola Valley, with Portola Valley 94028 addresses, Town planning and permits, and the Portola Valley School District. The Town of Woodside line is just to the north, at Family Farm Road.
How old is Woodside Highlands?
The Town archive dates the subdivision to 1926, with 179 lots, and an archive account counts about 55 houses built by 1940, mostly as summer cottages. Hayfields came in 1978 and Portola Redwoods (Wyndham Drive) in 1931.
How big are the lots?
Small for Portola Valley: about a third of an acre on a typical Woodside Highlands street and about a quarter acre on Wyndham Drive, versus roughly 1.5 to 2.2 acres on Hayfields Road (county parcel maps).
Are homes on sewer?
Mostly not, on county maps: all but two homes in the outline sit outside the West Bay Sanitary District boundary. Assume septic until records show otherwise, and get an inspection.
Which schools serve it?
The Portola Valley School District and the Sequoia Union High School District. Check the exact address with each district, since boundaries can change.
talk to a property nerd
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