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woodside neighborhood guide · property nerds® at compass
Skywood, Portola Hills & Skylonda, Woodside Homes for sale, recent sales and a Property Nerd’s guide
Woodside's wooded southwest corner, climbing from Portola Road up La Honda and Old La Honda roads to the Skylonda crossroads at Skyline Boulevard, plus the unincorporated Sky Londa streets just west of the Town line.
Skywood, Portola Hills & Skylonda by the numbers
skywood, portola hills & skylonda by the numbers · live from the mls
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Calculated in your browser from MLS data for Skywood, Portola Hills & Skylonda (approximate outline traced from the boundary streets). Sales are single-family homes, townhomes and condos.
homes in skywood, portola hills & skylonda · live from the mls
Homes for sale, for rent and recently sold in Skywood, Portola Hills & Skylonda
Every active listing, rental and closed sale in Skywood, Portola Hills & Skylonda 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 (Skywood, Portola Hills & Skylonda (approximate outline traced from the boundary streets)); it may not match every local definition.
the story
How Skywood, Portola Hills & Skylonda came to be
The Town's subdivision table traces this corner to two county-era tracts. Portolla Hills (the 1909 plat uses the double L) covered about 418 acres in 97 parcels, and the Woodside Country Club tract of 1926 covered about 449 acres in 166 parcels. A 2006 local news history explains the second name: investors bought about 400 acres in 1926 to build a club with a golf course near Searsville Lake and home sites running up toward Skyline along what is now Old La Honda Road. The course never got past preliminary grading after the 1929 crash, and some lots were later combined into three- and four-acre parcels.
Skywood Acres came next. Recorded in 1957, the year after Woodside incorporated, it is the first Town-era subdivision in the General Plan's table: about 212 acres in 89 parcels averaging 2.4 acres, on the hillside between La Honda Road and Wunderlich Park. Thornewood, in the middle of the lobe, was a 1908 estate purchase; Midpen says architect Gardner Dailey designed its house in the 1920s, and the land is now a public preserve.
Up on the ridge, La Honda Road (Hwy 84) meets Skyline Boulevard (Hwy 35) at Skylonda. The Town's 1985 Skylonda Center Area Plan covers the few businesses on the Town side of the crossroads and asks that buildings stay informal, small in scale and reviewed by the Architectural and Site Review Board. Across Skyline, the Town's maps label the unincorporated streets 'Sky Londa,' and the county's planning maps include them in its North Skyline area. The county held the ribbon-cutting for its rebuilt Skylonda Fire Station 58 there in September 2018; CAL FIRE staffs it under contract for Kings Mountain, La Honda, Upper Woodside and Skyline Boulevard.
streets and homes
The streets and the houses
Inside the Town, three road systems climb the hill. Off La Honda Road near Skyline, the Skywood Acres streets are Skywood Way, Ranch Road, Stadler Drive, Sunrise Drive, Friars Lane and Still Creek Road. In the middle, Map H1's Portolla Hills area takes in Grandview Drive, Espinosa Road, Preston Road, Phillip Road and Forrest View Road. Along Old La Honda Road, the Woodside Country Club lots line Martinez Road, Upenuf Road, Echo Lane, Summit Road, Medway Road, Big Tree Road, Morshead Road and Orchard Hill Road. Near Portola Road are Upper and Lower Lake Roads, Montecito Road, Meadow Road, Home Road and Dennis Martin Road. Old La Honda Road runs about four miles from Portola Road (about 390 feet, USGS) to Skyline.
West of Skyline and south of the crossroads, the unincorporated streets sit higher, around 1,600 to 1,750 feet: Skylonda Drive, Bret Harte Way, Fremont Way, Sequoia Way, Calaveras Way, Big Tree Way, Chapman Road, Skyline Drive, Elk Road, Redland Road, Morse Lane, Blakewood Way, Linwood Way, Kebet Ridge Road and Starwood Drive. Lots here are much smaller: the county parcel median is about half an acre, against about 2.1 acres on the Town side. County address records give most of them a Woodside mailing city and a few Redwood City, all ZIP 94062.
County parcel maps count about 470 single-family parcels across both parts and about 145 vacant parcels. The Town's 2017 zoning map puts most of the Town side in Special Conservation Planning districts (five-, 7.5- and ten-acre minimums for new lots), with open space at Thornewood and a small commercial district at Skylonda; most existing lots are well under those minimums. County zoning on the Sky Londa streets is mostly R-1 single-family with S-10 or S-11 lot-size combining districts, and Resource Management (RM) on larger outer parcels.
streets in skywood, portola hills & skylonda
- La Honda Road
- Old La Honda Road
- Skyline Boulevard
- Portola Road
- Skywood Way
- Ranch Road
- Stadler Drive
- Sunrise Drive
- Friars Lane
- Still Creek Road
- Grandview Drive
- Espinosa Road
- Preston Road
- Phillip Road
- Forrest View Road
- Martinez Road
- Upenuf Road
- Echo Lane
- Summit Road
- Medway Road
- Big Tree Road
- Morshead Road
- Orchard Hill Road
- Upper Lake Road
- Lower Lake Road
- Montecito Road
- Meadow Road
- Home Road
- Dennis Martin Road
- Skylonda Drive
- Bret Harte Way
- Fremont Way
- Sequoia Way
- Calaveras Way
- Big Tree Way
- Chapman Road
- Skyline Drive
- Elk Road
- Redland Road
- Morse Lane
- Blakewood Way
- Linwood Way
- Kebet Ridge Road
- Starwood Drive
parks and places
Parks, shops and landmarks near Skywood, Portola Hills & Skylonda
- park
Thornewood Preserve
A 167-acre Midpen preserve in the middle of the area. The gate is on the south side of La Honda Road, 1.6 miles past Portola Road, with a small lot; the 0.75-mile Schilling Lake Trail ends at a pond under redwoods. Hiking, horses on marked trails and leashed dogs on designated trails; no bikes.
- park
Wunderlich County Park
942 acres along the area's north edge (General Plan), entered at 4040 Woodside Road about 1.6 miles straight-line from the middle of the area, with hiking and riding trails.
- park
El Corte de Madera Creek Preserve
Midpen's 2,908-acre preserve west of Skyline has 34-plus miles of multiuse trail; its Skeggs Point lot is on Skyline about four miles north of Hwy 84. Bikes on designated trails; no dogs.
- shopping
Skylonda crossroads
The Skylonda Center Area Plan's photos show the handful of businesses at Skyline and La Honda Road: a restaurant, a market and deli, and a gas station. Woodside's town center is about 3 miles straight-line.
- landmark
Skylonda Fire Station 58
The county-owned station on Skyline Boulevard at the crossroads, staffed by CAL FIRE under contract; the county's 2018 release describes a two-story main building with quarters for 13 firefighters.
schools and commute
School districts and getting around
School districts
U.S. Census school-district maps, tested at every county address point, put all but four addresses here in the Portola Valley School District, on both the Town and unincorporated sides; the exceptions are two on Still Creek Road, one on Stadler Drive and one on Portola Road, which fall in the Woodside Elementary School District. Portola Valley's district lists Ormondale (TK-3) and Corte Madera (4-8), about 2.4 and 2.9 miles straight-line from the middle of the area. High school is the Sequoia Union High School District. Just beyond this guide, upper Old La Honda Road, La Honda Road west of Skylonda and most of Allen Road are in the La Honda-Pescadero or Cabrillo unified districts, on the coast side. Attendance boundaries change, so check the exact address with each district.
Portola Valley School District guide · Sequoia Union guide · Silicon Valley school districts
Getting around
- La Honda Road (Hwy 84) runs down to Woodside's town center, about 5.8 miles by road, and on to I-280 at Woodside Road.
- I-280: the Sand Hill Road interchange is about 3.2 miles and the Alpine Road interchange about 4.0 miles straight-line from the middle of the area.
- Skyline Boulevard (Hwy 35) runs north toward Kings Mountain Road and south along the ridge; it is a state scenic corridor in county records.
- Old La Honda Road links Portola Road to Skyline in about four miles (approximate, measured on public maps).
- Caltrain: Menlo Park station is about 6.3 miles straight-line; we found no bus service on these roads.
nerd notes
Buying or selling in Skywood, Portola Hills & Skylonda: what we check
Buying here
- Confirm the jurisdiction. The streets west of Skyline and south of the crossroads (Skylonda Drive, Blakewood Way, Morse Lane, Kebet Ridge Road, Big Tree Way, Chapman Road and others) are unincorporated San Mateo County, so county planning and building permits and county zoning apply, even with a Woodside address. Big Tree Road, Medway Road and Sequoia Way have parcels on both sides of the line.
- Check the fire zone and the responsible agency. CAL FIRE's maps put the Town side in a High zone (February 2025 local map) and the unincorporated side in the State Responsibility Area, also High (map effective April 1, 2024). The Town's 2012 map showed its part as Very High, so older disclosures may differ. Ask about defensible-space inspections and insurance early.
- Get geotechnical advice. County copies of the state seismic hazard maps put about 57% of the residential parcels in mapped earthquake-induced landslide zones, and the Town's geologic map shows nearly all of its part as a slope-instability zone.
- Plan on septic, and confirm water. The Town's 2022 sewer map shows no sewer service here; new or expanded septic systems need Town or county and Environmental Health permits. The county's water-district map puts these streets in Cal Water's Bear Gulch district; confirm service, storage and any well for the parcel.
- Check road access: whether the street is publicly maintained or private, any road maintenance agreement, and emergency access on narrow hillside roads. Skyline is a state scenic corridor, and the Town requires larger setbacks along it.
Selling here
- State plainly whether the parcel is in the Town or unincorporated county; the answer changes the permit history buyers will ask for.
- Collect fire records: defensible-space inspections, vegetation work, any home-hardening upgrades, and the parcel's current CAL FIRE zone.
- Have geotechnical reports, septic permits and pumping records, and water-service documents ready; on these lots they answer most buyer questions.
- On small Sky Londa lots, document lot coverage, setbacks and permits for decks and additions under county rules.
nerd noteCommissions are always negotiable, and we offer bundled services, so ask us what's included.
faq
Skywood, Portola Hills & Skylonda questions, answered
Is Skylonda in the Town of Woodside?
Partly. The Town's Skylonda Center Area Plan map puts the crossroads businesses on the east side of Skyline inside Town limits, while the residential streets west of Skyline and south of the crossroads (Skylonda Drive, Blakewood Way, Morse Lane and others) are unincorporated San Mateo County with Woodside-area addresses.
Which school district serves Skywood and Sky Londa?
Census maps put almost every address here in the Portola Valley School District, with high school in the Sequoia Union district. Four addresses near Still Creek Road, Stadler Drive and Portola Road are Woodside Elementary. Confirm the address with the districts.
Was there ever a Woodside Country Club golf course?
No. A 2006 local news history says the 1926 club planned a course near Searsville Lake, but it never got past preliminary grading after the 1929 crash. The name survives in the Town's subdivision records for the lots along Old La Honda Road.
How big are the lots?
On the Town side, county parcel maps give a median of about 2.1 acres; on the unincorporated Sky Londa streets, about half an acre.
Is this Portola Valley?
No. The area uses Woodside addresses and the Portola Valley School District. Portola Valley's town line is just south and east, and the Portola Hills tract name refers to a 1909 Woodside subdivision, not the neighboring town.
next door
More Woodside neighborhood guides
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