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hillsborough neighborhood guide · property nerds® at compass
Skyfarm & Oaksbridge, Hillsborough Homes for sale, recent sales and a Property Nerd’s guide
Northwest Hillsborough between I-280 and Eucalyptus Avenue: winding hill streets such as Skyfarm, Churchill and Summit drives, lots that run about half an acre and up, and town open space that stays closed.
Skyfarm & Oaksbridge by the numbers
skyfarm & oaksbridge by the numbers · live from the mls
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Calculated in your browser from MLS data for Skyfarm & Oaksbridge (approximate outline traced from the boundary streets). Sales are single-family homes, townhomes and condos.
homes in skyfarm & oaksbridge · live from the mls
Homes for sale, for rent and recently sold in Skyfarm & Oaksbridge
Every active listing, rental and closed sale in Skyfarm & Oaksbridge 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 (Skyfarm & Oaksbridge (approximate outline traced from the boundary streets)); it may not match every local definition.
the story
How Skyfarm & Oaksbridge came to be
The name comes from an estate. A university architecture database records that Skyfarm once covered about 500 acres and was reduced over time by subdivision, and that its house, designed by architect Arthur Brown Jr., was built in 1929 and 1930. That house still stands on Skyline Boulevard on private land, not a public site. Skyfarm Drive, which runs from Redington Road to Darrell Road and Skyline Boulevard, carries the name today.
The wider story is the town's. Hillsborough incorporated on May 5, 1910, after a 60-1 vote, and the town's history says the big estates were gradually cut into smaller lots between 1910 and 1938, often keeping the original house on a few acres. The half-acre minimum lot size dates from 1953 and still applies. Hillsborough has never drawn official neighborhoods, so this guide stitches together listing-record names (Skyfarm, Hillsborough Oaksbridge) with the town's own emergency-network map, which labels these blocks Upper, Mid and Lower Skyfarm, Upper and Lower Churchill, Butternut, Bella Vista, Upper and Lower Summit, Hillsborough Oaks and Forestview.
The land does a lot of the talking. Sanchez Creek runs through these hills on the county's stream map, and six of the town's nine open-space parcels sit here: Spencer Lake, Crocker Lake, Strawberry Hill, Cottonwood Court, Rowen Tree and Nueva/Macadamia. The town describes its roughly 259 acres of open space as rugged, heavily vegetated and undevelopable, and it does not allow public access, so think of them as green backdrops behind the lots, not trails.
streets and homes
The streets and the houses
Streets follow the hills rather than a grid. Skyfarm Drive is the spine, with Fir, Pine and Holly courts off it, while Macadamia Drive, Eugenia Way and Butternut Drive run through the middle. Churchill Drive and Privet Drive sit near I-280, Summit Drive follows the Burlingame line, and the north end around Baileyana Road, Oakdale Road, Jackling Drive, Forest View Avenue and Geri Lane runs toward Eucalyptus Avenue. Jacaranda Circle, Orange Court and New Place Road fill the southeast corner near Ralston Avenue.
Lots are big and uneven. County parcel shapes put the median at about 0.57 acre, with roughly one lot in nine at an acre or more and about 174 below half an acre. Any legally created lot can hold one house. The zoning code caps floor area at 25% of net lot area for the first acre plus 15% beyond, sets a 2,500 sq ft minimum house size and a 32-foot height limit inside a building envelope, and usually sends new homes of 8,000 sq ft and up to the City Council for the final design decision. The Architecture and Design Review Board reviews new houses and larger additions under the town's 2004 Residential Design Guidelines (amended for hillsides in 2015), and it warns buyers not to assume the maximum square footage can be built.
Edges need care. Summit Drive, Tiptoe Lane, Forest View Avenue and Carmelita Avenue each have addresses in more than one jurisdiction: county records list about 51 Hillsborough, 47 City of Burlingame and 17 unincorporated parcels on Summit Drive, and 23 of the 28 single-family parcels on Tiptoe Lane are unincorporated county land with a Burlingame mailing address. On the east edge, the private Burlingame Country Club's grounds fill the space between Skyfarm Drive and Eucalyptus Avenue; club membership is separate from owning a house.
streets in skyfarm & oaksbridge
- Skyfarm Drive
- Churchill Drive
- Summit Drive
- Forest View Avenue
- Butternut Drive
- Jacaranda Circle
- Oakdale Road
- Baileyana Road
- Macadamia Drive
- Geri Lane
- Privet Drive
- Bella Vista Drive
- Jackling Drive
- New Place Road
- Eugenia Way
- Rowan Tree Lane
- Redington Road
- Annescourt Drive
parks and places
Parks, shops and landmarks near Skyfarm & Oaksbridge
- open space
Town open space (Spencer Lake, Crocker Lake and four more)
Six of the town's nine open-space parcels lie in this area. The town says its open space cannot be developed or sold and is not open to public access.
- school
North Hillsborough School and Crocker Middle School
The district's campus at 545 Eucalyptus Avenue and 2600 Ralston Avenue sits just across the east edge, about 0.1 to 1.7 miles away (straight-line).
- park
Centennial Park and Town Hall
A small garden park on the Town Hall grounds at 1600 Floribunda Avenue, planted in 1989 as a low-water demonstration garden; about 0.6 to 2.1 miles away (straight-line).
- shopping
Downtown Burlingame
Hillsborough has no commercial zoning. The nearest shops cluster around Burlingame Avenue by the Burlingame Caltrain station, about 1.3 to 2.7 miles away (straight-line).
- library
Burlingame Public Library
Town residents get library service through agreements with Burlingame and San Mateo; the Burlingame main library at 480 Primrose Road is about 1.0 to 2.5 miles away (straight-line).
- landmark
Carolands
The Ernest Sanson-designed chateau to the south, about 0.3 to 1.7 miles away (straight-line), is private property, not a public park.
schools and commute
School districts and getting around
School districts
Homes here are in the Hillsborough City School District, which runs North, South and West elementary schools and Crocker Middle School (grades 6-8), and the San Mateo Union High School District. North Hillsborough School and Crocker Middle School share a campus just across the east edge. The district's 2024 street list splits this area: Churchill, Butternut, Macadamia, Privet, Eugenia, Rowan Tree and Jacaranda are listed for West; Forest View, Baileyana, Oakdale, Redington, Geri and New Place for North; Skyfarm, Summit and Bella Vista are split by house number. Residency guarantees a district seat, not a particular school, and attendance areas change, so check the exact address with the district.
Hillsborough City Schools guide · San Mateo Union High guide
Getting around
- I-280 runs along the west edge; the nearest ramps are at Golf Course Drive by Black Mountain Road, about 0.6 to 2.2 miles away (straight-line), and Skyline Boulevard parallels the freeway along the town line.
- Burlingame Caltrain, at Burlingame Avenue and California Drive, is about 1.3 to 2.7 miles away (straight-line); Millbrae station, with Caltrain and BART, is about 1.6 to 3.1 miles away (straight-line).
- The town lists bus stops on El Camino Real, about 0.4 to 2.0 miles away (straight-line), and at the commuter lot near I-280 on Golf Course Road.
- Eucalyptus Avenue and Ralston Avenue lead east toward Town Hall and El Camino Real; Skyline Boulevard and Black Mountain Road lead south to the I-280 ramps.
- Town rules allow street parking along frontages but not overnight parking without police permission, so plan on-site parking.
nerd notes
Buying or selling in Skyfarm & Oaksbridge: what we check
Buying here
- Confirm the city before anything else. Summit Drive, Tiptoe Lane, Forest View Avenue and Carmelita Avenue mix Hillsborough, City of Burlingame and unincorporated county parcels under the same 94010 ZIP, and permits, schools and fees follow the parcel, not the ZIP.
- Check fire maps by parcel. On CAL FIRE's 2025 local-responsibility map, about 52 single-family parcels here (by parcel center) are High and 72 Moderate, concentrated on Churchill Drive, Summit Drive, Skyline Boulevard, Live Oak Lane, Panorama Court, Privet Drive and Tiptoe Lane. Town planning handouts say new homes and teardowns in the wildland-urban interface or a High zone need fire-resistant construction and defensible-space landscape plans; Central County Fire's WUI map shows which parcels are in.
- Expect geotechnical questions. The state's seismic hazard maps (San Mateo quadrangle, 2018, and Montara Mountain, 2019) show earthquake-induced landslide zones touching roughly 360 of the 776 single-family parcels, heavy on Skyfarm, Butternut, Jacaranda, Summit, Macadamia and Churchill.
- Run the numbers before you plan an addition: floor area is capped at 25% of net lot area for the first acre plus 15% above an acre, structures plus hardscape are limited to half the lot, and every exterior change goes through design review. The town says county lot-size records are not always accurate, so get a survey.
- Trees with a trunk of 18 inches or more, measured 54 inches above grade, are protected under the town's 2023 ordinance update; check before you plan grading, a pool or a driveway.
Selling here
- Have a survey and net lot area ready. Buyers will run the 25% floor-area formula and the lot-coverage table, and the design review board cautions against assuming the maximum can be built.
- Central County Fire offers vegetation and defensible-space inspections and a natural hazard disclosure (AB 38) inspection for home sales; booking early helps with fire-zone disclosures here.
- The town FAQ says homes sold in Hillsborough must have the sewer lateral inspected and repaired or replaced if needed; schedule the inspection before listing.
- Signs are limited: one temporary real estate sign per property, no larger than 12 by 15 inches, in black and white (town FAQ).
nerd noteCommissions are always negotiable, and we offer bundled services, so ask us what's included.
faq
Skyfarm & Oaksbridge questions, answered
Is Skyfarm an official Hillsborough neighborhood?
No. The town has no official neighborhood map. Skyfarm is an estate name and a listing-record area, and the town's emergency-network map uses Skyfarm, Churchill, Butternut and Summit names for these blocks. The edges in this guide are approximate.
Can the public walk the Spencer Lake or Crocker Lake open spaces?
No. The town says its open-space areas are not open to public access. They are managed land behind the lots.
Which elementary school serves Skyfarm Drive?
It depends on the house number. The district's 2024 list puts 2160-2375 in North Hillsborough School's area and 2400 and up in West Hillsborough's. Check the address with the district.
Is every 94010 address on Summit Drive in Hillsborough?
No. County records show Hillsborough, City of Burlingame and unincorporated county parcels on Summit Drive, and Tiptoe Lane is mostly unincorporated. Check the parcel's jurisdiction before you rely on permit history or school information.
Does a house here include Burlingame Country Club membership?
No. The club is private and membership is separate from owning a home.
How large a house can be built on a half-acre lot?
Floor area is capped at 25% of net lot area for the first acre, so a 21,780 sq ft net lot tops out near 5,445 sq ft of floor area including the garage, subject to design review, the 32-foot height limit and setbacks.
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