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los altos neighborhood guide · property nerds® at compass
The Highlands Homes for sale, recent sales and a Property Nerd’s guide
A sloping pocket of late-1950s to early-1970s homes between St. Joseph Avenue and I-280 at the south end of Los Altos, inside city limits but served by Cupertino Union and Fremont Union schools.
The Highlands by the numbers
the highlands by the numbers · live from the mls
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Calculated in your browser from MLS data for The Highlands: St. Joseph Ave, Sierra Ventura and Stonehaven drives and I-280 (approximate). Sales are single-family homes, townhomes and condos.
homes in the highlands · live from the mls
Homes for sale, for rent and recently sold in The Highlands
Every active listing, rental and closed sale in the Highlands 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 (The Highlands: St. Joseph Ave, Sierra Ventura and Stonehaven drives and I-280 (approximate)); it may not match every local definition.
the story
How The Highlands came to be
The Highlands is the last stretch of Los Altos before the freeway and the foothills, and the name fits the ground: it rises from about 250 feet where St. Joseph Avenue meets Foothill Expressway to about 365 feet on the south side of Highlands Circle (USGS elevation data). We could not find a published history of the tract or the name of its builder. Listing services file these streets under 'Woodland Acres - The Highlands', and homes on St. Joseph Avenue, Lockhaven Drive, Highlands Circle and Oxford Drive show original build years of 1957, 1962, 1963 and 1972.
Its neighbor shares the label. Woodland Acres was developed on 86 acres a developer bought in 1948, with lots sold from 1950 to 1957, according to a history the Los Altos Town Crier published, and the city annexed the 79-acre Woodland Acres pocket from the county in 2006. The Highlands streets are inside Los Altos city limits today, with Cupertino on the far side of I-280.
Two public works shaped the edges. In 1990 the city filed plans to close St. Joseph Avenue at the Cupertino line by I-280 so it would stay a local street, with a locked gate for emergency vehicles and a pass-through for people on foot and bikes; current maps show that segment closed to cars. Just across the freeway in Rancho San Antonio County Park, Valley Water finished a flood detention basin in June 2021, the last piece of its Permanente Creek flood protection project.
streets and homes
The streets and the houses
The street names run to an English theme: Kent Drive, Oxford Drive, Regent Drive, Yorkshire Drive, Andover Way, Lockhaven Drive and Stonehaven Drive, organized around Highlands Circle, which loops through the middle of the tract. Curving streets and short courts such as Lockhaven Court, Longden Circle and Madelaine Court follow the slope rather than a grid. In OpenStreetMap's street network, every one of these streets reaches the rest of town by car only through St. Joseph Avenue, which meets Foothill Expressway and Grant Road at the northeast corner.
Most lots sit a little above 10,000 square feet: listing records show 10,010 to 11,102 square feet, and the average on Yorkshire Drive is about 11,300. Recent listings run from a 1,681-square-foot single-level ranch on St. Joseph Avenue to houses of about 2,000 to 2,600 square feet, several of them remodeled.
Because the ground slopes, lots can sit above or below the street, and any remodel has to work with the grade. Lockhaven Drive and the south side of Highlands Circle sit closest to the I-280 corridor, about 500 to 650 feet from the freeway (map measurement).
streets in the highlands
- Saint Joseph Avenue
- Highlands Circle
- Kent Drive
- Oxford Drive
- Regent Drive
- Yorkshire Drive
- Andover Way
- Scott Lane
- Lockhaven Drive
- Lockhaven Court
- Stonehaven Drive
- Sierra Ventura Drive
- Via Escalera
- Longden Circle
- Madelaine Court
- Wooded Glen Way
- Saint Joseph Court
parks and places
Parks, shops and landmarks near The Highlands
- park
Montclaire Park
A 1.1-acre city park at 1160 St. Joseph Avenue, next to Montclaire Elementary, with two tennis courts, picnic tables, barbecue pits and a preschool play area. City court reservations are limited to residents and nonprofit groups.
- park
Rancho San Antonio Preserve and County Park
About 0.7 mile away as the crow flies, across I-280: a 2,180-acre Midpeninsula preserve next to a 293-acre county park, with more than 25 miles of trail and Deer Hollow Farm. Drivers enter from Foothill Boulevard via Cristo Rey Drive; dogs are not allowed.
- landmark
Woodland Branch Library
A Santa Clara County Library District branch at 1975 Grant Road, about 0.6 mile east.
- shopping
Woodland Plaza
One of the city's seven shopping districts, on Grant Road about 0.7 mile east, with a Lucky supermarket at 2175 Grant Road.
- shopping
Foothill Crossing
The center on Homestead Road by Foothill Expressway, about a mile east, with Trader Joe's at 2310 Homestead Road plus Foothill Produce and Ace Hardware.
schools and commute
School districts and getting around
School districts
Although the Highlands is inside Los Altos city limits, it is not in the Los Altos School District. Census school-district maps place every street here in the Cupertino Union School District (TK-8) and the Fremont Union High School District, and recent listings on St. Joseph Avenue and Highlands Circle report the same. Cupertino Union's Montclaire Elementary is in the neighborhood at 1160 St. Joseph Avenue. Attendance boundaries change and the districts make the final assignment at registration, so check the exact address with Cupertino Union's school locator and Fremont Union's address check before you buy.
Cupertino Union guide · Fremont Union guide · Silicon Valley school districts
Getting around
- I-280: take St. Joseph Avenue to Foothill Expressway or Grant Road and head south to the Foothill Boulevard/Grant Road interchange, about 1 mile from the center (straight line).
- VTA Route 51 runs on weekdays between Moffett Field and West Valley College, using Grant Road, Foothill Expressway and Homestead Road nearby; check VTA for current stops and times.
- Caltrain: Mountain View station is about 3.7 miles and Sunnyvale about 3.9 miles away (straight line); there is no rail in Los Altos.
- Loyola Corners is about 0.8 mile northwest and downtown Los Altos about 3.2 miles (straight line).
- On foot or bike, the south end of St. Joseph Avenue is closed to cars at I-280; the city's 1990 plan kept a walk-and-bike pass-through, but check current access before counting on it as a route to Rancho San Antonio.
nerd notes
Buying or selling in The Highlands: what we check
Buying here
- Check schools by address. Highlands streets map to Cupertino Union and Fremont Union, not the Los Altos School District and Mountain View-Los Altos, despite the Los Altos address.
- City rules apply. This is City of Los Altos residential zoning (third-party records show R1-10); check the city's design review rules before planning a second story, and note that the city has added single-story (R1-S) overlays block by block elsewhere, so ask whether one has been proposed nearby.
- Mind the slope. The ground rises roughly 100 feet across the area; check drainage, retaining walls and the grading an addition would need.
- One road out: OpenStreetMap shows every street here exiting by car through St. Joseph Avenue, so time your commute at the Foothill Expressway/Grant Road corner. Near the freeway, also visit at rush hour and look at sound walls and window upgrades.
- Homes from 1957 to 1972 deserve a systems check: electrical panel, original plumbing, roof and sewer lateral condition. Also check the parcel on CAL FIRE's fire hazard severity zone map and the state seismic hazard maps, since disclosures and insurance depend on them.
Selling here
- State the school districts plainly (Cupertino Union and Fremont Union) with a verify note; buyers comparing Los Altos homes need to know this up front.
- Have City of Los Altos permits and finals for any remodel or addition ready.
- Show lot size and grade: say how much of the yard is level and usable.
- Give concrete distances to Montclaire Park, Rancho San Antonio and the I-280 on-ramp rather than adjectives.
nerd noteCommissions are always negotiable, and we offer bundled services, so ask us what's included.
faq
The Highlands questions, answered
Is the Highlands in Los Altos or Cupertino?
Los Altos. Census and OpenStreetMap boundaries put the Highlands streets inside the City of Los Altos; the Cupertino city line runs along I-280, so streets across the freeway such as Cristo Rey Drive and Via Esplendor are in Cupertino.
Which school districts serve the Highlands?
Cupertino Union School District for TK-8 and Fremont Union High School District for high school, per Census school-district maps and recent listings. Attendance boundaries change, so confirm the exact address with both districts.
Is the Highlands the same as Woodland Acres?
They are neighbors and listing services often lump them together as 'Woodland Acres - The Highlands'. Woodland Acres was developed from 1950 to 1957 and annexed from the county in 2006; the line between the two names is informal.
When were the homes built?
The listing records we checked show original build years from 1957 to 1972, so this is mostly late-1950s to early-1970s housing, with remodels and rebuilds since.
How close is Rancho San Antonio?
The county park is about 0.7 mile away as the crow flies, across I-280. By car you reach it from Foothill Boulevard via Cristo Rey Drive. The preserve and park together have more than 25 miles of trail.
next door
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