cupertino neighborhood guide · property nerds® at compass
Oak Valley, Cupertino Homes for sale, recent sales and a Property Nerd’s guide
178 homes clustered on the hills off Cristo Rey Drive, approved in 1997 and built 1999 to 2002, wrapped in public open space next to Rancho San Antonio County Park and Preserve.
Oak Valley by the numbers
oak valley by the numbers · live from the mls
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Calculated in your browser from MLS data for Oak Valley: off Cristo Rey Dr, west of Foothill Blvd (city neighborhood outline). Sales are single-family homes, townhomes and condos.
homes in oak valley · live from the mls
Homes for sale, for rent and recently sold in Oak Valley
Every active listing, rental and closed sale in Oak Valley 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 (Oak Valley: off Cristo Rey Dr, west of Foothill Blvd (city neighborhood outline)); it may not match every local definition.
the story
How Oak Valley came to be
The General Plan's history starts here: the Ohlone lived in the Rancho San Antonio area for more than 3,000 years, and Juan Bautista de Anza's expedition passed through in 1776. De Anza Knoll, a city commemorative site off Cristo Rey Drive, sits on public open space in the neighborhood. The ranch era left a name, too. The Snyder-Hammond House on Stevens Creek Boulevard, just south, is on the city's historic sites list, and the name turns up again on Hammond Way and the Hammond-Snyder Loop Trail.
The hillside joined Cupertino in a 387-acre annexation in 1986, according to the city's annexation map, and in 1997 the city approved partial development of the land. The plan clustered 178 homes on 67 acres, designated 145 acres as public parkland and steered building away from steep slopes, view sheds, creek corridors and tree cover. As part of that review, Santa Clara County acquired 133 acres of open space at no cost.
The houses followed quickly. County assessor records date nearly all of them to 1999 through 2002, the northern cluster mostly to 1999 and the southern cluster to 2000 through 2002, and listing records credit O'Brien Homes as the developer. The General Plan still treats Oak Valley as its own case. Goal LU-29 is to retain and enhance it as a unique neighborhood surrounded by natural hillside areas and private and public open space, and new development has to stay consistent with the development agreement, which covers building areas, styles, park dedication, tree protection, access and historic preservation.
streets and homes
The streets and the houses
Cristo Rey Drive is the main way in. It leaves Foothill Boulevard about 0.2 mile south of the I-280 exit and climbs west toward Rancho San Antonio, and the homes sit in two clusters off it. The southern cluster takes in Canyon Oak Way, Manzanita, Madrone and Peralta courts, Serra Street and Hammond Way. The northern one, reached by Oak Valley Road, includes Sycamore Drive, Sycamore Court, Black Oak Way and Juniper Court. Between them is open hillside, where OpenStreetMap maps the Hammond-Snyder Loop Trail.
County assessor data in the city's GIS shows about 165 detached single-family houses, roughly 70 percent of them two stories, on lots with a median near 14,500 square feet; most fall between 10,000 and 28,000. Hammond Way's houses are all single-story on lots of about 30,000 square feet, and Serra Street's lots run about 26,000. Sixteen smaller homes, mostly on lots of about 5,000 square feet, are recorded as below-market-rate units. The whole tract is zoned P(Res), a planned development, and the General Plan asks for traditional architectural styles with natural materials and colors that suit the hillside.
Changes go through planning review against the original approvals. A 2024 city filing, for example, covered a Director's Minor Modification for a 1,072-square-foot single-story addition to a two-story house in the Oak Valley Development. Nearly every parcel falls in the city's Hillside geologic zone, and the typical lot has an average slope of about 8 percent.
streets in oak valley
- Cristo Rey Drive
- Oak Valley Road
- Canyon Oak Way
- Manzanita Court
- Madrone Court
- Peralta Court
- Serra Street
- Hammond Way
- Sycamore Drive
- Sycamore Court
- Black Oak Way
- Juniper Court
parks and places
Parks, shops and landmarks near Oak Valley
- park
Rancho San Antonio County Park and Open Space Preserve
Midpen's 2,180-acre preserve and the 293-acre county park it manages sit just west, with more than 25 miles of trail. The county park entrance and parking lots are off the west end of Cristo Rey Drive. Dogs are not allowed, and bikes are limited to designated trails.
- park
Deer Hollow Farm
A working farm inside the preserve with turn-of-the-century ranch buildings, an organic garden, farm animals and the restored Grant Cabin, about a mile west of the middle of Oak Valley (straight-line).
- park
Canyon Oak Park
A 0.6-acre city park on Canyon Oak Way, built in the early 2000s, with play equipment, seating and a small lawn that looks out over open space.
- landmark
De Anza Knoll
A city commemorative site on public open space off Cristo Rey Drive, recalling the 1776 Anza expedition.
- landmark
Snyder-Hammond House
A city historic site at 22961 Stevens Creek Blvd., about 0.6 mile south of the middle of the neighborhood (straight-line).
- shopping
Homestead Road near Foothill Boulevard
The nearest commercial area, just north of I-280, which the General Plan lists among its small non-residential and mixed-use areas; about 0.9 mile from the middle of Oak Valley (straight-line). The corner of Foothill and Stevens Creek boulevards, another such area, is about a mile south.
schools and commute
School districts and getting around
School districts
Oak Valley is served by the Cupertino Union School District for kindergarten through eighth grade and the Fremont Union High School District for high school. No public school campus sits in or next to the neighborhood. Attendance boundaries change, so check the exact address with both districts.
Cupertino Union guide · Fremont Union guide · Silicon Valley school districts
Getting around
- Cristo Rey Drive meets Foothill Boulevard about 0.2 mile south of the I-280 interchange, where Foothill Expressway continues north. The interchange is about 0.8 mile from the middle of Oak Valley (straight-line).
- Hwy 85 is about 1.9 miles away at Stevens Creek Boulevard (straight-line), or a short run east on I-280.
- VTA Route 51 runs on Foothill Boulevard, with a timed stop at Cupertino Road about a mile from the middle of Oak Valley (straight-line) and weekday trips to the Mountain View Transit Center. The Silicon Valley Hopper, an on-demand shared-ride service, also covers Cupertino. Check current schedules.
- Caltrain: the Sunnyvale station and the Mountain View Transit Center are each about 4.3 miles away (straight-line).
- Trails start off the west end of Cristo Rey Drive: more than 25 miles in Rancho San Antonio, with bikes allowed only on designated trails and not west of Deer Hollow Farm.
nerd notes
Buying or selling in Oak Valley: what we check
Buying here
- Read the approvals for the lot. Oak Valley is zoned P(Res) and governed by its 1997 approvals (development agreement 2-DA-97, use permit 6-U-97, tentative map 4-TM-97 and rezoning 5-Z-97, per the 2005 General Plan), not the standard R1 rules. Ask the Planning Division what your lot allows before you plan an addition or ADU.
- Check the fire zone for the exact address. The city's layer of CAL FIRE's 2025 Fire Hazard Severity Zones tags the northern cluster (Oak Valley Road, Sycamore Drive and Court, Black Oak Way, Juniper Court) mostly High; the southern streets did not appear in that layer when checked in October 2026. Verify on the official map, plan for defensible space and get insurance quotes early.
- Mind the ground and the flood map. Nearly every parcel is in the General Plan's Hillside geologic zone, some lots on Sycamore Drive, Sycamore Court and Juniper Court are also mapped for liquefaction, and FEMA shows the southern cluster as Zone D, where flood hazard has not been determined. Ask for soils reports, and ask your insurer what Zone D means for coverage.
- Sixteen parcels are recorded as below-market-rate homes. If a listing is one of them, the city's BMR program rules and resale restrictions apply.
- Know the neighbors beyond the open space. The Lehigh cement plant and quarry lie roughly a mile southwest and border the preserve. Its kilns have been idle since 2020 and a county agreement made the stop permanent, while a 2023 reclamation plan amendment proposes ending new mining; follow the county's review.
Selling here
- Pull the lot's planning file: approved plans, any Director's Minor Modifications and permits for later work. Buyers will ask what the development agreement allows.
- Lead with what the lot backs onto. Open-space edges, views and slope set one Oak Valley lot apart from the next, so show them on a parcel map.
- Have the fire-zone status, any defensible-space work and the insurance history ready, especially on the northern streets.
- Give real distances to the Rancho San Antonio trailheads and parking, Deer Hollow Farm, Canyon Oak Park and I-280.
nerd noteCommissions are always negotiable, and we offer bundled services, so ask us what's included.
faq
Oak Valley questions, answered
When was Oak Valley built?
Cupertino approved it in 1997, and county assessor records date nearly all of the houses to 1999 through 2002. The 2005 General Plan counts 178 homes on 67 acres.
Why is there so much open space around the houses?
That was the deal. The approvals clustered the homes, designated 145 acres as public parkland and kept building off steep slopes, view sheds, creek corridors and tree cover, and the county picked up 133 acres of open space next to Rancho San Antonio.
Can I add on to an Oak Valley house?
Often, but under the planned-development approvals rather than standard R1 zoning. A 2024 addition, for example, went through a Director's Minor Modification, so check your lot's conditions with the Planning Division first.
How close is Rancho San Antonio?
Right next door. The county park entrance and parking lots are off the west end of Cristo Rey Drive, and Deer Hollow Farm is about a mile west of the middle of the neighborhood (straight-line).
Is this the same as the General Plan's Oak Valley area?
Not quite. The General Plan's Oak Valley planning area also takes in other streets west of Foothill Boulevard down to Stevens Creek Boulevard, plus the cemetery. This guide covers the 1990s tract and its open space, which matches the MLS area.
Which school districts serve Oak Valley?
The Cupertino Union School District (K-8) and the Fremont Union High School District. Boundaries change, so confirm the address with each district.
talk to a property nerd
Thinking about Oak Valley? Let's run your numbers.
Eric, Janelle and the Boyenga Team have sold more than 2,520 Silicon Valley homes, $2.6+ billion in all, since 1996. Get a value, a plan, or a straight answer about a street.
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