Homes for Sale in Hillsborough Oaksbridge, Hillsborough, CA
Homes for sale Hillsborough Oaksbridge draw buyers who want estate-style living in a lower Hillsborough setting that feels private, mature, and well-connected to Burlingame. The current listings in that pocket center on Fagan Drive and Sheldon Way, an area known for large parcels, gated entries, and a quieter residential feel than busier Peninsula corridors. This is the kind of location where privacy comes from land, setbacks, and established trees rather than distance alone, which is why the area fits the character buyers often expect from secluded Hillsborough wooded estates.
What makes the neighborhood especially appealing is its position near the Burlingame border and the Easton Addition area. That gives residents a practical mix of prestige and convenience, with Downtown Burlingame, schools, and commuter routes all relatively close by. In day-to-day terms, Hillsborough Oaksbridge upscale properties offer more than scale. They also deliver usable lots, strong curb appeal, and a setting that includes true private cul-de-sac homes Hillsborough buyers are often hoping to find. For buyers comparing lower Hillsborough against nearby Burlingame estates, this pocket stands out as a highly private residential enclave near the Easton Addition luxury neighborhood while still carrying the larger-lot identity that defines Hillsborough.
Privacy: This neighborhood works well for buyers who value separation from neighboring homes and a calmer residential atmosphere. Several current and recent properties sit on large parcels with mature landscaping, cul-de-sac placement, and heavily treed surroundings. That combination supports the type of day-to-day privacy that is harder to replicate on smaller in-town lots.
Lot size:
A major reason buyers focus on Oaksbridge is the amount of usable land attached to many properties. Even within the current listing pool, lots run from roughly half an acre to well over two acres, which creates room for pools, guest accommodations, recreation space, or future customization. For luxury buyers who want more than just interior square footage, land value is a real part of the appeal here.
Lower Hillsborough access:
The neighborhood gives buyers a lower Hillsborough address without pushing them far from downtown Burlingame and key Peninsula routes. One current listing notes a walk of roughly half a mile to Downtown Burlingame, which reinforces how this area blends privacy with convenience. That balance is one of the clearest advantages of buying here instead of choosing a more remote hillside pocket.
Hillsborough, CA Market Information
$6,000,000
$1,500
45/55
$5,300,000
93.9%
$3,500
5 Real Estate Facts About Hillsborough Oaksbridge, Hillsborough, CA
- The latest neighborhood market page shows a median sale price of $25 million and a median sale price per square foot of about $1,350, with 56 days on market in the most recent snapshot.
- Current inventory in the neighborhood ranges from a vacant lot listed at $8.99 million on about 0.90 acres to an estate asking $28.88 million with 13,490 square feet and about 2.18 acres.
- Established single-family homes in the area commonly fall in a broad luxury range of approximately 2,500 to 4,000 square feet, based on recent and recorded homes.
- Typical lot sizes for many improved homes in the neighborhood are around 0.5 acres, though larger estate parcels can exceed 2 acres, especially among trophy properties and historic estate holdings.
- Architectural styles are varied but consistently high-end. Verified examples include contemporary, French contemporary, and timeless estate-style architecture, reflecting a neighborhood shaped by substantial remodels, rebuilds, and custom luxury design.
Latest Homes for Sale in Hillsborough Oaksbridge, Hillsborough, CA
Hillsborough Oaksbridge Map
Hillsborough Oaksbridge sits in lower Hillsborough near the Burlingame border. A simple way in is from El Camino Real through Burlingame, then up toward the residential streets around Fagan Drive and Sheldon Way. For many buyers, the easiest reference point is Downtown Burlingame, since the neighborhood is just above that area and still feels tucked away once you enter the estate streets.
Ready to take the next step?
We pride ourselves on being accessible to our clients. We believe it is of the utmost importance that you feel informed, up to date, and confident in our business relationship. We run our team with efficiency, combining high tech with high touch and being available to you at all times of the day and on weekends. Please contact us to discuss your specific goals; we look forward to working with you.
Who Lives in Hillsborough, CA
11,499
47.9
$438,734
3,605
3.22
650.6%
Things to do around Hillsborough Oaksbridge
Burlingame Avenue
Walkable downtown destination with shops, dining, cafes, and everyday convenience.
Washington Park
Classic local park with lawns, playgrounds, courts, and family recreation.
Burlingame Country Club
Historic private club with golf, social events, and traditional Peninsula prestige.
Sawyer Camp Trail
Scenic trail for walking, biking, and reservoir-side Peninsula views.
Schools in Hillsborough Oaksbridge
| School Name | Grades | Admission |
|---|---|---|
| North Hillsborough School | K - 5 | Public |
| Crocker Middle School | 6 - 8 | Public |
| Burlingame High School | 9 - 12 | Public |
| The Nueva School | PK - 12 | Private |
| Crystal Springs Uplands School | 6 - 12 | Private |
