San Mateo · San Mateo County

Hillsdale

Hillsdale is a mid-century planned neighborhood in the central part of San Mateo, with consistent 1950s-1960s ranch architecture on roughly 5,500 to 7,500 square foot lots.

Median Sale
$2,375,944
March 2026 · 36 closings

Hillsdale Real Estate Market Snapshot

Median Sale Price
$2,375,944
+13.8% vs prior-year median
Avg. Days on Market
12
% List Price Received
111%
Months of Inventory
1.4
Homes Sold (March 2026)
36
Median price trend
2025 · $2,087,500 March 2026 · $2,375,944
List-price received
111%
90%100%120%+

As of March 2026 · Source: SAMCAR/MLSListings

Living in Hillsdale

Hillsdale occupies the central and southeastern flatlands of San Mateo, anchored by the redeveloped Hillsdale Shopping Center and the adjacent Bay Meadows mixed-use district built on the former racetrack site. The core residential fabric is mid-century ranch construction on roughly 5,500 to 7,500 square foot lots, with newer townhome and condominium product layered in along the Bay Meadows edge. The neighborhood reads more uniform in scale than the hillside pockets to the west and trades on commute access, retail proximity, and school enrollment in Hillsdale High.

Schools

Hillsdale falls within the San Mateo-Foster City School District at the K-8 level and is served by Hillsdale High School in the San Mateo Union High School District (San Mateo-Foster City School District; San Mateo Union HSD). Specific elementary and middle school attendance areas vary by parcel within the neighborhood; buyers should confirm assignments directly with the district before writing offers, as boundary lines between adjacent streets can shift.

Lifestyle

Daily life in Hillsdale revolves around the redeveloped Hillsdale Shopping Center and the Bay Meadows district, with restaurants, boutiques, and public gathering spaces concentrated on the neighborhood's southern edge. Bay Meadows added parks and trail connections to the neighborhood fabric, and downtown San Mateo's B Street and Third Avenue dining corridor sits a short drive north. San Mateo's heritage tree ordinance protects mature canopy throughout the area (City of San Mateo).

Commute

Hillsdale's signature advantage is its own Caltrain station, which provides express service to San Francisco's 4th and King in roughly thirty minutes and southbound access to Palo Alto, Mountain View, and Sunnyvale within fifteen to twenty-five minutes. US-101 sits within minutes via 25th Avenue or Hillsdale Boulevard, and I-280 is reachable in about ten minutes via State Route 92. The Millbrae BART interchange one station north adds direct East Bay and SFO connectivity.

Market

The Hillsdale Market Right Now

Hillsdale trades inside the broader San Mateo single-family market, where the 2025 annual median sat at $2,087,500 across 534 closings with a median price-per-square-foot of $1,235 and an average eighteen days on market (SAMCAR/MLSListings). March 2026 numbers ran tighter and more competitive, with a citywide median of $2,375,944, median PSF of $1,496, and list-price-received of 111% (SAMCAR/MLSListings). Hillsdale's ranch fabric on 5,500 to 7,500 square foot lots typically trades in the mid-tier of that distribution, while Bay Meadows townhomes and condominiums create lower entry points for buyers who want the location and Caltrain access without the detached-home price band.
Transactions

What Buyers and Sellers Should Know About Hillsdale

Hillsdale sits within San Mateo's R-1 Single-Family Residential framework, which includes multiple R-1 sub-districts with varying minimum lot sizes and floor-area limits depending on neighborhood (City of San Mateo R-1 Development Standards). The city's heritage tree ordinance protects designated trees, with permits required for removal of qualifying species and sizes, and Hillsdale's mature street tree canopy is materially affected (City of San Mateo). Bay Meadows townhomes and condominiums typically carry their own HOA assemblies with monthly dues and recorded CC&Rs, so buyers should request current HOA financials and meeting minutes during the contingency period. At closing, San Mateo County's base documentary transfer tax of $1.10 per $1,000 of consideration applies, plus the City of San Mateo's additional municipal real property transfer tax (San Mateo County Assessor-Clerk-Recorder; City of San Mateo) — confirm the current rate with escrow at opening.
Field Notes

Market Notes by Lisa M. Lum

Recent activity in San Mateo through early 2026 has shown competitive bidding on updated mid-century homes and continued absorption of newer Bay Meadows inventory, with citywide list-price-received running at 111% in March 2026 (SAMCAR/MLSListings). Lisa Lum observes that Hillsdale buyers tend to weigh Caltrain proximity and Hillsdale Shopping Center walkability alongside school assignment, and that sellers who pre-pack inspection and HOA disclosures generally see faster contract execution in this pocket.

Updated 2026-05-06

Frequently Asked Questions about Hillsdale

What kind of housing stock is typical in Hillsdale?
The core of Hillsdale is mid-century ranch construction on roughly 5,500 to 7,500 square foot lots, with newer townhome and condominium product layered in along the Bay Meadows mixed-use district built on the former racetrack site.
Does Hillsdale have its own Caltrain station?
Yes. Hillsdale Station serves the southern San Mateo neighborhoods including Hillsdale and parts of Baywood, with express service to San Francisco in roughly thirty minutes and direct connections south to Palo Alto, Mountain View, and Sunnyvale.
Which high school serves the Hillsdale neighborhood?
Hillsdale High School in the San Mateo Union High School District serves the eastern and southeastern portions of San Mateo, including the Hillsdale neighborhood (San Mateo Union HSD). Some western parcels can fall within Aragon High's attendance area.
How do prices in Hillsdale compare to the broader San Mateo market?
Hillsdale single-family homes typically trade in the mid-tier of the San Mateo distribution, with newer Bay Meadows townhomes and condominiums offering lower entry points than detached homes in the surrounding ranch fabric.
What is the transfer tax in Hillsdale, San Mateo County?
San Mateo County charges a base transfer tax of $1.10 per $1,000 of consideration, paid by the seller at close. Some cities add a local supplemental tax. Hillsdale does not impose an additional municipal transfer tax beyond the county base.
Does Hillsdale require a sewer lateral inspection at sale?
Several San Mateo County jurisdictions require a private sewer lateral compliance certificate before close of escrow. The requirement varies by city — confirm with your transaction coordinator early in the listing process.
What disclosures are required when selling a home in Hillsdale?
California requires Transfer Disclosure Statement, Natural Hazard Disclosure, lead-based paint (pre-1978), water-conserving plumbing fixtures, and smoke and carbon monoxide alarm certifications. San Mateo County properties may also require sewer lateral compliance and local supplemental disclosures.
What is the difference between median and average home price in Hillsdale?
Median price is the middle number when all sale prices are sorted — half of homes sold above, half below. It resists distortion from a few very expensive sales. Average price is the arithmetic mean and can be skewed upward by individual high-end transactions. Median is the more reliable indicator of typical Hillsdale home pricing.

Search Hillsdale Homes

Browse current listings in Hillsdale with Lisa M. Lum.

Search Listings
Last updated 2026-05-06 · By Lisa M. Lum, Realtor® · Coldwell Banker Realty · DRE 02005150