Homes for Sale in The Highlands, San Mateo, CA

The Highlands is a picturesque residential community located between Hillsborough and Belmont in San Mateo, California.

The Highlands offers expansive viewpoints looking west over the breathtaking scenery of Cahill Ridge, on Montara Mountain in the Santa Cruz Mountain Range. The landscape, structures, and atmosphere of a neighborhood may all make a difference when you wander or drive through it. The Highlands neighborhood is an excellent blend of serenity, sophistication, and convenience. Should you be more inclined to know more about The Highlands, you can reach out to us anytime.

SCENIC VIEWS: The Highlands residents can take advantage of the neighborhood’s long stretch of beautiful greenery and landscaping. The community’s roads are fairly broad and lined with mature trees and concrete pathways. The Highlands is bordered by vast swaths of open natural space, contributing to the neighborhood’s distinct character.

CUL-DE-SAC LAYOUT: Several cul-de-sacs may be discovered in The Highlands. This layout provides residents with additional privacy. It also creates a safe and tranquil atmosphere where families can develop a community spirit and camaraderie. Residents with a strong sense of community are more inclined to keep an eye on each other’s properties from a security standpoint.

CENTRAL LOCATION: The Highlands’ position is advantageous for folks who regularly commute to get to their work along the Interstate 280 and State Route 92 corridors. With minimal traffic, it takes around 25 minutes to get to downtown San Francisco and roughly less than 20 minutes to go to Sand Hill Road in Silicon Valley. Families are provided with ease of access to major roadways because of the strategic placement of the neighborhood in San Mateo, California.

Market Overview

San Mateo Market Information

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Homes in The Highlands

5 Real Estate Facts About The Highlands

  • Most residences in The Highlands go on the market with prices ranging from $160,000 to $3.15 million.
  • The majority of the houses in the area are equipped with three to five bedrooms and two to five-bath settings.
  • 1,360 sq. ft. to 3,300 sq. ft. are the typical interior living space offered by the homes in the area.
  • Residences are often built on lots ranging between 0.03 acres and 1.20 acres.
  • Homes in The Highlands are often one-story properties designed with Eichler or Tract architecture.
Find Your Home

Latest Homes for Sale in The Highlands

Open House


1439 Tarrytown St

San Mateo, CA, 94402
Open House


1268 Laurel Hill Dr

San Mateo, CA, 94402


2023 Ticonderoga Dr

San Mateo, CA, 94402
Open House


1484 Forge Rd

San Mateo, CA, 94402
Pending (Do Not Show)


1539 Forge Rd

San Mateo, CA, 94402

On the map

The Highlands Map

There are stunning vistas of mountains and rivers throughout The Highlands of San Mateo in California. The stretch of Polhemus Road defines the northern to the neighborhood’s eastern boundary. The Junipero Serra Freeway sets The Highlands’ western limit. The eastern boundary of the settlement is Polhemus Road, while Allegheny Way borders its southern region. Some notable landmarks around the area include Odyssey School, which is about 2.2 miles distant from the neighborhood’s north. It is about 4 minutes away by taking Polhemus Road and Ticonderoga Drive to reach. Residents and guests may also take advantage of San Mateo County Juvenile, located approximately 1.1 miles to the southeast of The Highlands. The San Juan Canyon Open Space Trailhead is roughly 1.8 miles southeast of the community via Ticonderoga Drive and may be reached in a 5-minute drive. The adjacent Interstate 280 access Fairview Crystal Springs Ceremony Site in approximately 8 minutes.

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Meet the locals

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Things to do in The Highlands

Highlands Recreation Center

The Highlands Recreation District is committed to delivering engaging, safe, and helpful activities and services to the Highlands Community.

The Field Club

A family-owned restaurant and pub specialized in artisan drinks, delicious food, and a warm and welcoming environment.

Dianda’s San Mateo

Tortes, panettones, cookies, cakes, and more can be found at this well-known bakery, which is housed in a typical setting.

San Mateo County Libraries

The San Mateo Public Library is a well-designed library with a lot of space and a broad range of art on exhibit. Several books and the Internet are readily accessible, as is a wide range of other information. For those of all ages, the San Mateo Library system offers a variety of various activities and services including movie screenings.


Schools in The Highlands

School NameGradesAdmission
Highlands Elementary SchoolK - 5Public
Ralston Middle School6 - 8Public
Carlmont High School9 - 12Public