The Highlands, San Mateo: What Makes This Neighborhood So Desirable?

If you are researching a San Mateo neighborhood that checks a lot of boxes—flat, walkable streets, easy freeway access, oversized lots, midcentury modern architecture and a true sense of community—the Highlands is one of the places you should be reading about. In this San Mateo neighborhood you get a rare combination: the practicality of single-level living on generous, flat lots plus the aesthetic and lifestyle benefits of Eichler-style homes that emphasize indoor-outdoor living. I want to walk you through what makes this San Mateo neighborhood special, what the homes are like, where they sit geographically, and what to watch for if you fall in love with one of these properties.

Table of Contents

• What Makes The Highlands Neighborhood in San Mateo So Unique?
• Where Is The Highlands Located?
• Shopping, Dining, and Local Amenities in San Mateo Highlands
• Lot sizes and topography: why the lots feel larger in The Highlands
• Understanding San Mateo’s Iconic Eichler Homes
• Key Construction Details to Know Before Buying an Eichler Home
• Why Homebuyers Love Eichlers
• Eichler Home Tradeoffs: Original Features vs. Modern Upgrades
• San Mateo Highlands Home Prices: What Buyers Can Expect to Pay
• San Mateo Highlands Community Amenities
• Inside a Renovated Eichler Home: A Modern Take on Mid-Century Design
• Practical Tips for San Mateo Homebuyers and Inspectors
• Who Buys in the Highlands and Why They Keep Coming Back
• FAQs About Living in The Highlands, San Mateo
• Is The Highlands the Right San Mateo Neighborhood for You?

What Makes The Highlands Neighborhood in San Mateo So Unique?

The Highlands is a San Mateo neighborhood tucked in the pocket where Highway 92 meets 280. Its location is one of the first things people fall in love with: close enough to downtown San Mateo to access restaurants and shops, yet set apart with quieter streets and larger yards. This San Mateo neighborhood is highly sought after for its flat, accessible lots—many of which range from 7,000 to 8,000 square feet—and for the unique midcentury Eichler-style homes that dominate the area.

Where Is The Highlands Located?

One of the practical strengths of this San Mateo neighborhood is the commute. Situated just east of 280 and north of 92, the Highlands offers convenient north-south access. If you work in the South Bay near Google, Apple, or other Big Tech campuses, 280 is a very direct route. If you need to get to San Francisco, heading north on 280 is straightforward. If your commute takes you toward the Peninsula or to 101, jumping on 92 is simple.

Commuters value this San Mateo neighborhood because it gives you quick freeway access without the feel of being on top of a freeway. Many homes look out across greenery and down toward 280, but the freeway sits below, out of immediate sight and often out of earshot. For people who want to balance a commute with neighborhood life, the Highlands hits a sweet spot.

Shopping, Dining, and Local Amenities in San Mateo Highlands

Living in this San Mateo neighborhood means you do not have to drive far for essentials. Crystal Springs Village and Crystal Springs Shopping Center are just a minute or two away and have a Safeway, Starbucks, and several popular breakfast and lunch spots. One exit south on 92 is the Laurelwood Shopping Center. Between those two hubs you can handle most grocery and dining needs without driving into downtown San Mateo.

That matters because it gives the Highlands a relaxed, almost suburban convenience while keeping you close to urban amenities when you want them. In this San Mateo neighborhood you can easily order deliveries, run quick errands, or spend a casual evening out without a long drive.

Lot sizes and topography: why the lots feel larger in The Highlands

A major selling point of this San Mateo neighborhood is the oversized, flat lots. In much of the Bay Area, lot sizes are often 5,000 to 6,000 square feet. The Highlands stands out because the majority of lots are 7,000 to 8,000 square feet and, importantly, flat. Flat lots are rare on the Peninsula and they offer practical benefits for accessibility and long-term living. If you prefer single-level homes or want a place without interior stairs for aging-in-place, this San Mateo neighborhood is ideal.

Flat lots make it easier to enjoy outdoor living, add landscaping, or expand a house with fewer grading challenges. In this San Mateo neighborhood, those larger flat yards are a major reason buyers choose to pay a premium.

Understanding San Mateo’s Iconic Eichler Homes

One of the most distinctive features of this San Mateo neighborhood is the prevalence of Eichler-style homes. These midcentury modern homes were developed by Joseph Eichler and his company in the postwar era to bring modernist design to middle-class families. The Eichler aesthetic emphasizes post-and-beam construction, open floor plans, a strong connection between inside and outside, walls of glass, and uncomplicated, functional design. In this San Mateo neighborhood you will find over 900 Eichler homes that carry that distinctive look and spirit.

Eichler homes tend to have fewer external windows at the street-facing facade and dramatic picture windows that look into private backyards or atriums. Many floor plans include a courtyard or atrium in the center, literally bringing the outside into the heart of the home. The interior layout emphasizes living spaces and family time, with a flow that was ahead of its time in the 1950s and 1960s.

Key Construction Details to Know Before Buying an Eichler Home

There are a few important construction characteristics common to Eichlers in this San Mateo neighborhood you should understand:

• Post-and-beam construction. The walls are not typically load-bearing in the same way as stick-built homes, allowing for large expanses of glass and open plans.
• Slab-on-grade foundations. Most homes in this San Mateo neighborhood are built on slabs, which means there is no crawl space. That keeps homes low to the ground and accessible, but it also makes access to plumbing and heating systems harder.
• Radiant floor heating. Many Eichlers have radiant heat supplied by a boiler in the garage with hot water running through pipes embedded in the slab. Radiant heat is even and comfortable, but the pipes are inside the slab which complicates repairs.

Because of radiant heating and slab construction, buyers in this San Mateo neighborhood should ask for a pressure test on the radiant heating system during inspections. A burst pipe embedded in the slab is an expensive problem and can be prevented or discovered before closing with proper testing. I tell every client this: if you buy an Eichler in this San Mateo neighborhood, get a pressure test on the radiant system if it exists.

Why Homebuyers Love Eichlers

Eichlers are not for everyone, and I always tell buyers that openly. If your heart is set on a Victorian or a Craftsman with ornate trim and narrow rooms, an Eichler will not be that house. But for buyers who love clean lines, modernism, and the indoor-outdoor living ethos, these homes are dream properties. In this San Mateo neighborhood Eichlers attract collectors and renovators who wait years for the right house to come on the market. Some buyers purchase multiple Eichlers over time to restore them because there is a satisfying, almost therapeutic process in bringing these homes back to their best.

This San Mateo neighborhood also has professionals—architects and contractors—who specialize in Eichlers. That specialization makes renovations smoother because the design and systems are distinct from conventional homes. When you love Eichlers, this San Mateo neighborhood feels like home in a way other neighborhoods may not match.

Eichler Home Tradeoffs: Original Features vs. Modern Upgrades

Many Eichlers were marketed as accessible modern homes for middle-class buyers in the 1950s and 1960s. That meant materials and construction were focused on affordability with style. As a result, the original builds sometimes had thinner walls, less insulation, and glazing that would not meet today’s tempered glass standards. Roofs and other systems from the original construction may be nearing end of life in many properties in this San Mateo neighborhood.

These are not deal-breakers, but they are things to factor into a budget. The good news is many of these elements are fixable with reasonable renovation budgets. Structural changes to the floor plan are more expensive, but replacing roofs, upgrading glass, adding insulation or reworking mechanical systems is often straightforward. In this San Mateo neighborhood buyers are willing to invest in upgrades because the lot, the plan and the style are so desirable.

San Mateo Highlands Home Prices: What Buyers Can Expect to Pay

Homes in this San Mateo neighborhood are not inexpensive. Over the last year the average and median sale prices have ranged from roughly $2.55 million to $2.7 million. You generally will not find anything under $2 million in the Highlands. Most houses are three or four bedrooms and sit on those larger flat lots that help justify the price. At the higher end of the market you will see low and mid $3 million sales for fully renovated Eichlers with great views, culde-sac locations and no freeway noise.

How price varies within this San Mateo neighborhood often comes down to renovation quality, view, location within the neighborhood and whether you can hear freeway noise from the backyard. A home closer to 280 with obvious freeway sound will trade for less than a quieter home on a culde-sac with a killer view and private backyard.

San Mateo Highlands Community Amenities

Beyond the houses themselves, this San Mateo neighborhood scores high for community amenities. Highlands Elementary is a top-rated school and is the neighborhood elementary for many families. There is also a community recreation center centrally located in the Highlands, which is a rare and valuable neighborhood asset on the Peninsula. Parks, trails and open space are nearby as well—Laurelwood Park and the Sawyer Camp Trail are within short drives or bike rides, giving residents access to hiking, running and long stretches of pleasant outdoor activity.

If you love being outdoors, this San Mateo neighborhood gives you easy access to the kinds of walks and rides that make day-to-day life feel richer.

Inside a Renovated Eichler Home: A Modern Take on Mid-Century Design

I want to describe a specific example to show you what a renovated Eichler in this San Mateo neighborhood can feel like. I visited a house built in 1956 that underwent a major renovation in 2017. The owners bought the home after it had been lived in by one family for decades. Their goals were practical and aesthetic: open up the plan to better support entertaining, celebrate the post-and-beam construction, and preserve the indoor-outdoor connection that defines Eichlers.

Originally, the kitchen was small and partially walled off. The first thing the owners did was remove a partial wing wall and open the kitchen into the main living area. Where the old layout forced you to see the refrigerator right when you walked in, the new plan creates a much cleaner arrival sequence and a much larger feeling living space. The fireplace remained the original element and anchors the room as it did for the prior owners.

The renovation honored Eichler details like the long redwood beams and post-and-beam structure. The ceilings were exposed and treated in a way that references the original redwood look. Where interior walls were originally mahogany, the owners chose modern materials that reflect the inside-outside motif—bringing exterior cladding materials inside and using consistent floor materials that blur the boundary between inside and outside.

One elegant trick the owners used was custom cabinetry to visually divide the kitchen from the living area without closing it off. Walnut-clad cabinets on the living room side provide warmth and texture while white cabinetry on the kitchen side keeps the cooking area bright. An appliance garage hides clutter, and a peninsula island includes a low box that obscures dirty dishes from the dining area when guests are present. These small design choices make daily life easier while keeping the home visually clean and modern.

Details and furnishings: respecting period pieces

The owners leaned into midcentury furnishings and period details. They highlighted things like globe pendant lighting that was original to Eichler developments. There are still manufacturers making replica globe lights and other period fixtures so you can restore or maintain an authentic look. They also preserved a couple of iconic pieces of furniture that fit perfectly into the spaces, like a Hans Wegner or a vintage sling sofa, which feels right in the postwar modern context.

Skylights, atria and walls of glass bring in light in ways newer homes often try to emulate. In the house I visited, skylights in the interior zones made up for areas that do not receive as much direct natural light, balancing bright living spaces with more intimate private zones.

Practical Tips for San Mateo Homebuyers and Inspectors

If you are considering buying in this San Mateo neighborhood, here are practical steps I recommend:

• Request a radiant heat pressure test if the home has radiant floor heating. This can reveal leaks in the slab lines before they flood the house.
• Budget for systems upgrades if the roof, glazing or insulation are original. These are common maintenance items in Eichlers.
• Work with an architect or contractor experienced with Eichlers if you plan structural changes. Post-and-beam homes behave differently than framed houses, and preserving the aesthetic while modernizing systems takes experience.
• Listen for freeway noise on site visits, especially in the backyard. Sound will affect value and livability in certain micro-locations within this San Mateo neighborhood.
• Consider the lot orientation and whether you want a private courtyard or large backyard. Lot size and flatness are some of the biggest assets in this San Mateo neighborhood, so align your priorities around outdoor living or expansion plans.

Who Buys in the Highlands and Why They Keep Coming Back

Buyers in this San Mateo neighborhood are a mix of design lovers, families who value single-level homes and empty nesters seeking easy living. Architects and creatives often gravitate toward Eichlers for the clarity of the design and the opportunities for tasteful renovation. Families appreciate the top-ranked elementary school and the community rec center. And for many buyers, the combination of flat large lots and this distinct architectural language is simply irresistible.

People who buy here often stay for the long term or return when the right property becomes available. That loyalty keeps demand strong for homes in this San Mateo neighborhood.

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FAQs About Living in The Highlands, San Mateo

How close is this San Mateo neighborhood to major tech employers?

The Highlands is right by Highway 280 and Highway 92, which gives very convenient north-south freeway access. You can reach the South Bay tech campuses quickly via 280 and get up to San Francisco on 280 as well. The location is one of the main reasons people choose this San Mateo neighborhood.

Are there good schools in this San Mateo neighborhood?

Yes. Highlands Elementary is a strong neighborhood school and is one of the reasons families choose to move to this San Mateo neighborhood. Always double-check current enrollment boundaries and policies online if school choice is a major factor for you.

What are typical lot sizes in this San Mateo neighborhood?

Most lots are larger than typical Peninsula lots, commonly 7,000 to 8,000 square feet, and importantly they tend to be flat. That flatness is rare and valuable, giving you easier single-level living and outdoor space options uncommon elsewhere on the Peninsula.

Do Eichler homes in this San Mateo neighborhood have basements or crawl spaces?

No. Most Eichlers here are slab-on-grade, meaning there is no crawl space. That makes them accessible and low to the ground but also complicates access to plumbing and radiant heating lines embedded in the slab.

What should I ask my inspector when touring an Eichler in this San Mateo neighborhood?

Ask specifically about radiant floor heating and request a pressure test if applicable. Check the state of glazing, the roof, insulation, and whether any structural modifications were done properly to preserve the post-and-beam system. Working with an inspector familiar with Eichlers is ideal.

What price range can I expect in this San Mateo neighborhood?

Over the past year the median and average prices have ranged roughly between $2.55 million and $2.7 million. Most homes list above $2 million, and fully renovated houses with great views can reach the low to mid $3 million range.

Is The Highlands the Right San Mateo Neighborhood for You?

If you value flat, walkable lots, love midcentury modern design and want convenient freeway access without living in a dense urban core, the Highlands is one of the strongest San Mateo neighborhood options on the Peninsula. It blends practical daily living needs with architectural distinction. The oversized flat lots make long-term living and accessibility easy, the Eichler homes provide a design language many people adore, and the nearby amenities and outdoor options round out a lifestyle that is hard to match.

If you are considering a move to this San Mateo neighborhood, take your time to tour several Eichlers so you can feel the differences in floor plans, lot positions, and renovation quality. Ask for specific inspections around radiant heat and slab plumbing, and work with contractors who understand post-and-beam preservation if you plan to renovate. When you find the right house in this San Mateo neighborhood, it can be a place to live beautifully for decades.

If you want to dive deeper into specific homes or need a local resource to evaluate listings in this San Mateo neighborhood, I am available to help guide you through the process and point out the neighborhood nuances that matter most when buying or renovating an Eichler-style home.