In this blog, we are pulling together my favorite underrated San Mateo neighborhoods into one practical guide. If you watched my video on this topic, you already know I grew up in San Mateo County and I’ve spent years helping families buy and sell homes here. In this article I’ll walk you through the pockets I think are the most overlooked, what makes them special, realistic price ranges, lifestyle perks, and a few trade-offs to consider when exploring San Mateo neighborhoods.
Table of Contents
- Introduction
- Hillsdale — “The Lanes”
- Parkside & Shoreview
- Laurelwood
- Sugarloaf (adjacent to Laurelwood)
- Barisford Park / Bearer Park area
- The Highlands
- Sunnybrae (Sunny Bray) & 19th Avenue Park
- Edgewater Isle
- How to Pick Among San Mateo Neighborhoods?
- Practical Tips for Homebuyers Exploring San Mateo Neighborhoods
- FAQ — Common Questions About San Mateo Neighborhoods
- Final Thoughts — Why These San Mateo Neighborhoods Are Underrated
- Want to Explore These San Mateo Neighborhoods in Person?
Introduction
San Mateo neighborhoods vary dramatically: from waterfront lagoon communities to mid-century modern enclaves, to flat, walkable parkside streets. With twenty-seven different neighborhoods in the city alone, many areas fly under the radar even though they offer excellent value or a unique lifestyle. In this guide I focus on pockets that often get missed by buyers but deliver big upsides — strong floor plans, good access to transit and freeways, great parks, and sensible pricing relative to the Peninsula market.
Throughout this article you’ll see photos tied to timestamps from my original neighborhood video so you can visualize the streets and places I describe. I’ll also include specific price ranges and practical notes — the real, on-the-ground intel I share with clients shopping San Mateo neighborhoods every week.
Hillsdale — “The Lanes”
If you want one of the best examples of a small, family-oriented pocket among San Mateo neighborhoods, start with Hillsdale’s “The Lanes.” This cluster sits north of Hillsdale Boulevard, east of Alameda de las Pulgas (Alam), west of El Camino, and just south of Highway 92. The nickname “The Lanes” comes from street names like Brier Lane, Arbor Lane, and Louise Lane — and more importantly, from a string of cul-de-sacs and small parks that thread through the area.
Why I love this pocket: the cul-de-sac layout gives kids safe places to play, and many of the lots are a comfortable size — often 5,000–6,000 sq ft — with generous backyards. Most homes are ranch-style, one-level floor plans with attached garages that open to the backyard. That layout is a huge selling point: you get a normal-sized lot, a usable backyard, and an attached garage — features that are often compromised in more expensive Peninsula towns.
Price snapshot for Hillsdale (The Lanes): expect starting prices in the high $1 millions, with many sales between about $1.8M and $2.6M. The median in recent periods has been around $2.1M. For buyers targeting smartly laid-out homes with park access, The Lanes is a standout among San Mateo neighborhoods.
Parkside & Shoreview
Parkside and Shoreview are two adjacent pockets east of 101, south of Coyote Point, and straddling Third Avenue (which continues east of 101). These areas are among the most affordable San Mateo neighborhoods for entry-level buyers — think $1.1M to $1.6–1.7M in many cases. Compared to places like South San Francisco, Daly City, or San Bruno, you get similar economics but with better Peninsula access and markedly nicer weather.
What to know about the land: Parkside and Shoreview are built on engineered landfill — essentially filled portions of the bay. That means liquefaction risk in a major quake is something to understand and weigh. However, every part of the Bay Area comes with trade-offs: hill neighborhoods can be in high fire zones or inundation zones from reservoirs. For many buyers, the balance of affordability, one-level ranch homes, and access to the Bay Trail and Seal Point Park outweigh the risks.
Special perks: many homes are single-story ranch designs due to FEMA and flood-insurance restrictions (which are in the process of being rezoned in some blocks). When second-story restrictions relax, expect to see ADUs and more two-story additions — likely pushing values up. For people who love walking, the Bay Trail, Seal Point Park (with a great dog park), and Ryder Park with its kid water feature make these pockets excellent choices among San Mateo neighborhoods.
Laurelwood
Laurelwood sits just south of Highway 92 and east of 280 — a small hill pocket with convenient access to 280 and quick connections to 101. For many commuters, Laurelwood hits a sweet spot: you're up on the hill but only 3–4 minutes down to 101 when you need to. The neighborhood’s homes are typically built in the last 30–50 years (so not brand new, but modern by Peninsula standards), with two-story homes, attached garages, and decent yards.
Price snapshot: Laurelwood ranges from mid $1M on the low end to roughly $3M at the top, with medians in the $2.1M–$2.2M area. The floor plans are often buyer-friendly — kitchens that open to the backyard, a family room and dining room, and layouts that don’t require major structural changes.
Local conveniences: Crystal Springs Village and Laurelwood shopping centers provide groceries and local shops so you don’t have to drive into downtown San Mateo for every errand. For nature and family time, Laurelwood Canyon provides hiking and a relaxing park vibe that feels a world away even though you’re close to shopping and freeways.
Sugarloaf (Adjacent to Laurelwood)
Sugarloaf is a smaller master-planned pocket near Laurelwood with a few hundred homes. The product type is “single-family attached” — essentially townhouse-style homes that feel like houses. You’ll find two-car attached garages, tall ceilings, and open floor plans. Backyards tend to be lower maintenance patios instead of big grassy yards — perfect for buyers who want less upkeep.
Why buyers like Sugarloaf among San Mateo neighborhoods: value. You can often find 1,700–1,900 sq ft homes with three bedrooms and a loft/workspace in the roughly $1.5M–$1.9M range. For many buyers on a sub-$2M budget who want a modern-feeling layout without expensive yard maintenance, Sugarloaf frequently tops their list.
Beresford Park / Bearer Park Area
What I call Beresford Park (you’ll also hear locals say Bearer Park) is the neighborhood centered around the park of the same name, just south of Highway 92. The area is flat, walkable, and has a great community park with ball courts, skate park, playground, and even a community garden (which famously has a long waiting list).
Commuting advantage: Beresford Park sits equidistant between 101 and 280, so north–south commutes are straightforward. Also, Hillsdale Shopping Center is very close — it’s not just a mall, it’s a local destination with an Apple Store, food court, Pinstripes bowling, and restaurants that make the area feel conveniently urban without being downtown.
House types and pricing: most homes are single-level, but the past decade has seen buyers add second stories and large renovations. Lot sizes mostly fall in the 5,000–6,000 sq ft range; you’ll see some larger 7,000–7,500 sq ft parcels in the neighborhood too. Prices range from around $1.4M on the low end to nearly $3.8M for larger or extensively remodeled homes — with a recent median around $2.0–$2.1M.
The Highlands
The Highlands is one of the most interesting pockets among San Mateo neighborhoods because of the strong concentration of Eichler-style homes. Developed in the 1950s–60s by Joseph Eichler, this pocket has roughly 900 homes and about 10% of the state's Eichlers within San Mateo. These homes are celebrated for their inward-facing courtyards, walls of glass, post-and-beam construction, and radiant-floor heating.
What to expect: Eichlers typically have radiant in-floor heating (water heated in a garage boiler circulating through the floor) and an architectural language that emphasizes indoor–outdoor living. Buyers either love them or don’t — if you love modern mid-century details, The Highlands can be life-changing.
Practical notes: original Eichler materials and construction aren’t always the highest-end by today’s standards, so many buyers renovate down to the studs. Typical ranges for most Eichler homes in recent sales are in the $1.9M low end up to $4M+ for fully renovated showpieces, with a median around $2.5M. Most homes are one level and in the 1,400–2,000 sq ft range.
Sunnybrae & 19th Avenue Park
Sunnybrae is a compact neighborhood just west of 101, north of 92, and within easy walking distance to downtown San Mateo. It’s a small area, tree-lined, and highly walkable — streets like Birch and Grant are particularly charming. Within Sunnybrae there’s a pocket called 19th Avenue Park that includes several Eichler homes as a smaller Eichler cluster.
Price and product: median pricing in Sunnybrae has been roughly $1.7M with a low around $1.2M and highs near $2.2M. Most homes are two- and three-bedroom houses in the mid-1M to low-2M range. The Eichlers in 19th Avenue Park are typically a touch less expensive than Highlands Eichlers — often in the $1.5M–$2M range depending on condition.
Why buyers choose Sunnybrae among San Mateo neighborhoods: location. You can walk to downtown San Mateo’s restaurants, parks, and Caltrain, while enjoying quieter residential blocks and great schools like Sunnybrae Elementary and nearby Borel Middle and Aragon High.
Edgewater Isle
Edgewater Isle sits in that pocket between 101 and south of 92 — geographically it feels close to Foster City but is part of San Mateo. The community is built around a lagoon system and has that wide-water feel similar to Redwood Shores and Foster City. Homes are mostly townhome-style, two stories with attached garages, and many units offer waterfront views.
Pricing and trade-offs: these are typically mid-$1M units up to higher $1M ranges depending on water view and finishes. Being on landfill is a factor — like other east-of-101 neighborhoods, Eastwater Isle sits on filled land — but the lifestyle bonus of direct lagoon access, bay trail connections, and proximity to Bridgepointe Shopping (Target, Home Depot, Costco) often offsets that for buyers seeking convenience and a waterfront vibe at a share-of-market price.
How to Pick Among San Mateo Neighborhoods?
Choosing among San Mateo neighborhoods comes down to priorities: budget, commute, school needs, yard vs. low-maintenance, and tolerance for natural hazards (fill/landslide/fire/inundation). Here are a few quick frameworks I use with buyers:
- Value + family parks: The Lanes (Hillsdale), Barisford Park
- Entry-level Peninsula options: Parkside & Shore View, Sunnybrae
- Hills & commute balance: Laurelwood, Sugarloaf
- Architectural lovers: Highlands (Eichler homes), 19th Avenue Park Eichlers
- Waterfront/townhome lifestyle: Edgewater Isle
Practical Tips for Homebuyers Exploring San Mateo Neighborhoods
- Visit pockets at different times of day — mornings, evenings, and weekends — to get a feel for traffic, noise, and the neighborhood vibe.
- Ask sellers for recent utility and flood/earthquake reports; confirm whether properties are in FEMA flood zones or on filled land.
- If you love modern Eichler details, budget for renovations; many Eichlers are restored and command top-dollar but originals often need updates.
- Consider future resale: neighborhoods with single-family-attached homes (e.g., Sugarloaf) can be easier to afford now, but single-family-lot neighborhoods may attract a broader pool when you resell.
- Factor in school catchments if schools are a priority — many of the neighborhoods above tie into strong local elementary and middle schools.
FAQ — Common Questions About San Mateo Neighborhoods
Which San Mateo neighborhoods are best for families?
For family-friendly pockets, I consistently recommend The Lanes (Hillsdale), Beresford Park, and Laurelwood. Those areas combine parks, quiet streets, good-sized yards, and relatively easy freeway access. Sunnybrae is also great for families who prize walkability and downtown access.
Are there affordable neighborhoods in San Mateo?
"Affordable" on the Peninsula is relative. Parkside and Shoreview typically offer the most entry-level pricing among San Mateo neighborhoods, with many houses in the low-to-mid $1M range. Sugarloaf’s single-family-attached product also gives great value for buyers sub-$2M.
Should I be worried about living on landfill east of 101?
Landfill areas require a different risk assessment, especially for liquefaction in major earthquakes. That doesn’t make them “no-go” zones—many buyers choose Parkside, Shoreview, and Edgewater Isle because of affordability and location. Work with a local geotechnical consultant and your lender to understand insurance options and necessary disclosures.
What makes Eichler homes special in the Highlands?
Eichlers emphasize open plans, indoor–outdoor living, walls of glass, and radiant in-floor heating. They’re architecturally distinct. Many buyers renovate Eichlers while preserving mid-century features. If you love modernist architecture, the Highlands is a standout among San Mateo neighborhoods.
How does proximity to 92 or 101 affect neighborhood life?
Being near Highway 92 or 101 gives easy commute access, but it can add noise or visual impacts for homes very close to the freeway. In most pockets I recommend aiming for a few blocks' distance from the freeway for a balance of noise reduction and still-short ramps to get on and off.
Why These San Mateo Neighborhoods Are Underrated
Each of these pockets brings something distinct to the table: The Lanes offers safe cul-de-sac parks and classic ranch floor plans; Parkside & Shoreview give Peninsula access at starter prices; Laurelwood and Sugarloaf combine hill living with practical layouts; Beresford Park gives walkability and convenience; the Highlands feed the Eichler-lover’s soul; Sunnybrae marries location with charm; and Edgewater Isle provides water-front townhouse living without the cost of single-family waterfront homes.
When I help buyers search San Mateo neighborhoods, I encourage a balance of data and feel: look at median prices and comps, but also walk streets, sit in parks, and imagine daily life. Hidden gems are hidden for a reason — they may lack the sizzle of a headline neighborhood, but they often deliver the substance most families need: great floor plans, parks, commute efficiency, and community.
Want to Explore These San Mateo Neighborhoods in Person?
If you’re thinking about buying or selling in San Mateo County and want neighborhood-by-neighborhood advice, I’d love to be your Peninsula real estate resource. Drop me a note at hello@burlingameproperties.com or call/text 650-822-7088. I help clients walk through what matters most — schools, commute, resale, and the real feel of a neighborhood.
Whether you’re looking for an Eichler, a ranch on a cul-de-sac, a tidy single-family-attached plan, or a lagoon-front townhome, San Mateo neighborhoods have hidden gems ready for buyers who know where to look.
