San Mateo Park vs Baywood: Two of the most expensive neighborhoods in San Mateo, CA

Table of Contents

• The Appeal Behind San Mateo’s Most Expensive Neighborhoods
• San Mateo Park: Architecture, Lot Sizes & Market Trends
• Baywood & Aragon: Schools, Styles & That “Classic San Mateo” Feel
• Lifestyle Trade-Offs: San Mateo Park vs. Baywood & Aragon
• What the Latest Data Says About Both Neighborhoods
• Smart Tips for Shopping in San Mateo Park or Baywood
• How to Decide: San Mateo Park vs. Baywood & Aragon
• FAQs About San Mateo Park, Baywood & Aragon  
• Final thoughts

The Appeal Behind San Mateo’s Most Expensive Neighborhoods

When you hear “most expensive neighborhoods in San Mateo, CA” think of three core strengths that draw buyers: location, lot size and privacy, and neighborhood character . 

The experience starts in downtown Burlingame and moves west through Burlingame Park into San Mateo Park. The transition is noticeable: from active retail corridors and bakeries to streets with islands, mature trees, and hedged frontages. These streets feel established. The islands and medians you see were originally designed for pre-automobile travel patterns, and they contribute to the quiet, residential feel that defines San Mateo Park.

That leafy ambiance matters. Tree density is one of the most underrated contributors to perceived neighborhood quality. San Mateo Park likely has the highest tree density among flat neighborhoods on the Peninsula, and that canopy not only elevates curb appeal but also helps maintain privacy and a sense of enclosure.

San Mateo Park: Architecture, Lot Sizes & Market Trends

San Mateo Park is over a century old. Expect stately homes, motor courts, pie-shaped lots, and Spanish or Mediterranean influences alongside classic shingle-sided houses. Typical lot sizes are meaningful — the median lot for recent sales sits near 9,000 square feet, with multiple sales over 10,000 square feet in the current year. That translates into a neighborhood where privacy and usable outdoor space are premium features.

Market patterns here reflect scarcity and desirability. There are only a handful of listings at any given time — historically around 2 to 3 new listings per month — and the average days on market for competitively priced homes is short. If an attractive house hits the market in San Mateo Park, expect offers quickly. Recent distribution of closed sales helps illustrate the range buyers are paying: most sales have clustered between the mid 3 millions and low 5 millions, with a handful pushing higher into the 6 to 8 million band.

What you get for price in San Mateo Park

• Lot size: median about 9,000 square feet, several lots over 10,000 this year.
• Home size: median square footage around 2,900 square feet.
• Sales volume: limited supply — roughly two to three new listings per month.
• Days on market: roughly 10 days for desirable listings.

Baywood & Aragon: Schools, Styles & That “Classic San Mateo” Feel

Baywood and Aragon are often grouped together as an alternative to pricier pockets like Burlingame or San Mateo Park. The full Baywood area includes multiple sub-neighborhoods: Baywood proper, Aragon, Homestead Housing, Foothill Terrace, and Baywood Knolls. Together, these pockets offer a wider range of housing types from condos to ranch-style single-level homes and larger Spanish-revival houses.

A standout advantage for many buyers is walkability to downtown San Mateo and the rare ability to walk to an elementary, middle, and high school from many neighborhoods in Baywood. That continuity is a huge win for families who want a long-term stay-in-place option for school-aged children. The area also benefits from a deep roster of restaurants and shops in downtown San Mateo, making it an appealing balance of convenience and residential calm.

Market snapshot: Baywood and Aragon

The greater Baywood Aragon area sees more inventory than San Mateo Park — roughly five to six sales per month across the combined neighborhoods. A typical home selling in the greater area this year has median characteristics around 2,100 square feet of living area and a median lot size near 6,100 square feet. Baywood proper often shows a larger median lot, roughly 7,600 square feet.

Price points in the greater Baywood Aragon cluster are generally more accessible than San Mateo Park. Where San Mateo Park’s median sale price sits in the high 3 millions, Baywood’s median sale price this year edged toward $3.9 million in some pockets, while Aragon’s median was lower, around the mid $2 millions. That spread makes the area attractive to buyers who want premium Peninsula living at slightly better value compared to the most expensive neighborhoods in San Mateo, CA.

Lifestyle Trade-Offs: San Mateo Park vs. Baywood & Aragon

When choosing between San Mateo Park and Baywood, the decision often comes down to two questions: do you prioritize larger, private historic lots or closer access to downtown amenities and schools? Think of San Mateo Park as a setting for buyers who value expansive shading trees, larger yards, and a quieter street rhythm. Baywood is better for buyers who prioritize walkability to downtown San Mateo, direct access to multiple schools, and a neighborhood that still offers gardens and mature landscaping but often at slightly lower price per square foot.

• San Mateo Park strengths: larger median lot size, strong tree canopy, historic character, a strong premium for privacy and charm.
• Baywood/Aragon strengths: closer access to downtown San Mateo, walkable school corridors, more frequent inventory and slightly more accessible price bands.

Commuting and location flexibility

Both neighborhoods enjoy excellent Peninsula connectivity. If one partner commutes to San Francisco and the other to Silicon Valley, the location of either neighborhood makes highway access straightforward. Baywood sits a little closer to downtown San Mateo and the Caltrain station options, while San Mateo Park gives you the Burlingame downtown feel on the northern edge. Choosing one over the other often boils down to a commute minute or two and whether you want a stronger downtown near your front door.

What the Latest Data Says About Both Neighborhoods

Numbers matter in markets that trade on scarcity. Here are concise, comparative metrics to help frame realistic expectations for buyers:

1. San Mateo Park: about 24 listings year to date, median sale price roughly $3.7 million, median size about 2,900 square feet, median lot size around 9,000 square feet, average days on market near 10 days.
2. Baywood & Aragon combined: about 55 sales year to date, median home size about 2,100 square feet, median lot size around 6,100 square feet, Baywood proper with a higher median lot size around 7,600 square feet, median prices varying from mid $2 millions in Aragon to roughly $3.9 million in Baywood pockets.

Those figures show why two homes that look similar on paper can trade for quite different prices depending on the neighborhood moniker and specific lot characteristics. For many buyers, a few thousand square feet of lot or the presence of a mature tree-lined street is the deciding factor between paying a premium or finding better value nearby.

Smart Tips for Shopping in San Mateo Park or Baywood

• Expect low inventory. When a desirable property lists in either neighborhood, prepare to act quickly. Offer timelines are often measured in days, not weeks.
• Look beyond photos. A lot’s usable area, topography, and privacy trees matter more than raw acreage in many Peninsula neighborhoods.
• Consider off-market opportunities. In tight markets, off-market or pocket-listing opportunities can be the route to finding a home before strong competition.
• Be realistic about size expectations. Two-bedroom homes are rare in these pockets; typical minimums run larger than in other parts of the Peninsula.

How to Decide: San Mateo Park vs. Baywood & Aragon

Answering the simple question “Which neighborhood is right for me?” is easiest when you stack preferences:

• If top priorities are large, private lots, a high tree canopy, and historic architecture, San Mateo Park is likely the better fit. It commands a premium for privacy and charm and buyers should be comfortable stretching budgets into the high 3 millions to 6 millions and beyond for the largest properties among the most expensive neighborhoods in San Mateo, CA.
• If walkability to downtown San Mateo, school proximity, and slightly more inventory are priorities, Baywood or Aragon offer excellent alternatives. Expect a range from high 2 millions up to the mid 4 millions depending on lot and home upgrades.

Small features matter. San Mateo Park islands, mature hedges, and motor courts give a unique streetscape that rarely appears elsewhere. Baywood’s wider streets and the ability to walk to Baywood Elementary and Aragon High provide family-oriented convenience that is rare on the Peninsula.

Want more neighborhood-level resources?

If you found this comparison helpful, I put together a complete San Mateo County city-by-city guide on my website with block-level recommendations, walkability scores, off-market tips, and more insider data you won’t find elsewhere. Visit burlingameproperties.com to explore the guide, sign up for neighborhood alerts, or join the free monthly newsletter at livinginsanmateocounty.com.

FAQs About San Mateo Park, Baywood & Aragon 

What price range should buyers expect in San Mateo Park?

Recent activity shows a median sale price in the high $3 millions with multiple sales in the $4 to $6 million range and a few approaching $8 million. Lot size, privacy, and historic character strongly influence value.

Is Baywood more affordable than San Mateo Park?

Baywood and Aragon are generally more accessible. Baywood median prices can sit near $3.9 million in the most sought pockets, while Aragon often shows medians in the mid $2 millions. The difference often comes down to lot size and proximity to downtown amenities.

How much inventory can I expect?

Inventory is limited in both areas. San Mateo Park averages roughly 2 to 3 new listings per month. The greater Baywood Aragon area sees about 5 to 6 sales per month across its neighborhoods.

Are there family advantages to living in Baywood?

Yes. Baywood is one of the few Peninsula areas where you can walk to an elementary, middle, and high school. For families who want a single neighborhood for their children's schooling from start to graduation, this is a major benefit.

How fast do homes sell?

Desirable, competitively priced homes in San Mateo Park often sell within a week or two. Baywood sales vary, but attractive listings also move quickly in the current market. Be prepared to move fast and be data-driven when making offers.

Final thoughts

Both San Mateo Park and Baywood represent what buyers are willing to pay for on the Peninsula: location, trees, and lifestyle. Choosing between them requires balancing the premium for large historic lots and privacy against the convenience of walkable schools and downtown life. Either way, you are looking at two of the most expensive neighborhoods in San Mateo, CA where a measured search strategy, quick decision-making, and an understanding of local inventory cycles will pay dividends.

If you want the combination of a leafy, private lot and stately architecture, San Mateo Park is worth the premium. If you would rather tilt toward walkability, schools, and slightly better value per square foot while staying in a prime Peninsula location, Baywood and Aragon deserve a close look. Either choice signals membership in the top tier of San Mateo, CA neighborhoods and the lifestyle that comes with it.