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CRMLSEXP Realty
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BuyRentSellAbout
    1. Home
    2. /Neighborhoods
    3. /San Mateo
    4. /Hillsdale
    Hillsdale neighborhood in San Mateo, California – real estate
    San Mateo NeighborhoodsSan Mateo, CA

    Live in Hillsdale

    Diverse neighborhood surrounding shopping center with mix of housing types from condos to single-family homes. Good schools, transit access, and more affordable Peninsula entry point.

    Connect with a San Mateo Expert

    By submitting this form, you agree to our privacy policy. We respect your privacy and will never share your information with third parties.

    Trusted partner for Hillsdale & San Mateo Real Estate
    ★★★★☆ 4.9/5 • Top Rated Local Agents

    Homes for Sale in San Mateo

    Showing San Mateo listings — no Hillsdale-specific listings found yet

    View all San Mateo listings
    For Sale
    Residential for sale at 555 Laurel Avenue 614, San Mateo CA featuring 3 beds and 3 baths
    Residential

    555 Laurel Avenue 614

    San Mateo
    $3,250,000.00
    listing price
    Built 1980
    HOA $1778.0/mo
    Rarely available penthouse unit in San Mateo's premier condo community Gramercy on the Park. This luxurious 3-bedroom, 2.5-bathroom residence offers a generous floor plan with commanding views of the San Francisco Bay, East Bay, and Downtown San Mateo. A grand marble foyer grabs your immediate attention upon entry. This area provides access to all the core living areas and private suites. Numerous skylights and raised ceilings allow for abundant natural light throughout the unit. The spacious chefs kitchen boasts a center island, stone counters, ample cabinetry, and pantry area. An expansive balcony stretches the rear of the home, with direct access from the formal living and dining rooms. The primary suite offers multiple walk-in closets and a private sun room. Gramercy at the Park has exceptional amenities, starting with an incredible heated pool spanning the length of the central courtyard. It also includes a well-equipped fitness room, a 24-hour door man, 2-car parking with EV charger, dedicated storage and much more. Great restaurants, specialty grocery stores, shopping, transportation, and parks are all within walking distance. The Central Peninsula location offers close proximity to SFO International Airport, San Francisco, and Silicon Valley.
    3 beds
    3 baths
    2,510 sqft
    View Details
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    For Sale
    Residential for sale at 301 Engle Road, San Mateo CA featuring 2 beds and 2 baths
    Residential

    301 Engle Road

    San Mateo
    $2,395,000.00
    listing price
    Built 1952
    Light-Filled San Mateo Park Living With Close-In Convenience! Set at the end of a lane in sought-after San Mateo Park, this move-in ready home offers privacy and close-in convenience to shops and restaurants. Lovingly maintained by the same family for more than 40 years, this picture-perfect home is bright and light with fresh interior paint, refinished hardwood floors, and new carpet. Beyond the two-story home is a detached 2-car garage with an adjoining extra-large bonus room offering flexible space for recreation, office, or potential for an ADU. The deep lot with an array of colorful flowering trees further enhances the setting whether enjoying as is or expanding to personalize over time.
    2 beds
    2 baths
    1,580 sqft
    View Details
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    For Sale
    Residential for sale at 731 Crystal Springs Road, San Mateo CA featuring 3 beds and 2 baths
    Residential

    731 Crystal Springs Road

    San Mateo
    $2,688,888.00
    listing price
    Built 1958
    Major Price Improvement! Exceptional Opportunity! Fully renovated and move-in ready, this 3 bed, 2 bath home offers 2,200 sq ft of thoughtfully updated living space on a beautifully secluded 9,090 sq ft lot. Surrounded by mature trees, the property features multiple private outdoor areas, including a spacious front patio ideal for entertaining and a serene backyard retreat. The home has undergone a complete top-to-bottom renovation, including new flooring with leveled subfloor, smooth retextured walls, and fresh interior and exterior paint. The brand new kitchen features solid wood cabinetry, quartz countertops, and all new appliances. Both bathrooms have been fully remodeled with new plumbing, tile, vanities, and fixtures. Additional upgrades include a new 200 amp electrical panel, sub-panel, full home rewiring, new plumbing throughout, recessed lighting, enlarged closets, and two new sliding doors to the backyard. Located near the Hillsborough border and zoned for highly sought-after Aragon High School (10/10 GreatSchools).
    3 beds
    2 baths
    2,200 sqft
    View Details
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    For Sale
    Residential for sale at 1094 Bermuda Drive, San Mateo CA featuring 3 beds and 2 baths
    Residential

    1094 Bermuda Drive

    San Mateo
    $1,688,000.00
    listing price
    Built 1954
    HOA $500.0/mo
    Welcome to 1094 Bermuda Drive! Nestled in the highly sought-after Fiesta Gardens neighborhood of San Mateo, this beautifully maintained single-family home offers the perfect blend of timeless character and everyday comfort. This is the opportunity you've been waiting for in one of the Peninsula's most beloved communities. This bright and inviting 3-bedroom, 2-bathroom home features a smart, functional layout with 1,240 sq ft of living space on a generous 4,994 sq ft lot, all on a convenient single level, perfect for easy living. The attached 2-car garage adds everyday practicality that is increasingly rare at this price point. Step outside and discover why Fiesta Gardens is so adored. Walkable streets, Steps from Fiesta Meadows Park and the Pool, and effortless access to Highway 92 and 101 make this location an absolute commuter's dream. Whether you're heading to San Francisco, the South Bay, or SFO, you're perfectly positioned. (Some images outside of the home have been digitally altered)
    3 beds
    2 baths
    1,240 sqft
    View Details
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    For Sale
    Residential for sale at 1057 Shoal Drive, San Mateo CA featuring 2 beds and 2 baths
    Residential

    1057 Shoal Drive

    San Mateo
    $1,588,000.00
    listing price
    Built 1976
    HOA $180.0/mo
    Stunning single level waterfront home set along a coveted wide-water position with serene westerly views of the hills. Light-filled interiors and vaulted living spaces create volume and openness, while expansive windows draw the outdoors in and connect the home to its tranquil setting. Extensively updated throughout, the home offers a balance of comfort and modern convenience, including central air, skylights, custom counters, quality appliances, smart home features, an EV charger (Level 2), and a private boat dock. Both bathrooms have been updated, with the primary elevated to a true spa-like retreat, anchored by a steam shower, Hansgrohe fixtures, and a thoughtfully designed lighting experience that brings a sense of calm and restoration to daily routines. A finished attic/loft space adds valuable flexibility for a home office, studio, or additional storage. Whether its quiet mornings by the water, time out on the dock, or evenings watching the light shift across the horizon, the home offers a lifestyle that feels relaxed, elevated, and easy.
    2 beds
    2 baths
    1,310 sqft
    View Details
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    For Sale
    Residential for sale at 4106 George Avenue 5, San Mateo CA featuring 1 bed and 1 bath
    Residential

    4106 George Avenue 5

    San Mateo
    $635,000.00
    listing price
    Built 1965
    HOA $625.0/mo
    Discover resort-style living in one of San Mateo's most sought-after communities. This bright & beautifully appointed 1-bedroom, 1-bath condo offers 826 square feet of stylish, comfortable living in the highly desirable Lauriedale community. This home is perfectly positioned in the complex near all amenities. Inside, enjoy a spa-like bathroom, fresh carpet, luxury flooring, recessed lighting, & new double-paned windows. The kitchen features beautiful cabinetry & a breakfast bar ideal for entertaining. The spacious bedroom boasts a custom full-length closet with lots of storage. Step out to your large private deck which overlooks lush, peaceful green space - your personal outdoor retreat for morning al fresco dining, evening unwinding, or simply soaking in nature's beauty. Practical conveniences include a deeded carport/garage, large storage room, and water and garbage covered by HOA fees. Lauriedale's resort amenities feature multiple pools, clubhouse, tennis courts, & a full fitness center with locker rooms & saunas, all set among beautifully maintained grounds. Ideally located near Hillsdale Mall, downtown San Mateo, Highway 101, & the Belmont border, with easy access to top Silicon Valley employers, San Francisco, and Half Moon Bay. This is the home you have been waiting for!
    1 bed
    1 bath
    826 sqft
    View Details
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    For Sale
    Residential for sale at 537 Hurlingham Avenue, San Mateo CA featuring 4 beds and 5 baths
    Residential

    537 Hurlingham Avenue

    San Mateo
    $6,950,000.00
    listing price
    Built 1897
    A historic beauty in San Mateo Park, this timeless Cape Cod residence blends classic character with exceptional updates throughout. Rich brown shingles, crisp white trim, charming flower boxes, and manicured landscaping create stunning curb appeal, while the private, park-like backyard offers the ultimate setting for relaxation and entertaining with a sparkling pool, spa, half-court basketball area, and detached legal studio ADU with its own kitchen and bath. Inside, elegant formal living and dining rooms are filled with natural light and overlook the picturesque gardens. The updated kitchen opens seamlessly to the family room and backyard, creating effortless indoor-outdoor living, while a charming eat-in banquette provides the perfect space for casual dining. Upstairs, the luxurious primary suite offers peaceful garden views, a spa-inspired bath, and private office. Three additional bedrooms and an upstairs laundry area complete the thoughtfully designed floor plan. Beautifully updated throughout, this exceptional home combines timeless character, modern comfort, and outstanding versatility. Realist reflects 3,640 sq. ft. Floor Plans Visuals measured approximately 4,210 sq. ft., including 3,725 sq. ft. in the main residence and 485 sq. ft. in the detached legal ADU.
    4 beds
    5 baths
    3,640 sqft
    View Details
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    For Sale
    Residential for sale at 2203 Allegheny Way, San Mateo CA featuring 4 beds and 2 baths
    Residential

    2203 Allegheny Way

    San Mateo
    $2,450,000.00
    listing price
    Built 1957
    Nestled in the coveted Highlands neighborhood, this cherished Eichler offers a rare opportunity to own a true piece of mid-century modern history. Lovingly enjoyed by the same family for decades & originally selected as one of the neighborhood's model homes, this home embodies the timeless appeal of Eichler design paired with the warmth of true community living. Ideally positioned on a flat lot, this open concept single-story residence is filled with natural light, skylights, & seamless indoor outdoor flow. The spacious kitchen features ample cabinetry, built in storage, stainless steel appliances including a gas range, eat up bar, & opens beautifully into the main living space. Custom built-ins & a media cabinet add both style & functionality. Walls of glass connect the indoors to a lush backyard opening to serene open space and a private front courtyard, creating the quintessential California lifestyle Eichler enthusiasts adore. The flexible floor plan offers 4 bedrooms plus a bonus room or walk-in closet off the primary suite. Enjoy the home's timeless character as is or personalize it over time. Moments from Crystal Springs Village, the Highlands Recreation Center, top commuter routes including 280, 92, and 101, and beloved neighborhood traditions.
    4 beds
    2 baths
    1,840 sqft
    View Details
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    For Sale
    Residential for sale at 1909 Polo Court, San Mateo CA featuring 3 beds and 2 baths
    Residential

    1909 Polo Court

    San Mateo
    $2,288,000.00
    listing price
    Built 1955
    Beautifully refreshed single-level home tucked away on a quiet cul-de-sac in desirable San Mateo. Filled with natural light, 1909 Polo Court features soaring beamed ceilings, expansive living spaces, hardwood flooring, new lighting throughout, stylish contemporary finishes, and seamless indoor-outdoor flow to a private backyard retreat with patio space and mature citrus trees. The thoughtfully updated kitchen offers abundant cabinetry, generous prep space, new stainless steel appliances, and a sunny breakfast area ideal for casual dining or morning coffee. Well-proportioned bedrooms include a spacious primary suite with refreshed ensuite bath, complemented by a beautifully renovated hallway bathroom with modern finishes. Recent improvements include a whole-house electrical rewire, new insulation, ducting, water heater, sewer lateral, gutters and downspouts, irrigation and two sump pumps. Conveniently located near shopping, dining, parks, and commuter routes, this move-in ready home offers comfort, style, and thoughtful upgrades throughout. Welcome home!
    3 beds
    2 baths
    1,760 sqft
    View Details
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    Page 2 of 24  ·  209 total listings

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    About Hillsdale

    Diverse neighborhood surrounding shopping center with mix of housing types from condos to single-family homes. Good schools, transit access, and more affordable Peninsula entry point.

    Diverse neighborhood surrounding shopping center with mix of housing types from condos to single-family homes. Good schools, transit access, and more affordable Peninsula entry point.

    Why Hillsdale?

    Nature & Parks
    Hillsdale offers beautifully maintained green spaces, parks, and a peaceful suburban atmosphere.
    Vibrant Community
    A welcoming mix of families, professionals, and long-time residents gives Hillsdale its distinctive character.
    Dining & Amenities
    Hillsdale boasts a curated selection of restaurants, cafés, boutiques, and everyday conveniences.
    Top-Rated Schools
    Highly regarded schools make Hillsdale a preferred destination for families planning for the future.

    Schools & Education

    Hillsdale is served by highly regarded schools within the San Mateo Unified School District, making it a popular choice for families. Many campuses nearby have earned recognition as California Distinguished Schools, offering strong academic programs alongside arts, athletics, and community activities.

    For higher education, residents benefit from proximity to world-class universities and community colleges throughout the greater San Mateo region, supporting lifelong learning and a highly educated local workforce.

    Neighborhood Highlights

    Community Type
    San Mateo Neighborhoods
    City
    San Mateo
    Median Home Price
    $1600k

    Lifestyle & Amenities in Hillsdale

    Hillsdale offers residents an exceptional Southern California lifestyle with a carefully curated mix of dining, shopping, parks, and recreational opportunities. From boutique cafés and farm-to-table restaurants to weekend farmers markets and scenic trails, daily life here combines comfort and character in equal measure.

    Whether you're exploring the local arts scene, catching a sunset at a nearby beach, or simply enjoying the mild year-round climate, Hillsdale delivers the kind of neighborhood experience that keeps residents committed for the long term. Its walkable streets, community events, and distinctive identity make it one of San Mateo's most sought-after places to call home.

    Investment Insights for Hillsdale

    Market Growth

    Hillsdale has shown consistent property value appreciation driven by strong demand and limited inventory.

    +5.2%avg. annual growth

    Rental Demand

    Strong rental market with high occupancy rates and competitive yields for investors in Hillsdale.

    96%avg. occupancy rate

    Economic Outlook

    Diverse local economy with growing job opportunities in tech, healthcare, and professional services.

    Strongjob market growth

    Investment Disclaimer: Past performance does not guarantee future results. Real estate values can fluctuate. Consult with financial advisors before making investment decisions.

    Buyer's Guide: Buying a Home in Hillsdale

    Purchasing in Hillsdale requires understanding the local market, financing options, and neighborhood dynamics. Our experienced agents provide end-to-end guidance — from your first visit to closing day.

    1

    Get Pre-Approved

    Understand your budget and financing options before you start looking.

    2

    Work with a Local Expert

    Our agents know Hillsdale and San Mateo and can help you find the right fit.

    3

    Schedule Property Tours

    View homes in person to get a true feel for the property and the streets of Hillsdale.

    4

    Make an Informed Offer

    We'll analyze comparable Hillsdale sales and market conditions so you can bid with confidence.

    Get Expert Buyer Guidance

    Year-Round California Weather

    ☀️

    Average Temp

    72°F

    Perfect year-round climate

    🌤️

    Sunny Days

    260+

    Days of sunshine annually

    🌊

    Ocean Breeze

    Coastal

    Mild ocean climate

    🌡️

    Mild Winters

    55–65°F

    Comfortable winter temps

    Transportation & Connectivity

    Public Transit

    Hillsdale residents enjoy easy access to San Mateo's transit network where available, including local bus service, regional rail, and nearby commuter corridors that connect the neighborhood to surrounding communities.

    Major Freeways

    Highway access depends on the exact property location, commute direction, and daily traffic patterns throughout the greater San Mateo region.

    Airport Access

    Airport access from Hillsdale depends on the nearest regional or international airport and typical traffic patterns from this part of San Mateo.

    Downtown San Mateo10–20 min
    Nearest airportVaries
    North County30–50 min

    More San Mateo Neighborhoods

    Continue exploring communities in San Mateo, California

    View all neighborhoods
    Baywood neighborhood in San Mateo, California
    San Mateo Neighborhoods

    Baywood

    San Mateo

    Highly sought-after neighborhood with tree-lined streets, Eichler homes, and mid-century architecture. Excellent schools, parks, and strong community identity. Popular with families seeking classic Peninsula living.

    Explore Baywood
    Park Manor neighborhood in San Mateo, California
    San Mateo Neighborhoods

    Park Manor

    San Mateo

    Premium hillside neighborhood featuring larger estates, Bay views, and proximity to golf course. Quiet, established area with mature landscaping and spacious properties.

    Explore Park Manor
    Aragon neighborhood in San Mateo, California
    San Mateo Neighborhoods

    Aragon

    San Mateo

    Family-oriented neighborhood with traditional homes, excellent schools, and community atmosphere. Well-maintained properties, tree-lined streets, and strong neighborhood association.

    Explore Aragon
    Shoreview neighborhood in San Mateo, California
    San Mateo Neighborhoods

    Shoreview

    San Mateo

    Bayfront neighborhood with water proximity, parks, and views. Mix of housing styles with easy freeway access. More affordable while maintaining San Mateo schools and amenities.

    Explore Shoreview

    Ready to Call Hillsdale Home?

    Our San Mateo experts know this neighborhood inside and out. Let us find your perfect property at the right price.

    Browse ListingsContact an Agent