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$5,420,000
4 Beds ⋅ 3 Baths ⋅ ML82047419 MLS
In the heart of sought after San Mateo Park, this stately circa 1924 Tudor reflects the enduring character and architectural grace that define one of the Peninsula's most treasured neighborhoods. Timeless details - richly paneled walls, leaded glass accents, decorative ceiling, and fine millwork - are complemented by thoughtful updates, including a remodeled kitchen, beautifully renovated primary suite bath, and upstairs carpet. Grand formal living and dining rooms are balanced by everyday comfort in the expansive family room, which opens fully to the kitchen for modern living, and the four bedrooms are all arranged upstairs. The entire home is bright and light with excellent proportions for today's lifestyle. The approximately one-third-acre lot offers exceptional outdoor space with a fireplace courtyard, large rear yard, raised garden beds, and a charming Western-themed barn. Ideally located between downtown Burlingame and San Mateo, the home offers classic elegance in a premier setting.

641 Crescent AVE, San Mateo

Listed by Mark Johnson, 650-685-7648 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Emma Elfving from APR
$3,805,000
4 Beds ⋅ 3 Baths ⋅ ML82047066 MLS
This magnificent home, situated on an oversized lot, combines stunning, renovated interiors and a timeless exterior to provide the perfect balance of style and comfort. Grand-scale living spaces bathed in a crisp, neutral palette offer a seamless indoor-outdoor flow, integrating the interior with the rear yard oasis and expansive deck. The beautifully updated, bright, and open floor plan revolves around a gourmet kitchen and great room featuring a generous central island, Thermador appliances, quartz counters, and two skylights. Light streams in from every direction, while glass doors flow effortlessly out to the resort-style outdoor patio areas and lush gardens ideal for entertaining. The main level includes a junior primary suite plus two additional bedrooms and an updated hall bath, all thoughtfully grouped together. The upper level features a private sitting area or office and the luxurious primary suite, complete with two walk-in closets and access to a private patio via glass doors. Finished with a two-car attached garage and ample guest parking, this property is truly the perfect "home sweet home." Located within the highly sought-after Baywood School District and just minutes from lively downtown San Mateo, shopping, dining, parks, and commute routes. Welcome home!

678 Barneson AVE, San Mateo

Listed by Ronda O'Leary, 650-520-8390 from Compass
(If provided) CoList: from

Sold listing courtesy of William Lister from CBR
$3,360,000
4 Beds ⋅ 3 Baths ⋅ ML82046069 MLS
With a gated front courtyard, framed by a rose garden, this home not only has curb apparel but also has an ideal layout with an expansive kitchen/family room, two-car garage and a swimming pool in the back. The updated kitchen means business with a Wolf range, large island and stainless steel appliances. The kitchen flows straight into the great room and to the outside patio for dining. There's also a formal living room and dining room along with a bedroom/bathroom on the main level. Upstairs, the primary suite has views, a walk-in closet and an ensuite bathroom. Plus there's two more bedrooms and a hall bath on the second level as well. In addition to the outdoor dining area in the backyard, there's also a spectacular swimming pool and a turf area for play. With the front lawn, rose garden, back patio and a pool this home lives large on all sides. Perfect for hosting a summer barbecue or just enjoying a quiet evening, Welcome home!

714 Barneson AVE, San Mateo

Listed by The Dwyer Group, (650) 931-2036 from Compass
(If provided) CoList: from

Sold listing courtesy of Anna J Wang from FQLT
$1,700,000
4 Beds ⋅ ML82046369 MLS
First time on the market in over 50+ years this rare Mid-Peninsula Duplex offers Investors and potential owner-users have the opportunity to acquire two homes on one parcel. 1015-1017 10th Ave is a well-situated duplex located in the thriving city of San Mateo, California. Situated on a 4,800 square foot parcel of land, the subject property was originally constructed in 1939 and has a gross building area of approximately 2,799 square feet, offering its tenants beautifully designed two-bedroom single-family floor plans. Tenants enjoy the privacy of single-family living with no shared walls and convenient amenities such as private garage parking and individual fenced backyards. San Mateo is strategically located between San Francisco and San Jose. The city is well situated and offers an ideal climate in a robust and successful community and region. San Mateo offers a vibrant business and retail environment with several major shopping centers and an active downtown area. Many notable attractions in the city include the many street retailers lined along North El Camino Real, the popular Hillsdale Shopping Center, and San Mateo Medical Center.

1017 10th AVE, San Mateo

Listed by Cole Simpson, 650-391-1735 from Marcus & Millichap
(If provided) CoList: from

Sold listing courtesy of Duydat Vu from DAT
$1,650,000
4 Beds ⋅ ML82044974 MLS
Pride of Ownership Duplex in Prestigious Hillsdale Neighborhood bordering Westwood Knolls. First time on the market in over 45 years! Excellent opportunity for owner-occupier or investor. Nicest property on the street strategically positioned on an oversized corner lot. Beautiful mature landscaping creates attractive curb appeal. Two very well maintained homes with private yard areas. Each home offers a private garage that includes a washer & dryer. Upgraded electrical system and newer water heaters. Opportunity to convert garage space into ADU! Prime location walking distance to Hillsdale Shopping Center and the newly improved Hillsdale Caltrain station. Best-in-class neighborhood amenities, easy commuter access, and major planned redevelopment activity create durable rental demand and long-term value capture. Hillsdale Shopping Center is a full-service retail destination with 130+ stores, a modern dining terrace and a luxury cinema, offering everyday conveniences and lifestyle retail minutes from the property.

34 & 36 W 38th AVE, San Mateo

Listed by Matthew Thomson, 650-515-6555 from Compass
(If provided) CoList: Bryan Danforth from Compass

Sold listing courtesy of Rachid Atie from SCPR
$2,050,000
4 Beds ⋅ 3 Baths ⋅ ML82044463 MLS
EXCEPTIONAL property with endless possibilities for multi-generational living or investment. This oversized lot, 2 parcel property features a 1934 3 bed 2 bath Tudor, large updated eat in kitchen w/ stainless steel appliances as well as an open airy dining room and laundry room. The home is highlighted by rich architectural details, vintage craftsmanship, and an abundance of old-world charm. The well-appointed ADU provides exceptional flexibility with 1 bedroom, 1 bathroom, and an additional large bonus space perfect for a home office, laundry room, or creative studio. The large property continues to impress outdoors with an expansive backyard designed for both relaxation and productivity. Enjoy a built-in BBQ for entertaining, established garden beds, and a charming chicken coop-perfect for those seeking a more sustainable, farm-to-table lifestyle. An extra-large two-car garage adds practicality and storage, completing this unique offering. Ideally situated in an excellent commuter location with easy access to major freeways and Caltrain. Close to downtown, shopping, dining & parks. Located within the boundaries of the highly regarded Baywood Elementary School (buyer to verify), this is a rare opportunity to own a piece of San Mateo history with room to live, work, and grow.

226 N Fremont ST, San Mateo

Listed by Julie Halpin, 650-315-4017 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Alice Chakhmazova from CBR
$2,750,000
2 Beds ⋅ 3 Baths ⋅ ML82043883 MLS
NEW PRICE!! Welcome to luxury living at the Towers in the heart of San Mateo! This stunning 2BR/2.5BA condo offers an expansive 2,800 SF of modern elegance. Step inside to find high ceilings, sleek hardwood floors, recessed lighting, and plenty of natural light streaming through a multitude of windows. The open layout features a spacious foyer, formal dining room, and a cozy library/den, perfect for working from home or unwinding. The sunlit kitchen is complete with a breakfast nook, cooktop, range hood, dishwasher, refrigerator, and even a wine cooler for entertaining. The private primary ensuite boasts a walk-in closet, a large shower and generous primary bedroom. A small private patio off kitchen offers a serene outdoor space, while the building includes shared rooftop deck, patios, and common outdoor areas. Amenities include pool/spa, sauna, gym, game room, and media/recreation room. With a doorman, elevator access, & security features like an electric gate and voice intercom, convenience and peace of mind are yours. Add'l features include central AC/heating, an in-unit washer/dryer and private storage Located near downtown San Mateo, this condo combines convenience, style, and easy access to downtown restaurants, shops and library

20 W 3rd AVE 601, San Mateo

Listed by Susan Herman, 650-400-4383 from Compass
(If provided) CoList: from

$1,825,000
6 Beds ⋅ ML82043896 MLS
A high-quality Peninsula duplex with stable income, minimal expense drag, and clearly defined long-term upside.117 N. Delaware Street presents a rare opportunity to acquire a well-located duplex in the heart of San Mateo. The property consists of two large units, each configured as 3 bedrooms and 2 bathrooms with garage parking offering strong fundamentals for both owner-occupiers and long-term investors. With tenants in place for over 20 years, the asset provides stable in-place income and a clear path for predictable rent growth under California rent control guidelines. The property currently generates $7,610 per month ($91,320 annually), with a highly efficient expense. Market rents for comparable units are estimated at approximately $4,500+ per month, indicating meaningful long-term upside. At market levels, the property would generate approximately $108,000. Generous layouts, strong rental demand and a desirable unit mix support long-term growth and income optimization. Don't miss this rare opportunity whether as an investment or a property you could occupy!

117 N Delaware ST, San Mateo

Listed by Tim Gilmartin, 650-348-2020 from Gilmartin Group
(If provided) CoList: Kathryn Gerhardt from Gilmartin Group

Sold listing courtesy of Kathryn Gerhardt from GILM
$4,595,000
4 Beds ⋅ 4 Baths ⋅ ML82043715 MLS
Bright, airy, and impeccably reimagined in beautiful San Mateo Park. This stunning single-level residence has been thoughtfully renovated with exceptional attention to detail, showcasing designer finishes, high-quality materials, and a cohesive, elevated aesthetic throughout. The home offers a desirable open-concept layout with four bedrooms plus a dedicated office, designed for both comfortable everyday living and effortless entertaining. The beautifully updated kitchen features premium appliances, honed marble countertops, and seamless flow into the expansive living and dining areas, where dramatic panoramic doors open to a bluestone terracecreating a true indoor-outdoor experience. The primary suite has been fully reimagined as a serene retreat, complemented by newly remodeled bathrooms throughout the home. Set on beautifully landscaped grounds, the property also features a sparkling pool with bluestone coping, offering a timeless and private setting for relaxation and entertaining. Ideally located just minutes from Burlingame Avenue, this exceptional home combines classic California living with modern luxury.

430 Hillsborough BLVD, San Mateo

Listed by Serena Conti, 650-619-8398 from Compass
(If provided) CoList: from

Sold listing courtesy of Denise Laugesen from KWPEN
$3,950,000
4 Beds ⋅ 4 Baths ⋅ ML82029852 MLS
A beautifully expanded and reimagined contemporary rancher offering relaxed Modern California luxury. The thoughtfully designed open floor plan showcases a sleek, light-filled kitchen that flows seamlessly into the family and dining areas, creating an ideal setting for effortless entertaining. Four generously sized bedrooms offer refined comfort, highlighted by an elegant primary suite featuring dual walk-in closets designed for effortless luxury. A dedicated office provides the perfect setting for sophisticated remote work or a private library retreat. The expansive utility room is thoughtfully appointed with walls of custom cabinetry, delivering exceptional storage with style and convenience. Expansive views extend to a lush, landscaped backyard, embracing the quintessential indoor-outdoor California lifestyle. Do not miss the opportunity to experience this exceptional home and discover elevated living at its finest.

412 Stephen RD, San Mateo

Listed by Ellen Vera, 650-862-8603 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Radha Rustagi from KWCU
$2,575,000
5 Beds ⋅ 4 Baths ⋅ ML82042394 MLS
Transparent pricing! Skylight House: among the larger homes in Fiesta Gardens, offering 2,820 sq ft with a well-designed two-story layout. With easy access to 92, 101, and moments from Trader Joe's, Whole Foods, and Bay Meadows Park, yet tucked into Fiesta Gardens, 1028 Bermuda offers an exceptional combination of convenience and setting. Rare 5-bed, 4-bath floor plan with two bedrooms and two full baths on the main level. The flexible layout with main-level bedrooms is ideal for guests or multi-generational living. At the heart of the home is a dramatic double-height living space where skylights flood the interior with natural light, anchored by a striking glass orb chandelier. The open layout flows to the outdoors, with direct access to the garden and patio from the family room, and side yard access from the dining area. Upstairs, vaulted ceilings extend through three bedrooms & two baths, including the primary suite, enhancing the sense of space and light throughout. Ideally located across from College Park Elementary, home to a Mandarin immersion program, and moments from the pool, clubhouse, tennis courts, and play area amenities exclusive to Fiesta Gardens residents. Plus an EV charger in garage. A rare opportunity to own one of the larger Fiesta Gardens homes.

1028 Bermuda DR, San Mateo

Listed by William Cheung, 650-759-8779 from Compass
(If provided) CoList: from

Sold listing courtesy of Julie Baumann from APR
$3,150,000
4 Beds ⋅ 3 Baths ⋅ ML82042374 MLS
Classic Craftsman, beautifully updated to reflect how we live today. This remodeled and expanded 4 bed, 3 bath corner lot home blends 1930s character w/ modern updates. Living/dining rooms feature courtyard views, detailed millwork, framed openings w/ decorative molding, fireplace, casement windows, and red oak hardwood floors w/ inlaid strips. Kitchen with defined spaces for prep, cooking, and gathering, custom cabinetry, Absolute Black granite, hand finished Beech wood ceiling, and Italian low voltage lighting. It flows into a breakfast nook w/ French doors to a pergola covered deck. A butcher block island w/ bar seating, Thermador 8 burner gas range, double oven, and wine bar complete the space. Ensuite on its own level w/ casement windows and views of the grounds. Bath features a floating vanity and glass enclosed shower. Lower level w/ separate access includes a permitted junior ADU, family room, bedroom, full bath, laundry, wine cellar, and courtyard access. Outdoor living w/ multiple areas, winding pathways, pergola covered deck/patio, custom wood-fired pizza oven, courtyard, raised garden beds, citrus trees. Detached garage w/cabinetry. Upgrades: TPO flat roofing, electrical 200 amps, copper plumbing, sewer, tankless water heater, and energy-efficient furnace - AC ready!

1120 Palm AVE, San Mateo

Listed by Christopher Eckert, 650-627-3799 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Ranya Kaileh Francis from SIR
$2,950,000
4 Beds ⋅ 3 Baths ⋅ ML82041557 MLS
This beautifully updated, split-level gem is in the coveted Baywood/Parrott Park neighborhood. The lower-level floor plan includes a bright living room, formal dining room, primary bedroom suite and bedroom. The gourmet eat-in kitchen opens to a sensational private patio with firepit, lush landscape and sprawling level lawn providing a seamless transition between the interior spaces & the incredible grounds. Fabulous grand staircase leads to the upper level that boasts 2 additional bedrooms and bathrooms. Explore the possibilities in this esteemed neighborhood just blocks to vibrant downtown San Mateo with shops, restaurants, cinema entertainment, parks and recreation. Easy access to both US 101 and 280, CALTRAIN and transportation makes this any commuters dream for San Francisco, SFO and Silicon Valley. The 4th bedroom is staged as an office the county shows 3 bedrooms 1 den

21 De Sabla RD, San Mateo

Listed by The Dwyer Group, 650-703-1183 from Compass
(If provided) CoList: from

Sold listing courtesy of The Dwyer Group from APR
$3,000,000
4 Beds ⋅ 3 Baths ⋅ ML82040752 MLS ⋅ SM Highlands BLDG.
This gorgeous custom built SM Highlands home offers privacy & Zen like experiences w/ a babbling creek in the rear yard. Located next to protected county land. 4BD/2BA upstairs. Large office could be 5th BD and full BA downstairs. Family room, 2 gas/wood burning fireplaces, formal dining, Gourmet kitchen, Radiant heat, central vacuum, integrated sound system, custom lighting. Much more! Don't miss out! Rec center includes community pool, tennis courts, & after school programs. Sawyer Camp road close by for walking, jogging, & bike trails along the Crystal Springs reservoir. Great school district. Location! Location! Location!

2060 Bunker Hill DR, San Mateo

Listed by Glenn Sennett, 650-208-7355 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Daniel Smith from APR
$5,495,000
5 Beds ⋅ 5 Baths ⋅ ML82040647 MLS
Brand New Luxury Residence in the highly sought-after Bel Aire Heights community of San Mateo. This exceptional home tryly has it all, nearly 4000 sq ft of thoughtfully designed living space featuring 5 bedrooms and 4.5 bathrooms, including two luxurious primary suites, one on each level, ideal for multi generational living or ultimate flexibility. The open-floor concept floor plan is light filled and expansive, seamlessly blending modern design with everyday functionality. A Chef's Dream kitchen showcases top of the line Thermador stainless steel appliances, including a built in espresso machine and wine refrigerator, perfect for both daily living and entertaining. Elegant finishes throughout, highlighted by a gas fireplace and walls of windows that capture stunning mountain and water views from most rooms. Set on approximately 9000 sq ft lot, the home also offers a spacious 3 car garage with multiple EV charging outlets. Located in one of San Mateo's premier new developments, Bel Aire Heights offers a rare opportunity to own a brand new, luxury home in a truly special setting.

18 Bel Aire LN, San Mateo

Listed by The Laugesen Team, 650-465-5742 from KW Advisors
(If provided) CoList: from

$3,450,000
3 Beds ⋅ 3 Baths ⋅ ML82040316 MLS
For nearly four decades, this home has quietly lived a life of devotion, the kind you feel the moment you step inside. Chosen 38 years ago for more than just its location, it became a place where life unfolded in meaningful ways, from mornings by the fireplace to evenings that lingered long past dinner. In 2003, it was thoughtfully expanded, not simply to grow in size, but to evolve with its owners, opening spaces, inviting in natural light, and creating a seamless connection between the kitchen, family room, and backyard where gatherings effortlessly flowed. It's a home that grew alongside a family, where children once walked to Baywood Elementary, then on to Borel Middle, and eventually to Aragon High, celebrating first proms, cheering at Friday night games, and marking milestones just moments from the front door, all set in San Mateos premier neighborhood. Upstairs, softly lit stairs lead to private retreats, including a refined primary suite and a tucked-away office that reflects changing times and needs. Every update since, from new systems to careful improvements, was made with intention and pride of ownership. This is not just a home that has been lived in, but one that has been deeply cared for, ready now for its next chapter with someone who will continue its story.

307 Aragon BLVD, San Mateo

Listed by Eva Chen, 415-971-5171 from Compass
(If provided) CoList: Jeff Chen from Compass

Sold listing courtesy of Sternsmith Group from APR
$2,990,000
4 Beds ⋅ 3 Baths ⋅ ML82039543 MLS
Welcome to this beautifully remodeled traditional home in the Woodbridge Park neighborhood of San Mateo, zoned to top-rated Belmont schools. Flooded with natural light, this rarely available 2-story residence offers a versatile floor plan. Upstairs, you will find a primary suite featuring high ceilings & a seating area along with 2 additional bedrooms each with their own walk-in closet. A bedroom & a full bath on the main level provide flexibility for guests or a home office. A grand entry opens to an elegant living room with vaulted ceilings & a formal dining area, creating an inviting space for everyday living. At the heart of the home, you will find an open layout where a fully remodeled kitchen flows effortlessly into a sunny eating area & an inviting family room. Double sliding doors open to the flat backyard perfect for indoor-outdoor living & entertaining. The stunning kitchen showcases white cabinetry, quartz counters, SS appliances, tile backsplash & a center island. Other highlights include newly installed white oak engineered hardwood floors & carpet, fresh paint, chic light fixtures, recessed lighting, laundry room & 2 car garage. Ideally located near parks, Hillsdale Mall, freeways, Caltrain & SFO. First time on the market, this is the one you have been waiting for!

269 Woodbridge CIR, San Mateo

Listed by Sanit Bordeianu, 650-430-3500 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Steven Wen from KWCU
$2,500,000
3 Beds ⋅ 3 Baths ⋅ ML82039491 MLS
Located in a sought-after San Mateo neighborhood, this spacious 3-bedroom + office, 2.5-bath home offers approximately 2,530 sq ft of flexible living space on a beautifully landscaped 6,600 sq ft lot. Designed for both everyday comfort and entertaining, the home features a large family room seamlessly connected to the kitchen perfect for gatherings, movie nights, or hosting guests. The dedicated office provides an ideal work-from-home setup or optional guest space. The expansive, flat backyard is a true highlight, offering mature landscaping, room to play, garden, or create your own outdoor retreat. With its generous layout and solid footprint, the home presents a rare opportunity to update, expand, or customize to match your vision and lifestyle. Ideally located near parks, top-rated schools, shopping, dining, and major commuter routes, this property combines convenience with long-term upside. Whether youre looking to move right in or design your dream home over time, this is a unique opportunity in one of San Mateos most desirable areas.

341 Sylvan AVE, San Mateo

Listed by Sternsmith Group, 650-678-5455 from Compass
(If provided) CoList: from

Sold listing courtesy of Magic Li from CBR
$3,300,000
4 Beds ⋅ 3 Baths ⋅ ML82039454 MLS
Located in the highly desirable Baywood Park neighborhood of San Mateo, this beautiful updated home offers an exceptional blend of comfort, convenience, and everyday amenities. Just moments from Crystal Springs Village with access to Safeway, Starbucks, CVS Pharmacy, and popular local dining including Rainbow Pizza. Conveniently situated near Highways 92 and 280 with easy access to Highway 101, Hillsdale Shopping Center, and Downtown San Mateo. Set within highly regarded school boundaries. This elegant Neo-Mediterranean residence features a spacious front lawn and inviting curb appeal. Inside, a grand open-concept foyer, living room, and dining area are highlighted by soaring double-height ceilings and abundant natural light through large windows. The well-appointed eat-in kitchen offers granite countertops, stainless steel appliances, ample cabinetry, a center island with breakfast bar, and a breakfast nook, opening to a generous family room with fireplace and backyard access. The main level includes a guest bedroom, office, full bath, and laundry room. Upstairs are three bedrooms and two baths, including a spacious primary suite with dual vanities, soaking tub, walk-in shower, and ample closet space. Private backyard with patio, lawn, and circular hillside deck.

117 Lakewood CIR, San Mateo

Listed by Stanley Lo, 650-373-0007 from Green Banker Realty
(If provided) CoList: from

Sold listing courtesy of Max Lo from GRBA
$4,800,000
4 Beds ⋅ 4 Baths ⋅ ML82039233 MLS
Architectural treasure in the heart of prestigious San Mateo Park! Built in 1924 and influenced by the timeless elegance of Julia Morgan, this single level 4-bedroom, 4-bathroom home offers over 3000sf of refined living space, artfully arranged around a central courtyard that enhances privacy and natural light. Set on a large lot of lush, fragrant grounds, this home is surrounded by fragrant jasmine and vibrant bougainvillea, gardenias, azaleas and abundant greenery. Rich with character and detail, curved double doors, intricate woodwork, brass patina finishes, and leaded glass windows speak to its historic charm and craftsmanship. This home features a large kitchen with stone floors & countertops with state-of-the-art appliances. TWO spacious suites are situated on opposite wings of the home, creating ideal separation for guests, family, or multi-generational living. A grand living room with a stately fireplace and a formal dining room provide gracious spaces for entertaining. French doors invite you outside to the backyard, where a sparkling pool and entertaining patio awaitperfect for gatherings or relaxing in the California sun. This is a lovely blend of classic sophistication, thoughtful design, and timeless charm in one of San Mateos most desirable neighborhoods.

626 Occidental AVE, San Mateo

Listed by Jean Joh, 650-636-3147 from Perisson Real Estate, Inc.
(If provided) CoList: from

Sold listing courtesy of Matthew Rogers from ELI
$2,400,000
3 Beds ⋅ 4 Baths ⋅ ML82038316 MLS
Located on a lovely, tree-lined street, this truly exceptional home is just a short walk to vibrant downtown San Mateo, known for its excellent restaurants, shopping & nearby Central Park. Blending timeless character with modern comfort, the home offers a spacious & highly versatile floor plan with multiple living areas. The main level welcomes you through a striking carousel-shaped entry that opens to a bright & inviting living room, a formal dining room, office, full bathroom, and laundry room. The open kitchen flows seamlessly to the beautifully landscaped backyard. Upstairs are two spacious bedrooms, an additional full bathroom & a cozy bonus room currently set up as a nursery. The lower level features an expansive bonus space with a full bathroom, dining area & a kitchenette (without stove). This flexible area is ideal for guests, a family or media room. Outside, the property offers beautifully landscaped front & back yards, along with a long, electronically gated, driveway perfect for RV parking. The driveway leads to a large two-car garage. Above the garage is a charming, light-filled one-bedroom in-law unit, adding even more flexibility to this remarkable property. With its unique character, generous space and prime location, this special home is not to be missed.

809 E 5th AVE, San Mateo

Listed by Kathy Wall, 415-608-4168 from Intero Real Estate Services
(If provided) CoList: Michael Darling from Intero Real Estate Services

Sold listing courtesy of Christopher Eckert from KWPEN
$4,200,000
4 Beds ⋅ 3 Baths ⋅ ML82037465 MLS
Unsurpassed quality defines this reimagined home at 638 Oregon Avenue. Rebuilt from the ground up, it features top-shelf construction, craftsmanship, and woodwork. The entryway includes a striking staircase. The high-end, open kitchen is filled with natural light, crafted with the finest materials, and includes an eat-in bar. The family room is an elegant living area with high ceilings, built-ins, natural light, and lots of space. Glass doors open to a beautifully landscaped backyard with a two-tier stone patio, extending the living space outdoors. One bedroom and one and a half bathrooms are downstairs. The upstairs primary suite has a stunning closet with high-end built-ins and an elegant en suite bathroom. Crown molding, wainscoting, and custom cabinetry combine functional design and quality materials. Integrated smart lighting, whole-home audio, and remote-controlled shades add convenience. Other features include central air, whole-house water filtration, tankless water heater, and a two-car garage.

638 Oregon AVE, San Mateo

Listed by Maria Scott, 650-207-9841 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Greg Damelio from SGP
$5,650,000
ML82036937 MLS ⋅ Crystal Springs Apartments BLDG.
Price reduced 4/29/2026. Crystal Springs Apartments is a generational multifamily asset, held by the same family for decades after establishing deep roots in San Mateo County more than 90 years ago. Constructed in 1978 by the developer of the adjacent Crystal Springs Village Shopping Center, the property reflects a level of care, intention, and permanence that is increasingly rare. Both in construction and interior character, the residences offer an experience more akin to a single-family home than a conventional rental property. It is 10-units consisting of (2) 2 bed / 2.5-bath townhouses, (5) 2 bed / 2 bath, and (3) 1 bed / 1 bath units. The property is two separate buildings located in a primarily single family residential neighborhood. It is situated on two separate parcels (041-203-010 and 041-203-020) that combine for ~0.35 acres of land. Residents enjoy amenities such as enclosed garage and covered parking, vaulted ceilings in second floor units, fireplace in each unit, and balconies and/or patios. The property's Peninsula location is near the midpoint of San Francisco and the Silicon Valley allowing for easy access to all major Bay Area employment centers. The neighboring multifamily property at 2005 Parrott Dr sold for $769,533 per unit on 2/20/2026.

2001-2003 Parrott DR, San Mateo

Listed by Carlos Azucena, 408-205-2679 from Marcus & Millichap
(If provided) CoList: from

Sold listing courtesy of Carlos Azucena from M&MKW
$3,550,000
4 Beds ⋅ 3 Baths ⋅ ML82036747 MLS
This beautifully preserved home showcases rich wood detailing, elegant millwork, and charming vintage touches at every turn. Sun-filled living spaces feature hardwood floors, classic fireplace, stained glass accents, and oversized windows that frame lovely neighborhood views. The inviting dining room, cozy bedrooms, and thoughtfully designed living areas blend historic craftsmanship with comfortable everyday livingcreating a warm, character-filled home that feels both refined and welcoming. Close to Silicon Valley, San Francisco and top-rated public and private schools. Disclosure link: https://app.disclosures.io/link/250-Harvard-Road-oh6wdpwz Open house Sat 3/28 2-4pm Sun 3/29 1-4 or tex Ting at 415.359.8419 or Trish at 650.808.0972 for showings.

250 Harvard RD, San Mateo

Listed by Ting Wang Conway, 415-359-8419 from Compass
(If provided) CoList: Trish Power from Compass

Sold listing courtesy of Mariana Pappalardo from COMPS
$2,860,000
5 Beds ⋅ 3 Baths ⋅ ML82036587 MLS
PRICE ADJUSTMENT!! Welcome to 1521 Cherrywood Dr - A standout 5 bedrooms + office, 2.5 bath retreat nested in one of San Mateos most sought-after Laurelwood neighborhoods. Set on a generous ~8700 sq. ft. lot. This 1975 built home offers ~2710 sq. ft. of thoughtfully designed living space, perfect for families & entertaining. The home welcomes you with a spacious floor plan, an elegant staircase, a sun filled living room with a fireplace & an inviting formal dining room with sliding doors to the lush gardens. The heart of this home is a well-appointed kitchen with a majestic inviting island - a place to create memories with family & friends. The cozy family room flows directly into a large private oasis backyard. Imagine hosting a private party within a serene garden space under mature trees and a waterfall. Office conveniently located on ground level and 5 private bedrooms upstairs. Additional features include, cherrywood hardwood floors, gourmet granite countertops, custom cabinetry, stainless steel appliances, radiant flooring in the primary bath, putting green, seperate laundry & attached 2 car garage. This centrally located Laurelwood enclave features premium schools, shopping destinations, scenic trails, parks and major commuter routes. OFFERS DUE, Tuesday 4/21/26 at 10am.

1521 Cherrywood DR, San Mateo

Listed by Dzovig Derounian, 650-302-3288 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Rumana Jabeen from KWPEN
$3,000,000
6 Beds ⋅ 4 Baths ⋅ ML82036584 MLS
Commanding a premier position in one of San Mateos most sought-after neighborhood. This classic two-level Tudor-style home spans an impressive 2,712 sq ft, offering a versatile layout that features 6 spacious bedrooms and 4 bathrooms. The true crown jewel of this property is the expansive 10,990 sqft lot. Behind the home lies a massive, sun-drenched backyard that serves as a private sanctuary and a blank canvas for your imagination. It is the ideal setting to build the escape of your dreams....a resort-style pool and spa, a professional outdoor kitchen for entertaining, or a lush sustainable garden. Complementing the homes interior is a functional three-car garage, providing ample space for vehicles and additional storage. Beyond the property lines, the location offers an unparalleled quality of life. Families will appreciate the close proximity to top-rated San Mateo schools, known for their academic excellence and community focus. For the modern professional, the home provides seamless access to the 280 freeway, offering a scenic and efficient commute to both San Francisco and the heart of Silicon Valley. Award winning San Mateo Schools...Aragon High School.

2056 Fairmont DR, San Mateo

Listed by The Laugesen Team, 650-465-5742 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Denise Williams from SRXW02
$7,300,000
4 Beds ⋅ 5 Baths ⋅ ML82036113 MLS
Set on a magnificent 30,851± sq ft flat estate parcel in coveted San Mateo Park, this timeless residence offers beautifully scaled living space and resort-style grounds designed for indoor-outdoor living. A sweeping circular motor court and detached 3-car garage create a grand arrival. Inside, hardwood floors, classic millwork, and formal living and dining rooms establish warmth and presence. The updated kitchen features custom cabinetry, stone countertops, professional-grade appliances, generous island, and a light-filled breakfast area opening to the family room and rear grounds. Upstairs includes spacious four bedrooms highlighted by a junior suite and a serene primary suite with office. Three full baths serve the upper level, complemented by a powder room and additional half bath downstairs. A finished basement adds flexibility. The grounds feature a sparkling pool, spa, expansive patios, private Entertainer's Cabana, level rear turf lawn, and lush front lawn framed by mature trees for privacy. Flat parcels of this scale in San Mateo Park are increasingly rare. Combined with a detached garage, circular drive, pool, spa, and move-in livability, this represents a compelling opportunity in one of the Peninsula's most prestigious neighborhoods.

124 W Poplar AVE, San Mateo

Listed by Dan Gilmartin, 650-796-3971 from Gilmartin Group
(If provided) CoList: from

Sold listing courtesy of Tatiana Narkiewicz from APR
$2,766,000
4 Beds ⋅ 4 Baths ⋅ ML82035874 MLS
Welcome to this inviting San Mateo home that offers a thoughtful blend of character, comfort & versatility. Classic charm is preserved throughout, while key spaces have been tastefully updated, including a renovated kitchen & fully remodeled bathrooms. The homes layout flows easily, with a front living room anchored by a wood-burning fireplace, a dedicated dining area & a comfortable family room adjoining the kitchen. A short set of steps leads up to a private bedroom wing. The primary suite features its own bathroom & opens to a private rear balcony, creating a quiet place to unwind. There are two additional bedrooms and bath. A standout feature is the versatile downstairs "apartment," complete with a kitchenette, living area, bedroom, and bathroom; with access from both the main home & a separate exterior entrance, this space is ideal for guests, extended family, or potential rental use. The home also includes a unique attic area that adds personality & usable flexibility. The landscaped backyard provides a peaceful retreat, highlighted by a built-in gazebo ideal for outdoor enjoyment. Centrally located, this charming home offers exceptional convenience just moments from Hillsdale Shopping Center, vibrant downtown San Mateo and popular Beresford Park.

319 30th AVE, San Mateo

Listed by Johnny Heckenberg, 650-776-5779 from Coldwell Banker Realty
(If provided) CoList: Kari Eden Schaiman from Coldwell Banker Realty

Sold listing courtesy of Joe Polyak from RISE
$6,500,000
4 Beds ⋅ 5 Baths ⋅ ML82035872 MLS
Polished and poised meets lively and fun. Set behind formal gates in prestigious San Mateo Park, this 1929 Spanish Colonial Revival estate makes a striking first impression. Color-rich tile details hint at the warmth and personality within, where timeless architecture and modern livability coexist beautifully. Thoughtful renovations and major system upgrades, including a 1,100 sq+/- ft San Francisco style garage, preserve original character while providing contemporary comfort. Arches, ironwork, rich wood detailing, and dramatic scale define the interiors. The grand living room with cathedral ceiling and statement fireplace, formal dining room, and chefs kitchen designed for gathering create an ideal setting for everyday living and entertaining. The main level also includes an office, pantry, and inviting family spaces. Spacious bedrooms. Custom designed Primary. A large lower-level rec room offers ideal hangout and game space. Set on nearly half an acre, the fully landscaped grounds connect multiple play and entertaining areas, including a level lawn and elevated front patio designed for memorable gatherings. San Mateo Park is prized for its tree-lined streets, architectural charm, and central Peninsula location with convenient access to SFO, San Francisco, and Silicon Valley.

414 Edgewood RD, San Mateo

Listed by Mike Bohnert, 650-504-2378 from Coldwell Banker Realty
(If provided) CoList: Heidi Maierhofer from KW Advisors

Sold listing courtesy of Marc Roos from SGP
$10,400,000
4 Beds ⋅ 6 Baths ⋅ ML82035852 MLS
2023 new build. A magnificent three-story estate of striking stature that embodies the pinnacle of luxury. On the most prestigious, tree-canopied street in The Park, backing onto Hillsborough's storied estates on Brewer Drive. Stroll to Burlingame Ave. Expansive lot, over one-third of an acre of beautifully curated grounds providing privacy and an impressive sense of arrival. Step inside and experience the grandeur, 6070 sq. ft. of stylish living. Light-filled rooms. Oversized windows framing peaceful treetop views. 6 cooling and heating zones. Professional chef's kitchen, 4 ovens, 72-inch fridge, 2 dishwashers. 2 wine coolers. Pristine marble adorns the 15-foot island. Butler's pantry. Office. 4 ensuite bedrooms, marble bathrooms with heated floors. Dreamy primary suite, large custom closet and sumptuous bathroom with double showers. Vibrant gardens with an orchard, gas heated pool. Jacuzzi. Cabana. Pergola. Fireplaces. Outdoor bar. Full outdoor kitchen. 1,000 sq. ft. hosting patio. A bench, perfect for quiet reflection, capturing unforgettable sunsets over the spa, all to nourish the body, mind and spirit. Gym. Wine tasting lounge. Wine cellar. Bespoke cocktail bar with a sweeping marble counter. Billiards room. 4 car garage. So new, a rare offering in the most coveted area.

830 Bromfield RD, San Mateo

Listed by Margaret Duffy, 650-676-0294 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Gurveer Bains from SZPR01

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