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$2,402,000
4 Beds ⋅ 2 Baths ⋅ ML82041331 MLS
Designed with both comfort and functionality in mind, this residence features three spacious bedrooms plus a dedicated office, offering flexibility for todays lifestyle. Vaulted ceilings create a sense of volume and openness, while new hardwood flooring throughout brings a fresh, cohesive feel. The home offers a classic yet versatile layout with a formal living room and dining room, along with a welcoming great room and breakfast area for everyday living. The kitchen has been refreshed with new countertops, and the light-filled primary suite provides a peaceful retreat. A back deck extends the living space outdoors, ideal for al fresco dining and entertaining. An attached two-car garage adds convenience, all set within a charming neighborhood with sidewalks, just minutes from Highway 92 and Laurelwood Shopping Center.

3408 Spyglass DR, San Mateo

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

Sold listing courtesy of Eric McCafferty from GGSIR

$2,401,888
4 Beds ⋅ 3 Baths ⋅ ML82033884 MLS
Your dream home awaits in San Mateo! This spacious 4 BED / 3 BATH home offers ~2,020 sq ft of well-planned living on a quiet, highly desirable street. The home's heart is the Family Great Room that flows to the Kitchen as well as the serene outdoors. A large open stadium kitchen with stainless steel appliances, granite countertops and breakfast bar opens to the dining area and family great room, which flow out to a fabulous landscaped backyard with 2 patio areas, perfect for everyday living and easy alfresco entertaining. The flexible floor plan includes two primary suites, (one on each level) perfect for multigenerational living plus there are 2 additional bedrooms & a generous formal living room with a fireplace. This home has abundant space to live, work, and play! Located blocks from George Hall Elementary with easy access to Caltrain, Hillsdale Shopping Center, Whole Foods, Bay Meadows, Downtown San Mateo Dining, Parks, and Conveniences. Quick commuting via Highways 101, 92, & 280 makes this an ideal central Peninsula location. Welcome home to 3936 Regan Drive!

3936 Regan DR, San Mateo

Listed by Yelena Lepina, 650-288-2815 from Luxuriant Realty
(If provided) CoList: from

Sold listing courtesy of Jennie Lok from KWPEN

$2,400,000
4 Beds ⋅ 3 Baths ⋅ ML82047386 MLS
Location, location, location! Nestled on an expansive 12,327 sq. ft. lot, this sought-after single-level home offers four bedrooms, two and a half baths, and breathtaking views of the Crystal Springs Reservoir and surrounding canyon. With its serene setting and lush mature landscaping, this property captures a rare country living in the city feel. The spacious living room features a fireplace and sweeping views, creating the perfect space for both relaxing and entertaining. A comfortable family room flows seamlessly off the kitchen and dining areas, while refinished wood floors, fresh interior paint, and abundant natural light enhance the homes warm and inviting atmosphere. Step outside to a beautiful deck and private hot tub surrounded by tranquil greenery, offering a true retreat-like setting. With tremendous upside potential, this home provides the opportunity to add your own personal touches and create something truly special. Additional highlights include a separate laundry area and attached two-car garage. Ideally located with easy access to Highway 92, Interstate 280, San Francisco, Silicon Valley, and San Francisco International Airport.

112 Linden LN, San Mateo

Listed by David Tapper, 415-370-7195 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Lili Chen from CBR

$2,400,000
4 Beds ⋅ 2 Baths ⋅ ML82042415 MLS
A rare mid-century retreat with sweeping bay and mountain views is offered for the first time in over 45 years. This well-maintained 4BR/2BA home sits on an expansive 24,000 sqft lot at the end of a quiet cul-de-sac in one of San Mateo's most desirable Hillside neighborhoods. Enjoy panoramic views of San Francisco, the Peninsula, & the East Bay. The home blends classic mid-century character with a functional, inviting layout. Sunlit living spaces feature all new double paned windows, hardwood floors and a fireplace, complementing a formal dining area ideal for gatherings. Updated kitchen offers generous counter space, ample storage, & new appliances. Four well-sized bedrooms and two full baths provide flexibility for living, guests, or a home office. A dedicated laundry room adds convenience. The oversized lot offers a rare sense of privacy and openness. The peaceful secluded backyard features a pool, areas for entertaining, & offers a calm space to recharge with daily opportunities for wildlife viewing! Located near Laurelwood Park & Sugarloaf Open Space, with access to hiking trails, top-rated schools, shopping, dining, & easy access to Hwy 92. A unique opportunity to own a classic mid-century home with exceptional space, privacy, & views in a sought-after San Mateo location.

723 Linda CT, San Mateo

Listed by Rick Barrelier, 650-573-5961 from eXp Realty of California Inc
(If provided) CoList: from

Sold listing courtesy of Yulia Goyal from PNN

$2,400,000
3 Beds ⋅ 2 Baths ⋅ ML82040327 MLS
A beautifully updated, sun-drenched home in one of San Mateo's most desirable neighborhoods, this residence offers the perfect blend of modern style and everyday comfort. With a sought-after south-facing orientation and three thoughtfully placed skylights in the kitchen, hallway, and office, the home is filled with natural light throughout the day, creating a bright and welcoming atmosphere. The heart of the home is the stunning kitchen, featuring premium appliances, an oversized island ideal for gathering and entertaining, and elegant wood cabinetry that adds warmth and sophistication. The open layout flows seamlessly into the living spaces, making it perfect for both relaxing and hosting. Step outside to a private backyard retreat with a beautiful wood deck and a mature plum tree, offering a serene setting for outdoor enjoyment. Ideally located just minutes from top-rated schools and near Beresford Park with its playgrounds and tennis courts, this home delivers both convenience and lifestyle in an unbeatable location.

765 Sequoia AVE, San Mateo

Listed by Charmaine Wang, 650-521-4756 from Compass
(If provided) CoList: Joy Rong from Intero Real Estate Services

Sold listing courtesy of Maggie Chien from COMPS

$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

$2,400,000
3 Beds ⋅ 2 Baths ⋅ ML82032945 MLS
Expansive Bay and San Francisco views from both inside and outside the home set the tone for this beautifully updated Mid-Century Ranch. The home sits on a generous lot on a quiet, sought-after street in San Mateo. Backing directly to Indian Springs Park and lush greenery, the property offers exceptional privacy and a serene setting. The light-filled interior showcases classic mid-century character, including a distinctive step-down living room that adds architectural interest and warmth. Hardwood floors run throughout much of the home, complemented by large windows that frame sweeping outlooks. The updated kitchen and refreshed bathrooms provide modern comfort and functionality. A finished basement adds valuable flexible space, ideal for a workshop, home gym, or studio. The home also offers abundant storage throughout, enhancing everyday convenience and functionality. The oversized lot provides generous outdoor space and excellent potential for expansion, creating long-term flexibility and value. Ideally located near highly regarded San Mateo schools, parks, shopping, dining, and convenient commuter routes. A rare opportunity to own an updated, view-oriented Mid-Century home with privacy, space, flexibility, and iconic Bay and San Francisco views.

3909 Leona ST, San Mateo

Listed by Betsy White Dalkert, 650-861-0082 from eXp Realty of California Inc
(If provided) CoList: Eileen O'Reilly from eXp Realty of California Inc

Sold listing courtesy of Heather Hansen from APR

$2,400,000
3 Beds ⋅ 4 Baths ⋅ ML82031327 MLS
Welcome to 1100 9th Ave, a beautifully renovated single-family home on a desirable corner lot in San Mateo. This 1,580 sq. ft. residence features 3 bedrooms, 3.5 baths, and 9 well-designed rooms blending comfort and style. If extraordinary detail is important to you this special home is a must see! Inside, bright spaces with engineered hardwood floors, and tile floors are illuminated by recessed lighting. The modern kitchen includes high-end appliances, a gas stove, refrigerator, washer/dryer, pantry, and a spacious eat-in design perfect for entertaining. Each beautiful bedroom has its own ensuite bathroom with a separate shower and walk-in closet. Dual-pane windows provide natural light and energy efficiency, while central heating ensures year-round comfort. A stylish half bath on the main level is great for guests. The newly landscaped private yard and patio, complete with 2 large patios, are perfect for relaxing or entertaining. Fenced front and backyards add privacy, and theres ample parking with on-site, guest, and street options. With practical features like a dedicated laundry area, crawl space storage, and access to common storage, this more than turnkey home is ready for you to move in.

1100 9th AVE, San Mateo

Listed by Gillian Kilroy, 650-868-2644 from Compass
(If provided) CoList: from

Sold listing courtesy of Danny Mok from NTERO

$2,400,000
3 Beds ⋅ 2 Baths ⋅ ML82022906 MLS
Find Your Haven in Laurelwood. At the quiet end of a Laurelwood cul-de-sac, 1656 Oakwood Drive is the kind of home that makes weekends feel like vacation. Sunlit living and family rooms spill onto three separate outdoor decks, down to a sparkling, solar-heated pool and a detached studio with half bath which is perfect as an office, gym, or pool cabana. Inside, hand-hewn engineered floors, old-world textured walls, and LED lighting set a warm, modern tone. The kitchen delivers stainless appliances with convection oven, microwave, and induction cooktop, plus smart in-drawer outlets for a tucked-away coffee station or appliance garage. Three bedrooms and two baths include a serene primary with a custom closet system; dual-pane Low-E windows and sun tunnels keep everything bright and efficient. A rare 3-car garage with loft swallows gear and weekend projects with ease. Moments to Laurelwood Park trails, the Laurelwood Center & CSM Farmers Market, Crystal Springs, and fast highway 92,280, and 101 access, this is a private retreat with great neighborhood vibes, everyday convenience, and true indoor & outdoor living.

1656 Oakwood DR, San Mateo

Listed by Olivia Mcnally, 650-576-6666 from Real Brokerage Technologies
(If provided) CoList: from

Sold listing courtesy of Joe Polyak from RISE

$2,400,000
8 Beds ⋅ ML82022896 MLS
SC Properties is pleased to present. This multi-family property offers a total of 5,740 square feet of living space on a generous 13,500 square foot lot. The property features a beautifully remodeled duplex, each unit offering 2 bedrooms and 2 baths with tasteful finishes throughout. TPO roof on the duplex was installed in 2025, and the sewer lateral was replaced in 2024. The duplex and single-family home have separate utilities. Additionally, there is a spacious 3,500 square foot single-family home with two stories and a basement, providing ample space for a large family. Built in 1935 and recently remodeled in 2016, this property is equipped with modern amenities and individually metered units. The private yards offer a secluded outdoor space for each unit. Located in a desirable neighborhood, this property provides convenient access to Bay Meadows, Hilldale Mall, local schools, parks, and dining options. With parking available in the carport and on the street, tenants will never have to worry about finding a space. Offered at $2,395,000, this multi-family property is the perfect opportunity for investors or those looking to live in one unit and rent out the others. Don't miss out on this rare find.

58 E 39th AVE, San Mateo

Listed by Rachid Atie, 650-868-0202 from SC Properties
(If provided) CoList: Chris Giotinis from SC Properties

Sold listing courtesy of Rinat Kaufman from CBR

$2,400,000
3 Beds ⋅ 2 Baths ⋅ ML82021365 MLS
Charm, Style & Natural Light to this updated home home with curb appeal and great space! This light filled updated home also features an amazing ADU that was just completed. In the main home you will find a lovely living room & formal dining area. The updated crisp white kitchen is filled with natural light, an abundance of cabinet space & quartz counters with an open concept casual dining space in the spacious family room that has high ceilings, sky light, and large sliding door to the backyard. The primary bedroom has an updated bathroom w/separate tub, and stall shower. In addition to all this home has to offer, the big bonus is the just completed fantastic ADU with standout features, enter into a generous bedroom with soaring ceilings, complemented by a darling eat in kitchen with comfortable sitting space. The ADU also includes a laundry room, large walk-in closet and a stunning bathroom with double sinks and oversized stall shower. This versatile addition is ideal for guests, extended family or as a source of rental income. This home has so much to offer with modern updated features & flexibility with the ADU. A must see!! The main house was originally a 3 bedroom/2 Bath and now is a 2/Bed/2 Bath with a flex room. Just minutes from Laurelwood Plaza & Hillsdale Mall.

715 31st AVE, San Mateo

Listed by Arlene Sullivan, 650-703-1830 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Traci Hornbaker from SGP

$2,375,000
3 Beds ⋅ 2 Baths ⋅ BE41114876 MLS
Welcome to 430 27th Ave, a beautifully remodeled ranch-style home in San Mateo's desirable Beresford Park neighborhood. This single-level residence offers an inviting open floor plan with spacious living and dining areas, a modern chef's kitchen with premium finishes, and abundant natural light throughout. The primary suite features a stylish ensuite bath and ample closet space. Two additional bedrooms and a full bath provide flexibility for family, guests, or a home office. Enjoy seamless indoor-outdoor living with a private backyard perfect for entertaining, gardening, or relaxation. Conveniently located near top-rated schools, Beresford Park, Hillsdale Shopping Center, and major commute routes. Move right in and experience the best of San Mateo living.

430 27th Ave, San Mateo

Listed by Richard Chang, (510) 333-6198 from ABC Commercial Realty
(If provided) CoList: from

Sold listing courtesy of Aladdin Kanawati from APR

$2,368,000
2 Beds ⋅ 2 Baths ⋅ ML82054571 MLS
Beautiful 2BR/2BA home in a prime Westside San Mateo location! This spacious single-story residence blends timeless charm with modern updates. The bright living room features a cozy fireplace, while the formal dining room showcases elegant wood wainscoting. Updated kitchen includes granite countertops, a skylight, and stainless steel appliances, and flows seamlessly into the adjacent family room. French doors open to a covered porch overlooking the private backyard, creating the perfect indoor-outdoor living space. The spacious primary suite features a large walk-in closet and a private en-suite bath. A generously sized second bedroom and a full hall bath with a soaking tub provide comfort for family and guests alike. Additional highlights include hardwood floors, crown molding, recessed lighting, dual-pane windows, central heating, and a massive attic with insulation. A detached two-car garage with a workshop and additional attic space adds even more versatility. Highly sought after school district. Ideally located within walking distance of vibrant downtown San Mateo, the Caltrain stations, restaurants, and grocery stores, with easy access to major freeways and tech shuttle stops, this home offers the perfect blend of character, comfort, and convenience.

1429 Maple ST, San Mateo

Listed by Angie Ni, 650-863-0879 from Coldwell Banker Realty
(If provided) CoList: Bali Liu from Coldwell Banker Realty

Sold listing courtesy of John Sayage from APR

$2,361,000
3 Beds ⋅ 2 Baths ⋅ ML82017624 MLS
Light-Filled and Spacious Baywood Knolls Gem! Located in desirable Baywood Knolls, just minutes from shopping and dining in vibrant downtown San Mateo, this lovely home offers timeless appeal for comfortable living today, and potential to transform into a dream home. Beautiful hardwood floors enhance the light-filled interiors, where a spacious living room with fireplace flows to a formal dining room and bright eat-in kitchen. Three bedrooms include a primary suite, while a spacious hallway bath serves two additional bedrooms and the main living areas. Outdoor living is inviting with a welcoming covered front porch and landscaped front and rear yards framed by lush gardens. An attached two-car garage with laundry area adds convenience, and excellent nearby San Mateo schools complete this wonderful opportunity.

525 Colgate WAY, San Mateo

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

Sold listing courtesy of Cindy Moscaret from APR

$2,360,000
3 Beds ⋅ 2 Baths ⋅ ML82022804 MLS
Presenting a timeless residence in the heart of San Mateo. Upon entering, you are greeted by a generous living and dining area that seamlessly connects to an elegant brick courtyard an ideal space for entertaining or enjoying outdoor living. The home features refined yet welcoming finishes, including warm wood flooring and a striking fireplace. Kitchen offers granite counters, high-end appliances and an ample sized eat-in area. There are three well-appointed bedrooms and two stunning bathrooms; the hallway bathroom offers marble finishes, a separate bathtub and shower, and a double vanity, while the primary bath features a marble shower & floors and premium fixtures. This property is conveniently located just minutes from shopping, restaurants, schools, and major commuting routes. This house is a wonderful place to call home.

445 23rd AVE, San Mateo

Listed by Connie Gerlach, 408-242-0500 from Intero Real Estate Services
(If provided) CoList: Eva Yao from Coldwell Banker Realty

Sold listing courtesy of Ivy Liang from CBR

$2,350,000
3 Beds ⋅ 2 Baths ⋅ ML82052229 MLS
This is it, YOUR NEW HOME! Welcome to this beautifully updated Eichler home in the highly desirable Sunnybrae neighborhood of San Mateo. Boasting numerous high-end upgrades and immaculate attention to detail throughout, this stunning property features a bright and open floor plan, brand new exterior and interior designer paint, gorgeous engineered wood flooring, stylishly renovated bathrooms, and a truly exquisite kitchen with custom quartz countertops, custom cabinets with auto-sensor LED lighting, and top-of-the-line appliances. Technical upgrades include all new electricals, new copper plumbing, new tankless water heater, new HVAC and AC unit, Milgard windows and sliding doors, Hansgrohe fixtures, designer ceiling lights, luxurious Porcelanosa brand floor and bathroom tiles, brand new pavers and low-maintenance artificial grass in backyard, new redwood fence in front, and so much more. Whatever your lifestyle, Sunnybrae's ideal location and distinctive community lets you create a life uniquely you, and this beautiful modern home will have you and your family living the good life for years to come. WELCOME TO YOUR NEW HOME!

1751 Celeste DR, San Mateo

Listed by Alana Lam, 408-981-6012 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Ranya Kaileh Francis from SIR

$2,350,000
8 Beds ⋅ ML82051839 MLS
An extraordinary find in the heart of the Peninsula, this large, meticulously configured fourplex located at 711-717 Highland Avenue presents a rare combination of immediate cash-flow and long-term appreciation. Situated across two independent buildings on a single parcel, the property balances structural versatility with extensive tenant appeal. The front building consists of two massive 2 bedroom 1.5 bathroom townhome style units spanning approximately 1,770 square feet each. These two-story spaces are designed for premium living, featuring an expansive first floor with a spacious living room, formal dining room, private breakfast nook, kitchen, laundry area, and a convenient half-bathroom, while the upper level hosts two bright bedrooms, a bonus room and a full bath. The rear building houses two flat-style 2 bedroom 1 bathroom units measuring a generous 1,000 square feet each. The ground-floor flat enjoys direct access to a private backyard space, while the upper unit benefits from an expansive balcony. Each unit is fully equipped with washer and dryer, refrigerator, range/oven, garbage disposal as well as four dedicated carports. Perfect for owner occupied and multifamily operators looking to capture top-tier Bay Area rents.

711 Highland AVE, San Mateo

Listed by Michael Hecht, 408-250-3442 from Intero Real Estate Services
(If provided) CoList: Shawn Jones from Intero Real Estate Services

Sold listing courtesy of Michael Hecht from NTERO

$2,350,000
3 Beds ⋅ 2 Baths ⋅ ML82049103 MLS ⋅ SM Highlands BLDG.
recently updated in a desirable location! With approximately 1500 square feet of living space, plus an additional approx. 300 square foot bonus room. This house is perfect for those who value both comfort and convenience with a spacious feel of this Eichler home! The living room is cozy and inviting, with large windows that let in plenty of natural light. Wood burning fireplace for extra comfort. The kitchen is well-appointed, with a galley kitchen & plenty of counter space for meal preparation. The dining area is conveniently located adjacent to the kitchen, making it easy to entertain guests. The bonus/hobby room can easily double as a home office or utility room. The house is situated on a big Level lot providing a peaceful and serene environment. The backyard is spacious and perfect for expansion or an ADU. The property also features a two-car garage 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!

1571 Forge RD, San Mateo

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

Sold listing courtesy of Soofie Jadallah from CBR

$2,350,000
3 Beds ⋅ 2 Baths ⋅ ML82045479 MLS ⋅ Fiesta Gardens Homes Association BLDG.
Welcome to 806 Fiesta Drive, a beautifully reimagined ranch-style home in sought-after Fiesta Gardens where timeless charm meets modern luxury. Expanded and thoughtfully remodeled, this light-filled residence offers an open-concept floor plan with refinished original hardwood floors and curated high-end finishes throughout. The stunning chefs kitchen features quartz slab counters, custom cabinetry, Wolf range, SubZero refrigerator, Miele dishwasher, wine fridge, and a dedicated larder cabinet/coffee station. Spa-inspired bathrooms were remodeled with custom vanities, quartz slab surrounds, and designer fixtures. Major upgrades include A/C, roof, fire sprinkler system, and solar. Outside, enjoy mature landscaping, accent lighting, fountain, pavers, and a private hot tub; creating an ideal setting for relaxation and entertaining. Located in the vibrant Fiesta Gardens community, residents enjoy access to the neighborhood pool, cabana, kiddy park, tennis courts, and beloved social events. Ideally positioned near major commute routes, shopping, dining, and top employment centers, 806 Fiesta Drive offers the perfect blend of lifestyle, luxury, and convenience.

806 Fiesta DR, San Mateo

Listed by David Martin, 650-743-2398 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Benjamin Chirko from CBR

$2,350,000
3 Beds ⋅ 2 Baths ⋅ ML82038492 MLS
Move right in and start enjoying life in the San Mateo Village. This beautifully updated 3-bedroom, 2-bath home blends comfort, charm, and an unbeatable neighborhood setting known for its strong sense of community and highly regarded George Hall Elementary. Inside, refinished oak floors, vaulted ceilings with skylights, modern lighting, dual-paned windows, and fresh interior and exterior paint create a bright, polished feel throughout. The living room with fireplace flows into a dining area with French doors opening to the patio and gardens, while the granite-finished kitchen features a dining island and stainless steel appliances. The spacious primary suite offers lofty ceilings, a cozy window alcove, walk-in closet, and bath with elevated soaking tub. Two additional bedrooms sit along a private hallway for comfortable living. Outside, stone pathways wind through colorful botanicals, fruit trees, and dry creek beds, creating a peaceful garden retreat. A charming stand-alone cottage adds flexible space for hobbies, work, or relaxation. Perfectly located in one of the Peninsulas most beloved neighborhoods, with easy access to parks, shopping, and major commute routes, you don't want to miss this turn-key gem.

3612 Santiago ST, San Mateo

Listed by Maria Baker, 415-412-2590 from Compass
(If provided) CoList: Julie Baumann from Compass

Sold listing courtesy of Hira Bakhsh from SZIR01

$2,350,000
3 Beds ⋅ 2 Baths ⋅ ML82035652 MLS
Nestled in the highly sought-after San Mateo Highlands, this fully remodeled California rancher offers the perfect blend of timeless architecture and modern turnkey living. Thoughtfully redesigned throughout, the home features a stunning new kitchen, beautifully updated bathrooms, new flooring, windows, doors, and fresh interior and exterior paint. Major upgrades including a new heating system, and water heater, provide lasting comfort and peace of mind. Set on a hillside lot, the uniquely shaped backyard presents multiple outdoor living possibilities ideal for entertaining, gardening, or creating private lounge spaces that embrace the natural surroundings. Located near scenic parks, hiking trails, a top-rated high school, and convenient access to Hwy 280, this exceptional Highlands residence delivers elevated Peninsula living in a move-in-ready setting.

1276 Laurel Hill DR, San Mateo

Listed by Martin Santiago, 415-850-7704 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Tiffany Stickle from CBR

$2,350,000
3 Beds ⋅ 2 Baths ⋅ ML82033976 MLS
Welcome home to this light-filled, beautifully updated single-level residence on a quiet street in the rarely available and highly sought-after Lauriedale neighborhood, just steps to Laurie Meadows Park and top-rated Belmont/Redwood Shores schools! The home offers an oversized, sun-filled backyard and a versatile, highly functional floor plan with the flexibility to accommodate a formal living room, an oversized dining room, or both. The spacious, updated kitchen features expansive quartz countertops with generous bar seating, stainless steel appliances, & an electric range with the option to convert to gas. The light and bright great room includes a wood-burning fireplace and sliding glass doors that open to a covered patio, creating a seamless indoor-outdoor setting ideal for everyday living & entertaining. Three large bedrooms and two full bathrooms provide comfort to family and friends alike. Additional highlights include a finished attached two-car garage with a laundry closet & abundant storage, central A/C and heating, rich hickory laminate flooring, dual-pane windows, & professionally landscaped grounds. An unbeatable location on a peaceful street! Enjoy nearby shopping & dining plus convenience to nearby commuter routes!

327 Rosilie ST, San Mateo

Listed by Laura Bryant, 650-888-0772 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of George Xie from KWSN

$2,350,000
3 Beds ⋅ 2 Baths ⋅ ML82024873 MLS
Welcome to this charming home located in the heart of San Mateo, offering comfortable living with 1,510 square feet of space. This beautifully updated home features three bedrooms and two full bathrooms, providing ample room for family and guests. Entertain in style with a private leveled yard featuring beautiful cobblestone and grass areas, multiple fruit bearing trees and an office shed in the back perfect for work from home days. Additional features include a laundry area, two-car garage, marble counter tops, hardwood floors custom closets throughout, double pane windows and radiant heated bathroom flooring. Located in one of San Mateo's most sought-after neighborhoods with great schools, including Aragon High. Enjoy a short walk to the College of San Mateo where you will find a year-round farmers market, cultural festivals and sporting events. Centrally located between the Crystal Springs and Laurelwood shopping centers, as well as the Hillsdale Shopping Mall, this home offers easy access to the 280, 92 and 101 Freeways.

1575 Parrott DR, San Mateo

Listed by Fitan M. Khalil, 408-406-0870 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Michael Haywood Jr. from EXPCA

$2,350,000
3 Beds ⋅ 2 Baths ⋅ ML82021175 MLS
Welcome to this beautifully remodeled 3-bedroom, 2-bath home (1620sf) with the ADDED BONUS of a detached ADU (341sf), providing a total of 1961sf of living space. Designed for modern living, the open-concept kitchen features a large island with seating and flows seamlessly into the dining and living rooms, perfect for everyday living and entertaining. The private bedroom wing includes a spacious primary suite with backyard views and two additional bedrooms sharing an updated bath. A versatile playroom adds extra flexibility. The detached ADU, complete with kitchenette and full bath, offers ideal space for guests, extended family, or a home office. Outdoor living shines with an expansive yard featuring a fire pit with built-in seating, a deck, lawn, and dedicated play space. Additional highlights include a two-car garage and prime location across from a pocket park and just a short walk to the newly reimagined Hillsdale Shopping Center. Move-in ready and thoughtfully upgraded, this home truly has it all.

300 31st AVE, San Mateo

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

Sold listing courtesy of Mattie Wei from RMACC

$2,350,000
5 Beds ⋅ ML82015006 MLS
A rare and exceptional opportunity to get two properties on one lot. 1401 Woodberry Avenue is a two-bedroom, two-bath home with spacious yard and two- car garage. Enjoy the outdoor space and manicured yard year-round. 3400 Glendora is a three- bedroom, two- bath home with a sun-filled patio and spacious living room. Enjoy easy access to Laurelwood Shopping Center, parks and open space - all just steps from your front door. Easy access to shopping, restaurants, and freeways make this a wonderful place to call home. Rental income or multi-generational living are just a few options for the owner of this unique property. Property Highlights: Home #1 3 Bedrooms / 2 Bathrooms Comfortable, well-proportioned layout perfect for families Home #2 2 Bedrooms / 2 Bathrooms Ideal for extended family, guests, rental, or home office Expansive Lot 9,150 Sq Ft Ample outdoor space, mature landscaping, and potential for further customization or ADU (buyer to verify) Prime Location Just minutes from Laurelwood Shopping Center, parks, top schools, and the College of San Mateo Quick access to highways 92, 101, and 280 for easy commuting Truly Unique Offering Two full homes on one parcel Live in one and rent the other, or enjoy both under one ownership

1401 Woodberry AVE, San Mateo

Listed by Dan Lyons, 650-892-2736 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Anna Lam from GSTAR

$2,345,000
3 Beds ⋅ 3 Baths ⋅ ML82035580 MLS
Opportunity knocks! Built in 1977, this Whitecliff built home offers three bedrooms with two and one half baths with 1,880 square feet of living space, set in the San Mateo hills in a serene canyon setting. Spacious living room with high ceilings, separate dining area, eat in kitchen and family room. Huge primary suite with a dry sauna and large walk in closet. This lovely home needs TLC with tremendous upside to put your own personal touches to make it your dream home. There's a three car garage with a huge attic, that could offer endless possibilities or even expansion. Close to shopping, with easy access to 92, 280 101 and the San Francisco International airport.

2026 Fairmont DR, San Mateo

Listed by David Tapper, 415-370-7195 from Coldwell Banker Realty
(If provided) CoList: Beata Swiderska from Coldwell Banker Realty

Sold listing courtesy of Morgan Aiello from CBR

$2,345,000
3 Beds ⋅ 2 Baths ⋅ ML82026316 MLS
Welcome to 472 Gymkhana Road, a beautifully updated single-level home that perfectly combines comfort, style, and convenience in one of San Mateos most desirable neighborhoods. Spanning approximately 1,840 square feet, this 3-bedroom, 2-bath residence offers an inviting layout designed for modern living. Step inside to discover a bright and spacious great room filled with natural light, creating the perfect setting for both relaxing and entertaining. The open floor plan flows seamlessly to a gorgeous patio and private backyard, ideal for al fresco dinners and gatherings under the stars. The beautifully remodeled kitchen and living areas exude warmth and sophistication, while the spa-like primary bathroom provides a serene retreat at the end of the day. Just a block from the Peninsula Golf & Country Club and minutes from Beresford Park, this home offers an unbeatable location close to award-winning schools. Centrally positioned between Silicon Valley and San Francisco, 472 Gymkhana Road captures the essence of effortless California livingbright, open, and beautifully refined.

472 Gymkhana RD, San Mateo

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

Sold listing courtesy of Jocelyn Xie from FQLT

$2,335,000
3 Beds ⋅ 3 Baths ⋅ ML82041551 MLS
Nestled in the charming neighborhood of Sunnybrae, this beautifully remodeled 3-bedroom, 3-bath contemporary home offers modern living with the added benefit of an attached ADU. A thoughtfully landscaped front yard welcomes you into a bright, open-concept living, dining, and kitchen area designed for both comfort and entertaining. The spacious living room is filled with natural light and anchored by a sleek, modern fireplace. The chefs kitchen features black stainless-steel appliances, quartz countertops, and an oversized island ideal for casual dining and gatherings. The primary suite serves as a private retreat, complete with a spa-inspired ensuite bathroom and a generous walk-in closet. The attached ADU includes a kitchenette and full bath, offering excellent flexibility for guests, extended family, or rental potential. Outdoor spaces in the side and backyard are perfect for seamless indoor-outdoor entertaining. A fully permitted 136-sq-ft detached flex room provides additional versatilityideal as a home office, gym, or art studio. This home truly has it allthis is one you dont want to miss before its gone.

1221 Carlisle DR, San Mateo

Listed by Gillian Kilroy, 650-868-2644 from Compass
(If provided) CoList: from

Sold listing courtesy of Jenna Chambers from APR

$2,330,000
4 Beds ⋅ 4 Baths ⋅ ML82024399 MLS
Welcome to this beautifully reimagined single-level residence, where storybook architecture and timeless curb appeal open to a thoughtfully remodeled interior designed for todays lifestyle. 4 beds, 4 baths including 3 ensuites and a detached 1 bed 1 bath studio ADU with a full kitchen, this home offers exceptional comfort, privacy and versatility. The main residence's airy floor plan highlights vaulted ceilings, hardwood floors, and a sleek fireplace as the centerpiece. The kitchen combines beauty and function with brand-new appliances, a gas stove with pot filler, pull-out pantry shelving, and a stylish island. Each bath is brightened by solar tubes, while the new primary suite features a curbless shower, double vanities, a spacious walk-in closet, and direct access to the deck for seamless indoor-outdoor living. The spacious ADU features 3 skylights, full kitchen, bath, and washer/dryer hook-up, ideal for guests, extended family, or rental income. Outdoors, the home offers lush landscaping in the front and a private backyard with a deck glowing under string lights, creating a magical retreat for gatherings or quiet evenings. All this, just steps from downtown San Mateo's shops and dining, nearby parks, and zoned for highly regarded Aragon High School.

909 S Grant ST, San Mateo

Listed by Kevin Peterson, 408-219-6963 from KW Santa Clara Valley Inc
(If provided) CoList: from

Sold listing courtesy of Ben Zhang from COMPS

$2,330,000
3 Beds ⋅ 3 Baths ⋅ ML82022807 MLS
Mid-century charmer in sought-after Beresford Manor near schools, parks, shopping, and the neighborhood Farmers Market. Traditional in style and well-cared-for, this single-level home boasts an 1890 sq. ft. layout with pleasant surprises indoors and out. Home highlights include a formal living room with floor-to-ceiling stacked stone fireplace and open dining area with modern chandelier, an eat-in kitchen anchored by striking stone countertops that add refinement and complement tones in the cabinetry and suite of stainless steel appliances, and a family room with a stunning wall of painted brick that integrates a fireplace, wet bar and barbecue, and opens to the side atrium (shared with kitchen) and private backyard oasis with a deck, emerald lawn and stately, verdant trees. Adding to the appeal, a privately situated bedroom suite also opens to the peaceful back yard for private rendezvous and late night stargazing. With a freshly painted interior and exterior, refinished hardwood floors, recessed lighting, and new light fixtures, kitchen counters, carpeting, fencing and refreshed landscaping, this turnkey home is ready for year-round enjoyment.

309 26th AVE, San Mateo

Listed by Julie Baumann, 650-576-8889 from Compass
(If provided) CoList: Peter Baumann from Compass

Sold listing courtesy of Taylor Kobayashi from APR

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