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2341 Ticonderoga Drive, San Mateo
$1,249,000
3 Beds ⋅ 3 Baths ⋅ ML82062609 MLS
Your own Tahoe-like retreat in the heart of San Mateo Highlands! Ideally situated in one of the community's most desirable locations, this beautifully maintained and upgraded 1,770 sq. ft. townhome offers a rare blend of architectural charm, peaceful surroundings, and everyday convenience. The dramatic main living area showcases soaring vaulted wood-beamed ceilings, expansive skylights, a fireplace, and an open-concept layout connecting the living, dining, updated kitchen with newer appliances, and light-filled breakfast nook. The lower level features a spacious primary suite, a bright guest bedroom, full bath, and laundry room, while the upper-level loft is ideal as a 3rd bedroom, family room, home office, media room, or fitness space. Private decks on both levels overlook a tranquil, tree-lined backdrop. Additional highlights include an attached one-car garage with additional storage space, an uncommon feature in the community, a designated parking space, and resort-style amenities including a pool, spa, tennis, and pickleball courts. Nestled near Crystal Springs Reservoir and just minutes from Crystal Springs Village, Laurelwood Shopping Center, the College of San Mateo, scenic trails, and Highways 92 and 280, this home offers the perfect blend of serenity and convenience.

2341 Ticonderoga Drive, San Mateo

Listing courtesy of April Zhao from Gaea Realty. 650-200-5221

755 Nevada Avenue, San Mateo
$4,599,000
5 Beds ⋅ 4 Baths ⋅ ML82058713 MLS
Modern living in sought-after Baywood Knolls. Extensively remodeled down to the studs, this 5-bedroom, 4-bath home offers approximately 3,124 sq. ft. of living space on a 6,000 sq. ft. lot. The comprehensive renovation included rebuilding the home's structural load-bearing shear walls from the foundation up. An open floor plan, high ceilings, 10 -inch-wide hardwood flooring, and solid modern doors with concealed hinges create a clean, refined aesthetic. The chefs kitchen features a 48-inch Thermador gas range and separate Thermador refrigerator and freezer columns. Dual-zone heating and cooling provide year-round comfort. The versatile layout includes three bedrooms and two baths upstairs, plus two bedrooms and two baths on the main level. A second-floor family room with a wet bar offers additional space for relaxing and entertaining. The primary suite is a stylish retreat featuring a minimalist walk-in closet and a full-wall, glass-front display closet. Thoughtfully designed and beautifully finished, this exceptional home blends modern style, quality craftsmanship, and flexible living.

755 Nevada Avenue, San Mateo

Listing courtesy of Sophia Wang from Alliance Bay Realty. 206-669-8029

435 Portola Drive, San Mateo
$2,395,000
6 Beds ⋅ 7 Baths ⋅ ML82061552 MLS
Discover an expansive San Mateo property in the desirable Beresford area, offering an impressive 6 bedrooms, 2 full bathrooms, and 5 half bathrooms. With a versatile layout and abundant space, this property presents a variety of possibilities for buyers seeking room for extended family, guests, a home office, or flexible living arrangements. Previously used as a care home, the property offers a unique opportunity to reimagine the space to suit your needs and lifestyle. The generous bedroom and bathroom count provides flexibility rarely found in the area. Ideally situated in the Beresford neighborhood of San Mateo, the home offers convenient access to parks, shopping, dining, recreation, and everyday amenities. Enjoy being within walking distance of vibrant 25th Avenue, where you'll find local markets, grocery shops, restaurants, and a variety of stores for everyday essentials. You'll also be close to Hillsdale Shopping Center, nearby green spaces, Coyote Point, and the many attractions throughout San Mateo and the Peninsula. Whether you're looking for a spacious home, a flexible property with adaptable spaces, or an opportunity to create something uniquely your own, this property offers the space, location, and versatility to bring your vision to life.

435 Portola Drive, San Mateo

Listing courtesy of Guillean Arradaza from Kinetic Real Estate. 415-480-7738

400 Mariners Island Blvd Unit #115, San Mateo
$1,199,000
2 Beds ⋅ 2 Baths ⋅ 41149209 MLS
Welcome to Unit 115 at Tidelands — a bright, ground-floor residence in one of Mariners Island’s most sought-after communities. This 2-bedroom, 2-bath home offers about 1,353 square feet of open living with hardwood floors, large windows, and an easy indoor-outdoor flow to a private balcony. The living, dining, and kitchen share one generous space. The kitchen is built for everyday cooking and entertaining, with a quartz island, gas cooktop, stainless appliances, and room for stools at the breakfast bar. A built-in bookshelf alcove off the main living area works as a den, office, or reading nook. The primary suite is a true retreat: generous bedroom, walk-in closet, and an ensuite with dual vanity and a glass walk-in shower. The second bedroom and full bath with tub/shower combo give guests or work-from-home space their own wing. In-unit laundry adds convenience. Tidelands living includes a gym, clubhouse with billiards and table tennis, community kitchen and lounges, and outdoor BBQ areas. Assigned garage parking and guest parking keep daily life simple. Walk or bike the Marina Lagoon trails, reach Seal Point Park and Foster City dining in minutes, and connect quickly to Highway 101, SFO, and the Peninsula job centers. A rare first-floor Tidelands home — open, light, and ready for its next chapter. Information provided is deemed reliable but is not guaranteed. Buyer and Buyer’s Agent are advised to independently verify the accuracy of all information, including but not limited to square footage, lot size, property features, permits, schools, taxes, HOA information, and any other matters material to Buyer’s decision to purchase.

400 Mariners Island Blvd Unit #115, San Mateo

Listing courtesy of Asif Kazi from EXP Realty of California, Inc. 415-580-2962

2225 Kent Street, San Mateo
$1,850,000
3 Beds ⋅ 2 Baths ⋅ ML82062377 MLS
Welcome to a home that feels inviting and wonderfully familiar from the moment you arrive. Located in beloved Fiesta Gardens, this 3 bedroom, 2 bath home offers 1,830 square feet of classic character and thoughtfully designed living spaces. The spacious living room features a charming bay window with a window seat, plantation shutters and a fireplace. The classic kitchen offers double ovens and flows to a dedicated dining room, while the separate family room provides a second fireplace and access to the backyard. One bedroom features built ins, adding useful storage and character. Outside, a custom shed and covered outdoor dining area create an ideal setting for summer dinners, casual gatherings and relaxed weekends. The low maintenance front yard features artificial turf. Fiesta Gardens offers a wonderful neighborhood setting with a community pool, tennis courts, park and cabana, while nearby Bay Meadows provides shopping, dining, parks and everyday conveniences. Easy access to Highways 101 and 92 makes getting around the Peninsula a breeze. A home with timeless appeal and spaces designed for everyday living and making memories.

2225 Kent Street, San Mateo

Listing courtesy of Julie Flouty from Compass. 650-504-6900

1139 Shoreline Drive, San Mateo
$1,148,000
2 Beds ⋅ 2 Baths ⋅ ML82062013 MLS
RARE single-level waterfront condominium ideally located within Harbortown NO STAIRS! The exquisite kitchen is a culinary delight, thoughtfully appointed with all the bells and whistles. The adjoining dining area opens through sliding glass doors to a private waterfront patio overlooking the tranquil lagoonperfect for morning coffee or relaxed outdoor dining. A spacious living room features a wood-burning fireplace, plantation shutters, and a comfortable sitting area. Newly installed carpeting and fresh paint throughout create a bright, move-in-ready setting. The primary bedroom offers generous closet space and a beautifully remodeled bath. The second bedroom and the hall bath echo the home's refined aesthetic. DOG FRIENDLY community with 3 pools, spa, sauna, 3 pickleball & 1 tennis court. Boat docks for your kayak & paddle-board. Convenient to freeways, shopping & dining. SELLER WILL COVER FIRST YEAR OF HOA FEE(S)

1139 Shoreline Drive, San Mateo

Listing courtesy of Nonnie Dinges from Engel & Voelkers Burlingame. 650-218-3353

340 W 39th Avenue, San Mateo
$1,899,900
3 Beds ⋅ 2 Baths ⋅ ML82061186 MLS
Beautifully-maintained San Mateo home perched in the foothills with a SF city skyline and bay views! The bright, sunny main floor features 2 BR + full BA, large dining/living room with fireplace, eat-in kitchen, hardwood floors throughout, and a large deck off the back to take in the view. Kitchen features cherry cabinets and granite countertops, plus a sunny bay window looking at Indian Springs Park across the street. The full bath features marble shower and floors, a soothing whirlpool bath and spacious luxurious countertop. Downstairs is an additional ~700 sq.ft unpermitted finished walkout basement area with a private master bedroom that opens to the backyard, 3/4 bath, and a family room with bar and fireplace. An oversized two-car garage, loads of storage space, new paint inside and out, plus a lower-maintenance yard with turf round out this special home just waiting for the right family.

340 W 39th Avenue, San Mateo

Listing courtesy of Marc J Romer from Romer Real Estate. 650-364-2922

2425 Alameda De Las Pulgas, San Mateo
$2,198,000
5 Beds ⋅ 2 Baths ⋅ ML82061838 MLS
Space, character, and endless potential come together at 2425 Alameda de las Pulgas! Lovingly cared for by the same family since the 1960s, this 5Bed/2Bath, 2,785 sqft residence is ready for a new owner to bring their own vision to life. The main level features a spacious living room with fireplace, dining room, kitchen, 2BRS/1BA. Upstairs, 3BRS/1BA & a finished attic/playroom. Upstairs has potential for an ADU or separate living space. (Buyer to investigate feasibility.) Beautifully landscaped front and back yards create a peaceful, garden-like setting filled with mature plantings and multiple areas to relax, play, or entertain. A charming waterfall feature adds to the tranquility of the backyard, while a two-car garage provides additional parking and storage. This property presents a rare opportunity in San Mateo's sought-after Beresford Park neighborhood. Conveniently located near all that San Mateo has to offer, including shopping, dining, parks, recreation, schools, and everyday amenities, with easy access to Caltrain,Major freeways for commuting throughout the Peninsula, Silicon Valley, and San Francisco.

2425 Alameda De Las Pulgas, San Mateo

Listing courtesy of Allison M Fujimoto from Golden Gate Sotheby's International Realty. 650-888-3863

1586 Lexington Avenue, San Mateo
$4,498,000
3 Beds ⋅ 2 Baths ⋅ ML82060534 MLS
A rare architectural offering, this one-of-a-kind 1956 Mid-Century Modern X-100 prototype, designed by an acclaimed team of architects, represents a pivotal moment in mid-century modern design. The home showcases six exposed steel I-beams, eliminating interior load-bearing walls and creating a dramatic open, light-filled environment with seamless indoor-outdoor flow. Thoughtfully restored while honoring its original vision, recent updates include fresh interior/exterior paint, recoated foam roof, refinished vinyl and concrete floors, updated radiant heating, curated furnishings, and refreshed landscaping. The home is organized around two private garden atriums with in-ground planting beds, while 32 feet of skylights flood the interiors with natural light. Signature materials, steel, glass, and Formica, highlight the home's authentic modernist character. Built-ins and kitchen elements are fully integrated into the architecture. Debuted in 1956, the X-100 gained national attention and influenced generations of modern residential design, set against the backdrop of Crystal Springs Reservoir. Listed on the National Register, this is a true collector-grade property ideal for design enthusiasts, historians, and those seeking a singular living experience. A legacy of visionary design.

1586 Lexington Avenue, San Mateo

Listing courtesy of from Compass. 408-373-1660

414 E 16th Avenue, San Mateo
$1,900,000
ML82061457 MLS
414 E 16th Ave (the Property) is a four-unit multifamily asset built in 1959, situated on a two-story, slab-on-grade structure of stucco and wood construction in San Mateo's Hayward Park submarket. The Property features a unit mix of two (2) studio floorplans and two (2) one-bedroom/one-bathroom floorplans, averaging 775 square feet. The Property is 100% occupied as of August 2026. The Property offers a new owner a rare combination in this submarket: a fully occupied, free and clear fourplex with copper supply lines, dual-paned vinyl windows building-wide, on-site laundry, and covered tuck-under parking. In-place rents average $2,129 per unit, against market rents of $2,375 per unit, a loss-to-lease of 11.5%. A light interior renovation program, budgeted at $18,750 per unit, supports renovated rents of $2,750 per unit, or a 15.8% premium to current market. The Property's location places residents between Highway 101 and Interstate 280, within a short drive of Peninsula employers including Sony Interactive Entertainment, Roblox, GoPro, and Franklin Templeton in San Mateo, Oracle in Redwood Shores, and Meta in Menlo Park. Hillsdale Caltrain and the Bay Meadows mixed-use development are both nearby, and Hillsdale Shopping Center provides additional dining and retail options.

414 E 16th Avenue, San Mateo

Listing courtesy of Adam Foley from CBRE, Inc.. 408-893-8063

213 Estrella Way, San Mateo
$1,725,000
3 Beds ⋅ 2 Baths ⋅ ML82061003 MLS
Welcome to 213 Estrella Way, ideally situated on one of the premier streets in desirable San Mateo Village. This expanded single-story home blends classic charm, thoughtful updates, and wonderful indoor-outdoor living. Mature landscaping, colorful gardens & a charming covered front porch create an inviting first impression. Inside, hardwood floors flow through the living room, where a classic fireplace creates a warm focal point and double-pane windows bring in abundant natural light. The eat-in dining area opens to the kitchen featuring granite countertops, generous cabinetry, and sun tunnel. Step down to the spacious family room with vaulted ceiling, bar seating, freestanding fireplace, and sliding doors opening to an expansive Trex deck. Three bedrooms feature hardwood floors, including the primary with direct deck access. 2 full bathrooms include an updated bath with decorative tile and frameless glass shower. The spacious backyard offers Trex deck, lawn, mature landscaping, and plenty of room for outdoor dining and entertaining. A substantial detached shed with electricity provides flexible space for a home office, workshop, hobbies, or private retreat. Close to George Hall Elementary, Hillsdale Shopping Center, Whole Foods, Roblox, Fieldwork Brewing, and highways 92 & 101.

213 Estrella Way, San Mateo

Listing courtesy of Debbie Wilhelm from Coldwell Banker Realty. 650-400-3111

no property photo
$1,599,000
2 Beds ⋅ 1 Baths ⋅ ML82048876 MLS
Beautifully updated and exceptionally bright, this San Mateo Village ranch offers a thoughtful blend of modern upgrades and comfortable living. Featuring an open, functional floor plan with 1,300 Sq Ft, the home includes 2 spacious bedrooms and 1 fully remodeled bathroom, along with a third room perfect for a home office. The remodeled kitchen is designed for both style and function, complete with quartz countertops, soft-close cabinetry, and stainless steel appliances and wine fridge. The bathroom has been tastefully renovated with quartz surfaces, a tiled shower, and sleek, modern finishes. The light-filled living room is anchored by a beautifully updated fireplace and charming arched doorway, adding warmth and character. Recent improvements include air conditioning, a new electrical panel, added laundry area, contemporary doors and baseboards, fresh interior/exterior paint, and renovated landscaping. Set on an oversized, flat lot, the backyard has been transformed into an inviting outdoor retreat with decomposed granite, a pergola, fire pit, and BBQ areaperfect for entertaining or relaxing. Ideally located near Bay Meadows and Hillsdale Shopping Center, with convenient access to shopping, a turnkey home offering both lifestyle and location in the heart of the Peninsula.

45 E Hillsdale Boulevard, San Mateo

Listing courtesy of John Sayage from Compass. 650-346-9480

185 Waters Park Circle, San Mateo
$1,298,000
2 Beds ⋅ 3 Baths ⋅ ML82059710 MLS
Built in 2021, this stylish San Mateo residence delivers the rare combination of newer construction, modern design, generous living space, and a private 2-car tandem garage - all in a convenient Peninsula location. This thoughtfully designed three-level home offers nearly 1,600 sq ft of bright, comfortable living with large windows and an open, airy feel. The main living level brings together the kitchen, dining, and living areas for effortless everyday living and entertaining, while a covered deck extends the space outdoors. Upstairs, two spacious bedrooms provide privacy and flexibility, including a generous primary suite with a walk-in closet and private bath. The second bedroom with its own en-suite bath is ideal for guests, a home office, or a private retreat. Contemporary finishes, energy-efficient features, smart-home technology, and an attached garage add to the ease of modern living. Enjoy a beautifully maintained community setting with convenient access to shopping, dining, major commute routes, and everything San Mateo and the Peninsula have to offer.

185 Waters Park Circle, San Mateo

Listing courtesy of from KW Advisors. 650-627-3700

228 State Street, San Mateo
$1,999,000
ML82060377 MLS
Excellent five-unit investment opportunity ideally located between Downtown San Mateo and Downtown Burlingame, offering convenient access to shopping, dining, Caltrain, major transportation routes, and Peninsula employment centers. The property features two one-bedroom units, one two-bedroom unit, and two studios, with current annual rents of approximately $122,580. Several units are rented below current market levels, creating significant long-term upside through future rent growth and thoughtful renovations. Renovated market rents are projected at approximately $181,800 annually, highlighting the property's compelling value-add potential. A rare opportunity to acquire a well-located Peninsula multifamily asset with strong in-place income, below-market rents, and meaningful future upside.

228 State Street, San Mateo

Listing courtesy of John Sayage from Compass. 650-346-9480

409 Longden Ave, San Mateo
$1,539,000
2 Beds ⋅ 3 Baths ⋅ 41147649 MLS
Welcome to this stunning, light-filled townhome perfectly situated on desirable Longden Avenue! Enjoy the ultimate blend of private, upscale living and urban convenience, located just steps from Paddock Park, the community garden, top-rated schools, shopping, and major commuter routes.Extensively upgraded throughout, the residence showcases gleaming hardwood flooring, modern recessed lighting, and oversized dual-pane windows that bathe the entire home in beautiful natural light.The main level features a bright, open-concept layout designed for seamless indoor-outdoor living. French doors effortlessly connect the living area to a charming view patio overlooking a lush, manicured lawn, while a convenient kitchen terrace provides the ideal setting for an outdoor electric BBQ or a personal plant nursery. The contemporary kitchen is a chef's dream, complete with abundant cabinetry, generous stone counter space, a custom backsplash, a premium stainless steel Bertazzoni hood, and an expansive breakfast bar. An inviting dining space, a main-floor half bath, and a dedicated laundry area complete this level.Upstairs, two generously sized en-suite bedrooms offer maximum comfort, privacy, and flexibility. The bright primary suite serves as a true retreat, featuring a dual vanity, a sleek glass walk-in shower, and ample closet space.Don't miss this turnkey property offering top-tier San Mateo schools, fantastic walkability, and effortless freeway access for an easy Bay Area commute! Offers due on Tuesday September 22 at noon. Seller reserves the right to accept preemptive offer

409 Longden Ave, San Mateo

Listing courtesy of Kristine Reyes from Bridges Real Estate. 925-899-0448

616 S Amphlett Boulevard, San Mateo
$2,495,000
ML82060083 MLS
616 S Amphlett Blvd represents a unique opportunity to acquire a well-located mixed-use investment property in the heart of San Mateo. Situated along the established Amphlett corridor, the property benefits from a central Peninsula location, excellent accessibility, and proximity to some of San Mateos most active commercial, residential, and employment areas. The property features an +-4,260sf warehouse/commercial building along with a separate +-1,670sf apartment building, creating a versatile mix of commercial and residential space. The residential component includes a 2-bedroom / 1-bath apartment unit, while an on-site income-producing billboard with a long-term lease through 2050 provides an additional revenue stream. This diversified configuration creates an attractive opportunity for an investor, owner-user, or business, with the ability to benefit from commercial, residential, and billboard income. The propertys layout also provides flexibility for a variety of potential commercial uses and offers additional long-term upside potential, subject to applicable zoning and approvals. Strategically located just off US-101, 616 S Amphlett Blvd provides excellent regional connectivity with convenient access to Highway 92, I-280, and El Camino Real.

616 S Amphlett Boulevard, San Mateo

Listing courtesy of Kevin J. Phillips from SC Properties. 650-380-2868

191 Waters Park Circle, San Mateo
$1,798,000
4 Beds ⋅ 4 Baths ⋅ ML82059533 MLS
Fully-upgraded former model home overlooking Borel Creek, an end unit with only one shared wall and windows on three sides. Open and versatile main floor with living, dining, and kitchen naturally flowing from one room to the next and out to a private deck. Silestone quartz counters in Charcoal Soapstone Suede, oversized island, Whirlpool stainless built-in oven, cooktop and hood, and three-zone heating and air conditioning with each level controlled independently. Upstairs there are 3 bedrooms with generous storage. Primary suite features two walk-in closets, double vanities, and an oversized seated shower. A fourth bedroom and full bath downstairs doubles as the guest room or perfect work-from-home enclave. Recessed lighting and CAT6 ethernet wiring throughout. Large 429 sq ft 2-car garage with 220V EV outlet, plus owned solar, no lease and no PPA. $70k+ in builder upgrades on a $100k premium end-unit lot, including accent walls, designer Winter White shaker cabinetry, and custom Shade Store window treatments. Coveted location within a short walk to the community dog park, lighted creek path, play structures and BBQ lawn, and minutes to Bridgepointe and Hillsdale Shopping Center for Whole Foods, Trader Joe's and Target, Hillsdale Caltrain, and Highways 101 and 92.

191 Waters Park Circle, San Mateo

Listing courtesy of Sophia Wong from KW Advisors. 408-438-2902

555 Laurel Avenue Unit #122, San Mateo
$2,988,000
4 Beds ⋅ 3 Baths ⋅ ML82059114 MLS
Welcome to Gramercy on the Park, one of San Mateo's most prestigious addresses, where luxury living meets downtown San Mateo convenience. Discover a spacious, townhouse-style residence with 3 bedrooms/den or office, 3 bathrooms, a private patio, and access to exceptional building amenities. A bright, open-concept layout with high ceilings and a cozy fireplace defines the interior. A sleek designer kitchen features stainless appliances and stone countertops, flowing naturally into a spacious living area. It is a space meticulously designed for both relaxation and effortless entertaining, extending to a private terrace, the ideal sanctuary for an evening glass of Cabernet. The primary suite serves as a true retreat, complete with generous wardrobe space and a spa-like ensuite. Every corner of this home ensures a harmonious balance of style and function. Beyond your front door, the very best of San Mateo is yours to explore. Located just moments from the lush greenery of Central Park, you are a quick trip from downtown dining, the cinema, and upscale boutiques. With the Caltrain station and major commuter corridors blocks away, you are perfectly positioned for effortless access to both San Francisco and Silicon Valley.

555 Laurel Avenue Unit #122, San Mateo

Listing courtesy of Jacklyn Friedland from Compass. 650-766-0791

216 8th Avenue, San Mateo
$1,230,000
2 Beds ⋅ 2 Baths ⋅ ML82052776 MLS
Warm, inviting contemporary home in the heart of San Mateo! With its own private & spacious 2-car garage complete w/ room for a workbench or hobby area, this residence offers the feel & privacy of a single-family home. The light-filled living & dining areas open through sliding glass doors w/ folding shutters to a private patio, creating the perfect space for relaxation. The beautiful kitchen features granite countertops, a Casa Dolce Casa porcelain tile backsplash, custom cabinetry, bar seating w/ designer pendant lighting, & high-end stainless steel appliances. Premium finishes continue throughout w/ Mirage engineered hardwood flooring from Canada & hand-poured Casa Dolce Casa porcelain tile from Italy. Two spacious bedroom suites offer custom-organized closets & spa-inspired bathrooms w/ stylish finishes, including a walk-in shower with massage shower head, soaking tub/shower, sauna & designer fixtures. Additional highlights include a dedicated laundry room with custom shelving and built-in desk, generous storage with a deep coat closet, & thoughtfully designed living spaces throughout. Ideally located within walking distance to San Mateo downtown, restaurants, shopping, and Caltrain. Welcome home!!!

216 8th Avenue, San Mateo

Listing courtesy of Vicky Yu from Coldwell Banker Realty. 650-701-5058

220 Waters Park Circle Unit #101, San Mateo
$1,149,000
3 Beds ⋅ 2 Baths ⋅ ML82058555 MLS
NEW PRICE! Beautiful single-level condo featuring three bedrooms, two bathrooms, and a nearby detached, enclosed two-car garage. Enjoy modern living in this four-year-old complex. Window coverings with Sheer and Black-out options. The sheers provide natural light along with privacy from the outside. The open-concept kitchen features a spacious island, white cabinetry, and white-and-gray stone countertops, flowing seamlessly into the living and dining areas. Three generously sized bedrooms include a primary suite with a private bathroom. Additional highlights include an in-unit laundry room, an elevator, and a rooftop common area ideal for entertaining. This move-in-ready home is conveniently located near Bridgepointe Shopping Center and Apple Fritter Restaurant, with easy freeway access. Don't miss the opportunity to see this fabulous home.

220 Waters Park Circle Unit #101, San Mateo

Listing courtesy of Susan Berry from KW Advisors. 650-464-3454

153 N San Mateo Drive Unit #201, San Mateo
$1,099,800
2 Beds ⋅ 2 Baths ⋅ ML82058321 MLS
Rarely available 2-bedroom, 2-bathroom condominium in one of San Mateo's most desirable buildings. This spacious home offers no-step entry, high ceilings, custom Venetian plaster walls, generous bedrooms, and new in-unit laundry machine. The recently updated kitchen features modern finishes, gas range and appliances. Some furnishings may be available for purchase, making this a great move-in-ready opportunity. Community amenities include an elegant lobby, clubhouse, fitness center, sauna, and bicycle storage. The secure underground garage offers two assigned parking spaces with an electric vehicle charger, guest parking, and private storage. Two elevators provide convenient access throughout the building. Ideally located within walking distance of vibrant downtown San Mateo, Caltrain, shopping, dining, and parks, with easy access to major commute routes, this home offers comfort, convenience, and a prime Peninsula location.

153 N San Mateo Drive Unit #201, San Mateo

Listing courtesy of Bradley Lent from Pacific Crest Properties. 650-766-7552

3 Bay Landing, San Mateo
$1,388,000
3 Beds ⋅ 3 Baths ⋅ ML82057925 MLS
A Great Value! Why buy a Condo when you can own a detached Single Family Home?! A Rare Opportunity to own A New England Style Bungalow in an Exclusive Private Enclave of just 10 Homes built in 1997! Located on a Peaceful Private Street steps from the Bay Trail, this 3-BR, 2.5-Bath Gem features an Updated Kitchen w/Coastar Engineered Stone Countertops, New SS Appliances, Sink, Faucet, GD. LRG Combo LR/DR, WBF w/Gas Starter, New Interior Paint Throughout, complimented by New High Quality Engineered Flooring w/ Commercial Grade AC4 Waterproof Rating w/ Advanced Scratch Protection on Entire Lower Level, Stairway and Upper Hall. New Carpet and Pad in Bedrooms. A Luxurious Primary Ste. welcomes the Morning Sun with Views of the SF Bay and SM Bridge, boasting a High Sloped Ceiling, Mirrored Closet Doors, and Double Sinks, Walk-In Shwr. The 3rd Bedroom serves perfectly as an Office w/ Built-In Cabinets and Shelving. Recessed LED Lighting and Upgraded Lighting Fixtures Throughout. Additional features include an Interior Lndry RM and a LRG 2-car Garage with Built-In Storage, Addtl Attic Space, and an 84-Bottle Wine Rack. Enjoy the Afternoon Sun in your Private Rear Yard featuring a Pergola Shaded Patio, and Built-In Natural Gas BBQ and Sink. Dual-Pane windows, fire sprinklers throughout.

3 Bay Landing, San Mateo

Listing courtesy of Victor M. Zolezzi from Coldwell Banker Realty. 650-868-3495

20 Madison Avenue Unit #213, San Mateo
$1,099,000
2 Beds ⋅ 2 Baths ⋅ ML82055885 MLS
Just moments from Downtown San Mateo, this beautifully designed second-floor end-unit retreat blends timeless architecture with modern comfort. Set within a Craftsman-inspired community, the light-filled home features high ceilings, abundant windows, and an open floor plan ideal for living and entertaining. The inviting living room is anchored by a fireplace and flows seamlessly into the dining area, where French doors open to a private covered balcony overlooking the central courtyard. Peaceful green views from the living room and both bedrooms create a tranquil setting. The kitchen features rich wood cabinetry, stainless steel appliances, a Viking gas range and hood, abundant storage, and a breakfast bar. The spacious primary suite offers an ensuite bath with a dual vanity, glass shower, and separate soaking tub. A secondary bedroom and full hall bath provide comfort and privacy. Additional highlights include plantation shutters, in-unit laundry, two deeded parking spaces, and secure building access. Enjoy a landscaped courtyard with a fountain, outdoor fireplace, a community room, and secure indoor mailboxes. Located less than 1 mile from Downtown San Mateo's acclaimed restaurants, boutique shopping, Cinemark, Caltrain, Central Park, and major commuter routes. Welcome home!

20 Madison Avenue Unit #213, San Mateo

Listing courtesy of Laura Lee from Compass. 650-455-5326

869 Woodside Way, San Mateo
$1,648,000
41144497 MLS
Recently remodeled (2023) and never occupied commercial space, offering a rare move-in ready mixed-use opportunity in the heart of San Mateo Village and a central Peninsula location. This property features a street-level commercial unit with strong visibility and direct street access, along with a separately accessed upper-level residential unit. The ground-floor commercial space offers an office/storefront-style frontage with large display windows, providing abundant natural light and excellent street presence. Front and rear entrances provide ADA-accessible sloped entry conditions. The commercial space has been extensively reconfigured, including demolition of prior interior improvements and the addition of newly designed storage and break rooms. Electrical upgrades include enhanced commercial-grade 220V power capacity, while existing wiring was partially retained and supplemented as needed. New Title 24–compliant lighting has been installed throughout. Additional improvements include an integrated HVAC system, a new hot water heater, commercial-grade laminate flooring, and an updated restroom. The flexible interior layout allows for immediate occupancy and supports a variety of business uses. The upper-level residential unit has been remodeled with fresh interior paint, a new kitchen, and a tastefully updated bathroom featuring a new vanity, mirror, lighting fixtures, and updated tile flooring. On-site parking is located at the rear of the property and accessed via the alley. Well-maintained and thoughtfully configured, this property is ideal for an owner-user or investor seeking a professional, service-oriented, or long-term investment opportunity. AI-generated virtual staging shown for illustrative purposes use inspiration only. Actual property condition and layout may differ.

869 Woodside Way, San Mateo

Listing courtesy of Ting Yu Zhu from BHG RE Reliance Partners. 510-282-9898

Bay East © 2026. CCAR © 2026. BridgeMLS © 2026. Information Deemed Reliable But Not Guaranteed. This information is being provided by the Bay East MLS, or CCAR MLS, or bridgeMLS. The listings presented here may or may not be listed by the Broker/Agent operating this website. This information is intended for the personal use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on:

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