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39 Live Oak DR, San Mateo
$2,520,000
3 Beds ⋅ 3 Baths ⋅ ML82058484 MLS ⋅ Verona Ridge Homeowners Assoc. BLDG.
Located in the hills of San Mateo, welcome home to this beautifully appointed detached single-family residence featuring 3 bedrooms and 2.5 bathrooms.Whether preparing everyday meals or entertaining guests, enjoy gourmet cooking with built-in Monogram Series stainless steel appliances and a professional-style six-burner range. A dedicated wine refrigerator provides convenient storage for your favorite bottles.Enjoy movie nights with in-ceiling surround sound, or step outside to the inviting back patio where you may catch a glimpse of deer wandering nearby. Spend the afternoon barbecuing, then gather around the fire pit for a relaxing evening under the stars. Energy and technology features include solar panels with two battery storage units, two EV chargers in front, and an additional charging option inside the garage. The home also features dual-zone air conditioning, security cameras, and an alarm system. Conveniently located near supermarkets, restaurants, College of San Mateo, The Peninsula Golf & Country Club, and Highway 92, providing easy access throughout the Peninsula.

39 Live Oak DR, San Mateo

240 Briar LN, San Mateo
$2,510,000
3 Beds ⋅ 2 Baths ⋅ ML82038596 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath home in The Lanes, a highly sought-after tree-lined cul-de-sac community in San Mateo. Thoughtfully refreshed & impeccably maintained, the home blends modern style, comfort, & effortless California living. At the heart of the home is a stunning chef's kitchen with an expansive island, high-end appliances, & elegant finishes-perfect for everyday living & entertaining. The open layout flows seamlessly into the main living spaces, filling the home with natural light & creating a warm, inviting atmosphere. The spacious primary suite offers a private retreat with a spa-inspired bathroom & a walk-in closet. Additional bedrooms provide flexibility for family or guests. What truly sets this property apart is its park-side setting. The backyard backs directly to open green space, offering rare privacy & tranquil views. With the park just beyond your yard, it feels like an extension of your outdoor living space-ideal for relaxing mornings or entertaining. A detached backyard studio adds versatility for a home office, gym, or creative space. Ideally located near commute routes, shopping, dining, & highly regarded schools, this home offers a rare opportunity to enjoy park-side living in one of San Mateos most desirable neighborhoods.

240 Briar LN, San Mateo

331 Sonora DR, San Mateo
$2,510,000
3 Beds ⋅ 2 Baths ⋅ ML82025186 MLS
Set on one of the most coveted streets in the Aragon area, this exceptional residence perfectly blends timeless character with modern sophistication. From the moment you enter, youre greeted by beautifully refinished hardwood floors, dramatic high ceilings, and a grand living room with a classic fireplace and stained-glass Dutch doors opening to a private patio. The formal dining room leads to a newly updated kitchen featuring quartz countertops, double ovens, a wine refrigerator, and a sunlit breakfast nook. Three generous bedrooms and two newly updated baths provide comfort and elegance, while the lower-level office or guest retreat adds flexibility. Outside, the lush backyard offers a private sanctuary framed by mature trees and colorful gardens ideal for entertaining or unwinding. Complete with a two-car garage, this one-of-a-kind home embodies the best of Bay Area living.

331 Sonora DR, San Mateo

1100 Ramblewood WAY, San Mateo
$2,508,000
3 Beds ⋅ 2 Baths ⋅ ML82027028 MLS
This is the home you've been waiting for! This beautifully updated, single level home is located in a secret pocket of San Mateo, right on the border of Belmont. The 3 bedroom, 2 bathroom property has been meticulously renovated with waterproof LVP flooring, designer light fixtures, beautiful stone countertops, a new refrigerator and a new bathroom vanity and toilet. This home will keep you warm in the winter with a cozy fireplace and cool in the summer with an energy efficient whole house fan. The backyard is ready for entertaining with a sparkling pool and fountains that are heated by solar roof panels. The walking opportunities here are limitless - go for a stroll around the friendly neighborhood, head across the street to a lovely park or walk to school, shopping, dining or the train station. This home is located in the highly rated Belmont-Redwood Shores School District and Carlmont High School. This home is ready for its new owner - welcome home to 1100 Ramblewood Way!

1100 Ramblewood WAY, San Mateo

453 26th AVE, San Mateo
$2,505,000
3 Beds ⋅ 2 Baths ⋅ ML82045318 MLS
Tastefully renovated in the heart of Beresford Park! This thoughtfully designed layout with seamless transitions and modern architecture checks all the boxes. The open floor plan blends the cozy living room and wood-burning fireplace with the spacious dining room and walk up eating counter. Chefs kitchen includes ample custom cabinetry, extensive granite counter space, 6 burner Viking range, a designer farmhouse sink, and recessed lighting. The generous family room and primary bedroom feature 10' high vaulted ceilings and tons of natural light with large sliding doors leading to the outdoor patio. No expense was spared in the primary suite and bathrooms including a seamless glass enclosed stall shower in the primary and a hall bath with double sinks. Additional features include a solar system, EV Charger, hardwood floors and a custom loft in the garage set up as a playroom. Low maintenance mature landscaping front and rear. A short 2 block walk to 25th Avenue and its wonderful selection of restaurants and shops. Easy access to Hillsdale Shopping Center, Beresford Park, Peninsula Golf Club, Caltrain, plus an easy commute to Highways 92, 101, and 280.

453 26th AVE, San Mateo

313 W 25th AVE, San Mateo
$2,500,000
3 Beds ⋅ 3 Baths ⋅ ML82052443 MLS
An exceptional residence thoughtfully reimagined through a fully permitted interior renovation, blending timeless architecture with modern luxury. Filled with natural light, the open-concept floor plan features wide-plank hardwood flooring, designer lighting, custom millwork, and premium finishes throughout. The stunning chefs kitchen is the heart of the home, showcasing custom cabinetry, premium stone countertops, top-tier appliances, and an oversized island that flows seamlessly into the spacious living and dining areas. The luxurious primary suite offers a peaceful retreat with a beautifully appointed spa-inspired bath, while the additional bedrooms and designer bathrooms provide comfort and versatility for family and guests. Step outside to a private backyard designed for Californias indoor-outdoor lifestyle, offering the perfect setting for entertaining, dining al fresco, or simply relaxing. Ideally located just minutes from vibrant downtown San Mateo, premier shopping and dining, parks, Caltrain, major commuter routes, Silicon Valley, and San Francisco International Airport. A rare opportunity to own a beautifully renovated home where timeless design, modern luxury, and exceptional craftsmanship come together in one remarkable residence.

313 W 25th AVE, San Mateo

2203 Allegheny WAY, San Mateo
$2,500,000
4 Beds ⋅ 2 Baths ⋅ ML82048838 MLS
Nestled in the coveted Highlands neighborhood, this cherished Eichler offers a rare opportunity to own a true piece of mid-century modern history. Lovingly enjoyed by the same family for decades & originally selected as one of the neighborhood's model homes, this home embodies the timeless appeal of Eichler design paired with the warmth of true community living. Ideally positioned on a flat lot, this open concept single-story residence is filled with natural light, skylights, & seamless indoor outdoor flow. The spacious kitchen features ample cabinetry, built in storage, stainless steel appliances including a gas range, eat up bar, & opens beautifully into the main living space. Custom built-ins & a media cabinet add both style & functionality. Walls of glass connect the indoors to a lush backyard opening to serene open space and a private front courtyard, creating the quintessential California lifestyle Eichler enthusiasts adore. The flexible floor plan offers 4 bedrooms plus a bonus room or walk-in closet off the primary suite. Enjoy the home's timeless character as is or personalize it over time. Moments from Crystal Springs Village, the Highlands Recreation Center, top commuter routes including 280, 92, and 101, and beloved neighborhood traditions.

2203 Allegheny WAY, San Mateo

731 26th AVE, San Mateo
$2,500,000
3 Beds ⋅ 2 Baths ⋅ ML82048421 MLS
Welcome to this beautifully updated 3-bed, 2-bath westside home in sought-after San Mateo Terrace, where modern refinement and pride of ownership shine throughout. Gleaming refinished floors flow through the bright, open living spaces, anchored by an expansive living room with a cozy fireplace that leads seamlessly to the formal dining room and out to the yard. At the heart of the home, the remodeled kitchen impresses with quartz counters, stainless steel appliances, and a sun-drenched eat-in nook framed by charming bay windows. The primary suite is a true haven, featuring a remodeled ensuite with a chic vanity and walk-in shower, while two additional bedrooms are served by a stylishly updated hallway bath. Step outside to a meticulously manicured backyard oasis on an expansive ~7,013 SF flat lot - a rare find and perfect for summer entertaining or simply enjoying the tranquil privacy of lush, verdant landscaping. Additional highlights: fully paid-off solar panels with a Tesla Powerwall, upgraded HVAC with A/C and heat pump, a newer 50-year roof, fresh interior paint, recessed lighting, a remodeled 2-car garage with extra storage, and seismic foundation upgrades. Moments from top schools, Beresford Park, Hillsdale Mall, 25th Avenue's dining and shops, and major commute routes.

731 26th AVE, San Mateo

341 Sylvan AVE, San Mateo
$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

3611 Kingridge DR, San Mateo
$2,500,000
3 Beds ⋅ 2 Baths ⋅ ML82025807 MLS
Welcome to 3611 Kingridge a spectacular single-level farmhouse-style rancher set on an oversized, private lot with a sparkling pool and spaThis beautifully updated home offers a perfect, flowing floor plan with a spacious dining room and family room featuring a wood-burning fireplace and French doors leading to the backyard. The gracious living room includes a second fireplace and large picture windows that fill the space with natural light. The updated kitchen overlooks the front garden and provides ample storage and functionality. The expansive primary suite opens to the yard through French doors and includes a luxurious spa-style bathroom. Two additional generously sized bedrooms share a stylish second bath. Outdoors, enjoy sprawling entertainment spaces with three patio seating areas surrounding the pool and spa ideal for relaxing or hosting. The oversized garage includes a workspace, and the large driveway provides ample parking. Serene, private, and full of charm this is the one youve been waiting for. Welcome home.

3611 Kingridge DR, San Mateo

330 41st AVE, San Mateo
$2,500,000
4 Beds ⋅ 3 Baths ⋅ ML82021639 MLS
Welcome to 330 41st Avenue, a beautifully maintained residence nestled in San Mateos highly sought-after Westwood Knoll neighborhood. This elegant 4-bedroom, 3-bath home offers 2,410 sq. ft. of refined living space on an expansive 11,088 sq. ft. lot, highlighted by stunning views of the Bay and San Francisco skyline. Lots of natural light, the interiors feature a warm and inviting flow, perfect for both everyday living and entertaining. The chef-inspired kitchen is equipped with stainless steel appliances and a Wolf stove, ideal for the gourmet cook and anyone who loves to entertain. The first 4 photos are AI enhanced with a color change of the walls being white. Outside, the terraced grounds provide four distinct patio areas, offering multiple options for outdoor dining, gatherings, or simply relaxing while enjoying the tranquil setting. A new sewer lateral installed in 2024. With easy access to San Francisco, SFO Airport, Highway 280, and 101, the location is ideal for commuters and travelers alike. The homes layout also offers excellent potential for multi-generational living, providing flexibility and comfort for a variety of lifestyles. A true gem in the heart of San Mateo.

330 41st AVE, San Mateo

308 42nd AVE, San Mateo
$2,500,000
4 Beds ⋅ 3 Baths ⋅ ML82018247 MLS
Stunning Westwood Knolls home with panoramic bay views from nearly every room. A 53-foot-wide composite deck with stainless-steel cable railings and gas/electric outlets spans the back -- ideal for entertaining. The upper level features vaulted ceilings, large windows, engineered maple hardwood floors, and an open living and dining area. The family room includes a gas/electric fireplace, built-in cabinetry, and sliding doors to the deck. The kitchen offers granite counters, stainless steel appliances, and a breakfast bar. The en-suite primary has ample closet space and a modern bath with double vanity and walk-in shower. A powder room is near the foyer. The lower level includes 3 bedrooms, a full bath, a 1,000-bottle wine cellar, and a theater with 5.1 surround sound, 82" screen, bar seating, and room for 12. Additional features: reinforced foundation, step-free ramp, double-paned windows, clay tile roof, 2-car garage with 240V outlet, wide driveway, custom cast iron gates, CCTV, Ring® system, and mature fruit trees. Convenient to schools, shops, and Hwy 92.

308 42nd AVE, San Mateo

2322 Red Oak CT, San Mateo
$2,490,000
4 Beds ⋅ 3 Baths ⋅ ML82040945 MLS ⋅ Elevate at The Heights BLDG.
This tranquil enclave of homes nestled amongst lush green space with stunning panoramic views of the peninsula with proximity to San Francisco, Silicon Valley, and Half Moon Bay.  It is conveniently located within a few blocks of Laurelwood Plaza with a grocery store, vibrant restaurants, coffee, tea, and shopping. A few minutes drive from access to 92, 101, or 280 and highly ranked schools.  Lifestyle enhancing amenities include outdoor fitness areas, dog park, community gardens, picnic areas, tot lot, and walking trails.  Close to the Peninsula Golf, downtown, Cal train station, Hillsdale Mall, Costco, Whole Foods, and Crystal Springs hiking trails.  Eleven miles to SFO.  Luxury designer finishes include quartz countertop, gorgeous full kitchen backsplash, upgraded cabinets, premium wood floors, and lux bathroom finishes. *Photo of model home not of actual home*

2322 Red Oak CT, San Mateo

1622 Eleanor DR, San Mateo
$2,470,000
4 Beds ⋅ 2 Baths ⋅ ML82030691 MLS
Welcome to 1622 Eleanor Drive. This exceptional residence has been completely remodeled from roof to floor, enabling the discerning buyer to enjoy a post-modernist home with brand new contemporary features. This sophisticated home has been reborn with a combination of practicality and elegance. The practical enhancements include new insulation, new interior drywall, new energy efficient doors, a new concrete apron, new electrical, and a newly repaired roof (which carries a 5-year warranty). The elegance includes new hardwood floors, designer lighting inside and out, and clean, uncluttered landscaping - and even a new modern garage door to add to the curb appeal. At the heart of the home, the chef's kitchen blends timeless elegance with modern sophistication: designer crystal lighting, the modern cabinetry, the quartz countertops and the built-in wine fridge. In addition, the discerning chef will love the sleek high-end Bosch appliances, especially the 800 Series Induction Bosch range, which deploys the latest magnetic technology to heat fast and efficiently. The private quarters provide a tranquil escape, and the rejuvenated bathrooms feature Delta rain shower fixtures, James Martin designer vanities and the master bath boasts a rare soaking tub.

1622 Eleanor DR, San Mateo

1718 Eleanor DR, San Mateo
$2,460,000
3 Beds ⋅ 2 Baths ⋅ ML82032149 MLS
Welcome to the beautifully reimagined Eichler home that honors its iconic mid-century modern design while offering a fully turnkey, contemporary living experience. It features classic post-and-beam ceilings, crisp white paneling, expansive walls of glass, and abundant natural light. The open-concept living and dining areas feature wide-plank flooring, designer lighting, custom millwork. The brand-new chefs kitchen is showcasing custom two-tone cabinetry, quartz countertops, tile backsplash, high-end SS appliances, waterfall island. The adjacent living area is anchored by a sleek modern fireplace, creating a warm and stylish focal point. The private living quarters include spacious bedrooms and a fully renovated primary suite with a spa-inspired bathroom featuring a custom vanity, designer tile, and contemporary fixtures. Additional bathrooms have also been updated. Sliding doors open to a redesigned backyard with low-maintenance artificial turf, outdoor fireplace, integrated lighting. Additional highlights include fresh interior and exterior paint, new HVAC systems, and two-car garage. Conveniently located near downtown San Mateo, shopping, dining, parks, Caltrain, and major commute routes. This home offers architectural significance, modern luxury, and prime Peninsula living.

1718 Eleanor DR, San Mateo

1632 Toyon CT, San Mateo
$2,455,000
3 Beds ⋅ 3 Baths ⋅ ML82049914 MLS ⋅ Sugarloaf BLDG.
Elegant Beauty! This gorgeous home boasts 3 bedrooms, 2.5 bathrooms and is lovingly perched in a Cul-De-Sac. This is a beautiful show piece filled with natural light. Newly updated kitchen including cabinets with granite counters, crown moldings, remodeled bathrooms, hardwood flooring upper and lower levels, wood spindle staircase, fireplace, and a den with a closet knockout that can easily become a 4th bedroom. Walk out from the living room to the quiet, serene, lush back yard for guest entertainment filled with trees and beauty. Nature at its best with hikes and walks to Sugarloaf and Laurelwood Parks. Don't miss this turn key opportunity. Convenient access to highway 280/92 and is zoned for highly sought after Carlmont High School District including Belmont/ Redwood Shores Schools....

1632 Toyon CT, San Mateo

1710-1712 Gum ST, San Mateo
$2,450,000
4 Beds ⋅ 6 Baths ⋅ ML82060061 MLS
Rare opportunity to own a contemporary duplex offering two executive-style townhouse residences on one lot, built in 2004. Live in one, rent out the other, create an ideal multi-generational setup, or explore the potential for condo conversion. Both residences are exceptionally bright with abundant natural light and quality finishes throughout. 1710 Gum, the owner's residence, offers 2 bedrooms and 2.5 baths, with both bedrooms featuring en-suite baths. Wood flooring, soaring ceilings, recessed lighting, and a gourmet kitchen create an inviting environment. The spacious primary suite features a custom closet, luxurious bath with soaking tub, and private balcony. The backyard is perfect for entertaining, with a built-in BBQ gas line and vegetable garden beds with drip irrigation. One car garage with extra storage, A/C, and in-unit laundry. 1712 Gum offers 2 bedrooms, 2.5 baths, plus a versatile loft that could be a 3rd bedroom. The open floor plan features wood flooring, soaring ceilings, recessed lighting, gourmet kitchen, and a primary suite with gorgeous bath and soaking tub. Private balcony, side patio, attached one car garage, and A/C. A commuters dream! Steps from Hayward Park Caltrain, Starbucks, restaurants, shopping, and easy access to all major freeways. Welcome home!

1710-1712 Gum ST, San Mateo

1708 Monticello RD, San Mateo
$2,450,000
4 Beds ⋅ 2 Baths ⋅ ML82057712 MLS ⋅ Highlands BLDG.
Mid-century modern Highlands Eichler on a large Approx. 7,778 square foot landscaped lot with room for expansion or an ADU! Entertaining living room w/10-foot high soaring ceilings. Updated Sliding doors and dual pane windows. Nicely maintained original wood paneled walls. Four bedrooms Two baths, sitting room/office, plus additional space in garage ideal for game room. New carpets, new interior/exterior paint. Foam roof. Kids playroom in backyard. Outdoor covered patio for a relaxing shaded space. Rec center includes community pool, tennis courts, and after school programs. Sawyer Camp Road close by for walking, jogging, plus bike trails along the Crystal Springs reservoir. Close to Highlands Elementary School. In the Aragon High School district. Location! Location! Location!

1708 Monticello RD, San Mateo

311 W Hillsdale BLVD, San Mateo
$2,450,000
3 Beds ⋅ 3 Baths ⋅ ML82038538 MLS
This stunning remodeled home in the heart of San Mateo's popular Hillsdale neighborhood is filled with thoughtful upgrades throughout! Set on a large, picturesque lot, the property enjoys a beautiful private Creekside setting that creates a nature-filled backdrop. Mature landscaping and generous outdoor space provides endless possibilities for relaxing, gardening and entertaining. A lovely formal entry greets you, step into the open living/dining room combination that features a large picture window to enjoy the stunning garden views. A gourmet kitchen that any chef would be delighted to call their own, featuring stainless steel appliances, wine fridge, sleek granite counters, a large pantry, 5 burner stove top and built-in dining area. The spacious family room includes a cozy corner fireplace, sliding doors to the outdoors and a conveniently located half bath. The primary bedroom features 3 closets, one being a large walk-in, the attached primary bathroom has an over-sized shower w/seating area. The front bedroom has custom built-in cabinets with a desk area that could be a great office for those that work from home. This stylish upgraded home with a comfortable layout & lush landscape has so much to offer! Located near Hillsdale Mall, Trader Joe's, parks, schools, & Library

311 W Hillsdale BLVD, San Mateo

417 36th AVE, San Mateo
$2,450,000
3 Beds ⋅ 3 Baths ⋅ ML82037646 MLS
Exceptional split-level San Mateo home, proudly owned by the same family for 62 years. Charming curb appeal with front porch, colorful landscaping, and private entry. The tiled foyer opens to a bright living room with oversized bay windows showcasing beautiful hill views, a classic fireplace, and gleaming hardwood floors. Formal dining room with designer chandelier and sliding glass doors opens to a covered patio and sunny backyard. The updated kitchen features skylight, stainless appliances, double oven, pantry, wet bar, granite counters, and custom cabinetry, flowing into a breakfast area and spacious family room with gas fireplace and sliding doors to the yardideal for everyday living and entertaining. Upstairs are three bedrooms with views and two baths, including a generous primary suite with stall shower, soaking tub, and bonus space for an office or walk-in closet. The lower level offers flexible living space with private exterior access, half bath, laundry area, storage, and attached two-car garage. South-facing backyard with mature fruit trees, lawn, and patio. A/C and central heat. Conveniently located near parks, schools, shopping, and transportation.

417 36th AVE, San Mateo

347 Rolling Hills AVE, San Mateo
$2,450,000
3 Beds ⋅ 3 Baths ⋅ ML82031825 MLS
Welcome to 347 Rolling Hills Avenue, a beautiful 3-bedroom, 3-bathroom home in one of San Mateos most desirable neighborhoods. Offering approximately 2,100 SF of thoughtfully designed living space, this home blends timeless character with modern updates and enjoys stunning views from nearly every window. The light-filled living and dining areas feature hardwood floors, a cozy fireplace, and elegant finishes, creating a warm and inviting atmosphere. The updated kitchen is equipped with stainless steel appliances, granite countertops, and an island with bar seating perfect for everyday living and entertaining. The spacious primary suite includes a spa-inspired en-suite bath, while two additional bedrooms and full baths offer flexibility for guests, a home office, or multigenerational living. All renovations, including the third bathroom addition, were fully permitted and finalized. Step outside to a resort-style backyard designed for relaxation and entertaining, featuring a built-in BBQ kitchen, spacious seating area, and a private putting green. Additional highlights include central heating and cooling, and a prime location close to schools, parks, shopping, hospital, and major commuter routes. This move-in-ready home offers the perfect blend of comfort and outdoor living.

347 Rolling Hills AVE, San Mateo

105 Louise LN, San Mateo
$2,438,000
4 Beds ⋅ 3 Baths ⋅ ML82042341 MLS
Lovely home in San Mateo's desirable Lanes neighborhood offers 4 bedrooms and 3 full baths, including two primary En-suites. This light-filled residence shows pride of ownership and features an open floor plan with an updated kitchen and island that opens seamlessly to the living and dining areas complemented by folding glass doors that go to the backyard. Beautiful refinished wood floors, fireplace, fresh interior paint, recessed lighting and a den/office that could be used as a 5th bedroom. A deck off the main living space provides the perfect setting for relaxing, entertaining, or enjoying your morning coffee. The beautiful landscaped backyard offers additional room to unwind or play, and less than 12 houses away on Louise Lane is East Hillsdale Park where you have tennis, a walking trail, park benches and play area, and approximately half mile from West Hillsdale Park in the Lanes. Spacious two-car garage includes pull-down stairs for convenient extra storage. Ideally located near shopping and dining, including Safeway, Trader Joes, and the Hillsdale Shopping Center, with easy access to Highways 280, 101, and 92 for a seamless commute to both San Francisco and Silicon Valley.

105 Louise LN, San Mateo

2055 Ticonderoga DR, San Mateo
$2,425,000
4 Beds ⋅ 3 Baths ⋅ ML82019751 MLS ⋅ Highlands BLDG.
Stunning 4-bedroom, 3-bath courtyard model Eichler on a rare 9,600± sq ft lot in San Mateos coveted Highlands. This architectural gem blends timeless Eichler design with modern updates, creating a home that is both iconic and highly livable. Soaring tongue-and-groove ceilings, dramatic post-and-beam lines, and signature floor-to-ceiling glass flood the interiors with natural light while framing sweeping mountain views. The flexible layout includes two primary suites and three full baths, offering ideal space for multigenerational living, guests, or a private home office. A central courtyard serves as the heart of the homeperfect for entertaining or peaceful relaxation. Recent updates include fresh interior and exterior paint, brand new SPC flooring, an updated kitchen with sleek finishes and new stainless appliances, refreshed baths, new accent lighting alongside original globe fixtures, and fresh landscaping. Original Eichler elementsradiant heat, a floor-to-ceiling brick fireplace, and seamless indoor-outdoor flowpreserve the homes architectural authenticity. Enjoy the Highlands lifestyle with access to the Recreation Center (pool, tennis, fitness), nearby hiking trails, and excellent schools: Highlands Elementary, Borel Middle, and Aragon High (buyer to verify).

2055 Ticonderoga DR, San Mateo

909 Sunnybrae BLVD, San Mateo
$2,420,000
4 Beds ⋅ 2 Baths ⋅ ML82039588 MLS
Welcome to this beautifully designed 1-story home with an open, modern floor plan that has been thoughtfully remodeled & reimagined. The heart of the home offers an open-concept great room that blends the living, dining & kitchen areas beneath vaulted ceilings w/ skylights, large floor to ceiling windows, recessed lighting & wide-plank white oak wood flooring. A fireplace with wood mantle creates a warm focal point. French doors open from the dining to the yard, creating effortless indoor-outdoor living. The great room flows naturally into the contemporary kitchen featuring clean-lined cabinetry, dramatic Porcelain Calacatta Viola countertops & backsplash, Bosch SS appliances, & a large center island. The spacious primary suite features picture windows w/ modern en-suite bath w/ a sleek vanity, contemporary fixtures, glass-enclosed stall shower & a large wardrobe closet. 3 additional bedrooms offer flexible living space. The hall bath is tastefully updated with a shower-over-tub, tile surround, & contemporary vanity. The yard provides a private outdoor setting with a lawn & spacious patio ideal for entertaining. Located on one of Sunnybrae's most desirable streets & close to the parks, vibrant downtown dining, Hillsdale mall, Caltrain & major commute routes. This is a RARE FIND.

909 Sunnybrae BLVD, San Mateo

1485 Ascension DR, San Mateo
$2,420,000
4 Beds ⋅ 3 Baths ⋅ ML82029725 MLS
EXTENSIVELY REMODELED OVER TIME! This corner-lot home with LOTS OF PRIVACY & hillside views/greenery sits on an oversized lot in one of San Mateo's most sought-after neighborhoods, w/ great schools including Aragon High. Beyond the double doors, a bright living room features large windows, a brick fireplace, hardwood floors, baseboard / crown molding, & cove lighting. The floor plan flows into a formal dining room & remodeled kitchen w/ custom cabinetry, marble counters, center island, breakfast nook, pantry, & Miele appliances including a steam oven, microwave, gas stove, range oven, & dishwasher. A spacious family room offers built-ins, French doors, & a hidden wet bar. Primary suite has an updated bath w/ frameless walk-in shower. 3 additional bedrooms includes a guest retreat w/ half bath. Updated hallway bath has frameless glass shower & wood-paneled tile. Other features: attic fan, LG washer/dryer, pantry w/ 2nd fridge, newer AC, hi-eff heater, performance water heater, new sewer line, attic/basement insulation, seismic shear walls. Spacious garage w/ abundant storage. Backyard sanctuary w/ redesigned landscaping, paver patio, deck, covered seating, & gardens. Close to Hwy 92/280/101, College of San Mateo, Crystal Springs trails, Crystal Springs Village, & Laurelwood shops.

1485 Ascension DR, San Mateo

3408 Spyglass DR, San Mateo
$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

3936 Regan DR, San Mateo
$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

112 Linden LN, San Mateo
$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

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This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego MLS®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego MLS®,