luxury houses for sale San Mateo County, United States

Warm and inviting four-bedroom, two-bathroom home in prime Belmont location, offering a spacious, thoughtfully designed floor plan with comfort, versatility, and functionality throughout. Beautiful hardwood floors and a welcoming living room with fireplace set the tone. The generously sized kitchen features abundant counter and cabinet space, a convenient breakfast bar, and opens seamlessly to the dining area and inviting family room, with direct access to the back patio and yard, perfect for effortless indoor/outdoor living and entertaining. Just a few steps up, a versatile sitting area offers the ideal setting for a library, study, or home office. The private primary suite provides a peaceful retreat, while two additional bedrooms share a full hall bathroom. Downstairs, a spacious fourth bedroom offers exceptional flexibility as a guest room, recreation room, or additional living space, complete with direct backyard access. An oversized attached two-car garage features laundry facilities and an abundance of workshop and storage space. Ideally located near excellent schools and within walking distance of local restaurants and shops, with convenient access to streamlined commute routes.

A stunning Craftsman, quintessential in charm throughout, embracing today's modern lifestyle. Situated on an oversized lot in coveted San Mateo Park. Behind a private gate, you have endless manicured grounds perfect for your very own retreat. A trellised entry beneath towering redwoods includes timeless character and guest accommodations. Inlaid hardwoods, arched openings, and abundant light throughout. The vaulted living room centers on a fireplace with chevron surround, opening to a skylit dining room to French doors leading to a private office. Your chef's renovated kitchen flows to a breakfast area and family room with wood-burning stove opening an intimate yard. A main-level guest suite opens to the garden. The primary suite offers a skylit ceiling, sitting nook, walk-in closet, private terrace, and spa bath with soaking tub; two more bedrooms, a full bathroom, and laundry complete the level. Above the garage includes additional quarters for guest staying or an office with a kitchen, bedroom, bathroom, and terrace. Outside, your expansive yard includes a brick-paved terrace, lawn for play, gated motor court, and multi-car garage - moments from Burlingame Avenue, downtown San Mateo, and Caltrain.

Spectacular home in the heart of Redwood City! Showcasing charm and personality, this delightful 3-bedroom, 1-bath home offers a wonderful blend of storybook character, inviting living spaces, and incredible indoor-outdoor living! Step inside to discover a beautiful living room that flows effortlessly into a fabulous, open dining area with plenty of room for hosting memorable dinners and special celebrations. The adjoining beautifully appointed kitchen offers generous workspace and convenient access to the side yard, creating a seamless connection between indoor and outdoor living. The charming side yard is ideal for dining al fresco, while the spacious backyard offers endless possibilities for gardening, outdoor fun, and relaxation. And there's more! A delightful detached bonus shed, complete with power and lighting, provides a fantastic space for a home office, art studio, or creative workspace. Ideally located near incredible restaurants and vibrant downtown Redwood City, this captivating home delivers timeless appeal, effortless elegance, and an extraordinary lifestyle!

This charming single-story home offers two bedrooms, one beautifully appointed bathroom, and a versatile bonus room. Freshly painted inside and out, the home blends classic character with stylish modern updates. Handsome refinished hardwood floors, new lighting, elegant crown molding, and substantial new baseboards create a polished feel throughout. The welcoming foyer features crown molding and opens to a spacious living room highlighted by recessed lighting, a beautifully retiled fireplace, and a wall of windows and French doors that fill the space with natural light while capturing views of the private rear garden. The remodeled kitchen showcases crisp white cabinetry, a pantry, stainless steel appliances, quartz countertops, a stylish tile backsplash, and attractive tile flooring. Just off the living room, the dining area is accented by a contemporary drum light, creating an inviting setting for everyday dining and entertaining. The generously sized rear bedroom enjoys peaceful garden views, while the front bedroom is filled with natural light from its many windows. The beautifully appointed bathroom features a separate tiled shower and bathtub, dramatically accented by striking blue tile. A special bonus room offers wonderful flexibility as a home office, additional bedroom, or creative space. Handsome wood-paneled walls and ceiling add warmth and character, while a Dutch door opens directly to the rear patio. Step outside to a private garden sanctuary, an ideal setting for relaxing, dining al fresco, or entertaining family and friends. . One-car garage with washer and dryer completes this appealing home. The bonus room is not included in the reported interior square footage. When the bonus room is included, the total square footage is approximately 1,230 square foot. Ideally situated on a quiet cul-de-sac, this home is just steps from the hidden gem of East Hillsdale Park and within easy walking distance of the movie theater, bowling, restaurants, and the many conveniences and amenities of Hillsdale Shopping Center.

Bay views and tucked behind mature landscaping on a private, tree-lined lot, this home offers a rare combination of classic elegance and resort-style outdoor living - all in one of the Peninsula's most coveted addresses. Inside, freshly painted, sun-filled principal rooms with newly refinished hardwood floors are designed for both everyday living and effortless entertaining: a gracious foyer opens to a formal Living Room with fireplace, an equally elegant Dining Room, and a Family Room anchored by its own fireplace and walk-out access to a private deck. The updated kitchen flows seamlessly into a sunny entertaining area. Upstairs, the primary suite is a true retreat, with a spa-inspired bath featuring a soaking tub and heated floors. Three additional bedrooms and an office complete the second floor. A lower-level room with wet bar and an additional bedroom offer flexible space for guests, media, or play. Outside, the grounds are spectacular - a sport court, batting cage, outdoor kitchen, fire pit, and sprawling lawn create an entertainer's paradise, all framed by newly refreshed landscaping. Perfectly located in Hillsborough, minutes to top-rated schools, downtown Burlingame, Highway 280, San Francisco and Silicon Valley, this is the Peninsula lifestyle at its finest.

Welcome to this exceptional home in sought-after Emerald Hills, beautifully situated on an expansive creek-side lot spanning over half an acre. This inviting three-bedroom, three-bath residence showcases open-beam ceilings, expansive picture windows and elevated living spaces designed for effortless living and entertaining. A welcoming formal entry leads to the living room with fireplace with access to a spectacular wraparound deck offering peaceful views and a seamless connection to the outdoors. The eat-in kitchen, formal dining room and versatile open office area provide inviting spaces for gathering and relaxation. The primary suite enjoys private access to the deck, while an additional bedroom and full bath are conveniently located down the hall. Downstairs, a spacious third bedroom, full bath, kitchenette and dining area create an ideal retreat for guests or extended family. The expansive backyard is truly an entertainer's paradise, featuring a sparkling pool, sauna, multiple seating areas and serene garden spaces surrounded by natural beauty. An oversized detached two-car garage completes this exceptional property. Ideally located just moments from Edgewood Park trails, minutes to downtown Redwood City, San Carlos and Highways 280, 101 and 92.

Welcome to Rancho San Gregorio, a coastal retreat perched on the bluffs overlooking the Pacific Ocean with direct beach access to be enjoyed with family and friends. Proximate to Silicon Valley and San Francisco, this rare compound is equal parts secluded hideaway and seaside playground. A place where one can experience the natural meditation of ocean waves among the magical sights and smells of fragrant eucalyptus groves. Anchoring the property is a fully renovated main residence featuring bold interiors designed by the renowned Ken Fulk. Thoughtfully furnished with custom art and all the luxury comforts required for an unforgettable stay, this home serves as the ultimate gathering hub. It boasts a chef's kitchen, lush media lounge, rooftop entertaining venue, a barbecue and picnic space, and two whimsical six-bunk en-suite bedrooms. A nearby garage, known as the Beach Shack, provides dedicated storage for everything needed to enjoy a full day of coastal recreation. Completing the compound, five private Airstream trailers, each with their own exterior dining and lounging areas, are nestled across the grounds to offer guests their own secluded accommodations. With its thoughtful design and bespoke artistic details, Rancho San Gregorio is a coastal escape unlike anything else.

Newly renovated throughout! This luxury California rancher offers three bedrooms, two and a half baths, and resides on a nicely sized lot. The home has an open concept, a kitchen family room combination, has white oak flooring, a striking fireplace with an ambient fire feature, elevated ceilings, an expansive yard, and a well appointed kitchen. The kitchen entails a large island with seating, premium appliances, custom built cabinetry, ample counter space, and top of the line finishes. Adjacent is the outdoor area with an inviting patio with large square pavers, and a lengthy lawn area. The primary features vaulted ceilings with a penny wood ship lap detail, walk in closet, and a spa like bathroom. All three bedrooms are nicely sized. The home has many attributes, natural light throughout, a quaint porch, and a separate laundry + mud room. Located on a quiet street, close proximity to down town Laurel Street, fun filled Laureola Park, and Caltrain station. Resides in the highly regarded San Carlos School District. This extraordinary home has it all, location and comfort.

Extensively renovated throughout, this bright and sunny home is located in the prestigious Farm Hill Estates neighborhood of Redwood City. The interior features gleaming hardwood floors and a freshly painted palette with custom colors. Designed for effortless entertaining, the open-concept designer kitchen is equipped with a large center island and premium Thermador appliances, connecting seamlessly to the main living space and an expansive deck with filtered Bay views. A spacious lower-level room offers versatile potential as a fourth bedroom, home office, or accessory dwelling unit (ADU). Outdoors, multiple entertaining patios surround a lush grassy yard complete with a play structure. Located just blocks from the top-rated elementary school, local parks, and hiking trails, the property combines proximity to vibrant downtown Redwood City with convenient access to Interstate 280 for an easy commute across Silicon Valley and San Francisco.

Cherished by the same family since the 1960s, this single-story gem occupies a generous corner lot in one of Millbrae’s most desirable neighborhoods, offering subtle peek-a-boo bay views and endless potential. The highly functional single-level layout features a bright, wrap-around floor plan that seamlessly connects the living room, dining area, kitchen and breakfast nook like only an authentic Mid-Century Modern can. A bonus family/media room with a separate entrance, along with four bedrooms and two bathrooms, completes the ample living space. Outside, an extra-long driveway accommodates four to five vehicles and leads to a versatile detached garage—ideal for an ADU conversion, home office, or personal gym. Situated minutes from Millbrae schools, bustling downtown Broadway dining scene, San Francisco International Airport, and ideal Peninsula weather, this blank canvas is the ultimate renovation project ready for its next owner to realize their dream vision.

Perched in the oaks of coveted Haskins Estates, this reimagined residence pairs a whole-house remodel with views toward San Francisco and the Bay. The vaulted main level features a dramatic living room opening to the view deck and a showpiece kitchen with cobalt cabinetry, a Vetrazzo waterfall island, quartz counters, and Bosch appliances including gas and electric ovens. It also has a light-filled dining room, a family room or office, and a Mondrian-inspired powder room. The lower level offers a primary suite with deck access, a custom walk-in closet, and a spa bath with a curbless dual-head shower, plus two more bedrooms, a remodeled full bathroom, and laundry. A vaulted upper bedroom makes an ideal studio or fourth bedroom. Updates include new windows, doors, roof, plumbing, electrical, two-zone HVAC, a tankless water heater, hardwood floors, and composite decks with cable railings. The home also has an attached two-car garage and driveway, and its close to Highways 92, 101, and 280, Caltrain, and downtown Belmont.

The San Francisco feel you love, right here on the Peninsula! This captivating, newly remodeled home offers three bed/two bath with two bonus rooms – thoughtfully designed living spaces and modern finishes throughout. The second floor showcases an open-concept layout featuring sleek white and gray high-gloss cabinetry, GE Café appliances and wine/beverage center. At the heart of the home, a stunning nine-foot quartz island with a waterfall edge creates the perfect setting for entertaining. Two bedrooms share a spa-inspired bathroom complete with a double concrete vanity, LED mirror, walk-in shower and separate toilet room with laminated glass. The lower level expands your living possibilities with a second living area/home office, dedicated fitness room, and private primary suite with private entrance. Ideal for extended family, guests, or potential rental income, this flexible space includes plumbing, electrical, and washer/dryer hookups already in place. Pre-plumbed/wired for a kitchenette. Step outside to a beautifully designed backyard featuring porcelain tile pavers, a patio, lush artificial turf and ambient outdoor lighting. Gas hookups for a fire pit and barbecue make outdoor dining/entertaining effortless. Enjoy walkable location near downtown San Bruno’s shops/restaurants, Bayhill Shopping Center, new San Bruno Recreation/Aquatic Center with pools, indoor basketball, fitness center and exercise studios. Nearby Caltrain and BART connections, convenient access to Highways 101 and 280 and a short drive to downtown Millbrae put the best of the Peninsula within easy reach. Stylish, versatile and ideally located, this exceptional home offers a rare combination of contemporary finishes, flexible living space and indoor-outdoor appeal. A must-see!

An incredible opportunity awaits in the highly sought-after White Oaks neighborhood! Situated on a generous lot, this charming single-level three-bedroom, two-bathroom home offers timeless appeal, a fantastic floor plan, and endless possibilities to make it your own. A welcoming formal entry leads to the inviting living room, featuring beautiful hardwood floors, a classic fireplace, and picturesque views of the backyard. The adjoining dining area offers direct access to the patio and backyard, creating a wonderful setting for indoor-outdoor living and entertaining. Just steps away, the eat-in kitchen provides convenient access to the oversized attached two-car garage. Down the hall, the primary bedroom and two additional spacious bedrooms offer comfort and versatility. The expansive backyard features a patio and sprawling lawn, with plenty of room to relax, entertain, or bring your outdoor vision to life. Enjoy excellent walkability to highly regarded schools, neighborhood parks, and the vibrant downtown restaurants and shops. Conveniently located near major commute routes. A rare opportunity to create something truly special in one of San Carlos' most desirable neighborhoods!

Exceptional new construction in sought-after Emerald Hills offers sophisticated design, beautiful architectural details, and an inviting atmosphere for luxurious everyday living and effortless entertaining. A welcoming covered front porch leads to the grand formal entry, where soaring ceilings and expansive picture windows fill the home with natural light. Step down to the elegant living room with fireplace and formal dining room, perfect for memorable gatherings. The stunning chefs kitchen features a large center island with breakfast bar, butlers pantry, and dining area, open to the inviting family room. Oversized sliding doors create a seamless connection to the covered back deck, patio, and yard, ideal for indoor-outdoor entertaining. A centrally located powder room and private en-suite bedroom tucked off the entry complete the main level. Upstairs, the grand primary suite offers a peaceful retreat with spa-like bath and custom walk-in closet. A second en-suite, two additional bedrooms with shared full bath, and perfectly placed laundry room complete this level. An attached two-car garage adds convenience. Ideally located near excellent schools, parks, and scenic hiking trails, just moments from vibrant downtown restaurants and shops, with easy access to commuter routes.

Located in the desirable WESTRIDGE Neighborhood, this impressive 2.62+/- ac. property offers views, room for expansion, a vineyard, separate ADU, and a freshly updated home with 4 bedrooms & 3 remodeled baths. The kitchen has new appliances, & flows into a family living space. The large dining area sets the stage for entertaining. The Primary Suite has tall beamed ceiling, 3 closets, & deck that overlooks the property & Windy Hill views. Additional bedrooms enjoy a private wing that centers around a flexible space This space is served by a separate entrance for flexibility. A lower level is a blank slate. Finishedit has a work-shop, lots of storage, 2 rooms with sliding glass doors, a large well-lit space thats ideal as a game room or exercise center. Potential for a wine cellar. And there is a full bath. The ADU is 1 bed. 1 bath & has an open living/dining/kitchenette space, + private deck & entrance. There is a small upper pasture or a large area at the front of the property that could be used for horses or pool, possibly a tennis court or just let nature share its beauty with you. Central Portola Valley location, convenient to shopping, Alpine Hills Swim & Tennis club, The Alpine Inn, excellent PV schools, & just 5+/- min. to Hwy. 280.

Situated on a preferred street in the highly sought-after Beverly Terrace neighborhood, this refined 2016 home seamlessly blends classic elegance with turnkey modern functionality. Inside, high ceilings, wide-plank hardwood floors, and custom cabinetry create a warm, polished backdrop flooded with natural light. The main level is designed for effortless living and entertaining, featuring a welcoming living room anchored by a gas fireplace with a marble surround and elegant formal dining room. The layout flows naturally into an open-concept family room and chefs kitchencomplete with marble countertops, a central island, and premium Bosch, Sub-Zero, and Wolf applianceswhich opens directly onto a covered patio for fluid indoor-outdoor enjoyment. A main-floor bedroom and full bath offer ideal flexible space for guests or multi-generational living. A dedicated laundry room and attached two-car garage offers ease and functionality. Upstairs, the primary suite is complete with two walk-in closets and a granite bath with a soaking tub, dual vanity, and separate walk-in shower. Outside, the low-maintenance grounds are framed by mature oak trees. Located just a mile from the vibrant Laurel Street, with easy access to Highways 101, 280, and top-rated local schools.

Sunlight Among the Redwoods Some houses announce themselves. This one does the opposite, settling quietly into the redwoods of Skylonda so that what you notice first is the light, then the trees, and only after that the house itself, a 1967 mid-century modern with dark-stained walls that recede into the forest the way good architecture should. Arrival is unhurried, a gravel court gives way to an entry courtyard of decking, trellis, and tree ferns. In true mid-century character, a bright orange door opens to a main entry where high wood ceilings and heavy beams carry your eye straight out to the forest beyond the glass. Walls of glass wrap the corners of the living and dining rooms, so you look out at the redwoods with trunks rising past the windows and sunlight filtering down through the canopy. The sunken living room, a quiet step down beside a stone fireplace, feels sheltered without ever feeling closed in, while the formal dining area on the other side connects to the outdoors through floor to ceiling windows and a sliding door, and to the kitchen through a handy pass through. On the other side of that pass through is a large kitchen, open to a spacious breakfast area with views of the trees. On cooler mornings a freestanding wood-fired stove warms the area, while a skylight fills the prep areas with natural light, making it easy to picture mornings when nobody is in a hurry. The decks, reached from the dining room, kitchen, and office, work as additional rooms, built for coffee at first light, long dinners under the trees, and the kind of conversation that keeps going after the plates are cleared. Gravel paths and stone steps lead down through the garden and wind through the trees. In the sunny area in the middle of the compound, raised beds with irrigation are waiting for the next gardener. The rooms are generous throughout, an office that opens to the deck, a family room, and two more bedrooms on the main level. Upstairs the primary suite feels like a separate apartment with a separate outdoor entrance, sitting up in the canopy with corner windows, two walk-in closets, and sliding doors to balconies on either side. The recreation room, once a carport, has its own entrance from the gravel court and plenty of space for fitness, games, or guests, and next to it a small detached office offers a quiet place to work, read, or think, or to use as additional storage. The plans carry the name of Edwin Wadsworth, a Menlo Park architect who opened his practice in 1951 and became best known for pole houses, the foundation-free designs that rest lightly on steep, wooded sites, and who received the American Institute of Architects' highest national residential design award for three of his Peninsula houses, two of them in Woodside. This is not one of his pole houses, but it shares the high ceilings, open floorplan, exposed beams, and respect for outdoor views and terrain. In 1989 the house was remodeled and expanded, the original carport became the recreation room, and a three-car garage, a laundry room, and the upper-level primary suite were added. It has now been refreshed with new flooring through much of the home, interior paint, updated lighting, deck repairs, and a tidied, trimmed landscape. The setting is rural, sunny yet surrounded by redwoods, and the comforts of town are close at hand, with Alice's Restaurant, a favorite stop at the corner of Skyline and Highway 84, and the Skywood Trading Post and Deli, for both human and vehicle fuel, nearby. Buyers in the hills understandably ask about wildfire, and it is worth knowing that County Fire Station 58 is close by. With approximately 3,420 square feet, four bedrooms, and three baths on approximately 0.91 acres, 160 Redland Road doesn't ask you to choose between privacy and convenience, or between sunlight and shade, or between feeling away from it all and having the comforts of town nearby, and it offers all of it quietly, the way the best properties in these hills tend to

Panoramic Views and Exceptional Peninsula Living! Wake up to breathtaking views of San Francisco and the Bay from this exceptional multilevel townhome perched atop San Carlos' desirable Crestview Park neighborhood. The inviting main level features a spacious living room and dining area with access to a private rear deck, perfect for entertaining or enjoying the views. The adjacent kitchen and family room create a warm gathering space with access to the deck. The middle level offers a laundry room, half bath, and direct access to the attached two-car garage with abundant storage. Upstairs, the private sleeping quarters include two spacious bedrooms, a full guest bath, and a generous primary suite featuring multiple closets, luxurious en-suite bath, and captivating Peninsula views. Nearby guest parking adds convenience. Community amenities include a private pool, hot tub, tennis courts, and playground. Ideally located near top-rated schools, parks, walking trails, downtown San Carlos, Caltrain, and Highway 280. Downtown San Carlos is approximately nine minutes away. Come experience the views, space, and lifestyle this special Crestview Park townhome has to offer!

Stunning Mediterranean-style home in the coveted Sunrise community of Redwood Shores — minutes from Oracle's Redwood Shores campus, the Electronic Arts global headquarters, Nintendo, Shutterfly and Box, with Meta in Menlo Park, Stanford University and SFO a straight shot on Highway 101. This elegant two-story residence offers 4 bedrooms, 2.5 baths and 2,490 sq ft. A formal entry with dramatic high ceilings opens to a light-filled living room with vaulted architecture and a cozy fireplace, flowing into a formal dining room and a tastefully updated kitchen with bright breakfast area and adjoining family room. Upstairs, the sprawling primary suite is a private sanctuary with dedicated dressing area, dual closets and a spa-like double shower. Private, low-maintenance yard and attached 2-car garage. Sunrise residents enjoy exclusive access to a private park and tennis courts, with the San Francisco Bay Trail, Redwood Shores lagoons, Bay Club Redwood Shores, Nob Hill Foods and the Redwood Shores Library all close at hand.

Space, character, and endless potential come together at 2425 Alameda de las Pulgas! Lovingly cared for by the same family since the 1960s, this expanded residence is ready for a new owner to bring their own vision to life. Offering five bedrooms, two bathrooms, and approximately 2,785 square feet, the home provides an impressive amount of space to live, entertain, work, and grow. The main level features a spacious living room with fireplace, dining room, kitchen, two bedrooms, and a full bathroom, complemented by beautiful hardwood floors and abundant natural light. Upstairs, three additional bedrooms and a second full bathroom provide flexibility for family, guests, or home office space. Upstairs has potential for an ADU or separate living space. (Buyer to investigate feasibility.) Outside, 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. The property may also offer potential for an ADU or separate living space, creating more possibilities for the future. Buyer to investigate feasibility. Conveniently located near all that San Mateo has to offer, including shopping, dining, parks, recreation, schools, and everyday amenities, with easy access to Caltrain, Highways 92 and 101, and Interstate 280 for commuting throughout the Peninsula, Silicon Valley, and San Francisco.

Set on 8.5 private acres in coveted Half Moon Bay, this beautifully remodeled contemporary ranch offers the rare combination of refined living and exceptional equestrian amenities just minutes from town. The home has been thoughtfully redesigned with a clean, modern aesthetic and an effortless indoor-outdoor flow. A dramatic living room anchored by an architectural steel fireplace opens to serene views of the creek and mature landscaping, while the formal dining area creates an elegant setting for entertaining. The chef’s kitchen is finished with sleek European cabinetry and top-tier appliances including a Gaggenau stove and steamer, Miele dishwasher, oven and refrigerator, and a built-in wine fridge. A spacious family room and dedicated office add flexibility for both relaxed living and working from home. The property is equally impressive for equestrian use. A well-designed barn offers three stalls, tack room and hay storage, complemented by paddocks, an arena, and open pasture. Direct trail access makes it ideal for riders seeking both privacy and immediate connection to the coastal trail system. Additional features include a detached two-car garage and a separate one-bedroom mobile home with kitchen, living room and bath—perfect for guests, extended family, or caretaker use. Gated and peaceful, yet just minutes from the charm of downtown and the coast, this is a rare opportunity to own a turnkey ranch property in one of the most desirable areas along the San Mateo County coastline. Offered at $3,098,000

Own a remarkable 1.4 acre parcel in Atherton, nestled at the end of a tranquil cul-de-sac. A perfect opportunity to build your dream home without compromise. The lot offers natural beauty and privacy in a park-like setting, creating a tranquil oasis that feels far from the hustle and bustle yet is close to the coveted Las Lomitas school district, prestigious private schools, Highway 280, and nearby shopping districts. Just minutes from Stanford University and Sand Hill Road, this property combines convenience and exclusivity.

There is a particular quiet at 411 Glenwood Avenue, and it has nothing to do with the address and everything to do with what is missing from the view. Stand on the main level and look out through walls of glass, and the first thing you notice is the treetops. The second is what you do not see: neighbors. Oak canopy, dappled light, and the open expanse of the Joan Olson Preserve fill the windows instead, so the sense of being tucked into the trees, private and unbothered, follows you from the kitchen to the deck to the primary suite upstairs. Friends who visit tend to call it the treehouse. The name sticks. The house itself is a genuine mid-century original, built in 1959 and gently modernized without losing its bones. Mohagany wood paneling, a brick fireplace, and warm cork and hardwood floors carry the era through the main living spaces. The kitchen is open to the great room, with stone counters, a gas cooktop, and seating for the kind of morning where nobody is in a hurry. Walls of glass open the indoors onto a broad deck built for slow dinners and longer conversations, with the preserve as a backdrop instead of a fence line. Upstairs, the bedrooms offer that same treetop view that defines the rest of the house. Downstairs, the floorplan offers so many possibilities. An open room with a slider to a flat yard surrounded by greenery could be an office, play room or flex space. Next to it is an en suite bedroom with a sliding door opening to a private patio. There is also a storage room that could function as a cozy office, plus laundry and additional storage areas. Cross the street and you are not on a street anymore. A trailhead into the Joan Olson Preserve sits directly across from the house, and it functions less like a scenic bonus and more like a second driveway. Regulars use it as a shortcut into downtown Woodside on foot, coffee in hand, oaks overhead the entire way. It is the kind of amenity that is nearly impossible to find on the Peninsula: genuine nature access, at the front door, that also happens to be the fastest way to town. Speaking of town, downtown Woodside is close enough to be a daily habit rather than a special trip. The Village Bakery, Buck's, and the everyday rhythm of small-town Woodside life are minutes away, while Highway 280 keeps the rest of the Peninsula and the city within easy reach. The property also sits within the Woodside Elementary School District, a TK through 8 program that consistently draws some of the strongest ratings in the state, a rare thing to find paired with this kind of privacy and land. 411 Glenwood is not a house that asks you to choose between nature and convenience, privacy and walkability, an easy commute and the feeling of being away from it all. It offers all of it at once, quietly, the way the best Woodside properties always have.