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240 Glenwood AVE, Woodside
$2,925,000
3 Beds ⋅ 2 Baths ⋅ ML82032025 MLS
Discover a blend of charm and modern living in this beautifully updated Woodside home, nestled beneath a canopy of majestic oak trees. Originally built as a summer cottage in 1927, this 3-bedroom, 2-bathroom residence has been thoughtfully expanded and renovated while preserving its vintage character. The heart of the home features a recently remodeled kitchen designed for both everyday living and entertaining. Natural light pours through skylights and a large sliding door that opens to a private patio, seamlessly connecting indoor and outdoor spaces. The dining room showcases a wall of windows framing views of the lush yard and filtered sunlight through the surrounding oaks. A private primary retreat, completed in 2017 with foundation and seismic retrofitting, offers a peaceful sanctuary with luxurious appointments and imported stone floors. A standout feature is the fully equipped guest house with its own kitchen and full bathroom, perfect for extended family, guests, a home office, or rental income potential. Located in the desirable Woodside Glens neighborhood, this home offers exceptional proximity to downtown Woodside and Woodside Elementary School. Roberts Market, charming cafés, and local favorites are just a short stroll away.

240 Glenwood AVE, Woodside

Listed by Chris Iverson, 650-450-0450 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of John Shroyer from TODAY
112 JANE DR, Woodside
$3,325,000
4 Beds ⋅ 3 Baths ⋅ ML82030869 MLS
OPEN HOUSE SAT. 1/17 & SUN. 1/18 2-4PM. SET ON A ONE-ACRE PARCEL IN DESIRABLE WOODSIDE, THIS 4-BEDROOM, 3-BATHROOM HORSE PROPERTY OFFERS EXCEPTIONAL SPACE, PRIVACY, AND OPPORTUNITY. SUN-FILLED INTERIORS SHOWCASE GLEAMING HARDWOOD FLOORS AND A FLEXIBLE FLOOR PLAN THATS IDEAL FOR EVERYDAY LIVING. THE EXPANSIVE DECK SITS OFF THE MAIN LIVING AREAS AND OFFERS INDOOR/OUTDOOR ENTERTAINING VERSATILITY. THE LUSH GROUNDS INVITE ENDLESS POSSIBILITIESEQUESTRIAN USE, GARDEN OASIS, EXPANSION, OR CUSTOM ESTATE VISIONMAKING THIS AN IDEAL CANVAS FOR BUYERS SEEKING TO CREATE SOMETHING TRULY SPECIAL. AN OVERSIZED GARAGE PROVIDES AMPLE ROOM FOR VEHICLES, STORAGE, OR WORKSHOP NEEDS, AND AN UNFINISHED LOWER-LEVEL AREA OFFERS EVEN MORE ROOM FOR STORAGE. WHETHER ENJOYED AS-IS OR REIMAGINED, THIS PROPERTY PRESENTS POTENTIAL GALORE IN ONE OF THE PENINSULAS MOST SOUGHT-AFTER COMMUNITIES, WITH EASY ACCESS TO TOP SCHOOLS, SCENIC TRAILS, WOODSIDE SHOPPING & RESTAURANTS, AND ALL MAJOR SILICON VALLEY CONVENIENCES.

112 JANE DR, Woodside

Listed by Maxine & Michelle Dumas, 650-591-8000 from Dumas & Company
(If provided) CoList: from

Sold listing courtesy of Angie Wolff from NTERO
205 Grandview DR, Woodside
$1,650,000
3 Beds ⋅ 2 Baths ⋅ ML82024935 MLS
Handcrafted California adobe-style home nestled among towering redwoods with sweeping Bay views. Built in the mid-century era, this residence blends timeless craftsmanship with natural tranquility. Exposed beam ceilings, brick and adobe walls, and terracotta tile floors create warmth and authentic character throughout. The open living and dining areas feature expansive windows and French doors that frame panoramic vistas and open to patios for seamless indoor-outdoor living. The original kitchen showcases artisan tile counters and solid wood cabinetry with easy flow to the main living areaideal for entertaining or everyday comfort. The spacious primary suite enjoys stunning Bay views and direct patio accessperfect for morning coffee or evening sunsets. Set on a private, fenced lot just minutes from downtown Woodside, this property offers architectural integrity, peaceful surroundings, and exceptional potential to update or expand while preserving its handcrafted charm.

205 Grandview DR, Woodside

Listed by Stephanie Nash, 650-995-3820 from Compass
(If provided) CoList: from

Sold listing courtesy of Lucy Goldenshteyn from RDFIN
131 Croydon WAY, Woodside
$7,645,000
5 Beds ⋅ 6 Baths ⋅ ML82024868 MLS
Experience the Woodside Lifestyle in this exquisite single-level 5 bedrooms and 5.5 bathroom residence. Fully reimagined and updated in 2025, this thoughtfully designed 3,580 sq. ft. residence offers a modern, open layout that perfectly balances style and comfort. The spacious living areas are ideal for both family gatherings and quiet relaxation. A private lower-level suite includes its own kitchen and bath providing a perfect setup for guests or a live-in au pair (currently staged as a game room). From sunrise to sunset, the captivating views of the Kings Mountain Hills and Skyline will leave you in awe. A home you will never tire of - welcome to Woodside living at its finest.

131 Croydon WAY, Woodside

Listed by David Young, 650-315-8989 from Coldwell Banker Realty
(If provided) CoList: Victoria Surles from Coldwell Banker Realty

Sold listing courtesy of Victoria Surles from CBR
6 Friars LN, Woodside
$4,850,000
4 Beds ⋅ 4 Baths ⋅ ML82024655 MLS
Sweeping views across the San Francisco Bay take center stage at this beautifully remodeled home on more than 3 acres of predominantly level land. Minute to downtown Woodside and Stanford. Designed for entertaining and recreation, the property features a large pool and separate spa framed in Connecticut bluestone, an expansive synthetic lawn for recreation and play, and broad decks with built-in seating and cable-strung railings. A brick-walled garden courtyard with Art Deco metal and glass front doors introduces the interiors highlighted by soaring ceilings and skylights. Wall-to-wall windows capture the panorama of the glorious views immediately upon entering. Multiple gathering spaces include a dramatic living room with stone-clad fireplace, a remodeled kitchen and dining area, and a family room with full bar and fireplace. A flexible use room between the foyer and kitchen offers versatility for a home office or playroom. Four bedrooms in a separate wing include a spacious primary suite with Bay views and steam shower, three bedrooms and a remodeled bath, plus there are two half-baths. Solar power with four Tesla Powerwalls, reclaimed San Francisco cobblestone paths, and a three-car garage are added features. Highly Rated Portola Valley Schools. Minutes to Woodside Village.

6 Friars LN, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Elena Tsukanova from APR
168 Sunrise DR, Woodside
$2,390,000
2 Beds ⋅ 2 Baths ⋅ ML82024519 MLS
Peaceful Woodside Retreat with Sweeping Bay Views Welcome to 168 Sunrise Drive, a serene retreat in the heart of Skywood Acres where you'll enjoy breathtaking panoramic views of the Bay, stretching from San Carlos to San Jose. Set on a spacious 53,577± sq. ft. lot, this home offers both privacy and connection to nature. A long driveway leads you to the inviting residence, surrounded by mature landscaping, lush foliage and the quiet beauty of Woodside's countryside. Inside, the home features 2 bedrooms, 2 baths, and a versatile bonus room perfect as an office, studio, or guest space. Vaulted ceilings and floor-to-ceiling windows fill the open living areas with sunlight, creating a warm, inviting space with stunning views from nearly every room. Step outside to a sunny deck and sparkling pool, the perfect place to relax, entertain, or take in the peaceful surroundings. Experience the best of Woodside living - privacy, natural beauty, and views that truly take your breath away. Just minutes from Menlo Park, Palo Alto, and top schools, it offers the rare blend of privacy, prestige and convenience.

168 Sunrise DR, Woodside

Listed by Deanna Reudy, 650-759-2986 from Compass
(If provided) CoList: from

Sold listing courtesy of Sam Habib from C21MM
170 Hardwick RD, Woodside
$4,262,500
4 Beds ⋅ 3 Baths ⋅ ML82023027 MLS
Absolutely the BEST VIEW of the Bay. Wake up early and catch the stunning panoramic view of the sun rising from this 4 bed/3 Mid-Century Modern home in Woodside Hills. Sit back relax and enjoy expansive views of the San Francisco Bay. On a clear day looking a bit Northwest youll catch a glimpse of the Bay Bridge as well as Treasure Island. One of the iconic features of a Mid-Century Modern home is their floor to ceilings windows that provide one with scenic views as well as bringing in an abundance of natural light. As the day transitions from day to night your view will be filled with lights from the bay that can leave you breathless. This 2,430 sq. ft. home on a mostly flat one-acre lot provides an excellent opportunity for one to remodel or design/build the home of your dreams with spectacular priceless views in one the most desired locations on the Peninsula. It's just 35 miles from The City and only 26 miles from Silicon Valley. A short drive from downtown Woodside shops and restaurants. Fine dine at The Pub or enjoy a meal at Bucs of Woodside a fixture of Silicon Valley. Nature lovers can explore the nearby vast open spaces,parks and preserves which provide an abundance of hiking and biking trails. Don't miss your opportunity to make this your forever home. Virtually Staged

170 Hardwick RD, Woodside

Listed by Eliot Beja, 408-506-3788 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Matthew Rogers from ELI
155 Normandy LN, Woodside
$5,525,000
4 Beds ⋅ 4 Baths ⋅ ML82021333 MLS ⋅ Woodside Hills Home Association BLDG.
Set on approximately 1.4 acres with views stretching out to the Bay, this beautifully remodeled 4-bedroom, 3.5-bathroom home offers timeless traditional style with elevated designer finishes. The 3339 sq ft interior features oak hardwood floors with inlaid borders, decorative moldings, and three fireplaces, creating a refined yet comfortable ambiance throughout. The floor plan is ideal for everyday living and entertaining, with formal and casual living spaces, a spacious kitchen, and light-filled rooms that open to the outdoors. Each bedroom offers privacy and flexibility, including options for a home office or guest accommodations. Outside, enjoy the peaceful setting with a sparkling pool, a charming pool house, and beautifully landscaped grounds framed by mature trees. A rare opportunity for style, space, and serenity just a short drive from town and local conveniences.

155 Normandy LN, Woodside

Listed by Tim Kerns, 650-430-4052 from Coldwell Banker Realty
(If provided) CoList: Kyle Katz from Coldwell Banker Realty

Sold listing courtesy of JJ Team:Jones/Cassel from NTERO
3323 Woodside RD, Woodside
$6,495,000
3 Beds ⋅ 3 Baths ⋅ ML82016045 MLS
Mid-Century Modern Style on 1.3 Acres Blocks from Town Center. Classic mid-century modern architecture is showcased on beautiful grounds of approximately 1.3 level acres just blocks from Town Center. Complete privacy is offered behind gates, where a long driveway leads past a fenced tennis court to the home and detached garage. Inside, the ambiance is airy and light-filled with soaring wood-paneled ceilings, skylights, and an entire wall of glass that frames the natural surroundings. Beautifully appointed throughout, the home has hardwood floors, dazzling modern lighting, and a sleek open layout with 3 bedrooms, an office, and 2.5 baths. The formal living & dining rooms as well as the kitchen share a dramatic wood-paneled cathedral ceiling and the wall of glass. A fireplace plus floor-to-ceiling library shelves with moveable ladder access are highlights. A separate family room anchors one wing with two bedrooms and a bath, while the primary suite and office are privately positioned in a separate wing, which has access to a patio with large spa. The grounds are a true retreat with redwood groves, creekside sitting areas, raised vegetable beds, tennis court, plus expansive areas for outdoor entertaining. Access to acclaimed Woodside Elementary School (K8) adds the finishing touch.

3323 Woodside RD, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Michael Warren from APR
13890 Skyline BLVD, Woodside
$2,425,000
4 Beds ⋅ 3 Baths ⋅ ML82019227 MLS
Discover the perfect blend of space, comfort, and natural beauty in this Woodside retreat. A scenic meadow highlights the property, plus a flat, usable acreideal for recreation, gardening, or expansion. The log cabin exterior with river rock accents evokes timeless curb appeal and a true Tahoe-inspired feel. Inside, the open floor plan, formal dining, breakfast room, and large bonus room provide flexibility for entertaining and everyday living. With 3 bedrooms upstairs and 1 downstairs with separate entry, the layout is perfect for families, guests, or multigenerational living. Enjoy top-of-the-mountain living in a park-like setting with redwoods, meadows, and direct access to hiking and equestrian trails in nearby Huddart Park. Sunset views from the expansive deck, a wood-burning stove, hardwood floors, and spa tub in the primary suite add charm and comfort. Amenities include central AC with dual zones, Generac whole-house generator with propane hookup, RV parking, ADT security, gutter guard filters, and a tranquil fenced yard. Just 6 miles from Hwys 92 and 84, youre minutes from the Peninsula or coast while enjoying the privacy and community spirit of Kings Mountain.

13890 Skyline BLVD, Woodside

Listed by Teri Rossetto Shaughnessy, 650-504-4016 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Gina Nibbi from COMP12
115 Toyon CT, Woodside
$3,800,000
4 Beds ⋅ 3 Baths ⋅ ML82019068 MLS
Great cul-de-sac location, this sunny, designer-updated home is as charming as it is comfortable. Just minutes from downtown Woodside and top-rated K-8 Woodside School, this location in the Glens is coveted. Step inside to discover the main level, featuring three bedrooms, including two with en-suite baths. The primary suite is a peaceful sanctuary with a generous footprint, sitting area, and direct access to the deck. A third full bath accommodates guests and the third bedroom. The heart of the home is open-concept, with a family room that flows seamlessly into an updated kitchen. Flow into the formal dining room and the inviting living room, where picture windows, custom built-ins, and one of two elegant stone fireplaces create a welcoming atmosphere. Step outside onto the expansive deck for effortless indoor-outdoor living and entertaining. Downstairs, discover a flexible fourth bedroom that can also serve as a home office or bonus room. With exposed beam ceilings, French doors leading to a private patio and fire pit, this may become your favorite space. A separate laundry room and two-car garage add functionality. The landscaped, tiered, and fenced backyard is perfect for entertaining, playing, or enjoying the serene natural surroundings.

115 Toyon CT, Woodside

Listed by Kimberly Hansen, 415-806-8230 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Ginna Lazar from LHG
120 Miramontes RD, Woodside
$4,000,000
5 Beds ⋅ 5 Baths ⋅ ML82018950 MLS
Private ~half-acre property is prime for redevelopment with an existing 3,365+/- sf house and ADU* with 5BDs and 5BAs, a carriage house with studio, paddock, two access gates and multiple outbuildings. This highly coveted location is within 0.5 mile of Woodside Village with Roberts Market, Bucks, the library, The Village Pub (Michelin starred), Village Hub and Village Bakery and Cafe, and near top rated schools, miles of hiking, biking and horseback riding trails and surrounding open space preserves. Nestled in the foothills of the Santa Cruz Mountains between the Pacific Ocean and SF Bay, Woodside is one of the wealthiest communities in Silicon Valley and the U.S. It is renowned for its natural beauty, redwood forests, equestrian culture, sprawling estates, high-profile residents and proximity to Stanford, venture capital firms and tech hubs like Palo Alto and Menlo Park. It is about 30 minutes from San Francisco and the coast, 1.5 hours from Napa Valley and located between two international airports and private jet centers. Affluent, private and understated, this scenic rural town of about 5,100 residents offers a low-key lifestyle and tranquil retreat within easy reach of thriving epicenters. *Some structures may have been built without permits; buyer to investigate.

120 Miramontes RD, Woodside

Listed by Michael Silva, 650-515-2388 from Compass
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS
19 Preston RD, Woodside
$4,900,000
4 Beds ⋅ 3 Baths ⋅ ML82011671 MLS
Surrounded by natures beauty... on 5.4 acres on a private street yet just 3 miles from Sand Hill Road venture capital centers this home offers complete privacy, organic architecture, and spa-like amenities. Oaks and wildflower-strewn meadows create a serene setting deeply connected to the natural landscape with enchanting walking paths. Inside, warm wood finishes, soaring paneled ceilings, and walls of glass establish a tranquil, Zen-like atmosphere that invites the outdoors in at every turn. The layout unfolds with multiple stone fireplaces, outdoor access from nearly every room, and refined materials that reflect the homes high-end craftsmanship. A spa-inspired primary suite features an all-marble bath with cedar-lined sauna and sliding glass doors to the outdoor spa. The flexible floor plan includes one bedroom with a fireplace, en suite bath, and private entrance making it ideal for guest quarters or a possible family room. There is also a detached studio and a lower-level wine cellar with outside access. Outdoor living is equally well considered with a spacious deck overlooking the natural landscape. This one-of-a-kind property offers a close-in location just minutes to miles of hiking and biking trails, town centers, and access to excellent Portola Valley schools.

19 Preston RD, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Kemper Ray from COMPS
125 Grandview DR, Woodside
$1,790,000
3 Beds ⋅ 3 Baths ⋅ ML82011144 MLS
Welcome to Five Acre Woods - A Magical Retreat in Woodside! Nestled on 5.6 private acres, this enchanting property offers sweeping Bay views framed by majestic redwoods. Combining seclusion with convenience, its just minutes from Hwy 280 and the town center of Woodside. Originally built in 1915, this 3-bed,3-bath home has been thoughtfully updated for modern living. With approx. 2,300 SF of single floor space, recent upgrades include a new metal roof, fresh paint, & flooring. The open kitchen flows into a great room that leads to a wrap-around deck, perfect for entertaining or enjoying the serene setting. 2 en-suite bedrooms are off the great room, while a 3rd bedroom & bath open directly to the deck. An office/bonus room offers inspiring redwood views, and the lower level features large, partially finished spaces ideal for a workshop, gym, or studio. Outside, explore your own stream, swing, and private trail connecting to the Thornewood Open Space Preserve. The ppty enjoys a mostly fog-free climate, making outdoor living a year-round pleasure. Located just 2 minutes from Four Corners, home to Alices Restaurant, gas station, and Skywood Trading Post -this home is also in the PV Sch Dist. Offering charm, privacy, and potential, this classic Woodside retreat is a rare find.

125 Grandview DR, Woodside

Listed by Lisa Keith, 650-703-8644 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Disen Cai RE Group from KWPEN
1207 Godetia DR, Woodside
$3,005,000
4 Beds ⋅ 3 Baths ⋅ ML82009528 MLS
Western hill views take center stage... at this updated farmhouse on 1.2 acres, just minutes from the heart of Woodside. The multi-level home, set back in complete privacy, is filled with character, featuring gleaming hardwood floors and generous gathering spaces, all with expansive windows oriented to the views. The kitchen and family room combination opens directly to a spacious view-side deck for indoor/outdoor living. There are 4 bedrooms and 2.5 baths, including a main-level primary suite and three bedrooms upstairs. A 3-stall barn connects to fenced pastures, there is ample room for a dog run or chickens, and additional highlights include a charming playhouse and an oversized one-car garage with laundry. Located just 1.5 miles from the town center and with access to acclaimed Woodside Elementary School (K-8), this property celebrates rural tranquility and offers the opportunity to enjoy as-is or thoughtfully renovate for the future.

1207 Godetia DR, Woodside

Listed by Erika Demma, 650-888-6558 from Compass
(If provided) CoList: Deborah Kehrberg from Compass

Sold listing courtesy of The Patty Dwyer Group from APR
12960 Skyline BLVD, Woodside
$2,037,000
4 Beds ⋅ 2 Baths ⋅ ML82008982 MLS
Perched on a peaceful mountain with breathtaking views of the Pacific Ocean, this updated 4-bedroom, 2-bath home offers the perfect blend of privacy and convenience. Just minutes from Half Moon Bay and San Mateo, this gated property is tucked within the cozy Kings Mountain community and designed for flexible living. With two spacious living rooms, two kitchens, and a bonus room, the home has excellent potential for separate living spaces; ideal for multigenerational living or guest quarters. The main kitchen features sleek Bosch appliances and modern finishes, while large windows throughout the primary living space capture breathtaking ocean vistas. Enjoy outdoor entertaining and evening sunsets on the deck, soak in the hot tub under the stars, and embrace the quiet, coastal mountain lifestyle. Whether you're looking for a serene full-time residence or a versatile retreat with income potential, this home offers comfort, flexibility, and unmatched views in a truly special setting. Just steps from Purisima Creek Redwoods Open Space Preserve and minutes to local favorites like The Mountain House and Alice's Restaurant, this home offers nature, charm, and versatility in one stunning package.

12960 Skyline BLVD, Woodside

Listed by David Skokan, 650-200-7420 from RE/MAX Gold Redwood Shores.
(If provided) CoList: from

Sold listing courtesy of Emily Baratzadeh from CBR
275 Eleanor DR, Woodside
$7,125,000
4 Beds ⋅ 4 Baths ⋅ ML82008127 MLS
Located in the desirable Woodside Heights neighborhood adjacent to Atherton, this dramatic Mid-Century Modern home on 1.05-acres showcases a top-to-bottom designer transformation that elevates every aspect of the home's features. Single-level floor plan offers 4 bedrooms & 4 baths, 2 spacious bedroom suites (one with its own separate office) positioned at opposite ends of the home for optimal privacy with guests or extended family. High-end Walker-Zanger Italian porcelain tile floors throughout provide the look of hardwood with the superior durability & easy maintenance of porcelain. Outdoor designed for entertaining & everyday enjoyment & landscaped to enhance privacy. Sparkling pool, expansive lawn, flagstone terrace with firepit, & separate-level flagstone terrace with fireplace for gatherings. Large poolside cabana open on three sides with its own stone fireplace adds architectural interest & functionality, while the vast undeveloped space at the bottom of the property extends the sense of space & privacy & provides great potential for additional use. Private front courtyard includes an antique marble fountain & a large, wisteria-covered arbor. Complete privacy, a close-in location, & access to top-rated Las Lomitas schools further elevate this one-of-a-kind designer home.

275 Eleanor DR, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Sanaz Khalili Malek from CBR
350 Grandview DR, Woodside
$1,875,000
3 Beds ⋅ 2 Baths ⋅ ML82008056 MLS
Morning light pours through redwoods onto white oak floors at this 3BR/2BA retreat on 2.44 private acres. Updated kitchen and marble baths blend comfort and style. A bright barn office and workshop offer flexible use easily converted for equestrian needs with an existing corral. A fenced dog run adds convenience. Enjoy sunrises on the expansive deck or quiet moments on a meditation deck tucked in a redwood fairy ring. Just 10 minutes to Roberts Market, 15 to Stanford, and close to Facebook (20 min), Google (25 min), and Apple (25 min). Top Portola Valley schools and Woodside High.

350 Grandview DR, Woodside

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: from

Sold listing courtesy of Jennifer Pollock from COMPS
3570 Tripp RD, Woodside
$3,935,000
4 Beds ⋅ 3 Baths ⋅ ML82007527 MLS
This light-filled country home in the heart of central Woodside, on just over one acre, is privately positioned at the top of a gentle knoll beyond picturesque equestrian facilities. Inside, every room opens to the outdoors through sliding glass doors with views of surrounding redwoods. Formal living room features fireplace & opens to expansive front terrace, while the adjoining formal dining room connects to the rear grounds. Bright & light kitchen with breakfast bar seating opens to the inviting family room with a charming wood stove &access to the rear patio. Separate bedroom wing is arranged for privacy & guest suite with solarium tub that takes full advantage of the redwood views. Luxurious primary suite has access to both front & rear grounds, extensive customized closet space, plus a spa-inspired marble bath with vanities, jetted tub & shower. Equestrian amenities include a 3-stall barn with tack room & white fenced corral amid sun-swept open grounds and perimeter redwoods. An attached 3-car garage & adjoining large covered workshop complete the offering. Located just 1.5 miles from Woodside town center and with access to acclaimed Woodside School, this is a special opportunity to enjoy the best of country living in a premier location.

3570 Tripp RD, Woodside

Listed by Hugh Cornish, 650-619-6461 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Christina Hengehold from CBR
380 La Questa WAY, Woodside
$3,500,000
4 Beds ⋅ 4 Baths ⋅ ML82006889 MLS
Bring your builder and architect!! First time on the market in 50 years - incredible value, priced to sell. Four beds and 4 baths in original ranch home plus more recent addition and ADU above garage. Beautiful in ground pool. Horses allowable and close to Woodside trails. Almost three acres!!!! Close to all Central Woodside has to offer including highly desirable Woodside elementary school.

380 La Questa WAY, Woodside

Listed by Andrea Ivarsson, 949-933-0219 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Andrea Ivarsson from CBR
789 Canada RD, Woodside
$1,924,911
3 Beds ⋅ 2 Baths ⋅ ML82002229 MLS
Welcome to this charming updated 3-bedroom, 2-bathroom home located in the beautiful city of Woodside. This inviting residence sits on a spacious 15,400 sq ft lot, offering plenty of room to enjoy the outdoors. Inside, the well-appointed updated kitchen features modern amenities including a gas cooktop, dishwasher, microwave, oven range, and refrigerator, making meal preparation a breeze. The dining area, conveniently situated in the living room, creates a cozy atmosphere perfect for entertaining. Updated ADU with additional 3rd bathroom separate entrance. Large barn-like 2 car garage with extra room for storage workshop/office or more. This home is located within the Woodside Elementary School District. Lush and serene grounds with quiet and privacy inside this beautifully done home. Easy access to HWY 280 and downtown Woodside, close proximity to the Filoli Historic House and Garden. Don't miss the opportunity to make this lovely Woodside home your own. Large price reduction..Motivated Sellers!

789 Canada RD, Woodside

Listed by Tammy T-Cole, 650-683-0426 from Compass
(If provided) CoList: from

Sold listing courtesy of Sharad Gupta from LY55V
1491 Canada LN, Woodside
$12,600,000
4 Beds ⋅ 5 Baths ⋅ ML82003378 MLS
Striking Modern Retreat near Town Center. In the heart of central Woodside, this modern home retains secluded privacywith convenience to shopping & dining just down the road. On a private country lane off the main road, the just over 1-acre setting presents sweeping western hill views from its gentle knoll beyond custom gates. Sophisticated architecturalelements define the home, from Ann Sacks tiles and radiant-heated French oak and marble floors to dazzling designerlighting and Fleetwood doors and windows. The open floor plan balances spacious gathering areas with options for privacyand flexibility plus indoor/outdoor living all around. A dramatic fireplace is shared by the family room with the living anddining room, all oriented to the majestic views. The open kitchen is a hallmark of the design, blending warm wood toneswith French limestone and designer tiles, while an adjacent den/study center offers versatility. There are 4 bedrooms and4.5 baths plus an equally well-appointed 1-bed, 1-bath guest house with full kitchen and laundry, perfect as an ADU orpoolside entertaining. At the center, a sparkling infinity-edge pool is surrounded by level lawn and sun-drenched terraces.A rare combination of modern luxury, a premier location, plus access to Woodside School (K-8).

1491 Canada LN, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: from

Sold listing courtesy of Michael Warren from APR
171 Old La Honda RD, Woodside
$2,700,000
3 Beds ⋅ 3 Baths ⋅ ML82003150 MLS
Lakeview Lodge: A Storybook Sanctuary with Iconic Views and a Surprisingly Convenient Location. Every now and then, a property comes along that feels pulled from the pages of a storybook. Lakeview Lodge is one of those rare places, loved and nurtured by its owners for 29 years for the simplest reason: its just that special. Perched above the treetops with sweeping views of Stanfords Jasper Ridge, and originally named for its view of Searsville Lake, this peaceful retreat offers a front-row seat to natures changing beauty. From golden sunrises to dusky twilight, the vistas inspire reflection. Located near the bottom of Old La Honda Rd at Portola Rd, your minutes from Stanford, top schools, commute routes, and dining - seclusion without sacrifice. Nearby Dennis Martin Creek trails offer tranquil walks under the redwoods. The main home features 2BD/2BA, and a private-entry suite below with kitchen, living area, bedroom, and bathideal for guests or a home office. With high-speed internet, you can Zoom by day and stargaze by night. Lakeview Lodge is more than a home, its a soulful escape with a country feel and unbeatable convenience.

171 Old La Honda RD, Woodside

Listed by Kavanaugh Group, 650-850-1046 from Coldwell Banker Realty
(If provided) CoList: Steven Gray from Coldwell Banker Realty

Sold listing courtesy of Alexander Nichols from EXPCA
1477 Portola RD, Woodside
$5,750,000
4 Beds ⋅ 4 Baths ⋅ ML82002115 MLS
Welcome to a breathtaking estate crafted from heart redwood, where timeless elegance meets modern luxury. The beautifully updated main residence features four spacious bedrooms along with a renovated kitchen and baths, designed for both comfort and style. Two inviting guest houses provide flexible living options, while a third guest unit serves as a bright, inspiring studio/gym. Soak up the sun by the luxurious pool, unwind in the private spa just off the primary suite, or find serenity on one of the many garden patios. Skylights throughout the home flood the interiors with natural light, creating a warm and welcoming ambiance. For outdoor entertainment, enjoy friendly competition on the bocce ball court or stroll through the storybook grounds, complete with sweeping lawns and majestic oaks. Set on fully fenced, gated, and alarm-secured acreage with garage parking for three, this rare retreat offers privacy, beauty, and convenienceall within the acclaimed Portola Valley school district. A truly magical and one-of-a-kind offering.

1477 Portola RD, Woodside

Listed by Kristin Cashin, 650-387-2603 from Christie's International Real Estate Sereno
(If provided) CoList: from

Sold listing courtesy of Ankur Luthra from CATAPULT
258 Kings Mountain RD, Woodside
$13,500,000
5 Beds ⋅ 6 Baths ⋅ ML82001314 MLS
Panoramic Western Hills views set the stage for this stunning Central Woodside estate, nestled on approximately 3.2 flat, fully usable acres just moments from downtown shops, dining, and top-rated Woodside Elementary. Designed for both comfort and function, the primarily single-level layout includes a spacious primary suite, multiple living areas, and a bright eat-in kitchen opening to a large deck overlooking a sprawling lawn, pool, and spa. Work or unwind in the detached office near a private chipping and putting green, while the beautifully crafted barn features a 4-stall stable, tack room, hay storage, riding ring, and fenced turnouts surrounded by peaceful pastures. This estate is brimming with amenities: a rose garden, fountains, sports court, horseshoe area, hidden redwood trails, and vibrant landscaping throughout. The expansive ~2,700 sq ft basement offers incredible storage, along with a wine cellar. Separate guest quarters complete with a second kitchen and private entrance. A rare combination of luxury, land, and locationthis is Central Woodside living at its finest.

258 Kings Mountain RD, Woodside

Listed by David Bergman, 650-948-1100 from Intero Real Estate Services
(If provided) CoList: Angela Bergman from Intero Real Estate Services

Sold listing courtesy of Nicholas French from SGP
9 Summit RD, Woodside
$3,250,000
3 Beds ⋅ 2 Baths ⋅ ML82001305 MLS
Embrace Nature 5.19 Acre Gated Magical Woodside Retreat. Contemporary style, huge windows, soaring ceilings that reach to amazing heights, pyramid copper roofs, 10 gig network intra-structure, and skylights. Unique style/constructionset in the magical setting of a majestic Redwood grove, surrounded by Silicon Valley Views. 3 bed, 2 bath home of ~2,850 sf. The open plan has a kitchen with custom cabinets, luxury appliances, all wrapped by windows. Alfresco dining is just steps away, a tranquil oasis & just one of several venues for entertaining. Separate dining, family and living rooms. Huge primary suite with sitting area & office. Oversized 2-car garage & large workshop/art studio. Extras: Beautiful finishes, radiant heat, Ring doorbell, Advantage lighting system, excellent storage, Boise sound system, hidden panel to finished basement/laundry, whole house vac system, Tesla EV charging, Rumford fireplace, steam shower & much more. Excellent Schools. Just 6 miles from Hwy 280 & Menlo Park. This is just a hint of the treasures this property holds, schedule an appt. with Peter today.

9 Summit RD, Woodside

Listed by Peter Cowperthwaite, 650-207-4101 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Dana Cappiello from SIR
252 Raymundo DR, Woodside
$4,200,000
4 Beds ⋅ 3 Baths ⋅ ML82000241 MLS
Best Value in Woodside! 3 SUNNY acres- all usable. Spacious and expansive, the classically simple and refreshed one-level home is designed for effortless indoor/outdoor living. Highlights include a dramatic great room, extra-large kitchen, 4 bedrooms, and seamless access to the pool and enchanting outdoor living spaces. Enhancing the appeal is a separate guest cottage or ADU, equestrian facilities with direct trail access to 973-acre Huddart Park, plus access to acclaimed Woodside Schools. 3 sunny acres, all usable and ready for planting/farming and/or horses Spacious, refurbished one-level home with a design for indoor/outdoor living ( approx 3340 square feet) 4 bedrooms and 3 baths; approximately 3,340 square feet Guest cottage or ADU with full kitchen, bath, and large deck( approx 640 square feet) 3-car garage with workshop ( approx 970 square feet) Pool plus expansive entertaining patios and decks ( approx storage rooms 215 sq ft, dressing rm 90 sq ft,) Equestrian facilities with two barns ( approx 1175 and 190 sq ft) riding arena ( approx 50x100), and fully fenced horse pastures Woodside Elementary (K-8) School (total structure approximate square feet 6620)

252 Raymundo DR, Woodside

Listed by Don DeFranco, 415-722-7259 from Compass
(If provided) CoList: from

Sold listing courtesy of Michael Warren from APR
160 Alta Mesa RD, Woodside
$3,850,000
4 Beds ⋅ 2 Baths ⋅ ML81992626 MLS
Updated and renovated, this home is ideally located opposite the picturesque Kite Hill permanent open space. Introducing the home is a spacious great room that encompasses a living room, with modern stone gas fireplace, and a step-down seating area with an impressive wall-to-wall window view of the rock and cactus garden. Adjacent to this is a formal dining room and newly remodeled kitchen with quartz counters and all new stainless steel appliances. There are 4 bedrooms and 2 baths plus a detached bonus room ideal for today's remote office, or for a game room or fitness center. Outside, are sun-drenched spaces, a stunning rock and cactus garden complete with pathways and a seating area, plus a private rear garden with large deck for entertaining around the sparkling pool. Adding the finishing touch is this homes access to the highly regarded Woodside School (K-8) and proximity to the Woodside Village.

160 Alta Mesa RD, Woodside

Listed by Scott Dancer, 650-888-8199 from Compass
(If provided) CoList: from

Sold listing courtesy of Afsoon Shahrdar from TODAY
12 Skylonda DR, Woodside
$1,335,000
3 Beds ⋅ 2 Baths ⋅ ML81991484 MLS
Mountain Retreat with Valley Views, Ultimate Privacy, and Open-Concept Living! This 3-bedroom, 2-bath home offers the best of both worldsclose enough for a quick Silicon Valley commute, yet it feels like a secluded mountain escape. The open-concept design connects the kitchen, dining, and living spaces, creating an airy flow perfect for relaxing and entertaining. Enjoy stunning valley views from the kitchen, living room, upstairs bedroom, and spacious decks. The largest bedroom, with a private entrance, offers ADU potentialideal for a guest suite, rental, or a teens private space.The sun-drenched backyard features mature oaks, fruit trees, berry bushes, a greenhouse, and irrigated planting beds. The front yard, with a redwood ring and native plants, enhances the peaceful retreat feel. Inside, the home boasts updated bathrooms, wood floors upstairs, and heated tiles in the downstairs bedroom and bath. Skylights and double-pane windows fill the home with light, while fresh paint and newer decks make it move-in ready. Walking distance to Skywood Trading Post and Alices Restaurant, this home has a small-town vibe. With top-rated Portola Valley schools and nearby trails, and only 25 minutes from the beach, its a perfect blend of nature and convenience.

12 Skylonda DR, Woodside

Listed by Scott Hayes, 650-245-5044 from Compass
(If provided) CoList: from

Sold listing courtesy of Kelsey Takaha from COMPS
185 Harcross RD, Woodside
$4,410,000
4 Beds ⋅ 3 Baths ⋅ ML81989450 MLS
Beautiful 4 Bedroom 3 Bathroom Home with Attached 3-Car Garage. Formal Entry. Chef's Kitchen with Center Island, Wine Refrigerator, and Stainless Steel Appliances Opens to Dining Area with Skylights and Vaulted Ceilings. Spacious Family Room with Skylights, Vaulted Ceilings, and Fireplace. Primary Suite Retreat Features Double Sinks, Stall Shower, and Walk-in Closet. 4 Bedrooms. 3 Bathrooms. Inside Laundry Room with Storage and Sink. Separate Office. Interior Features Include High Ceilings, Ample Light, and Stunning Design Finishes Throughout. Lovely Landscaped Yard with Sauna and Patio.

185 Harcross RD, Woodside

Listed by Keri Nicholas, 650-533-7373 from Parc Agency Corporation
(If provided) CoList: from

Sold listing courtesy of Julie Hadidi from COMPS

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