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13660 Skyline BLVD, Woodside
$1,890,000
3 Beds ⋅ 2 Baths ⋅ ML82065423 MLS
ONE LEVEL LIVING- The Comfort of a Classic Discover life among the redwoods in this inviting single-level California ranch home, situated on approximately half an acre of level, fenced grounds along Woodside's Scenic Skyline Boulevard. Surrounded by towering redwoods and beautiful natural scenery, this private woodland retreat combines the warmth of solid redwood construction with natural stone accents, vaulted ceilings, skylights, and generous windows that bring the outdoors in. The dramatic living room features exposed beams, wood floors, and a handsome stone fireplace, with views of the woods/garden and flagstone patio. A remodeled kitchen with stainless steel appliances opens to a spacious dining area overlooking the surrounding forest. The thoughtfully designed floor plan includes three bedrooms with generous closets, two full bathrooms, a separate laundry room, ample storage, and an attached two-car garage. Just around the corner from the iconic Mountain House restaurant and nearby hiking trails, the property offers convenient access to the Peninsula, Silicon Valley, and the coast. Possible ADU and expansion potential.

13660 Skyline BLVD, Woodside

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

388 Albion AVE, Woodside
$14,800,000
2 Beds ⋅ 2 Baths ⋅ ML82064344 MLS
One of the most premier locations in Central Woodside! Within walking distance to the Town Center shops & restaurants and highly acclaimed Woodside Elementary K-8. This exceptional property is nestled on just over 4 acres (175,977sf) offering a rare combination of privacy with lovely views of the western hills. A private oasis, consisting of 3 separate cottages, offers a unique opportunity for a builder or developer to generate rental income while plans are designed and construction is underway. Located in one of the worlds most exclusive zip codes, nearby Venture Capital hub Sandhill Road, Stanford University & Silicon Valley. Set amid the natural beauty of Woodside, enjoy all of the renowned hiking, biking and horseback trails that make Woodside such a special place. Easy access to major commuter routes 280, 92 and 101 This is a rare opportunity to create a private estate!

388 Albion AVE, Woodside

Listed by Wendi Selig-Aimonetti, 650-465-5602 from Coldwell Banker Realty
(If provided) CoList: from

160 Redland RD, Woodside
$2,750,000
4 Beds ⋅ 3 Baths ⋅ ML82063276 MLS
Some houses announce themselves, this one settles quietly into the redwoods of Skylonda, a 1967 mid-century modern by architect Edwin Wadsworth where the light comes first, then the trees, and only after that the house itself. High wood ceilings and heavy beams carry the eye through walls of glass to the forest beyond, the sunken living room feels sheltered beside a stone fireplace, and the dining room opens to the decks through floor to ceiling windows and a sliding door, with a pass through to the island kitchen and a sunny breakfast area warmed by a freestanding wood-fired stove. Upstairs, the primary suite sits in the canopy like a separate apartment, with its own outside entrance, walk-in closet, and balconies on either side. The recreation room has its own entrance from the gravel courtyard, and a small detached office offers a quiet place to work. Approximately 3,420 square feet, 4 bedrooms, 3 baths, and approximately 0.91 acres, expanded in 1989 and refreshed with new flooring through much of the home, interior paint, updated lighting, and deck repairs, with Alice's, the Skywood Trading Post, and County Fire Station 58 close by.

160 Redland RD, Woodside

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

25 Corto LN, Woodside
$4,850,000
3 Beds ⋅ 3 Baths ⋅ ML82062831 MLS
Rarely available flat lot and ideally located close to Woodside Town Center, this inviting single-level ranch-style home combines timeless appeal with exceptional flexibility and private outdoor living. A welcoming front porch and newly refreshed interiors. The spacious living and dining room combination is anchored by a gas fireplace, creating an inviting setting for both everyday living and entertaining. The bright kitchen features white-painted cabinetry, granite countertops, a tumbled stone backsplash, and stainless-steel appliances, including dual ovens and a Bosch refrigerator. A skylight brings in abundant natural light, while a walk-in pantry provides excellent storage. The adjoining breakfast area opens directly to the rear grounds, where the stone patio, low stone detailed seating walls, and expansive level lawn create a private, sun-filled setting for outdoor enjoyment. Three bedrooms are located together, including the primary suite with views of the backyard, while two additional rooms and half bath in a separate wing offer tremendous versatility for a dedicated office, gym, recreation room, or other lifestyle needs. Just minutes from Roberts Market, Woodside Town Center, and Highway 280, the home also enjoys access to acclaimed Woodside Elementary School.

25 Corto LN, Woodside

Listed by Judy Citron, 650-400-8424 from Compass
(If provided) CoList: Talia Citron from Compass
63 Ridge CT, Woodside
$3,489,000
4 Beds ⋅ 3 Baths ⋅ ML82062642 MLS
Beautifully updated interiors & striking architectural character define this exceptional home in the Glens newly built in 2007. Tucked away at the end of a peaceful cul-de-sac just one mile from the Woodside town shopping & acclaimed restaurants as well as the highly rated TK-8 Woodside Elementary school. Framed by custom Corten-style fencing, terraced gardens, & underground utilities rarely found in this neighborhood, the property presents an added sense of privacy & refinement. Freshly painted interiors & hardwood floors introduce warm, inviting spaces filled with natural light. Original architectural details are complemented by contemporary finishes, custom cabinetry, granite surfaces, & expansive windows & sliding glass doors opening to the outdoor living areas. Cathedral ceilings enhance the open-concept design, creating wonderful scale for everyday living & entertaining. Flexible floor plan, spacious primary suite with fireplace, customized walk-in closet, & newly finished bath. There is also expansion & ADU potential (subject to Town approval & applicable development standards). Fully fenced front & rear yard offer expansive areas for entertaining & relaxation with a level rear lawn, expansive deck, paver stone terrace, & large spa, all in a tranquil park-like setting.

63 Ridge CT, Woodside

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

1100 Mountain Home RD, Woodside
$6,350,000
2 Beds ⋅ 2 Baths ⋅ ML82062379 MLS
This beautifully appointed residence blends warm natural materials with abundant windows and effortless indoor/outdoor living, on one of Woodsides most desired streets/locations. Expansive decks provide multiple areas for dining, entertaining & relaxing while overlooking the Cabernet Sauvignon vineyard. Stunning living room with vaulted wood beam ceilings, wood burning fireplace & wall of glass overlooking the vineyard. Separate family room features recessed lighting & gorgeous built-ins. Kitchen features Miele built in oven, Thermador gas cooktop, dishwasher drawers, & a glass door refrigerator. The serene primary suite features custom built-ins, a window seat, walk-in closet, private deck access w/hot tub & a beautifully detailed bath with dual vanities and freestanding soaking tub.Additional bedroom features a built-in desk and a sliding glass door to the deck. Separate den, office or wine room with wet bar & sliding doors to the back deck.Terraced gardens, level side and rear lawns, and raised beds for vegetables bring forth ultimate usability throughout the grounds.Mature landscaping and a striking outdoor water feature complete this extraordinarily peaceful setting.A rare opportunity to experience the privacy & natural beauty that define Woodside living in an A+ location.

1100 Mountain Home RD, Woodside

Listed by Zach Trailer, 650-906-8008 from Compass
(If provided) CoList: from

Sold listing courtesy of Jennifer Alfaro from COMPS
14826 Skyline BLVD 3, Woodside
$599,999
2 Beds ⋅ 1 Baths ⋅ ML82061335 MLS ⋅ Kings Mountain Association BLDG.
This 2-bedroom, 1-bath home in Woodside offers 1,110 square feet of comfortable living space. The updated bathroom features a stall shower and tile finishes. The kitchen includes an electric oven range, dishwasher, refrigerator, and a 220-volt outlet, with an eat-in area for casual dining. Flooring throughout combines hardwood and carpet for a balanced look. A separate family room provides additional living space. Additional features include a skylight that brings natural light into the living areas. A one-car garage adds to the functionality. This property falls within the Cabrillo Unified elementary school district. HOA is in the process of putting on a new roof, so home is under contruction. This is a shortsale home and will take a minimum of 3 to 6 months(minimum) for bank approval. This purchase is not for a buyer who might be in a hurry as we have two loans to get short-sale approval. Inspections will need to be done by buyers. Bank will NOT have any inspections.

14826 Skyline BLVD 3, Woodside

Listed by M&W Collective, 559-681-5477 from Ocean Element Real Estate
(If provided) CoList: from

232 Highland TER, Woodside
$3,350,000
4 Beds ⋅ 3 Baths ⋅ ML82060102 MLS
Set on approximately one-third acre in a serene Woodside setting, 232 Highland Terrace offers privacy, distinctive architecture, and exceptional indoor/outdoor living. Mature trees frame beautifully landscaped grounds with roses and fruit trees, while expansive patios and decks capture western hill views. The updated residence is rich in character, with wide-plank hardwood floors, a soaring paneled and skylit cathedral ceiling, hand-painted tilework, a distinctive pressed-metal ceiling, and French and Dutch doors opening outdoors. Just off the foyer is an office or playroom with multiple windows and mini-split ceiling HVAC. The primary suite features a steam shower and private deck with recessed spa. An authentic-style Japanese tea house, secluded koi pond, outdoor shower, and detached studio with bath provide flexible spaces for guests, work, wellness, or creative pursuits. Plans for an expansion of the main residence have been submitted to the Town of Woodside and remain active through approximately February 2027, offering the opportunity to further enhance the property. Just minutes from Woodside Town Center and acclaimed Woodside Elementary School, this distinctive property combines privacy, character, flexibility, and convenience.

232 Highland TER, Woodside

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

Sold listing courtesy of Helen Miller from APR
510 Woodside DR, Woodside
$4,758,000
3 Beds ⋅ 4 Baths ⋅ ML82057851 MLS ⋅ Woodside Hills BLDG.
High in the Woodside hills on a rare 1.36-acre parcel, this move-in-ready home offers sweeping bay and bridge views, complete privacy, and easy access to Silicon Valley and San Francisco's Financial District. Wide frontage and an elevated setting frame the view on arrival. The east-west orientation brings morning light into the main living spaces and afternoon sun to the rear. The plan divides into three sections: a soaring-ceiling living and dining room; a kitchen with Wolf range, Sub-Zero refrigeration, beverage and wine coolers, and an oversized pantry; and three en-suite bedrooms with custom closet organizers and Toto Washlets. Two-car attached garage. The land is the opportunity. At 1.36 acres, there's room for a pool, sport court, addition, or detached ADU buyer to verify with the Town of Woodside and San Mateo County. Turnkey, private, and view-driven. And room to make it yours.

510 Woodside DR, Woodside

Listed by Yu Chih Chiang, 408-818-0046 from Casa Nova Realtors Inc.
(If provided) CoList: from

Sold listing courtesy of Un Represented from NOBUY
496 Raymundo DR, Woodside
$3,175,000
3 Beds ⋅ 3 Baths ⋅ ML82054634 MLS
Woodside Retreat "Beside The Woods in Woodside" Peaceful end-of-road privacy and a rustic, eclectic retreat once featured in the Almanac, cherished by one family for 50+ years. 4 sunny, wooded acres with sweeping hill and redwood views. Private gate opens directly onto the trails of 900+ acre Huddart Park. Close to town and Woodside schools. This rustic 3600+ ft 3 beds/2.5 bths home is a study in Vintage Tahoe-style craftsmanship. The living room anchors the house with wood and brick walls, an open stone fireplace, and terracotta tile underfoot. Wooden beams carry into the country kitchen with Subzero and stainless appliances, and the dining room flows onto an expansive view deck over the gardens and pool. A home office overlooks the gardens, and a skylit staircase leads down to a gallery hallway with a stained glass window and a private family room/bedroom. The showstopper: a dramatic Great Room "tavern," host to gatherings of 150, with 19' ceils and grand fireplace of original SF cobblestones. Custom bar built from salvaged San Carlos post office and pharmacy. A reclaimed-barn-siding full bath with steam shower. Large billiard room completes the tavern vibe. Decks and brick paths trace the contour of the land to the pool, framed by redwoods on all sides. Sep 2-car garage.

496 Raymundo DR, Woodside

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

Sold listing courtesy of James Horn from JHORN
12180 Skyline BLVD, Woodside
$2,300,000
3 Beds ⋅ 1 Baths ⋅ ML82053963 MLS
Welcome to your own private retreat where modern comfort meets the beauty of nature. Set on a picturesque property surrounded by towering trees and breathtaking valley and ocean views, this beautifully updated home offers the perfect blend of tranquility and style. Inside, you'll find light-filled living spaces and quality finishes throughout. Large windows frame the natural landscape, creating a seamless connection between indoors and out. Step outside to discover thoughtfully designed grounds featuring lush landscaping, expansive lawns, inviting patios, and multiple areas for entertaining or relaxing. Wander along a charming walking path that winds through the property to a secret garden, an enchanting sanctuary with mature trees, unique sculptures, and peaceful spaces to unwind. Whether enjoying morning coffee overlooking the hills, hosting gatherings under the stars, or exploring your own private woodland retreat, every corner of this property offers something special. A detached garage provides room for vehicles, hobbies, or future expansion. This is more than a home it's a lifestyle where privacy, nature, and refined living come together in perfect harmony. Just minutes from Highways 92 and 280, for an easy commute to Silicon Valley, SFO, San Francisco, and the Peninsula.

12180 Skyline BLVD, Woodside

Listed by Karen C Hoffmann, 650-400-7409 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Wei-Pei Cherng from EXPN
140 Sheridan Way, Woodside
$4,395,000
4 Beds ⋅ 5 Baths ⋅ BE41140473 MLS
Tucked at the end of a peaceful cul-de-sac in Woodside Hills, this beautifully reimagined single-level retreat pairs timeless ranch design with an unbeatable connection to nature. Panoramic views stretch across Hoover Tower, Moffett Field, the Dish, and Mount Hamilton - a backdrop that changes with the light throughout the day. Set on a full acre with a creekside property line, the grounds feel like a private nature escape. Deer and songbirds pass through regularly, while four terraced garden beds await your green thumb. Outdoor living is at the heart of this property, with a spacious private deck, a bocce ball court, horseshoes, a swing set, and even a chicken coop - space to entertain, play, and unwind in equal measure. A large paved driveway offers ample parking for hosting guests with ease. Inside, the open floor plan is anchored by a custom kitchen featuring a large center island, stainless steel appliances, and timeless leathered granite countertops, prized for their easy maintenance, complete with a pantry for extra storage - all flowing seamlessly into the home's entertaining spaces. The thoughtfully remodeled layout (2013) also offers true separation between private and social areas. Two en-suite bedrooms and a Jack-and-Jill bath provide flexibility for family or guests,

140 Sheridan Way, Woodside

Listed by Ella Naylor, (650) 520-9864 from Compass
(If provided) CoList: Daniel Boot from Compass
17001 Skyline, Woodside
$3,150,000
4 Beds ⋅ 3 Baths ⋅ ML82049733 MLS
Truly extraordinary 10+ acre retreat offers a rare combination of privacy, usability, and natural beauty. Tastefully updated home sits on an elevated, level setting surrounded by mature trees and abundant sunshine, creating a peaceful sanctuary that feels far removed from the pace of everyday life. A private road winds down through the property, crossing a seasonal creek before opening to a spectacular sunny meadow below & connects to Horse and Hiking trails. This expansive area presents endless possibilities, from horses, barns, and riding facilities to orchards, gardens, recreational uses, or simply enjoying the open space. Outdoor enthusiasts will appreciate direct access to miles of nearby trails for hiking, horseback riding, and mountain biking right from the property. Combining turnkey living with exceptional land, tremendous sun exposure, remarkable privacy, and a setting that inspires exploration and relaxation, this is a truly special opportunity to own one of Skylines most compelling lifestyle properties

17001 Skyline, Woodside

Listed by Nino Gaetano, 650-207-1986 from The Agency
(If provided) CoList: from

Sold listing courtesy of Greg Damelio from SGP
855 Patrol RD, Woodside
$3,705,000
3 Beds ⋅ 2 Baths ⋅ ML82050036 MLS
Set on 1.5 acres at the end of a quiet cul-de-sac in Central Woodside, the property offers a beautifully completely updated estimated 2,105 sq ft retreat in the highly regarded Woodside School District. The refreshed home features wide-plank oak hardwood floors, new dual-pane windows, LED lighting, and a new metal roof with added skylights. The renovated kitchen showcases shaker cabinetry, white marble countertops, a Wolf induction range, Sub-Zero refrigerator, dual Wolf ovens, a deep corner pantry with microwave, and an island with seating, plus a Dutch door to the spacious rear patio. Enjoy a cozy family room with wood-burning fireplace, large-screen TV, and articulating door to outdoor entertaining and dining. The primary suite includes an expansive sleeping area with French doors to the nearby native plant garden and majestic Redwoods, a Mitsubishi split A/C, and an upgraded and spectacular bath with marble counters, freestanding tub, new shower, and improved walk-in closet. Additional highlights: new central forced-air system with Nest controller, Level 2 EV charger, security cameras, new septic system and gated trail access to Teague Preserve.

855 Patrol RD, Woodside

Listed by Helen Miller, 650-400-1317 from Compass
(If provided) CoList: from

Sold listing courtesy of Robert Luecke from SHOPI
300 Ridgeway RD, Woodside
$4,625,000
3 Beds ⋅ 3 Baths ⋅ ML82033724 MLS
Located in the highly desirable Woodside Hills, this exceptional gated estate offers the perfect blend of privacy, luxury, and bay views. Set on a level one-acre lot, the property features a thoughtfully designed main residence and a fully separate guest house, ideal for extended family, guests, or work-from-home flexibility. The main house offers approximately 3,247 square feet of living space with three bedrooms and two and half bathrooms, complemented by a three-car garage. Designed for both comfort and entertaining, the home opens to expansive outdoor amenities including a pool, hot tub, and sports court, all surrounded by mature landscaping and serene views. The guest house provides approximately 1,254 square feet, featuring two bedrooms, two full baths, its own one-car garage, and complete privacy from the main residence with its own private yard. Additional highlights include solar power, a gated entry, and sweeping Bay and mountain views, making this a rare opportunity to own a versatile estate property in one of Woodside's most sought-after neighborhoods.

300 Ridgeway RD, Woodside

Listed by Gregory Garcia, 650-771-0656 from Sequoia Realty Services
(If provided) CoList: from

Sold listing courtesy of Anuja Krishnan from KWPEN
260 Grandview DR, Woodside
$2,850,000
4 Beds ⋅ 3 Baths ⋅ ML82049221 MLS
Sunlit Sanctuary on 3.7 beautiful acres. Sky Hill Farm, a rare, retreat-like property that blends natural beauty, indoor-outdoor living & modern luxury minutes from the heart of Silicon Valley. This beautifully renovated home has been completely reimagined w/high-end finishes & exceptional craftsmanship, offering a lifestyle of comfort, privacy & effortless elegance. Seamlessly flowing open floor plan, refined aesthetics and meticulously upgraded systems that enhance comfort, efficiency and long-term peace of mind. Sun-filled living spaces open naturally to the outdoors. The heart of the home is a gourmet kitchen featuring premium appliances, custom cabinetry, expansive counter space and functional layout. Huge deck extends the living space outward. Set on 3.7 very usable acres provides endless possibilities gardens, play areas, outdoor lounges, or simply room to breathe. The primary suite feels like a private retreat, with serene views and redwood finishes, huge walk-in closet and luxurious bath. Charming 2 bed guest house w/kitchen. Historic updated carriage house can be used as 6-car garage, workshop a dream for car collectors, hobbyists, or anyone needing serious workspace. At the back of the property sits a restored barn for storage, projects ,animals. Plans show 2427 s.f.

260 Grandview DR, Woodside

Listed by Karin Bird, 650-207-0940 from Compass
(If provided) CoList: from

Sold listing courtesy of Daniel Chang from COMP
180 Phillip RD, Woodside
$4,300,000
3 Beds ⋅ 2 Baths ⋅ ML82047585 MLS
For Comp Purposes Only

180 Phillip RD, Woodside

Listed by Costantini Team, 650-430-8425 from Compass
(If provided) CoList: from

Sold listing courtesy of Costantini Team from APR
140 Dean RD, Woodside
$12,000,000
6 Beds ⋅ 5 Baths ⋅ ML82046443 MLS
Designer Transformation on 1.5 Private Acres Steps to Town A remarkable whole-home transformation has elevated this property into a showcase of design, quality, and livability. Spanning approximately 1.5 acres just minutes from the town center, the setting unfolds with park-like grounds that capture the essence of Woodside country living. Inside, a beautifully orchestrated floor plan offers predominantly single-level living with subtle elevation changes that define spaces while maintaining an open, flowing arrangement ideal for both everyday living and entertaining. Every detail reflects a designers eye, with cohesive finishes and thoughtfully selected materials creating a sophisticated yet welcoming atmosphere throughout. A well-appointed 2-bedroom, 1-bath guest house with full kitchen and laundry adds exceptional flexibility for extended family, guests, or even office use. Outdoor amenities are equally compelling, highlighted by a sparkling pool, vast lawn areas, and a bountiful orchard alongside a charming chicken coop that enhances the property's country appeal. All of this plus access to acclaimed Woodside Elementary School, offering a rare combination of privacy, scale, and convenience.

140 Dean RD, Woodside

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

Sold listing courtesy of Matt Zampella from SGP
330 Ridgeway RD, Woodside
$6,561,058
5 Beds ⋅ 5 Baths ⋅ ML82045206 MLS ⋅ Woodside Hills Association BLDG.
Set on a flat acre of gorgeously manicured grounds. This single story home borrows transitional architectural tones from the French countryside. The circular driveway leads up to a large 3 car garage. Five bedrooms that come with a separate guest house, sports court, large pool with covered grotto like spa, adjacent bath with changing room. Outdoor kitchen covered by a palapa, the perfect shade from natural elements while dining al fresco. Backyard is south facing and hosts the perfect weather all year long. The yard is an entertainers paradise. French oak engineered flooring throughout. Kitchen has an open layout with Thermador appliances and tuscan inspired limestone touches. Front living room has custom built shelving and cozy gas fireplace. Knotted Alderwood window and doors. Indoor surround sound. Generous master suite with walk in closet and wardrobes. Heated floors in bath and an oversized shower with tropical garden views. Enjoy the privacy this secluded subdivision provides. Hidden away, yet suburban enough hooked up to city sewer and close proximity to Sand Hill Road, Silicon Valley and San Francisco. Close to Menlo School, Sacred Heart Prep, Phillips Brooks, Woodside Priory amongst many other renown schools. Enjoy sunsets and the nature this lifestyle provides.

330 Ridgeway RD, Woodside

Listed by Mariana Pappalardo, 650-670-7888 from Compass
(If provided) CoList: from

Sold listing courtesy of Agnes Yu from BPRO
140 Northridge, Woodside
$5,080,000
3 Beds ⋅ 4 Baths ⋅ ML82041730 MLS
This is the forever home everyone hopes for! Exceptionally quiet and private, this gated single-level ranch home spans approximately 3,000 sq ft on over one acre of rare, level land in a prestigious Woodside Hills cul-de-sac. Offering a unique combination of serenity and convenience, the property is just minutes from Highway 280 for easy commuting. A gated entry opens to an expansive front yard with ample parking and a spacious motor court. This lot is ready for a pool, lawn games or an ADU. The home features a well-designed floor plan highlighted by a grand-scale living room, a separate formal dining room, and a sun-filled kitchen with wraparound windows overlooking the backyard. The kitchen flows seamlessly into the family room, creating an open-concept great room ideal for everyday living and entertaining. The bedroom wing includes three generously sized bedrooms, each with its own connected bathroom, including a primary suite. The grounds are park-like, featuring a large, flat lawn, mature trees, and partial view-an uncommon offering in this area. An exceptional opportunity to enjoy a peaceful setting with easy access to commute routes and nearby amenities.

140 Northridge, Woodside

Listed by Costantini Team, 650-430-8425 from Compass
(If provided) CoList: from

Sold listing courtesy of Linda Wang from AGNC
235 Hillside DR, Woodside
$2,150,000
3 Beds ⋅ 2 Baths ⋅ ML82032924 MLS
BEST VALUE IN WOODSIDE!! Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. The nearly 0.5 acre lot features abundant, verdant scenery and a wrap-around deck to take it all in. The main level boasts a large, open-beam living room anchored by a cozy wood-burning stove, and is surrounded by windows which bring the natural beauty of the Glens inside. The floor plan includes a vintage kitchen, a dining area overlooking the oaks, and two bedrooms -- one featuring its own fireplace. Central air-conditioning provides year-round comfort. Upstairs is a versatile loft with a storage area. The lower level features a large bedroom with a bathroom and shower, an oversize 2-car garage, plus driveway space for 2 additional vehicles. With the large lot, an ADU is possible (buyer to confirm with the town). Located in the district for top-rated Woodside Elementary (K-8) and Woodside High, this home is moments from Woodside Village and offers a convenient commute to the entire Bay Area via Hwy 280. Experience the quintessential Woodside lifestyle in this timeless woodland sanctuary.

235 Hillside DR, Woodside

Listed by Steve Rumberg, 408-981-2383 from Keller Williams Realty-Silicon Valley
(If provided) CoList: from

309 Olive Hill LN, Woodside
$11,000,000
2 Beds ⋅ 4 Baths ⋅ ML82039836 MLS
Discover an exceptional opportunity to create a dream home or reimagine the existing Neoclassical residence on one of central Woodsides most desirable streets. Spanning just over 3.4 acres, this expansive property showcases rare Bay views. There is an existing planning study for guidance in future opportunities. Positioned at the end of a private lane, the setting reflects the essence of Woodside country living, with lush perimeter trees and vast open land that offer a serene and private natural environment. The gated property includes an existing one-level home, a pool, and an original tennis court. Just one mile from Woodside Town Center and acclaimed Woodside Elementary School, and only minutes to Stanford University, Sand Hill Road venture capital firms, and the heart of Silicon Valley, this location offers both seclusion and convenience.

309 Olive Hill LN, Woodside

Listed by Brent & Mary Gullixson, 650-888-0860 from Compass
(If provided) CoList: from

391 Mountain Home RD, Woodside
$5,800,000
2 Beds ⋅ 1 Baths ⋅ ML82039615 MLS
Nestled in a prime location in the prestigious town of Woodside, this exceptional property offers a rare opportunity to create something truly extraordinary. Set on an expansive 58,893 square foot (1.35-acre) lot, the setting is both private & picturesque - surrounded by beautiful estates that define the areas renowned character and enduring appeal. Here, the possibilities are truly limitless, offering an ideal canvas to design and build your dream estate in one of the Peninsulas most sought-after communities. The property includes a quaint 2 bed/1 bath cottage, detached garage, plus a pool. Offered for the first time in over 75 years, this is a once-in-a-generation opportunity to secure a premier parcel in a location known for its elegance, natural beauty, and long-held generational ownership. Just minutes from Woodside Town Center (Roberts Market, acclaimed local restaurants, etc.) you'll enjoy a seamless balance of peaceful seclusion and close-to-town living. Outstanding Woodside TK-8 School and proximity to Highway 280 further enhance the property's exceptional livability and convenience. A truly rare offering in a coveted location, framed by distinguished neighboring estates - this is your opportunity to create a legacy property in the heart of Woodside.

391 Mountain Home RD, Woodside

Listed by Greg Celotti, 650-740-1580 from Compass
(If provided) CoList: Katherine Celotti from Compass

Sold listing courtesy of Brad Miller from APR
665 W Glen WAY, Woodside
$3,600,000
3 Beds ⋅ 2 Baths ⋅ ML82038616 MLS
A Private Setting with Sweeping Western Hill Views! Architectural character with a strong connection to the outdoors define this inviting Woodside home set on more than one-third of an acre. Across the front of the home, a dramatic wall of glass rises to a beamed and paneled cathedral ceiling, framing sweeping western hill views and tranquil garden outlooks. Living, dining, and kitchen spaces come together in a generous open area that extends out to a crushed stone patio oriented to the views. Three bedrooms and two baths are arranged for comfort and privacy. The primary suite is positioned just off the foyer and opens directly to the rear yard. Two additional bedrooms are located on the opposite side of the home, including one with an adjoining office or art studio and direct outdoor access. The grounds offer expansive gardens, a level lawn, and a detached studio with flexible use, creating inviting spaces for relaxation, creativity, or entertaining. A close-in setting near the center of town, along with access to highly regarded Woodside Elementary School, completes the appeal of this distinctive property.

665 W Glen WAY, Woodside

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

Sold listing courtesy of DeLeon Team from DLRPA
160 Phillip RD, Woodside
$10,988,000
5 Beds ⋅ 6 Baths ⋅ ML82037743 MLS
Set on more than 2.5 acres of quintessential Woodside grounds, this spectacular estate balances timeless elegance with easy comfort. Behind gates and surrounded by mature trees and lush foliage, it conveys a quiet sense of luxurious seclusion. Inside, more than 6,400 total SF includes a dramatic foyer with columns, expansive formal rooms, a chef's kitchen, private office, theater, and five bedrooms, including a sanctuary-like primary suite. Outdoors, resort-style grounds feature a pool, spa, pool house, patio with fireplace and grill, cascading waterfall with bridge, gardens, fruit trees, and a detached bonus studio for work or fitness. Tesla solar panels and 6 Powerwall batteries, a seamless Sonos sound system, and expert craftsmanship enhance every detail. Just minutes from Woodside, Sand Hill Road, Palo Alto, and top schools, it offers the rare blend of privacy, prestige, and proximity.

160 Phillip RD, Woodside

Listed by DeLeon Team, 650-900-7000 from Deleon Realty
(If provided) CoList: from

51 Cragmont WAY, Woodside
$5,750,000
4 Beds ⋅ 3 Baths ⋅ ML82037292 MLS
Gorgeous, unobstructed views of the bay and mid-century styling in a private setting in Woodside Hills. Situated on a 1.12-acre lot with 4 spacious bedrooms plus an office and 3 bathrooms, this single level home offers a terrific floor plan. Designed to embrace natural light with dramatic floor-to-ceiling windows and high ceilings that create an airy, open atmosphere while seamlessly connecting indoor and outdoor spaces. The large patio, seen through walls of glass throughout the home, overlooks the views and is the ideal spot for entertaining. The gardens feature mature fruit trees, charming landscaping, spaces for children to play, and a sparkling pool and spa. The 2-car attached garage and additional detached 1-car garage and a generous circular driveway provide ample parking.

51 Cragmont WAY, Woodside

Listed by Monica & Mandy Group, 650-823-8212 from Compass
(If provided) CoList: from

Sold listing courtesy of Judy Citron from COMPS
135 Harcross RD, Woodside
$4,200,000
3 Beds ⋅ 2 Baths ⋅ ML82034218 MLS
Set on approximately 1.65 acres in Woodside Hills, this rare single-story property presents an exceptional opportunity to create a custom estate in one of Silicon Valleys most coveted settings. The existing 3-bedroom, 2-bath residence built in 1955, features a classic footprint, swimming pool, and expansive groundsoffering endless potential for renovation, expansion, or a complete reimagining. Surrounded by mature trees and natural beauty, the property delivers privacy, scale, and a premier canvas for builders, developers, or visionaries seeking to craft something truly extraordinary. Whether restoring the homes mid-century character or designing a brand-new architectural statement, this is a rare chance to secure a sizable parcel in a prestigious enclave where world-class estates define the landscape.

135 Harcross RD, Woodside

Listed by David Kelsey, 650-388-2086 from Compass
(If provided) CoList: from

Sold listing courtesy of Jasmine Lee from CBR
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

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Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.


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