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$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

$5,690,000
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

$8,000,000
4 Beds ⋅ 6 Baths ⋅ ML82060993 MLS
Privately positioned at the end of a gated country lane, this elegant French Country estate combines sweeping Western Hills and sunset views with the convenience of a prime Central Woodside location. Set on approximately 1.11 acres, the grounds feature expansive terraces, mature landscaping, and inviting spaces for indoor-outdoor living and entertaining. The main residence features four bedrooms, five-and-a-half bathrooms, a dedicated office/library, a main-level primary suite with an adjoining flexible-use room, and a recently updated chefs kitchen with a sunny breakfast area. Patterned oak floors, high ceilings, and abundant natural light create a warm, sophisticated atmosphere throughout. A detached one-bedroom, one-bath guest house with a full kitchen, fireplace, and high ceilings provides an ideal setting for guests, extended stays, or a private workspace. Just moments from Woodside Town Center, Woodside School, Interstate 280, Sand Hill Road, and Stanford University, this exceptional property offers a rare combination of privacy, usable acreage, inspiring views, and close-in convenience.

55 Mission Trail RD, Woodside

Listed by Victoria Yang Surles, 415-818-3603 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Sally Li from CBR
$7,295,000
5 Beds ⋅ 4 Baths ⋅ ML82062065 MLS
An extensive remodel completed in 2023 transformed this classic New England Colonial with designer style and a fresh approach to modern living. The remodeling went well beyond new finishes, with the floor plan reconfigured to add a main-level bedroom and full bath for a total of 5 bedrooms and 4 baths. The kitchen and dining area were completely transformed with an open design and commercial-quality appliances, while all new windows, glass doors, and recessed lighting enhance the ambiance and connections to the surrounding three-acre grounds. Significant infrastructure improvements were completed as well, including upgraded electrical, new HVAC, a tankless water heater, earthquake retrofitting, and new irrigation.The setting is equally impressive with mostly level grounds, a 5-stall -1700 square foot barn, with hayloft and tack room, vast stretches of lawn, a newly fenced yard, and expansive brick terraces for outdoor living and entertaining. There is also a separately fenced and newly resurfaced pool featuring a 75-foot lap lane, elevated spa, and new owned solar heating system, plus equestrian facilities that include a 5-stall barn with paddocks. A detached 2-car garage with 2 EV charging outlets adds further convenience. Wonderful location close to Woodside and PV Town Centers

1543 Portola RD, Woodside

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

$5,988,000
5 Beds ⋅ 4 Baths ⋅ ML82062056 MLS
Set on a private acre in Woodside Hills, this exceptional midcentury residence offers more than 4,600 square feet of living space, spectacular Bay views, and a wonderful connection between indoors and out. Walls of glass, hardwood floors, and expansive living areas create a distinctive setting, complemented by two fireplaces and a stylish kitchen with black granite and appliances from top brands. The family room provides a comfortable gathering space, while five bedrooms plus an office offer flexibility for family, guests, and work. Multi-level grounds showcase the views with a large deck, inviting pool, and broad lawn, creating an ideal setting for entertaining and everyday enjoyment. Conveniently located near shops, restaurants, parks, nature preserves, and Interstate 280, the home is also just five minutes from acclaimed Woodside High School (buyer to verify eligibility).

160 Crest RD, Woodside

Listed by DeLeon Team, 650-407-0160 from Deleon Realty
(If provided) CoList: from

$2,100,000
3 Beds ⋅ 3 Baths ⋅ ML82056662 MLS
Perched high along Skyline Boulevard on 2.67 acres, this exceptional mountain retreat offers sweeping 180-degree views stretching from San Francisco to San Jose. Surrounded by the natural beauty and serenity of the Santa Cruz Mountains, its an ideal sanctuary for remote work, writing, creative projects, or simply escaping the everyday. Built in 2007, the 2,180-square-foot home features 3 bedrooms and 2.5 baths, with expansive walls of glass that flood the living spaces with natural light. Warm straight-grain fir trim and custom baseboards add timeless character throughout. The open floor plan flows onto a spacious view deck with hot tubperfect for sunset relaxation or casual entertaining. An outdoor shower makes returning from a morning hike or gardening especially refreshing. Practical amenities include a private well, backup generator, and attached 2-car garage with covered breezeway. Enjoy exceptional privacy and mountain tranquility while remaining connected to the Peninsula, with Stanford roughly 20 minutes away and easy access to Woodside, Portola Valley, and beyond.

20421 Skyline BLVD, Woodside

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

$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

$65,000,000
5 Beds ⋅ 6 Baths ⋅ ML82032838 MLS
Completed in 2023 on Woodside's most premier central corridor, a Cul De Sac off Mountain Home Road. This 3 acre Tuscan inspired estate property is a masterpiece of design that blends the finest materials from around the globe. Breathtaking displays of quartzite evoke artful elegance, while floors of marble and French oak exude timeless sophistication. Every detail is crafted with precision- French oak cabinetry, ceilings, and trim, coupled with Venetian plastered walls in the grand public rooms, softly illuminated by chandeliers from Spain. Designed to perfection for today's lifestyle, the great room serves as the heart of the home, offering a magnificent kitchen with a seamless flow to the loggia and vast private grounds. Five bedroom suites, including both main and upper level primary suites, provide ultimate flexibility and privacy. The guest house mirrors the main residence's impeccable standards, complete with a full kitchen, bedroom, two baths, and sauna. The estate's grandeur extends outdoors with a wrap around loggia with fireplace, 60 foot pool and spa with canopy jets, fully fenced tennis court, expansive lawns and meadows. Located in one of the country's most exclusive Silicon Valley zip codes, nearby Venture Capital hub Sandhill Road, Stanford Univ. & Silicon Valley.

7 Blue Ridge LN, Woodside

Listed by Steve Lessard, 650-704-5308 from Compass
(If provided) CoList: from

$6,880,000
5 Beds ⋅ 4 Baths ⋅ ML82056698 MLS
Elegant Woodside living in an exceptionally spacious and versatile 5-bedroom, 3.5-bath residence bordering Atherton. A gracious formal entry opens to the inviting living room with a fireplace and adjoining formal dining room, creating an ideal setting for entertaining. The gourmet eat-in kitchen features a generous center island, breakfast bar, premium appliances, and abundant workspace, and opens to a spectacular family room with soaring vaulted ceilings and a second fireplace. Three bedrooms are located on the main level, including a luxurious primary suite with a private fireplace, a walk-in closet, and a beautifully appointed en-suite bath with dual vanities. The lower level offers two additional bedrooms, an office/den, a large recreation room, a wine cellar and tasting room, and a flexible exercise space. Beautifully landscaped grounds extend the living experience outdoors, with a sprawling lot, an inviting patio, and a BBQ area, perfect for relaxed gatherings and outdoor entertaining. This exceptional residence offers a rare combination of elegance, scale, versatility, and indoor-outdoor living. Bordering Atherton, a coveted location, close to shopping, parks, great schools, and near commute routes. Welcome Home!

2120 Stockbridge AVE, Woodside

Listed by Jose Dos Ramos, 650-787-5568 from Berkshire Hathaway HomeServices DrysdaleProperties
(If provided) CoList: from

$2,995,000
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

$1,950,000
3 Beds ⋅ 3 Baths ⋅ ML82059245 MLS
Skyline corridor on nearly one-half acre with spectacular unobstructed ocean views and easy access to both the Peninsula and the coast. The two-story floor plan features vaulted beamed ceilings, angled transom windows, and abundant natural light. The main level has a spacious living room with fireplace, dining area opening to the view deck, an updated eat-in kitchen, plus the primary suite, two additional bedrooms, and a bath. The lower level includes a large family room with fireplace and wet bar, full bath, laundry room, and access to the 2-car garage. Detached bonus studio with wet bar and bath provides flexible space for guests, office, or hobbies. Expansive wraparound deck with ocean views plus covered and open patios extend the living space outdoors. Just one-half mile from a trailhead to Purisima Creek Redwoods Preserve with miles of hiking and equestrian trails, 5 miles to Highways 92 and 8 miles to Highway 84 for access throughout the Peninsula and to the coast. Excellent Kings Mountain Elementary School.

115 Forest View RD, Woodside

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

$3,389,000
3 Beds ⋅ 2 Baths ⋅ ML82059026 MLS
There is a particular quiet at 411 Glenwood Avenue. Stand on the main level and look through walls of glass. The first thing you notice is the treetops. The second is what you do not see: neighbors. The Oak canopy and the open expanse of the Joan Olson Preserve fill the windows instead. Friends who visit call it the Treehouse. Built in 1959, the home keeps its mid-century bones: mahogany paneling, a brick fireplace, and warm cork and hardwood floors. The kitchen opens to the great room, with stone counters and a gas cooktop. Walls of glass open onto a broad deck for slow dinners, the preserve as backdrop. Upstairs, the bedrooms share that same treetop view. Downstairs adds real flexibility: an open room with a slider to a flat, green yard, suited to an office or playroom, an en suite bedroom with its own patio, plus laundry and storage. Cross the street and you are on a trailhead into the preserve, a shortcut into downtown Woodside on foot, coffee in hand, oaks the whole way. Downtown, with the Village Bakery, Buck's, and Highway 280, is minutes out. The home sits within the highly rated Woodside Elementary School District, TK - 8. 411 Glenwood does not ask you to choose between nature and convenience. It offers both, as the best Woodside properties do.

411 Glenwood AVE, Woodside

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

$2,299,000
4 Beds ⋅ 3 Baths ⋅ ML82058136 MLS
Panoramic Views, Absolute Privacy Perched high above the valley on over six acres, this rare 4-bedroom, 3-bath mountain sanctuary pairs total seclusion with sweeping, unobstructed views stretching clear across the Bayfrom vibrant sunrises over the water to shimmering city lights at night. Inside, three thoughtfully designed levels of living space are anchored by soaring ceilings, expansive glass, and two cozy wood-burning fireplaces. The main floor centers around a functional kitchen with a central island and walk-in pantry, opening directly to a multi-level wraparound deck designed for effortless indoor-outdoor living and scenic dining. The layout includes a primary suite positioned to capture morning light, complete with an oversized bath and walk-in closet. Three additional bedrooms feature a built-in loft, a walk-in closet, and a ground-floor room with private outdoor entry ideal for a peaceful home office. Sprawling level lawn areas, mature trees, and a hot tub set for stargazing complete the grounds. Extras include an attached 2-car garage, large utility room, ample parking, Jackery backup battery, and a Tesla EV charger. Located minutes from trailheads, preserves, central Woodside, and I-280-a high-elevation retreat moments from Silicon Valley.

255 Allen RD, Woodside

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

$1,650,000
3 Beds ⋅ 3 Baths ⋅ ML82058172 MLS
Contemporary, eclectic, and like living in a treehouse, this home is secluded in the redwoods on 5+ acres just off Skyline with midway convenience to either Highway 92 or Woodside Road. Acclaimed Woodside Elementary School. Miles of hiking trails all around.

14 Blue Jay WAY, Woodside

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

Sold listing courtesy of Scott Dancer from APR
$14,900,000
7 Beds ⋅ 9 Baths ⋅ ML82057953 MLS
A rare, fully realized legacy compound offering the soul of a European retreat in the heart of Woodside. Hidden within 3.2 acres of curated gardens and ancient oaks, this meticulously renovated sanctuary blends old-world artistry, artisan tile, and beamed ceilings with the peace of mind of enterprise-grade infrastructure. The grounds are a private resort masterpiece designed for serene living, anchored by a rare clay tennis court, a waterfall grotto, a pool and spa, a pitch-and-putt green, and a bocce court. The main residence features four refined suites, a professional grade kitchen, a magnificent wine cellar,and a private executive office. Multi-generational living is perfected with a 2-bedroom family cottage, a 1-bedroom guest house, and a detached fitness center with sauna and Tonal strength training equipment.Beyond the charm, the estate offers total autonomy with redundant internet access, a backup generator, and advanced surveillance. This is the ultimate turnkey acquisition: an impossible-to-replicate blend of character and modern high-performance living, perfectly positioned minutes away from Silicon Valleys entrepreneurial eco-systems most iconic hubs.

600 Moore RD, Woodside

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

$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
$21,995,000
4 Beds ⋅ 5 Baths ⋅ ML82054839 MLS
Evoking the patina & permanence of a residence shaped over generations, this vineyard estate possesses an authenticity rarely achieved in contemporary construction. Completed in 2016 imbued with character of timeless European manor, it received the Julia Morgan Award for Classical Architecture, honoring its exceptional craftsmanship & architectural integrity. Hand-hewn beams, bespoke millwork, artisanal detailing, & imported Italian patterned terra cotta tile flooring define the interiors, while Mediterranean Revival influences create an atmosphere that is grand & welcoming. Arranged across two levels with elevator access, lower-level storage room with wine cellar potential, residence offers 4 bedrooms, dedicated office, & detached guest house. Formal & informal living spaces center around a chef's kitchen with a generous butlers pantry, while arched windows & French doors frame surrounding landscape. Set on approximately 4.33 acres in Woodsides coveted Hidden Valley, the estate enjoys sweeping views of Jasper Ridge, the Santa Cruz Mountains, the Western Hills, & Westridge. A pool, spa, rose gardens, crushed stone paths, dual-fuel backup generator, & professionally managed Pinot Noir vineyard producing up to 50 cases annually complete this extraordinary Silicon Valley retreat.

180 Farm RD, Woodside

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

$1,888,000
4 Beds ⋅ 4 Baths ⋅ ML82056831 MLS
An exceptional opportunity to own a premier property in the heart of Woodside, one of the Peninsula's most prestigious and sought-after communities. Located at 26 Big Tree Rd, this unique offering combines privacy, natural beauty, and convenient access to Silicon Valley, making it ideal for homeowners, investors, or those seeking a legacy property. Surrounded by mature trees and Woodside's renowned rural charm, it offers a peaceful retreat just minutes from downtown Woodside, Stanford University, Sand Hill Road, and major employment centers. Residents enjoy a rare balance of tranquility, open space, and access to world-class dining, shopping, and recreation. Whether creating a private estate, preserving a long-term investment, or capitalizing on one of the Bay Area's most desirable locations, 26 Big Tree Rd presents a rare opportunity in a market where exceptional properties are seldom available. Woodside remains one of Northern California's premier residential destinations, known for expansive estates, an equestrian lifestyle, enduring property values, and unmatched privacy, prestige, and long-term appreciation.

26 Big Tree RD, Woodside

Listed by Matthew Dapolito, 408-202-9202 from Intero Real Estate Services
(If provided) CoList: Scott Bishop from Intero Commercial
$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
$3,610,800
4 Beds ⋅ 2 Baths ⋅ ML82054316 MLS
Nestled on nearly two private acres in a coveted Woodside setting, this Mid-Century Modern home offers a rare blend of rustic charm, natural beauty, & breathtaking panoramic views. Thoughtfully designed to embrace its spectacular surroundings, the four-bedroom, two-bath residence features a sun-drenched living room framed by a dramatic wall of floor-to-ceiling windows that capture sweeping vistas & create an effortless connection to the outdoors. Adjacent to the living room, the open kitchen & dining area also flow seamlessly onto the expansive view deck which is an ideal setting for entertaining, sunset gatherings, or quiet mornings overlooking the horizon. The main level features the primary bedroom & a full bathroom, offering the ease and convenience of single-level living. Downstairs, three additional bedrooms, a full bath, dedicated laundry room, and a spacious bonus family room provides exceptional flexibility for a media lounge, home office, or recreation space. Set on 1.95 acres of serene grounds, the property offers a true sense of privacy and includes a charming barn, adding authentic Woodside character. Lots of possibilities! With access to acclaimed Woodside schools, this special property creates a lifestyle defined by tranquility, scenic beauty, and timeless appeal.

3635 Partition RD, Woodside

Listed by Jennifer Alfaro, 650-888-8338 from Compass
(If provided) CoList: Kimm Terpening from Compass

Sold listing courtesy of Grayson Martin from COMPS
$2,870,000
7 Beds ⋅ 6 Baths ⋅ ML82039818 MLS
A rare opportunity to own an expansive estate with breathtaking panoramic views, exceptional square footage, and incredible potential in a private hillside setting. From the moment you arrive, the home commands attention with its grand entry and impressive scale. Inside, soaring ceilings, dramatic open spaces, and walls of windows flood the home with natural light while showcasing sweeping valley views. The main level is built for both everyday living and entertaining, featuring a spacious living room, multiple gathering areas, and seamless access to a wraparound deckperfect for true indoor-outdoor living. The kitchen offers a large island, ample cabinetry, and a functional layout ready to be elevated into a stunning chefs space. Generous bedrooms and flexible living areas include a primary suite with scenic windows, dual vanities, and a soaking tub, creating a peaceful retreat with beautiful natural surroundings. The lower level offers an expansive bonus/game room with bar area and endless possibilities for entertaining, recreation, or extended living. A dedicated wine cellar adds a rare and desirable touch. Expansive decking and usable outdoor space complete this exceptional offering, blending privacy, scale, and opportunity in a truly unique setting.

245 Heacox RD, Woodside

Listed by Aaron Derbacher, 408-828-8114 from KW Bay Area Estates
(If provided) CoList: Benjamin Frieden from KW Bay Area Estates
$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
$4,000,000
4 Beds ⋅ 3 Baths ⋅ ML82053870 MLS
Central Woodside Opportunity on 1.11 Acres. Just over one mile from Woodside town center this 1.11-acre property presents an increasingly rare opportunity in a desirable Central Woodside setting. A seasonal creek at the rear of the property and stunning western hill views that may be further enhanced create a beautiful natural environment that reflects the scenic character for which Woodside is renowned. A secondary access point from Hillside Drive to the barn further enhances the property's flexibility and future potential. The mid-century ranch-style home has been recently refreshed with new paint inside and out, refinished hardwood floors, new carpet, and refreshed landscaping. Comfortable living spaces, flexible lower-level quarters with a bonus kitchen, and a detached two-stall barn with expansive upper-level space provide immediate enjoyment while offering numerous possibilities for the future. The true appeal extends beyond the home itself. Generous acreage, a close-in location, access to acclaimed Woodside Elementary School, and surrounding estate properties create an exceptional setting for renovation, expansion, or the creation of a significant new residence all while immediately enjoying the freshly updated home.

136 Jane DR, Woodside

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

Sold listing courtesy of Jackie Walker from SGP
$4,750,000
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
$4,625,000
4 Beds ⋅ 4 Baths ⋅ ML82051662 MLS
Inspired by traditional Norwegian farmstead architecture, this home was extensively rebuilt and expanded with views of the western hills and Kite Hill Wildflower Preserve across the street. The home showcases exceptional craftsmanship with solid cedar siding, windows, doors, and screens, a slate roof, old-growth redwood trim, wide-plank Tennessee longleaf pine floors, soapstone countertops, Venetian plaster around the fireplace, and salvaged Douglas fir beams. The flexible 3-level floor plan includes lower-level quarters with kitchenette and private bath, two main-level bedrooms and a bath, plus upstairs primary suite and second suite. Beautifully landscaped grounds feature winding paths, specimen plantings, numerous fruit trees, a rare bamboo grove, pond, flagstone terrace with fireplace, spa, and large chicken coop. Additional features include dual-zone air conditioning, EcoFlow battery backup system and generator, distributed sound, EV charging for 2, and a detached garage. Minutes to Town Center, miles of trails, and acclaimed Woodside Elementary School (K-8).

144 Alta Mesa RD, Woodside

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

Sold listing courtesy of Joan Cattermole from APR
$3,575,000
3 Beds ⋅ 2 Baths ⋅ ML82050810 MLS
Move in today, expand tomorrow. Nearly one-half acre of level land less than one-half mile from the Woodside town center. Fresh paint, refinished hardwood floors, and numerous updates make the home ready to enjoy, while the expansive property presents exceptional opportunities for future expansion or building new. The home has 3 bedrooms, 2 baths, an updated kitchen, living room with fireplace, attached 2-car garage, energy-efficient heat pump for heating and cooling, updated electrical service, and EV charging. Just down the street from renowned Woodside Elementary School (TK-8).

3270 Woodside RD, Woodside

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

$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
$4,588,000
4 Beds ⋅ 4 Baths ⋅ ML82050181 MLS
Nestled among majestic oak trees on nearly 1.2 acres in Woodside Hills, this home is set well back from the street via a long paver driveway. Spanning 4,150 SF, the interiors feature wide-plank hardwood floors, soaring ceilings, and refined finishes that create a light-filled, airy atmosphere in harmony with its natural surroundings. Expansive formal rooms are complemented by multiple fireplaces, a well-appointed kitchen, and a walk-out family room that opens to the outdoors. The four-bedroom layout includes a primary suite with a spa-inspired bathroom designed for comfort and retreat. Outdoor living is equally compelling, with a generous deck and patio featuring an outdoor kitchen, all framed by a verdant, oak-studded backdrop that emphasizes the home's connection to nature. A three-car garage completes the property, while the setting balances privacy with convenience, just minutes to downtown Redwood City, nearby nature preserves and trailheads, and easy access to Highway 280.

61 Oak Haven WAY, Woodside

Listed by DeLeon Team, 650-407-0160 from Deleon Realty
(If provided) CoList: from

$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
$4,075,000
4 Beds ⋅ 4 Baths ⋅ ML82050010 MLS
One Acre with Sweeping Bay Views in Woodside Hills! Sweeping San Francisco Bay views take center stage at this exceptional Woodside Hills property with fresh updates throughout. Spanning one acre, the elevated corner lot is positioned to capture the expansive views while also providing generous level areas for outdoor living. Enhancing the setting is the gentle sound of a meandering creek and strolling paths that create a distinctly parklike ambiance. Fresh interior updates include new paint, refinished hardwood floors, and new carpet, all complementing the living rooms signature vaulted ceiling, handcrafted with layered redwood cedar rising to a dramatic center peak. Multiple fireplaces add warmth and character, while glass doors open to several outdoor spaces oriented to enjoy the Bay views. The formal living room and dining room each have Bay views, plus there is a large open kitchen and family room for everyday gatherings. Four bedrooms, an office, and 3.5 baths are well arranged, featuring a main-level primary suite and a second suite comprising the entire lower-level with outside access and flexibility for future ADU conversion. An attached two-car garage and abundant off-street parking complete this inviting retreat with close-in convenience.

199 Brookwood RD, Woodside

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

Sold listing courtesy of Erika Demma from APR

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