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$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
$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

$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

$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

$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
$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
$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
$4,300,000
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
$3,195,000
3 Beds ⋅ 3 Baths ⋅ ML82045702 MLS
Luxury retreat offers a serene escape on 9+ acres, secured by an electronic gate. Under 2 miles and just minutes to Alices restarant. Stunning style on one level, the home features dramatic light-filled interiors with an open-concept design, SOARING CEILINGS, and abundant sliding glass doors and skylights. Bamboo floors, vertical grain cabinetry, and polished concrete counters. The main rooms revolve around a central patio with a stunning heritage oak tree, while an expansive rear deck with a large spa beneath the redwoods and a sunswept front yard for gardening enhance the outdoor experience. Three privately located bedrooms, each with its own bath, ensure comfort and flexibility. An equally well-appointed ADU above the garage includes a kitchen, bath, and laundry. Total privacy directly adjacent to MidPen open space. Flat useable grounds with large vegetable garden, ample of paved parking, large ground level deck and heritage oak entertainment area for large parties. Open sunny side toward views and beauty of Redwood forest on the oposite side of the house with heated spa under the redwoods. Main house 2870 sq.ft, plus ADU 550 sq.ft., plus attached garage 525 sq.ft for total of 3945 sq.ft.

1100 Old La Honda RD, Woodside

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

$7,495,000
4 Beds ⋅ 6 Baths ⋅ ML82044344 MLS
New Price! Set at the end of a private, gated country lane on approximately 1.11 fully usable acres, this elegant estate with French country architecture offers an exceptional blend of refined living and natural beauty, with sweeping views of the Western Hills and stunning sunsets. The main residence features 4 BR and 5.5 BA and a dedicated office/library with inspiring views. A recently updated chefs kitchen with a sunny breakfast area, main-level primary suite with connecting recreation room, patterned oak hardwood floors, and dual-paned windows throughout create a warm yet sophisticated ambiance. Designed for indoor/outdoor entertaining with expansive terraces and beautifully landscaped gardens this is a one of a kind home. A detached 1 BR 1 BA guest house has a full kitchen, wood-burning fireplace, and high ceilings, perfect for guests, extended family, or independent work space. An additional 520 square feet of garage space and 795 square feet of basement storage provide functionality alongside luxury. Ideally located within walking distance to Woodside Town Centers shops and restaurants, and close to Woodside School (Pre-K8th), Interstate 280, Sand Hill Road, and Stanford University, this home exemplifies the best of serene, convenient, and elegant Woodside living

55 Mission Trail RD, Woodside

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

Sold listing courtesy of Victoria Yang Surles from CBR
$5,450,000
5 Beds ⋅ 4 Baths ⋅ ML82044125 MLS
Tucked away on a private, gated cul-de-sac, 200 Todo El Mundo in Woodside offers the perfect balance of privacy, convenience, and natural beauty. Situated on approximately 1.5 acres of flat, usable land bordered by a seasonal creek, the property features expansive front and back irrigated lawns and a peaceful, park-like setting. The European-influenced traditional 4,885-square-foot main residence is designed for effortless indoor-outdoor entertaining, with several rooms opening through French doors to two sunny decks. A dramatic living room with soaring two-story ceilings and fireplace anchors the home, complemented by a spacious family room with its own fireplace and wet bar, a cozy kitchen and a private dining room ideal for intimate gatherings. The thoughtful five-bedroom, three-and-a-half-bath layout includes a serene upper-level Primary Suite with a full bath, sauna, fireplace and walk-in closet, two additional upstairs bedrooms and two main-level bedrooms with a full bath and tub. With its proximity to Woodside Town Center, Woodside Plaza shopping, Sand Hill Road, Stanford University, and nearby freeway access to major Silicon Valley destinations, this exceptional property offers a rare opportunity to enjoy the Woodside lifestylequiet, connected, and surrounded by nature

200 Todo El Mundo, Woodside

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

Sold listing courtesy of Larry Liu from APR
$5,350,000
4 Beds ⋅ 4 Baths ⋅ ML82043727 MLS
Set at the end of a private lane on more than one acre, this stylish contemporary retreat offers a rare sense of privacy just moments from downtown Woodside. Refreshed landscaping & a spacious, partially covered front deck introduce interiors defined by clean lines, hardwood floors, vaulted ceilings, & expansive walls of glass that fill the home with natural light. The flexible two-level floor plan features 4 bedrooms, an office, & 4 full baths, including a main-level primary suite. A dramatic living room with a fossilized limestone fireplace, formal dining room, & streamlined maple kitchen with honed black granite & butcher block surfaces create a modern yet inviting backdrop for everyday living & entertaining. Sliding glass doors open to a wraparound deck for seamless indoor-outdoor flow. The lower level expands the living space with a large recreation room with a built-in workstation for two, plus 2 additional bedrooms, one with an en suite bath. Terraced rear grounds include a free-form pool, barn with potential equestrian use, zip line, & refreshed landscaping, along with additional usable outdoor areas suited for recreation, play, or future possibilities. Just one-half mile from downtown Woodside & within the acclaimed Woodside School District.

35 Neuman LN, Woodside

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

Sold listing courtesy of Erika Demma from APR
$2,195,000
3 Beds ⋅ 3 Baths ⋅ ML82042155 MLS
Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view balcony. Lawn and mini orchard. A separate charming barn captures the Old West Woodside feel with a wood-beamed ceiling, full-sized bar, and French doors to a veranda with flowering vines. Just a mile to the Thomas Fogarty Winery and 8 minutes to Alice's Restaurant.

20255 Skyline BLVD, Woodside

Listed by Jennifer Paulson, 650-996-7147 from Christie's International Real Estate Sereno
(If provided) CoList: from

$16,000,000
5 Beds ⋅ 6 Baths ⋅ ML82041798 MLS
In one of the best locations in Central Woodside, easy walking distance to Town Center and acclaimed Woodside School (pre-K to 8th); this home captures California Country with East Coast Elegance with its breathtaking views of the Western Hills from the flat one-acre parcel. The open floor plan flows seamlessly for indoor/outdoor entertaining featuring a rear dining patio, built-in BBQ, 50 foot saltwater pool, bocce court, shaded pergola sitting area, spacious rear grass lawn and surrounding array of colorful gardens. Gorgeous oak hardwood floors unify the two-story home, with a comfortable family room adjacent to the chefs kitchen and large combined dining and living room, all with French Doors opening out to the sunny rear entertaining patio. The home has 5 spacious bedrooms, each with its own bath and ideally arranged for a variety of lifestyle needs. The main-level also has a separate home office. Upstairs a primary suite plus 3 additional en-suite bedrooms provide a perfect living area layout. This location offers it all: a private home and property on one of the best country lanes in Woodside while also being within walking distance to Woodside School, Town Center shops and restaurants, and all of the hiking, biking and horseback trails that make Woodside special.

180 Romero RD, Woodside

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

Sold listing courtesy of Katy Thielke Straser from COMPS
$2,750,000
4 Beds ⋅ 4 Baths ⋅ ML82041075 MLS
This Custom built home is perched high on the Skyline ridge (approx. 2000' elevation) with the Pacific Ocean on one side the SF Bay on the other. Located in the exclusive Woodside neighborhood of Kings Mountain, this modern retreat was built with natural filtered light through the Redwoods in mind surrounded by about an acre of wooded privacy. Think open floor plan flow, soaring ceilings, and a wall of glass framing endless redwood canopies. Gourmet kitchen opens to a family gathering area with wood burning stone fireplace. Spa-like baths with a steam shower in the master bathroom, large deck in back for your entertainment needs, a private heated lap pool below, and a separate entrance to an attached ADU/art studio/private office with it's own kitchen and bathroom - it's all here, your own mountain retreat wrapped on a rare level lot where hi-tech meets tranquility and serenity. Woodside's hidden gem where you can become part of a true community - minutes from a top rated elementary school, very active and vibrant community. Only 10-15mins drive to either San Mateo or Half Moon Bay, 20 min to SFO, 25 min to Stanford and 30-40mins to SF - yet worlds away from the chaos. Perfect for remote execs/workers, nature lovers, hikers/bikers, or anyone craving Elevation - literally!

13370 Skyline BLVD, Woodside

Listed by Jonathan Lee, 650-619-9255 from A 2 M Real Estate
(If provided) CoList: from

Sold listing courtesy of Brent Walsh from COMPS
$895,000
1 Beds ⋅ 1 Baths ⋅ ML82038622 MLS
Hidden at the end of a quiet country lane beneath a magnificent canopy of redwoods lies one of Kings Mountain's rarest opportunities, 3.63 private acres where nature, privacy, and possibility come together. Tucked away on picturesque Native Sons Road, this extraordinary property offers a peaceful woodland setting with an existing cottage and valuable infrastructure already in place, including a newer foundation, updated well, septic system, and pump. The home is served by electrical utility service, private well, septic, and delivered propane. Surrounded by towering redwoods and just moments from El Corte de Madera Open Space Preserve, this special property offers a rare opportunity to restore, thoughtfully expand, or create a personal retreat over time. The unfinished lower level presents exciting potential for additional living or bonus space, subject to buyer verification and applicable approvals. Whether envisioned as a weekend escape, artist's studio, writer's retreat, or future custom residence, this is a place where the pace slows, nature takes center stage, and imagination can flourish. A truly uncommon opportunity to own a private slice of Kings Mountain just minutes from the Peninsula's vibrant communities.

155 Native Sons RD, Woodside

Listed by Liliana Perazich, 415-297-0125 from Coldwell Banker Realty
(If provided) CoList: from

$8,900,000
4 Beds ⋅ 3 Baths ⋅ ML82037417 MLS
First time on the market in generations, this rare Woodside property offers a unique opportunity to own a piece of local history. The Victorian home, originally built in 1901 and remodeled in 2010, has remained in the same family for decades and sits on a private 3.4 acre lot, offering potential to split the lot and build your dream home. The home features 4 bedrooms and 2.5 bathrooms, blending classic architectural character with thoughtful updates for comfortable living. The size and location of the property create a distinctive setting that is increasingly rare in Woodside. Ideally located next to Woodside Elementary and just minutes from Woodside Village, with convenient access to Roberts Market, The Village Bakery, Bucks Restaurant, and the Woodside Village Church. A special opportunity offering space, privacy, and historic charm in a highly desirable location.

3215 Woodside RD, Woodside

Listed by Vivienne Kelvin, 650-291-7241 from Vabrato
(If provided) CoList: Mark Martinho from Vabrato

Sold listing courtesy of Michael Warren from APR
$800,000
2 Beds ⋅ 2 Baths ⋅ ML82033018 MLS
This property scores high on the unique scale! Just 5 minutes drive from Alice's Restaurant, nestled in a sorrel, fern and redwood gorge, this two bedroom, two bath home is an engineering feat to behold. Outstanding vehicular accessibility as the .87 acre property enjoys a horse-shoe looped driveway off Highway 84 which would be ideal for heavy equipment operators, or motorcycle enthusiasts. There is a large shop and multiple outbuildings. 20 minutes drive to Palo Alto yet a world away; think clubhouse, weekend get-a-way, or create your own Dwell Magazine worthy abode.

121 La Honda RD, Woodside

Listed by Mollie Whipp, 415-741-4012 from Coldwell Banker Realty
(If provided) CoList: Cameron Jeffs from Coldwell Banker Realty

Sold listing courtesy of Dante Razzini from NTERO
$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

$2,275,000
4 Beds ⋅ 4 Baths ⋅ ML82036766 MLS
A very special home among the trees with peekaboo views towards the ocean. An ideal escape from the bustle just down the hill. The chefs kitchen with center island is open to the spacious family room and breakfast nook. Just outside is an extensive deck and your eyes are drawn out to the natural beauty around. The formal dining room and adjacent living room are light filled with large windows and gracious views. Completing the main floor is a convenient bedroom and nearby full bathroom. Upstairs, the massive primary bedroom has double suite bathrooms, yes, TWO bathrooms attached to the primary. Two additional bedrooms, one decorated as an office/media room, a convenient bathroom with dual sinks, plus the adjacent laundry area with storage round out the second floor. Whether awakening to the mist drifting through the trees or falling asleep listening to the sounds of owls, nature is ever present.

6 Megans LN, Woodside

Listed by Janie Barman, 650-759-1182 from Compass
(If provided) CoList: John Barman from Compass

Sold listing courtesy of Alicia Sanguinetti from APR
$2,000,000
3 Beds ⋅ 3 Baths ⋅ ML82035391 MLS
Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The main floor features a gourmet kitchen with high-end appliances, sleek finishes, dining area, family room and dedicated home office offers the perfect space for remote work or creative pursuits. Upstairs, the bedrooms provide privacy and tranquility. A large, bright family room stands out as a favorite space, filled with natural light and a cozy, welcoming ambiance. Multiple large decks extend the living space outdoors, offering peaceful spots for relaxing, entertaining, or enjoying the majestic redwood surroundings. Additional features include a wine cellar and ample storage. Tucked just off the scenic Skyline Corridor with easy access to Hwy 92, 280/101, SFO, open space trails, restaurants, and award-winning Kings Mtn Elementary, this home offers a rare blend of privacy, convenience, and a strong sense of community fostered by friendly neighbors and the Kings Mtn Volunteer Art Fair.

13872 Silver Sky WAY, Woodside

Listed by Joakim Bye, 650-284-2080 from Ocean Element Real Estate
(If provided) CoList: from

Sold listing courtesy of Evan Walsh from EXPCA
$8,000,000
6 Beds ⋅ 9 Baths ⋅ ML82034677 MLS
One of the most extraordinary properties on the SF Peninsula on 17 acres. The property has endless potential and has been used to raise horses, to showcase a car aficionados collection, and to host philanthropic and social events easily up to 200 guests, all the while serving as a comfortable venue for everyday living. 5-floor main residence from the 10+ car garage to a viewing room at the top of one of the turrets. Personal quarters include multiple apartments plus tremendous, dedicated office space. The barn is a matching masterpiece with both buildings hand-crafted by local and international artisans with individual details taking up to a year to complete. Magnificent grounds include a 4-tee golf practice area, RC car track, resort-inspired pool and spa, and direct access to miles and miles of hiking and equestrian trails in bordering Wunderlich Park. 17 minutes to Woodside town center.

16351 Skyline BLVD, Woodside

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

Sold listing courtesy of Kavanaugh Group from CBR
$500,000
ML82033277 MLS
Lovely flat development spot near a seasonal creek. Excellent opportunity to build on this oak-studded parcel. 4000 ft2 home deemed possible by Lea and Braze engineers; price includes feasibility study, survey, and septic perc test results. This land could be a great location for your estate home or quiet get-away. One mile from Thomas Fogarty Winery. Plenty of room for horses, animals and/or hobby farm, you'll find that you are well-situated to access the hiking and riding trails that abound in the open space near this property. Seller has 2 lots for sale (0-220 and 0-250 Heacox) and the actual address is not yet determined. Electric pole on site. You add septic and well for water, which is plentiful here.

0-250 Heacox, Woodside

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

$550,000
ML82033274 MLS
Tranquil land. Excellent opportunity to build or ? on this sun-drenched parcel that has gentle grade for development. 3800 ft2 home plus 1000 ft2 ADU deemed possible by Lea and Braze engineers; price includes feasibility study, survey and septic perc test results. This land could be a great location for your estate home or quiet get-away. Plenty of room for horses, animals and/or hobby farm, you'll find that you are conveniently located to access the hiking and riding trails that abound in the area's open space. Seller has 2 lots for sale (0-220 and 0-250 Heacox); the actual address is not yet determined. Electric pole on site. Old well on-site (plentiful water here), you add septic system. Invest in your future!

0-220 Heacox RD, Woodside

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

$1,750,000
4 Beds ⋅ 4 Baths ⋅ ML82029010 MLS
Forever views of coastal hills and Pacific ocean at the very end of a small country maintained road. Adjacent to hundreds of Open Space acreage. 1,600 + sq. ft. upper floor Great-Room with floor-to-ceiling windows. Large open kitchen / dining area and open living room with wet bar and guest bath. Upper level deck wraps around the entire exterior. Bedrooms are all downstairs each with access to the deck. Bonus room (great for crafts, possible den or bedroom) and laundry utility area. Downstairs is also aprox.1600 sq. ft.. House was being remodeled, but was not completed. Truly a fixer upper. Complete set of remodel plans included.

47 Forest View RD, Woodside

Listed by Plank or Cline, 650-728-8080 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Richard Beale from BEAL

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