Other Real Estate, Homes, Condos for Sale in Woodside, CA

2 Beds ⋅ 3 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

$998,000

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

$2,900,000

5 Beds ⋅ 5 Baths ⋅ ML82023275 MLS

Perched a top of Skyline Ridge, this gated custom estate offers spectacular views of the San Francisco South Bay, including Mt. Diablo, Stanford, and San Jose. Nestled on a private 5+ acre east-facing parcel near the 942-acre Wunderlich Park, the home features 5 bedrooms, 4.5 bathrooms, 4 large decks, and a 2-car garage. The gourmet kitchen with center island, dining room, and large pantry opens to the great room with vaulted ceiling, skylights, and 3 French doors. Upstairs showcases imported slate floors, a central family/activity room, a guest half bath, a library/office, and a spacious primary suite with a walk-in shower, a 2-person jetted spa, a private deck, double sinks, a bidet, and a walk-in closet. A nearby flexible room could serve as a bedroom, nursery, or den. The laundry area opens to a flat yard suitable for a future pool, tennis court, or stables. Downstairs includes 2 bedrooms, a large bath, a sitting room, and a fully self-contained ADU with private entry and a deck. In the coveted Portola Valley/Woodside School District, the estate feels private yet is minutes from Alice's Restaurant, Fogarty Winery, central Woodside, Stanford, and the Coast.

16501 Skyline BLVD, Woodside

Listed by Hebe Li, 650-889-6649 from The Agency
(If provided) CoList: from

Sold listing courtesy of Alexandra Gilmartin from GILM

$6,495,000

3 Beds ⋅ 3 Baths ⋅ ML82016045 MLS

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

3323 Woodside RD, Woodside

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

Sold listing courtesy of Michael Warren from APR

$2,199,000

3 Beds ⋅ 3 Baths ⋅ ML82019950 MLS

Nestled among the redwoods, 13630 Skyline Blvd offers the perfect Woodside retreat. Recently refreshed with a brand-new roof, new decks, refinished hardwood floors, and new carpet, this 3,270 sq ft home is move-in ready. The floorplan includes 3 bedrooms plus a dedicated office, a huge main suite, and spacious living areas that balance privacy with flow. A 2-car garage provides convenience, while the 0.56-acre lot delivers peace and room to grow. Located in the Kings Mountain Elementary boundary, this home offers the serenity of mountain living with the accessibility buyers wantjust 15 minutes to Hwy 280 at 92 and 45 minutes to SFO. Whether youre seeking a full-time residence or a weekend retreat, this property combines natural beauty, thoughtful updates, and everyday practicality in one of the Peninsulas most desirable settings.

13630 Skyline BLVD, Woodside

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

Sold listing courtesy of David Skokan from RMXSP

$1,150,000

ML82019754 MLS

Exceptional Development Opportunity in Woodside, with panoramic views. Discover a rare and versatile opportunity in the heart of the Santa Cruz Mountains. This 2.55-acre vacant lot offers breathtaking views of the rolling hills, coastal mountains, and on clear days, sweeping vistas of the Pacific Ocean. Located in the town of Woodside, this property is ideal for visionary buyers seeking a private estate, a high-end residential development, or a unique commercial venture. Multiple Potential Building Sites, Ideal for a luxury home with expansive square footage and unobstructed views. New 3,000 Sq Ft Warehouse Featuring three 12'x16' roll-up doors, perfect for storage, workshop, or staging future development. Upgraded Infrastructure, including PG&E, propane gas, private well with water storage tanks, and a septic system already in place. Zoned Resource Management (RM), allowing for a variety of uses including residential, agricultural, and limited commercial. Whether you're envisioning a private retreat, a multi-use compound, or a strategic investment, this property offers the flexibility and infrastructure to bring your vision to life. Located minutes from Silicon Valley, yet worlds away in serenity and natural beauty.

12725 Old La Honda RD, Woodside

Listed by Matt Aragoni, 650-483-8949 from Coldwell Banker Realty
(If provided) CoList: Mollie Whipp from Coldwell Banker Realty

Sold listing courtesy of Matt Aragoni from CBR

$2,425,000

4 Beds ⋅ 3 Baths ⋅ ML82019227 MLS

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

13890 Skyline BLVD, Woodside

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

Sold listing courtesy of Gina Nibbi from COMP12

$3,088,000

4 Beds ⋅ 8 Baths ⋅ ML82017325 MLS

*NOW REDUCED FOR SALE* SKY VILLA: RE-IMAGINE ROYALTY IN THE WOODS. Sky Villa is an opportunity to dream big with unmatched grandeur & privacy. This is a bank-owned, non-livable development opportunity, approximately 70% complete, with expired permits. Buyer to verify with County of San Mateo the existence and status of any past permits and the ability to resume construction towards completion. Grand scale luxury features such as: 2-Story Lobby with Imperial Staircase | 4 levels of destinations inspire your finishing details | Library off the lobby | Two Enormous Primary Suites (one main level, one upstairs) | Multiple Offices | Immense walk-in closets | Unfinished lower levels of Rec Room, Wine Vault, Grand Loggia, & dreamy Mezzanine facing majestic Sequoia Forest | Flat rear grounds inspire a future pool & ADU | Off-street parking for the most grand events, plus 2 separate attached garages: a daily 3-car at the motor court, plus a lower level 2-car attached garage | Long the bastion for Silicon Valley founders and CEO's, Woodside blurs the line between timeless province and epicenter of wealth and innovation. SKY VILLA, prepare to take flight in one of California's most prestigious communities.

1 Reids Roost RD, Woodside

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: from

$2,525,000

5 Beds ⋅ 4 Baths ⋅ ML82019381 MLS

Experience the ultimate retreat, where majestic redwoods, sweeping canyon vistas, and ocean views provide a stunning backdrop for everyday living. This 3,323 sq ft custom home features 5 bedrooms and 3.5 bathrooms. The main level boasts soaring ceilings, expansive windows, and skylights that flood the space with natural light, highlighting the breathtaking scenery. The open-concept design connects the spacious living area to the kitchen, featuring Brazilian soapstone countertops, rich wood flooring, and stainless steel appliances, perfect for entertaining or relaxing. An adjoining family room offers more space to unwind. Head downstairs to access the expansive deck, versatile bedrooms, and flexible spaces. Outdoor living takes center stage as you step onto the oversized deck, soak in the hot tub under a canopy of stars, or explore the meticulously terraced yard, offering space to garden, relax, or let your animals roam free. Ideally located, a short walk to miles of open space trails,10 minutes to Hwy 280 with easy access to SFO, Silicon Valley, and the Half Moon Bay coast, this home offers the perfect blend of serenity and convenience. Come experience the lifestyle you've been dreaming of, surrounded by nature, tranquility, and the welcoming community of Kings Mountain.

103 Harkins RD, Woodside

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

Sold listing courtesy of Valerie Trenter from CBR

$3,125,000

3 Beds ⋅ 2 Baths ⋅ ML82019083 MLS

A rare and private 15+ acre estate blending equestrian excellence, vineyard living, and natural beauty. Perfect for riders, vintners, or those seeking peaceful country living. The Barn Pros barn includes 4 matted stalls with Euro fronts, individual runs, a heated wash rack with hot/cold water, tack room, and enclosed feed/hay storage. Above, a spacious apartment with 2 sleeping areas, tall ceilings, and sweeping viewsideal for guests, caretakers, or rental income. Equestrian features include 2 fenced pastures with matted double run-ins, a paddock with a single matted shed, ~95x198 Olympia Footing arena (fenced with sand/rubber footing), and a ~60 round pen. The vintage 3BR, 1.5BA farmhouse offers rustic charm, storage, a cellar, and a relaxing front porch with serene views. A newer guest house (separately addressed) features 1BR + office/bonus roomideal for family, guests, or rental. Enjoy ~1 acre of Pinot Noir vines, fully fenced and producing excellent estate wineperfect for personal use or boutique winemaking. Mid Pen has plans to add a lot and access to the La Honda Open Space Perserve, that is right across the street. This is more than a propertyits a lifestyle sanctuary just ~20 mins to Hwy 280 and 30 mins to Half Moon Bay.

11120 La Honda RD, Woodside

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

Sold listing courtesy of David Cline from CBR

$699,000

2 Beds ⋅ 1 Baths ⋅ ML82018470 MLS ⋅ Kings Mountain Association BLDG.

Tucked along Skyline Boulevard, this 2-bedroom, 1-bath Woodside condo with its own private one car garage and laundry offers a lifestyle thats becoming increasingly hard to find: quiet, privacy, and nature; without giving up proximity to Silicon Valley and the Peninsula. Only 10-15 minutes to hwy 280 and set among towering redwoods, open sky, an ocean view and steps away from trails. This home features a spacious, light-filled layout with comfortable living areas that feel both grounded and welcoming. Whether youre starting your morning surrounded by nature or coming home after a long day below the hill, this property delivers a sense of retreat that most condos simply cant. This is Woodside living at an attainable level; ideal for a first-time buyer, down-sizer, or anyone craving a peaceful escape with real long-term value. Inventory in this area is limited, and opportunities like this dont come along often. If youve been waiting for the right way into Woodside; this is it.

14826 Skyline BLVD 3, Woodside

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

$2,037,000

4 Beds ⋅ 2 Baths ⋅ ML82008982 MLS

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

12960 Skyline BLVD, Woodside

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

Sold listing courtesy of Emily Baratzadeh from CBR

$1,768,000

4 Beds ⋅ 2 Baths ⋅ ML81989321 MLS

Imagine a tranquil sanctuary highlighted by the splendor of nature, perfect for hosting gatherings in a lovely outdoor setting. This 4 BD & 2 BA home integrates indoor & outdoor living, boasting generous decks that overlook majestic redwood treeslocated just 20 minutes from Stanford! The living room & kitchen have vaulted ceilings & large picture windows throughout. The kitchen is equipped with premium SST appliances and custom cabinetry. Throughout the home, neutral tones & designer touches create a timeless and tranquil ambiance. The master bedroom serves as a private sanctuary, offering lush mountain views through oversized windows. Each additional bedroom also features large windows, providing peaceful views of the surrounding forest. Enjoy a built-in BBQ station, a private hot tub, and plenty of space for dining and loungingideal for soaking under the stars or enjoying quiet moments in nature's embrace. Conveniently located near Alice's Restaurant, local trails, and parks, midway between SF and San Jose, in the heart of Peninsula. Ormondale TK-3, Corte Madera 4-8, Woodside High School (buyer to verify all schools). This home is truly a Woodside gem!

13499 La Honda RD, Woodside

Listed by Wen Guo RE Group, 650-867-1128 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Paul Sabbagh from ZHB2X

$1,924,911

3 Beds ⋅ 2 Baths ⋅ ML82002229 MLS

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

789 Canada RD, Woodside

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

Sold listing courtesy of Sharad Gupta from LY55V

$1,935,000

3 Beds ⋅ 2 Baths ⋅ ML81998176 MLS

Secluded retreat in the redwoods on 6.1 acres just off Skyline with midway convenience to either Highway 92 or Woodside Road. Absolute privacy and perfect for a main residence or second home for weekend retreats. Gorgeous hardwood floors, dramatic great room with angular wall of windows, sliding glass doors to front and rear decks, and freestanding wood stove. Numerous skylights throughout. Well-equipped kitchen with adjoining flexible use room for wine, small office, or storage. Two main-level bedrooms, one with direct access to a dual-entry bath plus upstairs primary suite with loft-style bedroom and large bath with oversized tiled shower for 2. Additional finished room with outside access offers flexible space for office, fitness, or studio. Separate laundry area, detached 3-car garage, plus storage shed. Acclaimed Woodside Elementary School. Miles of hiking/biking trails all around.

101 Laughing Cow RD, Woodside

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

Sold listing courtesy of Scott Dancer from APR

$1,250,000

3 Beds ⋅ 3 Baths ⋅ ML81995667 MLS

Tucked among towering redwoods, this enchanting log cabin-style home offers a serene retreat in the heart of Woodside's verdant nature. Spread across two levels, this enchanting property features three bedrooms and 3.5 baths. Skylights bathe the interior with natural light, while rich wood floors and a grand stone fireplace create a warm and inviting ambiance. Step out onto the beautiful deck with forest views, establishing a cozy and private retreat. Comprising 3 parcels (075-092-040, 075-092-050, 075-092-060), this 1+ acre property slopes gently down to a tranquil creek. The great outdoors beckons with multiple usable areas, perfect for relaxation or entertaining. And with numerous open space trailheads accessible off Skyline Boulevard, you'll have plenty of opportunities to explore natures beauty. Conveniently located near Alices Restaurant, its just a 13-minute drive to Highway 280, 20 minutes to Stanford University or the San Mateo coast. Dont forget the excellent Portola Valley Schools. Experience the allure of mountain living with the convenience of Silicon Valley and coastal access just moments away.

139 Redland RD, Woodside

Listed by Francesca Lampert, 650-776-1581 from Coldwell Banker Realty
(If provided) CoList: James Milton from Coldwell Banker Realty

Sold listing courtesy of Bob Johnston from CBR

$1,263,688

3 Beds ⋅ 2 Baths ⋅ ML81995213 MLS

Located just steps from the famous Alices Restaurant, this charming cabin is a true retreat set amongst majestic redwoods on over half an acre. Offering a flexible floor plan with three bedrooms, two bathrooms, a very spacious living/dining room combination, and a kitchen with updated appliances. Walls and floors of rich wood carry throughout the home and are highlighted by expansive windows and high ceilings. The living room features a focal-point stone fireplace and sits beneath vaulted ceilings with handsome wood trusses. The dining room sits adjacent to the living room for easy entertaining with access to the deck. The kitchen is placed in the heart of the home with a center island topped in butcher block, tile countertops, a wood-burning stove, and a casual dining area. The primary bedroom has a wall of built-in storage plus two large closets, a sky-lit en suite bath with abundant storage, and sliding glass doors to the deck and spa. The secondary bedroom has a large skylight, a convenient sink, and a lofted area for even more living space. Outside, a vast deck surrounded by a majestic grove of redwoods has plenty of space to relax, and wraps around to a sunken spa off the primary bedroom. A cozy sanctuary, just a few miles away from the hustle and bustle of Silicon Valley.

227 Blakewood WAY, Woodside

Listed by Allison Howard-Smith, 650-334-5664 from Intero Real Estate Services
(If provided) CoList: Troyer Group from Intero Real Estate Services

Sold listing courtesy of Monica Newman from NTERO

$15,750,000

6 Beds ⋅ 7 Baths ⋅ ML81992668 MLS

Completely Renovated inside and out! This architectural Jewel with Dazzling Views! Originally imagined by the visionary architect Gardner Dailey in 1934, this exceptional estate is a testament to his architectural brilliance updated with a complete comprehensive renovation. The classic style of a country manor is presented, creating a visual symphony from the slate tile roof to the leaded glass windows and exceptional gardens. The views offered are nothing short of dazzling, encompassing verdant views of the bordering Menlo Country Club golf course, the sweeping panorama of San Francisco Bay, and the majestic silhouette of the East Bay hills. Set within a gated sanctuary of 1.5 acres, the home is adjacent to a 2.8 acre lot available for separate acquisition, enhancing the promise of exclusivity or with potential for further development. The palatial home spans more than 10,000 square feet of grace and sophistication. The journey into the home begins with a unique entrance a pedestrian gate beyond the gated driveway opens into a vast front courtyard with a magnificent heritage oak tree, lawns and patios, and pool, creating an enchanting space for grand celebrations or private relaxation. This is a once-in-a-lifetime property! Gorgeous Gardner Daley Home.

961 High RD, Woodside

Listed by Erika Demma, 650-704-7928 from Compass
(If provided) CoList: The Dreyfus Group from Golden Gate Sotheby's International Realty

Sold listing courtesy of Steve Lessard from APR

$125,000

BE41083418 MLS

Private lot in prime Redwood Park area of Woodside offers an extraordinary opportunity to build the home of your dreams! Its a perfect rustic hideaway! Private, yet not secluded setting close to 84 and easy access to 280 & 92. Don't miss the opportunity if you love nature and a quiet neighborhood! Prospective buyers are encouraged to do their own due diligence & investigations for building suitability and development with the County of San Mateo. Actual legal description to property is APN: 067-167-070 & 067-167-280. Two parcels merged in 1983.

229 Huckleberry Trl, Woodside

Listed by Jon Ahern, (925) 838-9999 from Coldwell Banker Realty
(If provided) CoList: Camille Ahern from Coldwell Banker Realty

Sold listing courtesy of Lauren Wolff from CCCOLD19

$1,335,000

3 Beds ⋅ 2 Baths ⋅ ML81991484 MLS

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

12 Skylonda DR, Woodside

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

Sold listing courtesy of Kelsey Takaha from COMPS

$210,000

ML81990722 MLS

Opportunity to build and live in the prestigious rural community of Kings Mountain. Lots of stunning Redwoods. Water is available via the local water district. Septic will be needed. Parcel includes Ap #'s 067-222-080 & 067-222-100 for a total of approx 5.5 acres. Property extends from Swett Rd to Tunitas Creek Rd.

0 Swett RD, Woodside

Listed by David Cline, 650-619-3369 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Chris Iverson from GGSIR

$950,000

ML81989854 MLS

THIS 21 ACRE COUNTRY ESTATE IS AN OASIS OF CALM PARADISE SET IN A PARK OF OAK, FIR & REDWOODS IN UNINCORPORATED SM COUNTY; AN EXPANSIVE FEELING OF TOP OF THE WORLD OVERLOOKING SOOTHING GREEN VISTAS IN THE ULTIMATE FAIRYTALE SETTING; A RARE OPPORTUNITY TO BUILD ON THE LARGEST & LAST REMAINING BUILDABLE LOT ON ALLEN RD BUILD A MOUNTAINTOP CASTLE ON EXPANSIVE GROUNDS W/TOTAL PRIVACY & SECLUSION IN AN ENVIRONMENT WHOSE NATURAL BEAUTY IS UNDUPLICATED; THE SILICON VALLEY VIEWS ARE CENTER STAGE & TAKE YOUR BREATH AWAY IN THIS SHANGRI-LA SPOT; DRAMATIC ROCK FORMATIONS ON THIS PRISTINE WOODLAND PICTURE POSTCARD SETTING OF ALMOST ALL USABLE LAND; THERE ARE MANY POSSIBLE BUILDING SITES AT THIS HEAVEN-ON-EARTH PROPERTY OF A LIFETIME W/SPECTACULAR SUNRISES & MOONRISES; WOODSIDE IS THE AREAS MOST DESIRABLE LOCATION; THE PARCEL IS SITUATED ON A SECLUDED COUNTRY RD SET AMONG BEAUTIFUL RUSTIC HIGH END HOMES; THE PARCEL IS IN THE MOST ACCESSIBLE PART OF SKYLINE; CLOSE TO WOODSIDE RD & CA-92 STEP BACK IN TIME TO A SIMPLER WAY OF LIVING WHEN YOU KNOW YOUR NEIGHBORS & HAD A HEALTHY RESPECT FOR PRIVACY & UNSPOILED ENVIRONMENT; HIKING TRAILS & NATURE WALKS ARE CLOSE BY; THE CURRENT FOREST TIMBERLAND PRESERVE ZONING(TPZ) STIPULATES CURRENT PROPERTY TAXES OF $209/YR UNTIL A RESIDENCE IS BUILT & COMPLETED

0 Allen, Woodside

Listed by Deborah Chelini, 650-868-9700 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Janis F. Grube from JANIS

$2,950,000

4 Beds ⋅ 4 Baths ⋅ ML81989328 MLS

ARCHITECTURAL DIGEST MODERN OF ULTIMATE VIEWS! EXCLUSIVE GATED COMMUNITY, WOODSIDE SCHOOLS, HEART OF SILICON VALLEY LIFESTYLE! Bespoke architecturally singificant modern overlooking the Bay. Private natural wonderland with the Peninsula's best Bay vistas. Custom designed in 1991 by celebrated architect Paul Gilger, it's no wonder this home takes on cinematic qualities: around the same time Gilger was crafting this modern opus, he was masterminding the film studio of George Lucas, the legendary Industrial Light and Magic in San Rafael. *3 bed/3 ba in main house + ADU with bed area, office area, kitchen & full bath. *Lower level of main home makes a Zen Office, Lounge, or Family Room * Bold Open Concept * Unobstructed water views * Extensive new landscaping of handpicked native plants and organic design *2-story staircase nearly 30 feet high as work of art * Indoor/Outdoor w/ view dining decks and flat pad to rear * Immersive privacy beyond circular motor court * Tons of Sunlight * New Fountain Courtyard * Backup Generator, Tesla Charger in huge 3-car garage *Architecturally significant bespoke caliber, served by two gates: one at Central Woodside's Bear Gulch/Woodside Road, and upper gate at Skyline, not far from Mountain House Restaurant and easy Highway 92 connection

33 Bear Glen DR, Woodside

Listed by Geoffrey Nelson, 650-455-3735 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Kavanaugh Group from CBR

$685,000

3 Beds ⋅ 2 Baths ⋅ ML81987587 MLS

Price Improvement! Bring your vision, contractor and agent and make us an offer! Picture yourself, immersed in nature, living amongst the redwoods and fruit trees in your own fully fenced, secluded compound. Hidden from the road allowing you the ultimate in privacy. Enjoy the fragrance of fresh air and the Coastal breeze. Sink into soulful bliss and surround yourself in the beauty of nature while enjoying your morning beverage or your telecommute on the sun filled deck. The large great room with stone fireplace is the perfect space to entertain, an additional fireplace in the primary bedroom. Bonus room downstairs. No freeways here, far enough away from the hustle and bustle of the Silicon Valley, yet a short drive to Highways 92 and 280. With a little TLC, this lovely, private and secluded, quiet home would transform into a true gem. Sitting on over a half an acre, this is a real opportunity for the buyer who wants to keep the history and nostalgia of the area while creating a beautiful sanctuary to call their own. Live here or make this your vacation home away from home, moderate drive from the East Bay or San Francisco. Forget Tahoe, live Woodside!

200 Star Hill RD, Woodside

Listed by Linda Crose-Andersen, 650-417-1545 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jazmine Ransom from REEXPERTS

$1,450,000

3 Beds ⋅ 2 Baths ⋅ ML81984955 MLS

Abundant skylights throughout this charming woodsy cabin fill the home with sunlight and create a peaceful, inviting retreat just moments away from the bustle of Silicon Valley. The newly remodeled kitchen offers crisp white counters, cabinets, and a contemporary tile backsplash plus a mudroom laundry area with updated appliances. There are natural hardwood floors and vaulted ceilings in the living room, kitchen, and bedrooms. A large bedroom, full bathroom, kitchenette, and family room on the lower level could be used as a guest suite or ADU with separate entrance. Upgrades include new electrical panel, AC, back-up generator, cast iron wood stoves, and outdoor pizza oven. Multiple fruit trees, a small meadow, and a seasonal creek grace the backyard and are lightly shaded by elegant redwood trees. This one-of-a-kind home is served by Portola Valley's highly acclaimed elementary and middle schools, and is a short stroll to Alices Restaurant, Four Corners, and stunning trails for hiking or biking. Come see all that 223 Blakewood has to offer!

223 Blakewood WAY, Woodside

Listed by Carrie Davis, 650-269-4768 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of RECIP from RCIP

$10,500,000

4 Beds ⋅ 4 Baths ⋅ ML81984920 MLS

Welcome to Woodside Big View Ranch! This legacy 162+ acre ranch has been in the same family for nearly a century - can now be yours. The large country home has a barn, workshop, lake for swimming and fishing and an unofficial,but well used air strip. The house is appx 4230 sq ft with amazing western views of the ocean.Built in 1983 by the patriarch of the family, it features 4 bedrooms 3 full and 1 half baths. A large, casual kitchen has views of the gardens and a spacious area for a big table. The formal dining room has paneled walls and looks out the back to the lake area and gardens. The living room is huge and takes a minute to believe that this beautiful of a setting is possible. You can feel the memories, the music and the possibilities for entertaining.There is a magnificent center veranda which has clear views of the lake and air strip. It is a remarkable view. There library that also can be used as a bedroom, with access to a full bathroom. Unfinished basement with laundry that has exterior access. One of the best fishing spots in all of Woodside, is the lake on this property. It is also a great swimming lake with a quaint deck for relaxing. Exuding personality and joy, this ranch is right out of an old Western movie - minutes to Sand Hill/Stanford. Williamson Act.

19600 Skyline BLVD, Woodside

Listed by Debora Smith, 650-580-8286 from Sotheby's Intl Rlty
(If provided) CoList: Dana Cappiello from Sotheby's Intl Rlty

Sold listing courtesy of RECIP from RCIP

$4,025,000

6 Beds ⋅ 6 Baths ⋅ ML81984105 MLS

13716 Skyline BLVD, Woodside

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

Sold listing courtesy of Joakim Bye from OCEA

$275,000

ML81983061 MLS

Priced to sell! This expansive 4.59-acre lot, zoned for Resource Management, offers endless possibilities for residential, agricultural, and accessory uses. Ideal for those looking to create a quiet retreat or build their dream home. The property offers ample space for agricultural projects, nurseries, livestock, grazing, kennels, catteries, and much more! Enjoy the charm of country living while being close to essential amenities. Surrounded by expansive estates and bordered by open space, this lot features paved road access and a serene atmosphere, providing the perfect blend of seclusion and accessibility. Conveniently located near Skyline, 20 minutes from Hwy 280, and less than 2 miles from Thomas Fogarty Winery. Buyer to verify all details and buildability with the San Mateo County Building and Planning Department. Topographic Survey is available. Don't miss this rare opportunity to shape your vision in a picturesque setting! Photo renderings showcased for inspiration.

0 Heacox, Woodside

Listed by Miriam Cruz, 408-644-4295 from eXp Realty of Northern California, Inc.
(If provided) CoList: from

Sold listing courtesy of Michael Warren from APR

$1,099,900

2 Beds ⋅ 1 Baths ⋅ ML81980445 MLS

Welcome to this charming Woodside home, cradled amongst a cathedral of Redwood trees, and loaded with character. Enjoy the relaxing ambiance of this home, featuring Pella windows, vaulted wood ceilings, skylights, and pine wainscoting. With the perfect balance of updated convenience and country charm, this lovely home boasts an open kitchen with an adjacent dining nook, a loft perfect for storage, guests, or office, and a living room with vaulted ceiling, perfect for curling up by the wood burning stove. Outdoor eating area, flagstone patio w/arbor, built-in benches, large shed, extra storage, detached garage

144 Creek TRL, Woodside

Listed by Ed Gory, 650-743-7645 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Michael Mendenhall from KWSV

$1,757,500

4 Beds ⋅ 3 Baths ⋅ ML81979968 MLS

Nestled in a serene redwood grove in the hills above Woodside, this 4-bedroom, 2.5-bath home offers a tranquil retreat with modern convenience. Set on a spacious mostly level 1/2-acre, this property blends the beauty of nature with sophisticated living. The open concept living area features vaulted ceilings, large windows, & a cozy fireplace, filling the space with natural light and framing breathtaking views of the towering redwoods. The kitchen boasts stainless steel appliances with granite countertops. The primary suite offers a private sanctuary with two story cathedral windows looking out onto the private back yard. Adjacent to it is an enclosed downstairs porch with a built-in hot tub with 3 additional bedrooms providing ample space for guests, or a home office. Outside, the half-acre lot offers endless opportunities for relaxation & recreation, with pathways, fruit trees a garden area and plenty of space to create your vision. Located just a short drive from the city, this home provides the perfect balance of seclusion and convenience, offering a unique lifestyle for those who value nature and privacy without sacrificing proximity to urban amenities. A rare find in the Bay Area, this home invites you to experience the perfect blend of rustic charm and modern luxury.

8 Big Tree WAY, Woodside

Listed by Brian Dakin, 650-483-5760 from Compass
(If provided) CoList: from

Sold listing courtesy of Norman Fung from COMP

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