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

155 Normandy LN, Woodside

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

Sold listing courtesy of JJ Team:Jones/Cassel from NTERO
$3,500,000
4 Beds ⋅ 3 Baths ⋅ ML82020106 MLS
Custom built in 1992 on one of the largest parcels in the area. Over 14,000 sq. foot lot. On the market for the first time! Sweeping western hill views, close-in convenience, plus pool and spa. A dramatic great room with soaring two-story ceiling, arched clerestory windows, and skylights highlights the open floor plan that connects living, dining, and kitchen areas to a spacious view deck. 4 bedrooms and an office are arranged across 3 levels, including a main-level primary bedroom with adjoining bath and bedroom ideal for office or nursery. The upper level has a office and skylit loft lounge, while the lower level has two bedrooms, a full bath, and recreation room with refreshment bar opening to the pool deck. Outdoor amenities include a large above-ground pool surrounded with vast decking for entertaining space plus a separate spa. All just minutes to Town Center, hiking trails, and acclaimed Woodside School. Room to add an ADU.

129 Hillside DR, Woodside

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

Sold listing courtesy of Cliff Whearley from WRLY
$18,900,000
7 Beds ⋅ 9 Baths ⋅ ML82019556 MLS
A magnificent transformation has redefined this 1929 French chateau into a modern estate of extraordinary light and sophistication. Once known for its European formality and ornate detail, the home has been renewed from top to bottom with the highest level of design, cabinetry, and finishes. Original millwork and moldings were meticulously preserved, now presented in a palette of light tones that elevate rather than overshadow the architecture. Exceptional lighting and carefully curated finishes bring contemporary elegance to every room, creating a residence that feels entirely new while honoring its historic character. The result is a home that stands among the finest expressions of luxury living today. Equally compelling are the dual-gated five acres of formal grounds that frame the estate. Vast lawns, parterre gardens, and farm-to-table gardens accompany resort amenities of a pool, spa, and tennis court, with multiple terraces providing an unparalleled setting for entertaining or private retreat. All of this unfolds within easy reach of Silicon Valley and San Francisco, establishing a rare estate property where history and modern vision meet at the highest level. among the finest expressions of luxury living today.

320 Harcross RD, Woodside

Listed by Michael Warren, 650-315-0224 from Compass
(If provided) CoList: from

Sold listing courtesy of Charles Liu from COMPS
$7,500,000
4 Beds ⋅ 5 Baths ⋅ ML82017471 MLS
Set on a 3.1-acre, private and gated lot in one of Woodside's most scenic settings, this exceptional, newly-updated residence offers the perfect blend of refined luxury and modern comfort - just minutes from town. Flooded with natural light from expansive floor-to-ceiling windows, the main home spans 3 levels and offers 4 bedroom suites, a library with fireplace, an office, and grand public spaces in +/-5,555sf. The open-concept living room boasts 24-foot ceilings, massive curved windows, a striking fireplace, and flows seamlessly into the sun-filled dining room. The chef's kitchen opens to a huge family room with 10-foot ceilings, a dramatic fireplace, bar, and French doors opening to a patio-perfect for indoor/outdoor living. Designed for everyday comfort and entertainment, the home offers multiple terraces, temperature-controlled wine storage, and an expansive lower level replete with a gym, home theater, and full bath. Outdoor amenities include a pool with spa, tennis court, meandering paths that encircle the property, level lawns, and a vineyard. A detached 2BR/2BA, +/-1,135sf guest house is ideal for extended family or visitors. Access to the top-rated Woodside Elementary School completes this rare opportunity to experience a lifestyle of elegance, privacy, and convenience.

333 Raymundo DR, Woodside

Listed by Jim Arbeed, 650-558-4248 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Jaswinder Gill from GILLJ
$4,750,000
4 Beds ⋅ 5 Baths ⋅ ML82011673 MLS
Designer Style with Pool and ADU on Large Level Grounds Classic and timeless architecture and beautifully remodeled interiors come together on more than one-half acre of level land with a pool and Accessory Dwelling Unit. Hardwood floors and multiple fireplaces add warmth and character across three levels designed for flexibility and comfort. The chefs kitchen and adjoining family room connect effortlessly to formal living and dining rooms, with glass doors throughout opening to expansive patios and vast rear grounds ideal for large-scale entertaining. There is also a dedicated office plus a lower-level laundry room and recreation room with full bath convenient to the tucked-away pool. Upstairs are four bedrooms, including a spacious primary suite with two full baths and two walk-in closets, plus sweeping western hill views. Just minutes from the natural beauty and trailheads of Edgewood Park, and offering access to top-rated Woodside School, this home balances timeless design with modern livability in a premier setting.

490 W Maple WAY, Woodside

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

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

275 Eleanor DR, Woodside

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

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

380 La Questa WAY, Woodside

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

Sold listing courtesy of Andrea Ivarsson from CBR
$8,849,000
4 Beds ⋅ 5 Baths ⋅ ML82006723 MLS
A stately retreat, this exquisite home offers complete privacy just blocks from Town Center and the acclaimed Woodside School. Set behind electronic gates on more than one acre of level land, the property is a showcase of timeless elegance and modern luxury with resort-like amenities. Sustainable living is effortlessly integrated with 32-panel solar power, four Tesla Power walls for energy independence, Tesla charging in the detached 3-car garage, and thermal solar power for the pool. The expansive rear grounds are designed for resort-style living, featuring a 54-foot pool with a beach entrance with water jet, lap lane, spa, plus infinity wall with waterfalls. A state-of-the-art Kalamazoo Outdoor Gourmet kitchen, with Hybrid Fire Grill fueled by any combination of gas, wood and charcoal, gas-fired pizza oven ready in under 45 minutes to make great Neapolitan pizza, and a gravity feed smoker with room for three whole packer briskets, nine whole rib racks or two large turkeys. A fire pit terrace, bocce court, and level lawn provide endless opportunities for entertaining. Offering the best of Californias indoor-outdoor lifestyle, this exceptional property is a rare find so close to the Town.

3295 Woodside RD, Woodside

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

Sold listing courtesy of Jennifer Alfaro from COMPS
$85,000,000
34 Beds ⋅ 26 Baths ⋅ ML81985961 MLS
The Green Gables Estate, in its entirety, is a 74 acre, spectacular, one of a kind, multi-generation oasis situated within walking distance from the Woodside Town Center. The estate is currently comprised of seven homes and 10 separate lots, featuring significant additional build out potential and may be purchased as a whole or in 6 potential lot combinations (see MLS listings for suggested lot combinations with Albion addresses 329-A, 329-AA, 329-C, 331, 333). The complete estates homes currently include 34 bedrooms, 26 bathrooms across approx. 23,900 existing square feet, with numerous options for expansion and/or redevelopment. The vast landscape includes world class gardens, magnificent vistas of the Western hills, its own large reservoir, three swimming pools, a tennis court and a breathtaking 100-yard Roman pool. Situated in the heart of Silicon Valley at the epicenter of venture capital, technology, and renowned educational institutions, the estates elegant blend of English and Italian design offers a bounty of elegant spaces to host retreats, social events, and cultural gatherings or to simply be a world class refuge from the pressure of the outside world. Green Gables is a truly remarkable estate and welcomes its next owner to the latest chapter of its amazing legacy.

329 Albion AVE, Woodside

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

Sold listing courtesy of from

$14,250,000
6 Beds ⋅ 8 Baths ⋅ ML82004065 MLS
Masterfully Renovated Bay-View Vineyard Estate. This extraordinary estate presents a masterfully executed whole-home renovation, captivating San Francisco Bay views, and resort-style amenities. Encompassing 1.8 acres of fully landscaped grounds, the property also includes a Chardonnay vineyard, two wine cellars, and expansive indoor and outdoor entertaining spaces designed for grand gatherings. The main residence was taken down to the studs with both levels reimagined with the ultimate in designer sophistication. Highlights include bespoke lighting, custom wall coverings, premium fixtures, exquisite finishes, and white oak floors throughout. The main residence has 6 bedrooms, 6 full baths, and 2 half-baths. As part of the renovation, an equally well-appointed 2-bedroom, 1-bath guest house was added along with a pool house with indoor barbecue center and ample space for entertaining.

140 Eleanor DR, Woodside

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

Sold listing courtesy of Pamela Culp from COMP32
$12,600,000
4 Beds ⋅ 5 Baths ⋅ ML82003378 MLS
Striking Modern Retreat near Town Center. In the heart of central Woodside, this modern home retains secluded privacywith convenience to shopping & dining just down the road. On a private country lane off the main road, the just over 1-acre setting presents sweeping western hill views from its gentle knoll beyond custom gates. Sophisticated architecturalelements define the home, from Ann Sacks tiles and radiant-heated French oak and marble floors to dazzling designerlighting and Fleetwood doors and windows. The open floor plan balances spacious gathering areas with options for privacyand flexibility plus indoor/outdoor living all around. A dramatic fireplace is shared by the family room with the living anddining room, all oriented to the majestic views. The open kitchen is a hallmark of the design, blending warm wood toneswith French limestone and designer tiles, while an adjacent den/study center offers versatility. There are 4 bedrooms and4.5 baths plus an equally well-appointed 1-bed, 1-bath guest house with full kitchen and laundry, perfect as an ADU orpoolside entertaining. At the center, a sparkling infinity-edge pool is surrounded by level lawn and sun-drenched terraces.A rare combination of modern luxury, a premier location, plus access to Woodside School (K-8).

1491 Canada LN, Woodside

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

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

1477 Portola RD, Woodside

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

Sold listing courtesy of Ankur Luthra from CATAPULT
$6,400,000
5 Beds ⋅ 4 Baths ⋅ ML82001319 MLS
An extended driveway meanders through more than 1.3 acres of Woodside grounds, leading to this spacious and inviting home offering nearly 4,200 SF of space. Bright and airy interiors, adorned with maple floors and intricate millwork, have been thoughtfully updated over the years with modern living in mind, providing ideal spaces for entertaining or quiet evenings at home. Expansive formal rooms, cozy fireplaces, a chefs kitchen, and five bedrooms, including two with en suite bathrooms, create a comfortable and functional layout. Designed for seamless indoor/outdoor living, the all-encompassing grounds feature a pool, outdoor kitchen, drought-friendly synthetic grass, and gorgeous views. Additional highlights include air conditioning, a 2-car garage with an attached workroom, and a prime location near the Atherton border. Youll enjoy convenient access to downtown Menlo Park, Menlo Country Club, the iconic Woodside Pub, Bucks, and top schools (buyer to verify eligibility).

2290 Stockbridge AVE, Woodside

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

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

258 Kings Mountain RD, Woodside

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

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

252 Raymundo DR, Woodside

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

Sold listing courtesy of Michael Warren from APR
$5,755,000
4 Beds ⋅ 4 Baths ⋅ ML81998202 MLS
Stunning 4 Bedroom, 4 Bathroom Home with Sparkling Pool and Tennis Court. Formal Entry. Living Room with Fireplace, Built-ins, and High Ceilings. Formal Dining Room. Chefs Eat-in Kitchen with Walk-in Pantry, Stainless Steel Appliances, and Breakfast Bar. Opens to Family Room with Vaulted Ceilings and Fireplace. Bonus Family/Media Room Features Wine Room, Wet Bar, Projector, Drop Down Screen and Full Bathroom with Steam Shower. Main Level Bedroom, Full Bathroom, and Laundry Room. 4 Spacious Bedrooms. 4 Bathrooms. Primary Suite Retreat Features Walk-in Closet, Radiant Heat, Jacuzzi Tub, Stall Shower, and Private Sun Room. Lovely Landscaped Acre Plus Lot. Sparkling Pool, Hot Tub, Waterfall, and Built-in BBQ. Tennis Court with Storage

110 Northridge LN, Woodside

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

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

160 Alta Mesa RD, Woodside

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

Sold listing courtesy of Afsoon Shahrdar from TODAY
$6,710,000
5 Beds ⋅ 5 Baths ⋅ ML81989774 MLS ⋅ Buck Estate Home Owners Assoc BLDG.
This charming home is tucked away on a private cul-de-sac,within the prestigious gated community of Buck Estates. Built in 2001, this home exudes the artistic allure of Carmel, w/unique architectural details throughout. Boasting a spacious office (or additional bedroom) and 1 bd/1 ba guest house w/granite kitchen and large entertaining area. Newly refinished mahogany floors in the main living areas of the main house with multiple French doors to professionally landscaped yard. Open-concept kitchen connects the family room w/gas fireplace and soaring wood-beamed cathedral ceilings. The kitchen offers 2 Bosch dishwashers, built-in Miele coffee system, wine refrigerator, and breakfast bar. Luxurious primary suite on main level has cozy seating area w/fireplace, French doors to private terrace, spa-like bath w/heated floors, dual shower heads, and soaking tub. Both the main house and guest house have 2-car garages, 4 total spaces. Expansive yard w/multiple terraces, Jacuzzi, saltwater pool, and beautiful lanai w/custom bluestone patio among a vibrant mix of fruit trees and florals. Infrared heaters, stone fireplace w/seating hearth, and ceiling fan, make it the perfect space for year-round enjoyment. Great access to commuter routes, Menlo Country Club, Stanford, Menlo Park, and more.

50 Buck CT, Woodside

Listed by Bogard-Tanigami Team, 650-924-8365 from The Agency
(If provided) CoList: from

Sold listing courtesy of Michelle Englert from COMP
$5,999,000
4 Beds ⋅ 4 Baths ⋅ ML81986876 MLS
On the corner of "Wall Street West" Sand Hill Road ( Venture Capital firms ) 3 level acres Prime Central Woodside with a very nice single level Ranch home and accessory structures. Pinot and Merlot wine vineyards which can be easily removed for a larger yard. Very convenient location near central town and commuting. Excellent Schools. Surrounded by larger estates of much higher value.

675 Manzanita WAY, Woodside

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

Sold listing courtesy of Joe Piazza from CBR
$4,480,000
6 Beds ⋅ 4 Baths ⋅ ML81987106 MLS
This fantastic new price makes it possible to create your own dream property on 2 tranquil acres! Conveniently located in true central Woodside with 2 homes, 2 private driveways and so much room to grow. The main house is 3,090 square feet, has 5 bedrooms, and 3 bathrooms. The large living room has huge windows overlooking the expansive lawn and pool area. The primary bedroom upstairs features a walk-in closet, fireplace, and a balcony with a jacuzzi overlooking your 2-acre property. The cottage can be accessed off of the first driveway and has been thoroughly remodeled. There is a lush green pasture, and pathways leading to the pool and patio area. 2 natural gas generators connected to each house. Experience the tranquility of Woodside, just 2 minutes from the town center and renowned horse trails. This is your chance to embrace a relaxed lifestyle in the heart of Woodside!

8 Oakhill DR, Woodside

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

Sold listing courtesy of Rachel Hardyck from DWELL
$4,887,500
4 Beds ⋅ 3 Baths ⋅ ML81986602 MLS
Woodside Gem! This expansive one+ acre property is a versatile estate offering endless potential to renovate, re-imagine entirely, or simply move in and enjoy. The property includes a light-filled ranch home with vintage details intact, blending classic appeal with modern upgrades, including fresh interior and exterior paint throughout. The main residence offers 4 spacious bedrooms and 3 and half bathrooms, formal dining, separate living room and kitchen / family combo providing ample space for family and guests. Additionally, a 1-bedroom, 1-bath ADU, complete with a full kitchen, is ideal for guest stays or rental opportunities. The vast grounds feature multiple outdoor zones, including a separately fenced pool and plenty of open space to accommodate equestrian use or future enhancements. Located within the acclaimed Woodside Elementary School district, this rare property captures the essence of rural tranquility with suburban convenience. Just minutes from the town center and school.

155 Ravine DR, Woodside

Listed by Christienne Hadley, 650-533-3766 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Bharath "Kumar" Talluri from NTERO
$5,573,000
4 Beds ⋅ 6 Baths ⋅ ML81984912 MLS
Embrace the sweeping views of the Western Hills from this stunning two-story home, perfectly situated on a 1.28-acre lot. The heart of the home is the gourmet chef's kitchen featuring a large center island, double dishwashers, wine fridge, 6 burner gas stove, bar seating, sub-zero fridge & tons of storage. The kitchen seamlessly opens to a spacious family room w/ window seating, a fireplace, soaring vaulted ceilings & access to the backyard. In addition, the main floor boasts 2 ensuite bedrooms, a formal dining room, a beautiful bright living room, cozy den with gorgeous built-ins, & a dedicated full bathroom w/ access to the yard. The rich hardwood floors, wonderful natural light, lots of windows & fabulous indoor/outdoor flow allows this home to cater to many lifestyles. Upstairs, the primary bedroom suite is a true retreat offering a fireplace, sitting area, spa like bathroom and walk-in closet. An additional ensuite bedroom & open office/play area complete the upper level. The expansive & private backyard is ideal for everyday relaxation and entertaining with a large flat area, garden beds, a sparkling pool & a patio featuring an outdoor kitchen. Located within in the excellent Woodside School district, this home offers both luxury and comfort in a serene convenient location.

662 W Glen WAY, Woodside

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

Sold listing courtesy of Kimm Terpening from COMPS
$10,495,000
4 Beds ⋅ 4 Baths ⋅ ML81981937 MLS
Just-completed one-level vineyard estate with San Francisco Bay views. Built with natural stone walls inside and out and vaulted all-wood ceilings in every room. Nearly every room has French limestone floors, cabinetry is waterfall-wrapped in natural quartzite, and handcrafted iron doors are inspired by Tiffanys in New York. Unique see-through wine cellar upon entry, formal dining room opens to a waterfall wall, and stunning great room for entertaining. The primary suite has a couture closet room and spa-inspired bath. There are 4 bedrooms and 3.5 baths in the main home plus 2 bedrooms and 1 bath in the updated original guest house with full kitchen. Outdoor living spaces are spectacular with a zero-edge pool and spa, kitchen/dining lounge with pizza oven, vast eco-friendly lawn, fire pit terrace, and bocce court in the vineyard. Exceptional dog run and custom tortoise enclosure for the animal lover. Square Footage Breakdown: Main Residence: 4,887 | Garage: 782 | Guest House: 1,184 | Total: 6,853. Buyer to verify.

2195 Greenways DR, Woodside

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

Sold listing courtesy of Joe Kwan from JODI
$4,600,000
4 Beds ⋅ 4 Baths ⋅ ML81981262 MLS
Opportunity abounds on over one acre just a mile from town center and with access to acclaimed Woodside Elementary School. Move in and enjoy, renovate, or build new. The sprawling mid-century ranch home is bright and light and has been freshly updated with all new paint while preserving its vintage charm in the kitchen and bathrooms. There are 4 bedrooms and 3 baths plus a 1-bedroom, 1-bath ADU with full kitchen for guest accommodations, rental potential, or a comfortable space while designing a future estate. Vast level grounds, separately fenced pool, and equestrian zoning.

155 Ravine DR, Woodside

Listed by Judy Byrnes, 650-208-2388 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Christienne Hadley from CBR
$4,250,000
4 Beds ⋅ 3 Baths ⋅ ML81980525 MLS ⋅ Woodside Hills BLDG.
Discover a Rare Gem in the Heart of Silicon Valley! This expansive 1-Acre Property with Breathtaking Bay Views offers a blend of potential and elegance, perfect for those ready to make it their own. 1-Acre Level, all-usable land provides endless possibilities for expansion, gardening, or creating your dream outdoor space. High Vaulted ceilings allow one to enjoy the grandeur of open, airy spaces in the family and living rooms, designed to enhance light and create a welcoming ambiance. Fabulous bay views of the bay from your own home is a daily reminder of the beauty and tranquility surrounding you. Dive into relaxation with a lovely, well-kept pool, perfect for enjoying sunny days or hosting outdoor gatherings. Seize the opportunity to customize and update the bathrooms and kitchen to your dream. Spacious and Functional 4 Bedrooms provide ample space for family, guests, or a home office. Enjoy a well-thought-out floor plan that balances comfort and practicality. Located in the heart of Silicon Valley, you're just minutes away from top tech companies, renowned schools, and vibrant local amenities. This property is a rare find and a fantastic canvas for your vision. Imagine the possibilities!

235 Crest RD, Woodside

Listed by Brenda Kim, 650-242-2220 from BEK Realty
(If provided) CoList: from

Sold listing courtesy of Joe N. Pollifrone from SGP
$4,270,000
4 Beds ⋅ 3 Baths ⋅ ML81980870 MLS
Located on one of Woodside Hills most sought after streets is this immaculate and well maintained single level home custom built for the original owners in 1969...in perfect harmony with its natural environment. Affording incredible privacy and spectacular, Top of the Hill, Panoramic Bay Views, this residence boasts an all usable .97 acre lot with sweeping lawns, an expansive terrace and resort style outdoor living...perfect for grand entertaining! Enjoy the home now or remodel/expand this property in this exceptional location! 4 Bedrooms including the Primary suite. Gracious Formal Living Room and Dining Room all facing the incredible Bay Views. Updated Kitchen with gas stove top, large pantry and breakfast area. Inviting Family Room adjacent to the Kitchen with built-in shelving, storage cabinetry and sliding door access to the rear terrace. Separate wood paneled Den with bookshelves. Perfectly positioned Sparkling Pool. Mature orchard with Apple, Lemon, Plum, Apricot and Orange trees. Newer Front Landscaping with circular driveway and plenty of guest parking. Morning and Afternoon sun all day...lots of natural light inside the home! Attached, two car garage with storage cabinetry. A prime Woodside Hills address with close proximity to Woodside Plaza & Stanford Shopping Center

180 CREST RD, Woodside

Listed by Anthony Galli, 650-219-0495 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of John Nguyen from CJP
$14,250,000
3 Beds ⋅ 4 Baths ⋅ ML81977591 MLS
Sophistication Meets Serenity. Nestled at the end of a cul-de-sac off the coveted Mountain-Home Road, this exceptional estate sits atop the ridgeline, offering breathtaking, ever-changing vistas of the lush mountainsa view unmatched in all of Woodside. Secluded amidst the natural rolling landscape of majestic Sequoias and Oaks, this property is one of the few that boasts its own vineyard, producing exclusive Chardonnay for the renowned La Honda Winery. Spanning 3.3 acres, this timeless Spanish-villa-style residence embodies the elegance of Woodside living. The home features three spacious bedrooms, with an additional study that can serve as a fourth bedroom option, 3.5 beautifully remodeled bathrooms, and a gourmet chefs kitchen with a large center island. Each bedroom suite provides private access to a serene outdoor area, leading to a large pool with a jacuzzi and a detached 3-car garage. The meticulously landscaped grounds enhance the estates allure, including a pathway to a newly renovated office or guest house complete with a full bathroom, kitchenette, and a viewing deck. This property is an embodiment of refined living while strategically placing you in the heart of Silicon Valleys thriving business ecosystem, with easy access to Highway 280, Stanford University, and SFO.

12 Vineyard Hill RD, Woodside

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

Sold listing courtesy of Hugh Cornish from CBR
$13,300,000
5 Beds ⋅ 8 Baths ⋅ ML81978456 MLS
Contemporary Woodside. Designed by William A. Churchill and inspired by Frank Lloyd Wright - an extraordinary architectural masterpiece. One of the most sophisticated living and entertainment homes in Silicon Valley! Private, located on 3.38 gated acres, expansive entry is surrounded by a professionally managed vineyard of over an acre of Pinot Noir, Cabernet Sauvignon and Vermentino grape varietals. Open floor plan, 35-foot ceilings. The approximate 8,660 sq ft home has 5 bedrooms/ 6 full/2 half baths. Primary suite - stunning retreat w/fireplace, secluded outdoor terrace and dramatic ceiling.All bedrooms have unique features - ceilings of glass, views of the gardens and large adjoining bathrooms. Living room has views of the magnificent grounds and Santa Cruz Mountains. Five seat wet bar and game area. Library/office includes hand crafted bookcases and fireplace. Formal dining room. Openkitchen has granite counters and top of the line appliances.Family room.Outdoor entertainment area w/big western hill views, cascading pool and spa, verandas, barbecue and dining areas. Garden vegetable planters.Private spa/massage room, wet and dry saunas, gym room, and a private entry office w/kitchen and bath.Temperature-controlled wine cellar for 1,000 bottles, 4 car garage w/EV charger.

6 Quail Meadow DR, 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
$4,950,000
4 Beds ⋅ 4 Baths ⋅ ML81973865 MLS
Central Woodside Oasis with Resort-Like Amenities. Located in Central Woodside within the esteemed Tripp Road neighborhood, this cherished property presents indoor/outdoor living in a glorious setting on more than one acre. Owned by the same family for 63 years, the home has been beautifully updated over the years with an organic designer style that includes oak and hickory floors, knotty alder cabinetry, and towering paneled wood ceilings. Almost every room opens to the grounds where a resort-inspired setting amid 200-year-old redwood trees unfolds with a sun-swept pool, secluded barn, putting green, and sport court. The home spans one level, with just a few steps between some rooms, and is filled with natural light from walls of glass and numerous skylights. A spacious formal living room & formal dining room are complemented by a fabulous chefs kitchen & open family room, where a secret door leads to the oversized primary suite with ample space for a nursery, office, and/or fitness center. In a separate wing of the home, there are two additional en suite bedrooms plus a fourth bedroom customized for an office. All around is the beauty of the setting in secluded privacy, yet close to town center and Woodside School, plus proximity to renowned scenic hiking and biking trails.

430 Summit Springs RD, Woodside

Listed by Erika Demma, 650-740-2970 from Compass
(If provided) CoList: Hugh Cornish from Coldwell Banker Realty

Sold listing courtesy of Kimm Terpening from COMPS

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