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$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

$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

$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

$4,250,000
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

$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

$1,500,000
4 Beds 3 Baths ML81977467 MLS
PRICE DROP! Discover this charming home built with love and designed to stand out. This unique 'round house' offers soaring open-beam wood ceilings and panoramic views of the stunning nature that envelops it. Built in 1978 and ready for you to renovate, or take advantage of the 1.6-acre lot and build your dream home. (Permits would be SMC, not City of Woodside.) Key features... Spacious Living: 2400 sq ft of living space with 4 bedrooms downstairs and 1 den/study/bedroom on the main level, providing ample room for family & guests. Outdoor Oasis: Wrap-around decks allow you to fully embrace the beauty of the surrounding landscape. This property also backs up to open space & Wunderlich Park, perfect for hiking enthusiasts. Expansive Lot: 1.6 acres adorned with a variety of beautiful trees, providing a harmonious balance of sun and shade. Prime Location: Located on a developed street with beautiful homes, you're just 5 minutes from the iconic Alice's Restaurant, local wineries & other attractions. Don't miss the opportunity to own this one-of-a-kind home in a desirable community! Take advantage of the price reduction and make this unique property yours today! (Note: Some images are digitally enhanced, with virtual staging to show furniture configurations. 3 bedrooms on record.)

76 Morse LN, Woodside

Listed by Stephanie Sills, 650-678-5707 from Compass
(If provided) CoList: Mark Palermo from Compass

Sold listing courtesy of Bryan Duong from RDFIN

$3,150,000
4 Beds 4 Baths ML81978201 MLS
Chic & Luxurious Retreat with Ocean Views. offering an unparalleled living experience, high-end luxury throughout, just 20 minutes to Woodside Village. Set on more than 8.2 acres with vast level areas, the entire home was extensively remodeled just 12 years ago and features a grand entrance via a long cobblestone-lined driveway. The open and flowing interiors showcase oak hardwood floors and a blend of modern / rustic design elements, including vaulted wood-paneled ceilings, paneled walls in some rooms, and contemporary designer light fixtures. Every room overlooks the ocean, accessing decks on each level lined in clear glass for unobstructed views. The home includes 4 spacious bedrooms, with the primary suite on the upper level and a second primary suite plus two additional bedrooms on the lower level revolving around a central lounge. Outside offers expansive decks, an ocean-view spa plus a regulation sand volleyball court for added relaxation and recreation. Nearby are miles of hiking and biking trails at Open Space Preserves plus acclaimed restaurants, such as Alices and Mountain House with a Michelin-star chef, along with a convenience market, deli, and gas station, all enhancing the lifestyle at this luxurious coastal-view retreat.

240 Allen RD, Woodside

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

Sold listing courtesy of Ian Batra from TRJRE

$2,500,000
4 Beds 3 Baths ML81975433 MLS
This spacious ranch home offers exceptional living on a beautiful lot with a gentle slope and a serene koi pond with a waterfall. The two-car garage, located at the back, has potential for conversion into an ADU. The home features four bedrooms, with one closet converted into an office and another into a hobby room. Nearly every room has outdoor access, enhancing indoor-outdoor living. The master bedroom includes a skylight and private garden access, with a master bath featuring double sinks, a jetted tub, a garden view, and a steam shower. Two additional bathrooms have convenient stall showers. Hardwood floors add elegance, while new carpeting in the living and dining rooms adds coziness. The large kitchen and family area, with two full-size refrigerators and a wine refrigerator, offers ample space for cooking and entertaining, with easy access to the side patio, front, and garage. Situated on a quiet cul-de-sac, just half a mile north of the 84 & Skyline intersection, this home combines comfort and nature, providing a peaceful and private environment. This is in a micro climate called the Banana Belt. (good weather)

25 Morse LN, Woodside

Listed by Nancy Palmer, 650-492-0200 from The Agency
(If provided) CoList: from

Sold listing courtesy of Rita Tang from YT62N

$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

$5,000,000
4 Beds 4 Baths ML81973117 MLS
This home has it all with close-in Woodside Glens convenience, entirely rebuilt luxury, and a glorious setting with over one-third acre of level grounds and Western hill views. Authentic Craftsman style is exemplified by peaked rooflines and a series of classic tapered columns that wrap around the inviting covered porch. Designed for seamless indoor/outdoor living, the setting is remarkable, featuring fully usable grounds for leisure, sports, and wellness in complete privacy. Rebuilt from the ground up in 2011, this two-story home exudes classic elegance with hardwood and travertine floors, refined millwork, and an expansive great room alongside a formal living room. Personal accommodations include 4 bedrooms, an office, plus 3.5 baths. On the main level, two bedrooms share a bath, while the primary and secondary suites are located upstairs. Bathrooms are beautifully appointed, each with fixed rain and hand-held sprays, and the primary suite includes the added luxury of heated floors. Additional highlights encompass owned solar panels, a rare attached 3-car garage, and potential for a pool and Accessory Dwelling Unit. The home's proximity to the town center and acclaimed Woodside School completes the picture.

115 Highland TER, Woodside

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

Sold listing courtesy of Deborah Kehrberg from APR

$2,000,000
4 Beds 2 Baths ML81972926 MLS
THIS IS YOUR CHANCE TO REMODEL TO YOUR SPECIFICATIONS OR REBUILD THE HOME OF YOUR DREAMS! SITUATED ON A FLAT, 13,144 SQ. FT. LOT, AND NESTLED ON A CUL-DE-SAC STREET, OPPORTUNITIES LIKE THIS DO NOT COME AROUND OFTEN! THE MAIN HOUSE FEATURES 4 BEDROOMS AND 2 BATHROOMS, AN ABUNDANCE OF STORAGE & CLOSET SPACE, AND AN OPEN-CONCEPT LIVING ROOM/DINING ROOM/KITCHEN FLOOR PLAN. WITH VAULTED CEILINGS AND LOTS OF NATURAL LIGHT THROUGHOUT, THIS HOME FEELS LARGER THAN IT IS. EXTERIOR HIGHLIGHTS INCLUDE DUAL DRIVEWAYS, TWO SEPARATE STORAGE/WORKSHOPS AT THE REAR OF THE PROPERTY, AND MATURE TREES FOR PRIVACY AND SHADE. WOODSIDE IS KNOWN FOR ITS TRANQUIL LIFESTYLE, AWARD-WINNING SCHOOLS, AND EASY ACCESS TO 280, DO NOT LET THIS CHANCE TO FINALLY LIVE CLOSE TO EVERYTHING BUT FAR FROM IT ALL PASS YOU BY!

5 PALM CIRCLE RD, Woodside

Listed by Maxine & Michelle Dumas, 650-591-8000 from Dumas & Company
(If provided) CoList: from

Sold listing courtesy of RECIP from RCIP

$3,478,000
4 Beds 3 Baths ML81969487 MLS
Located in the highly desirable Woodside Heights on a vast 41,000 sq ft lot! Featuring an open concept floor plan, soaring ceilings and an abundance of natural light this 4 bedroom, 3 bathroom, 2,990 sq ft villa sets the stage for gracious living and entertaining! Formal living room, fireplace and custom cabinets with access to the beautiful stone terrace. The large kitchen with dining bar opens to an inviting family room and adjacent spacious dining room. Paces away you have a separate laundry room, perfectly placed space for a home gym and beautiful wine cellar. Rounding out this level is a wonderful library/office and full bathroom. Just upstairs you have a private and spacious primary suite retreat with walk-in closet and spa-like bath! Down the hall, three additional bedrooms share a full hall bathroom. Relax or entertain outside in the elaborate yard with lush mature, landscaping boasting sweeping views and several seating areas. Located just minutes to Town Center, great schools and streamlined commute routes!

880 High RD, Woodside

Listed by John Shroyer, 650-787-2121 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

Sold listing courtesy of Cynthia Kodweis from APR

$13,000,000
4 Beds 5 Baths ML81967051 MLS
Situated in the heart of premier central Woodside, this magnificent estate combines the elegance of a classic country manor with boundless possibilities to live the lifestyle of your dreams. This is a rare opportunity to obtain a spacious & versatile home on a large, 3-acre plot of prime, level land just one-half mile from Woodside Town Center. The property is replete with resort-style amenities catering to a variety of alluring lifestyles, including outdoor living, entertaining, fitness, equestrian pursuits, gardening, & farm-to-table dining. Estate features a spacious main residence with classic Tudor architecture. Other rooms provide flexible space for additional offices, fitness rooms, & recreation. Tucked away on the lower level is an extraordinary 3,000-bottle wine cellar designed in European fashion with a dining & tasting area to uniquely entertain guests. Extensive grounds also include a magnificent, recently built barn with 4 stalls for horses, 2 work rooms, restroom, & extra space to store a horse trailer, extensive patio with bbq area, pergola, social fire pit surrounding a newly refinished pool & spa. An ideal retreat for the quintessential Woodside lifestyle, this exceptional property's offering of luxury, amenities, size, & location won't soon be seen again.

1210 Canada RD, Woodside

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

Sold listing courtesy of Michael Warren from COMPS

$5,800,000
4 Beds 6 Baths ML81966880 MLS
An exquisite modern farmhouse in Woodside, where luxury, comfort & functionality blend seamlessly amongst the verdant setting. Bordering Open Space & spanning over 3,800 sq ft & 1.5 acres, this stunning estate offers an unparalleled retreat with breathtaking views & top-notch amenities. Every bedroom is a private sanctuary with ensuite bathroom. The primary suite is a true oasis featuring a fireplace, custom walk-in closet & a spa-like bathroom with a BainUltra freestanding tub & walk-in shower. The gourmet kitchen is equipped with a Viking Tuscany range, marble countertops & chef favorites such as a built-in espresso machine, pot filler, microwave drawer, wine fridge & pantry. A statement temperature-controlled wine room, conveniently located off the kitchen, is perfect for wine enthusiasts. Elegant elements throughout include floor-to-ceiling windows throughout, trim & wall detailing, electric linen blinds, built-in Sonos system & designer fixtures. The 6+ car garage with a workshop & soaring ceilings is a dream come true for car aficionados. Outdoor serenity is epitomized by the center courtyard adorned with a koi pond & cascading waterfall. The surrounding low-maintenance landscaping & garden beds further enhance the natural beauty. Woodside Elementary.

595 Summit Springs RD, Woodside

Listed by Bob Johnston, 650-400-5039 from Coldwell Banker Realty
(If provided) CoList: Francesca Lampert from Coldwell Banker Realty

Sold listing courtesy of Marc Roos from SGP

$6,900,000
4 Beds 5 Baths ML81965664 MLS
Enjoy sweeping Western Hill VIEWS from this gorgeous turnkey Cape Cod style home in the Woodside Elementary School district ! Resort like living awaits with a sparkling infinity POOL & spa, picturesque pinot noir VINEYARD & bucolic horse pasture. Entertain in the gorgeous POOL CABANA w/ kitchenette, full bathroom & sauna, surrounded by a beautiful huge brick patio. The home features elegant & spacious separate Living and Dining rooms, gourmet Kitchen with vaulted ceiling adjacent to cozy Fam Rm --all with outstanding VIEWS! Large separate office. Luxurious, MAIN level primary suite with gorgeous white marble bathroom, huge walk-in closet and more views! Rich hardwood, French doors, Carrera marble, custom cabinetry throughout. 5 CAR GARAGE--2 car attached +3 car NEW detached garage. HUGE deck off all main rooms overlooks the Western Hills. This is an exceptional home and property !

1075 Godetia DR, Woodside

Listed by Liz Daschbach, 650-207-0781 from Compass
(If provided) CoList: from

Sold listing courtesy of Lynn Wilson Roberts from APR

$3,998,000
4 Beds 4 Baths ML81963414 MLS
This reimagined Woodside residence effortlessly blends organic living with modern luxury, all while enjoying marvelous western hill views on an expansive nearly 17,000 sq ft lot. The striking steel & glass entry welcomes you into a luminous, architecturally elegant space. The open-concept living area features a telescoping door that seamlessly connects the indoors with the spacious Batu wood deck overlooking the expansive backyard, creating an atmosphere for relaxation & entertaining. The chefs kitchen boasts matte porcelain countertops & backsplash, modern mixed oak & charcoal cabinets, along with convenient amenities such as a pot filler, large center island & two dishwashers, perfect for hosting gatherings with ease. Unwind in the primary suite, complete with a spacious walk-in closet, a spa-like bathroom featuring a custom oak vanity & glass slider leading to the deck- a true oasis. Additional amenities include a dedicated laundry room & pantry, updated systems including AC + an EV charger & an attached carport for convenient parking. A semi-attached ADU offers flexibility with a kitchenette, full bathroom & W/D hookups. This meticulously remodeled home offers the perfect combination of sophistication, comfort & functionality. Top rated Woodside Elementary mere moments away.

810 W California WAY, Woodside

Listed by Bob Johnston, 650-400-5039 from Coldwell Banker Realty
(If provided) CoList: Christienne Hadley from Coldwell Banker Realty

Sold listing courtesy of Mary Sanbrook from SIGNP

$2,755,000
4 Beds 2 Baths ML81962145 MLS
Majestic home set on 1.96 acre lot boasting with mature redwood trees, beautiful lush grounds with stunning views! Quaint entry porch & front door invites you into the spacious living room with cozy brick fireplace. Separate dining area, chefs kitchen with gas range and breakfast bar. Updated baths, recessed lighting, gorgeous hardwood flooring, dual-paned windows, 2 side storage sheds, large walkin basement accsessible from back yard under deck. Perfectly located in Central Woodside; this home is minutes to town center for convenient shopping, dining and the acclaimed Woodside School. Easy access to hiking trails, biking and horse back riding. Expansive deck to entertain guest while enjoying breathtaking views.

555 Summit Springs RD, Woodside

Listed by Diane Martin, 650-400-3555 from Keller Williams Palo Alto
(If provided) CoList: John W. King from Keller Williams Palo Alto

Sold listing courtesy of Denise Crosetti Schaul from DCBR

$7,800,000
4 Beds 5 Baths ML81958693 MLS
Location, location! This lush jewel estate is located along central Woodside's most exclusive Mountain Home Road corridor. A rarely available opportunity to own a 1.25 flat acre property in the heart of the town's most prestigious neighborhood, discover an effortless blend of fine craftsmanship with luxurious elements and a touch of Hollywood style: 4(+1) brs, 4.5 ba plus an array of multi-functional spaces: a main-level suite easily converts to lounge/5th bedroom, the primary suite is enhanced by a private library/office/ walk-in closet, nursery or 2nd bedroom. Venture to the wine cellar with its own tasting room through a potential home theatre. An entertainer's dream for elegant al fresco afternoons by the pool and easy indoor/outdoor living, and the expansive grassed yard is framed for utmost privacy by pristine mature landscaping, a romantic rose garden, olive and fruit orchards. A short walk to town and the Woodside Elementary School, this garden estate balances peaceful seclusion with close proximity to all commuter routes and less than 20 minute drive to SFO Airport.

290 Winding WAY, Woodside

Listed by Linda Hymes, 415-377-6061 from Intero Real Estate Services
(If provided) CoList: from

Sold listing courtesy of Josh Rubin from COMPS

$2,915,000
4 Beds 3 Baths ML81960256 MLS
Expanded by home owner to 2,479sq feet. This beautiful mission style, four bedroom smart home was built for both luxurious entertainment and family fun. From the imported knotty alder doors to the 50 speaker home entertainment system, attention has been given to each detail. A residence door separates the front house from the bedrooms for privacy. Enter through the double door to an open kitchen and dining which area leads into a sitting room and large office. The full guest bath features an exquisite Orinoco granite slab shower while the living room centers around the gorgeous wood burning fireplace. Behind the residence door are three bedrooms, two baths, a nursery/multi-use room and a dog run. The master bath boasts exotic Tanzanian Onyx stone slabs and an oversized Moen spa shower. The kids' bath has Alaskan white granite and an extra long jet tub. Nestled up against the Santa Cruz mountains just above Silicon Valley, with easy access to San Francisco, San Jose and Palo Alto, Woodside boasts California's top elementary school with 11 students per teacher.

4 Palm Circle RD, Woodside

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

Sold listing courtesy of Lihong Zhong from GNVR

$5,200,000
4 Beds 6 Baths ML81960173 MLS
Welcome to Woodside Whisper, a fully gated property stands as an epitome of refined luxury & tranquil living.This distinguished single-family home spans across 4050 square feet of meticulously crafted living space on a 1 acre parcel. Boasting 4 spacious beds & 4.5 baths, this residence offers ample room for both relaxation & entertainment. Upon entering, guests are greeted by an inviting formal entrance characterized by abundant natural light & tasteful finishes. The gourmet kitchen, equipped w/high-end appliances & custom cabinetry, serves as the heart of the home, inspiring culinary creativity & gatherings. The primary suite exudes sophistication & serenity, featuring a luxurious en-suite bath w/huge walk-in closet. Additional bedrooms offer comfort & privacy, each thoughtfully appointed to ensure restful nights & rejuvenating mornings. Get your game on at the on-site sports court, perfect for basketball, pickleball, or tennis. Post-match, plunge into the saltwater pool or jacuzzi, or detox in the outdoor sauna it's wellness on your doorstep. The outdoor space is a dreamy landscape for enjoying the Californian sunshine. Chill on the vast patios, gather around the fire pit under the stars, or wander through the lush gardens it's all about serene outdoor living.

165 Woodside DR, Woodside

Listed by Alan Canas, 415-298-8940 from Engel & Voelkers San Francisco
(If provided) CoList: from

Sold listing courtesy of Syed Baqar from MXR

$5,500,000
4 Beds 5 Baths ML81959261 MLS
3 acres in a superb close-in location with a wonderful combination of mid-century aesthetics and country amenities. Sleek and expanded main home has tile and hardwood floors, grand main living room, formal dining room, and eat-in kitchen with high-end Wolf and Sub-Zero appliances. 3 bedroom suites on the main level including primary suite with private office, plus lower-level suite with outside entrance and 2-bedroom, 1-bath Accessory Dwelling Unit with full kitchen and private garage. Pool, poolside recreation room, changing room with bath, large barn, solar-powered electricity, and beautiful serene grounds. Less than one mile from acclaimed Woodside School (K-8) and from trailhead access to 974-acre Huddart Park with miles of horse and walking trails.

259 Kings Mountain RD, Woodside

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

Sold listing courtesy of Dana Cappiello from SIR

$2,200,000
4 Beds 2 Baths ML81958417 MLS
Enjoy the relaxing ambiance of this custom home located in the redwoods above Woodside. This beautiful residence and its' surrounding garden is a perfect place for tranquility. Tastefully updated, home rests on .88 acres. Natural illumination from large windows & skylights flood the home in beautiful light. An open concept main level floor plan creates gathering areas that connect seamlessly to the chef-inspired kitchen featuring a suite of stainless appliances including a 48" Thermador range. Harwood floors run throughout the 2 level home & high, open beam ceilings accentuate this outstanding residence. There is an en-suite bedroom on the main floor, 3 additional bedrooms on the 2nd floor along with a stunning bath. A spacious family room, separate mudroom, laundry & surrounding decks are all additional features of this hi end home that is surrounded by a beautiful garden. Charming separate Artist studio, large decks, basement, storage sheds too. Seller is the Agent .DISCLOSURES AT ...https://app.disclosures.io/link/368-Ridge-Road-ulp04l2i

368 Ridge RD, Woodside

Listed by Valerie Trenter, 650-888-6930 from Coldwell Banker Realty
(If provided) CoList: from

Sold listing courtesy of Bonnie Romo from 01TWNO01

$6,600,000
4 Beds 4 Baths ML81957859 MLS
Wonderful sun-filled home on 1+ acre with STUNNING Western Hill VIEWS just blocks from downtown Woodside!! Within the serene embrace of a Cabernet vineyard, this enchanting Santa Barbara style home offers a unique blend of elegance and tranquility. Spanning just over one acre with western hill views, the home is predominantly arranged on one level with a spacious primary suite and office area comprising the upper level. French doors open at every turn to three separate courtyards, including a central one with sparkling pool. Natural wood ceilings in herringbone pattern are a focal point, and Spanish tile floors inside and out exemplify the Santa Barbara style. The natural beauty of the surroundings and the expansive vineyard wrap around the home creating a coveted setting that is classic Woodside. Highly acclaimed Woodside School.

211 La Questa WAY, Woodside

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

Sold listing courtesy of Billy McNair from CBR

$2,775,000
4 Beds 3 Baths ML81956847 MLS
Upgraded Compound on the Skyline Corridor. This incredible property rests above the fog line. Multiple rooms and its broad deck boast glorious sunsets and breathtaking views of the valley, coast and great Pacific. The updated single story home has four bedrooms and 2 ½ bathrooms. Its massive kitchen/great room takes advantage of the view with a bank of tall windows and a long comfortable window seat. Several rooms open to a spacious deck that seamlessly promotes a true indoor/outdoor lifestyle. Work efficiently indoors or out in an office with deck access, two work stations and built-in cabinets. Find your inner child or green thumb within a plethora of creatively planned outdoor spaces (treefort, zip-line, bocce, chess to name a few). Reach miles of Open Space trails within steps of your front door, or soak in the tranquility of your own private acre amongst majestic Redwoods and mature natural landscape. Appreciate its quiet serenity, or easily entertain a large gathering.Situate a guest or family member in the ADU, or enjoy the income stream.Drive a mere ten minutes to reach 280. Walk two minutes to Purisima Creek trails--hike in the morning; mountain bike in the afternoon! Realize your dream at this truly remarkable, one of a kind property in the coveted Skyline community.

13060 Skyline BLVD, Woodside

Listed by Chad Krakow, 650-222-7090 from Krakow Company
(If provided) CoList: from

Sold listing courtesy of Suzanne Bakhtiari from RDFIN

$8,498,000
4 Beds 5 Baths ML81955662 MLS
Through the private driveway at 11 Southgate Drive, something extraordinary awaits. Youre greeted by hand crafted iron gates which open to an expansive front courtyard, meticulously landscaped grounds, and an astounding, Ernest Coxhead designed 5,790-square foot Spanish Colonial home. The classic estate, built in 1929 as the original owners summer retreat, combines timeless design and luxury in a private, California setting with unmatched views of the Woodside hills, the sparkling Bay Area and beyond. Inside, youll find dramatic architecture, spacious living & entertaining areas, and distinct treatments throughout, with four bedrooms and bathrooms for family and guests. Outside, inspired by nearby historic Filoli gardens, youll enjoy the unique trees, plants, and flowers, as well as the resort-like backyard with large pool and entertainment areas. This is an extremely rare opportunity to enjoy the lifestyle of a more refined era all in the heart of world-renowned Silicon Valley. A world away, yet close to everything.

11 Southgate DR, Woodside

Listed by Granoski,Weil Assoc., 650-269-8556 from Compass
(If provided) CoList: from

Sold listing courtesy of Keri Nicholas from PARCA

$16,800,000
4 Beds 6 Baths ML81947147 MLS
New Price! This magnificent contemporary farmhouse is situated on 3+ flat acres with spectacular views of the Western Hills and is within easy walking distance to the Woodside School (preK-8th grade) and Town Center. A testament to timeless architecture, meticulous craftsmanship and designer details, the main home and guest house were newly constructed in 2012 by renowned builder, Pacific Peninsula Group. Nothing short of exceptional, the 4 bedroom main home has high end finishes and white oak floors throughout, a state-of-the-art chefs kitchen and a eye catching two-story great room with rustic wooden beams and a honed limestone two-sided gas-fed fireplace. This estate's flat 3+ acres, which include a detached 1,255 sf elegant one-bedroom guest house, are elegantly fully utilized between the natural front equestrian pasture, the rear pool, spa and large entertaining terrace, the wisteria-framed fire pit, a 6-raised bed vegetable garden, chicken coop, dog run and fenced corrals. Privacy, entertainment options and enviable location, this property has it all!

140 Olive Hill LN, Woodside

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

Sold listing courtesy of Liz Daschbach from COMPS

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