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$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
$4,170,000
4 Beds ⋅ 4 Baths ⋅ ML81997614 MLS
Welcome to 277 Grandview Drive, a contemporary Craftsman style haven in Woodside, CA offering privacy near Silicon Valley. The 4-bed, 4-bath main house with 2 offices spans 4920 sq ft on a 10+ acre lot. A 996 sq ft guest house, with an additional 1 bedroom and 1 bath, adds versatility (currently used as a music studio). The gated entrance reveals a welcoming design which includes an 8.4 kW solar system with battery backup. Inside, discover radiant heating, a chef's kitchen and two living rooms with surround sound. Outside, a fireplace, porch and deck offer relaxation and entertainment spaces, not to mention ultimate privacy. Adjacent to Thornewood Open Space, and built in 2008, this residence seamlessly combines modern amenities with eco-conscious features. Explore the harmonious blend of modern living and natural beauty.

277 Grandview DR, Woodside

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

Sold listing courtesy of Eddie Oberoi 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
$4,635,645
4 Beds ⋅ 5 Baths ⋅ ML81988046 MLS
Stunning turnkey contemporary, minutes from the village & Woodside Elementary. Gorgeous custom home was re-built & expanded in 2015 & upgraded/enlarged again in 2022, with a brand new attached ADU, sparing no detail nor expense. 4 CAR GARAGE plus additional parking! Vaulted ceilings, oversized windows & doors, views and patio/yard access throughout--- this home epitomizes California indoor/outdoor living in a beautiful, natural treed setting. Features include: Dramatic vaulted ceiling Living Room/ Dining Room combo w/ Fireplace* Chef's Kitchen with island* Huge Family Room with wall of built-ins and garden access* ADU Guest Suite w/living area, kitchenette, FP & Murphy Bed *Separate Laundry Room* 2 - 1/2 baths* 4 Car Garage--2 car Attached Garage PLUS 2 car Detached Garage w/ separate driveway* SOLAR with 2 TESLA Powerwall Back-up Batteries*. Outside: Large flat Patios & Yard off both Living & Family Rooms* Incredible Outdoor Kitchen with built-in BBQ, 2 burner Gas Stove, Refrigerator, Sink, long slab Stone Buffet* Hot tub. *Outstanding Woodside Elementary School !

900 Midglen WAY, Woodside

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

Sold listing courtesy of The Sharp Group from KWPEN
$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
$4,410,000
4 Beds ⋅ 3 Baths ⋅ ML81989450 MLS
Beautiful 4 Bedroom 3 Bathroom Home with Attached 3-Car Garage. Formal Entry. Chef's Kitchen with Center Island, Wine Refrigerator, and Stainless Steel Appliances Opens to Dining Area with Skylights and Vaulted Ceilings. Spacious Family Room with Skylights, Vaulted Ceilings, and Fireplace. Primary Suite Retreat Features Double Sinks, Stall Shower, and Walk-in Closet. 4 Bedrooms. 3 Bathrooms. Inside Laundry Room with Storage and Sink. Separate Office. Interior Features Include High Ceilings, Ample Light, and Stunning Design Finishes Throughout. Lovely Landscaped Yard with Sauna and Patio.

185 Harcross RD, Woodside

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

Sold listing courtesy of Julie Hadidi from COMPS
$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
$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
$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
$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
$6,820,000
5 Beds ⋅ 6 Baths ⋅ ML81983105 MLS
Serenity Hill Haven, a once-in-a-lifetime opportunity to own a stunning estate in the coveted Woodside Hills. A 6,200 sq.ft., 5-bedroom, 5.5-bathroom estate, perched on 2.180 acres & engulfs breathtaking Panoramic Bay Views. A sophisticated LR, highlighted by a fireplace & large windows that invite natural light, large walkout w/water feature & spectacular views. Separate DR & chef's eat-in kitchen, complete w/a center island & high-end Thermador appliances. The kitchen opens into a spacious FR w/another fireplace. The main level of Serenity Hill Haven boasts a luxurious Jr. suite, a convenient PR, & a separate office. The primary suite retreat features its own fireplace, walk-in closet, & a spa-like bath w/oversized tub & a separate shower. In addition there are 3 more spacious jr. suites & 5.5 bathrooms, ensuring ample space & privacy for all. The estate also includes a family/recreation room, a sauna, laundry room & lots of closet/storage space. The beautifully landscaped over 2-acre grounds include walking paths, a rear great lawn, & a large natural pond. The property features a wrap-around driveway leading to a 3-car garage w/cabinetry. Experience luxury living with stunning views & unparalleled amenities in this magnificent Woodside Hills estate.

7 Oak Haven WAY, Woodside

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

Sold listing courtesy of Susanne Bohl from RDFIN
$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
$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
$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
$4,550,000
5 Beds ⋅ 4 Baths ⋅ ML81975816 MLS
An exceptional estate and opportunity nestled at the end of a serene private cul-de-sac in central Woodside. This expansive 3-acre property boasts its own vineyard and bay views. The 3,590 square foot home features 5 bedrooms and 4 bathrooms, providing ample space for family and guests with amenities like an additional kitchenette upstairs and dedicated laundry room. The kitchen is equipped with high-end stainless steel appliances, perfect for gourmet cooking, and the formal dining room, complete with built-in cabinets, adds an elegant touch for entertaining. Each level of the home includes a primary suite, offering flexibility and comfort for multi-generational living. With the potential to split into two parcels under SB9, you can remodel, build new, or develop additional properties-the possibilities are endless! Enjoy the convenience of walking to local favorites such as Robert's Market, Buck's, the bakery, and Woodside Elementary. The welcoming circular driveway leads to a 3-car garage. Located in the highly-rated Woodside Elementary School district, this unique property offers a rare combination of luxury, convenience, and potential for future development.

50 Haciendas DR, 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 Leika Kejriwal from APR
$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
$1,935,000
5 Beds ⋅ 4 Baths ⋅ ML81949920 MLS
Welcome to tranquil home with an ocean view among the lush Redwood Forest off Skyline Blvd. in Woodside! Located about 15 minutes from HWY92, less than a minute from Kings Mt Road, you'll enjoy winding down on the multi-level deck on a warm afternoon or next to a cozy fire on a cold brisk night. Oak hardwood flooring throughout the main home with vaulted ceilings adding lots of natural light. The kitchen is equipped for a chef with a Wolf gas range, new quartz countertops, stainless steel sink, and goose neck faucet. The main house has 3 Bedrooms and 2.5 Baths encompassing 2,260sf of the 3,180 total including the dining room, 2 office spaces, a laundry room, and walk-in closet. The secondary unit is situated on the bottom floor with its own private deck, separate laundry, and walk-in closet in the primary bedroom. At 920sf there is plenty of space in the ADU; 2 Bedrooms and 1 Bathroom. New quarts counter tops and appliances, stainless steel sink and faucet. Motivated Seller

14732 Skyline BLVD, Woodside

Listed by Angela Burnett, 650-743-4950 from KW Advisors
(If provided) CoList: from

Sold listing courtesy of Allen Nazari from PKLNC
$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
$5,875,000
5 Beds ⋅ 3 Baths ⋅ ML81966535 MLS
Contemporary luxury with breathtaking San Francisco Bay views in Central Woodside. Extensively renovated open concept design on two levels, including modern kitchen, white oak floors, new metal roof, and designer baths. Tesla solar power, 5 battery backups, EV charging, and synthetic lawn. Every room opens to a deck for Bay or western hill views or just the natural beauty of the surrounding grounds. Elevated and private pool plus meditation/yoga area with sweeping views. Separately fenced farm with large barn and space for animals or garden. Direct access to hiking and equestrian trails at Wunderlich County Park. Excellent Woodside Elementary School (K-8). Recent upgrades over 500K of improvements including new standing seam metal roof, solar system & storage, HVAC systems, structural upgrades, plumbing, home A/V systems. Every detail updated and ready to be enjoyed!

15 Oakhill DR, Woodside

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

Sold listing courtesy of Rachel Zhang from COMPS
$5,200,000
5 Beds ⋅ 6 Baths ⋅ ML81966423 MLS
Rare new-build contemporary in Woodside! Designed by Steve Simpson/SDG Architecture and built by Milne Design and Build, both know for attention to detail, this spectacular dream home provides your own private sanctuary. Its total livable area of 3,875 sf, is comprised of a two story 4 BR / 4.5 BA Main Home (approx 3,175 sf) with an artful blend of wood finishes, large windows and dark steel beams. Its main level open floor plan has a large chefs kitchen connected to a light-filled living room and dining area and also features a separate office which can double as the fourth bedroom. A lower level boasts three additional bedrooms, including a large primary suite, walk-in closet, soaking tub, shower and dual sinks and a spacious laundry room. The main home also has a coveted attached two-car garage (approx 465 sf) along with several additional off street parking areas. An adjacent detached two level 1 BR/1BA Guest House (approx 700 sf) has a full kitchen and guest suite, lower bedroom and covered exercise patio, providing perfect optionality for a remote office, hosting visitors or indoor/outdoor exercising. The property is situated on a less traveled one way street within walking distance to Town Center shops, restaurants and the acclaimed Woodside School (pre-K to 8th)

327 Hillside DR, Woodside

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

Sold listing courtesy of Helen Miller from APR
$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
$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

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