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$4,050,000
3 Beds ⋅ 3 Baths ⋅ ML82048231 MLS
Nestled on a quiet, beautifully wooded lot in desirable Woodside Hills, this meticulously updated residence blends timeless elegance with modern comfort. Light-filled interiors showcase expansive windows, refined finishes, custom window coverings and seamless indoor-outdoor flow. The remodeled chef's kitchen (2019) features a quartz-topped island, custom cabinetry, and premium Thermador, Bosch, and LG appliances, while opening to inviting dining and family spaces. A gracious living room with a redesigned gas fireplace and access to a deck creates an ideal setting for entertaining. Up the grand staircase, a serene primary suite offers high ceilings, dual walk-in closets, and a spa-inspired bath with soaking tub, curb-less shower, and designer finishes. Two additional bedrooms enjoy natural light and peaceful views. Extensively renovated, the backyard presents a resort-like retreat with multiple entertaining areas, a saltwater pool, AZEK decking, stamped concrete patios, gazebo and stone retaining walls and box planters, all surrounded by majestic oaks. Smart home features throughout the home include an EV charger. This exceptional home is situated in a premier, ultra-private location while being close to the Town of Woodside, Redwood City, schools, shopping, dining and Hwy 280.

345 Harcross RD, Woodside

Listed by Jane Dew, 650-353-8899 from The Agency
(If provided) CoList: from

Sold listing courtesy of Carol Koffel from COMP41
$3,800,000
6 Beds ⋅ 3 Baths ⋅ ML82022347 MLS
A Six-Bedroom Modern Masterpiece in Woodside Glens. Discover a stunning 2024 reimagined home where modern design meets family functionality just one mile from Woodside Town Center. This 6-bedroom, 3-bath smart home offers 3,087 sq. ft. of beautifully expanded and remodeled living space on a ~7,000 sq. ft. flat lot. The dramatic entry with custom iron and glass doors opens to airy, vaulted living spaces and a great room with a sleek all-white kitchen featuring quartz counters and Bosch appliances. The flexible layout includes a lower-level wing with two bedrooms, an office, laundry, and a rec room opening to the terrace ideal for guests, work, or play. Upstairs, the private primary suite offers skylit ceilings, a spa-like bath, and a balcony with western hill views. Smart-home systems, whole-home audio, three-zone heat pump climate control, and full fire sprinklers ensure comfort and peace of mind. Outdoor living shines with an expansive terrace, full outdoor kitchen, and RV hookups. Located in the acclaimed Woodside Elementary School District.

118 Hillside DR, Woodside

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

Sold listing courtesy of Michael R. Perrelli from CBR
$3,125,000
3 Beds ⋅ 2 Baths ⋅ ML82019083 MLS
A rare and private 15+ acre estate blending equestrian excellence, vineyard living, and natural beauty. Perfect for riders, vintners, or those seeking peaceful country living. The Barn Pros barn includes 4 matted stalls with Euro fronts, individual runs, a heated wash rack with hot/cold water, tack room, and enclosed feed/hay storage. Above, a spacious apartment with 2 sleeping areas, tall ceilings, and sweeping viewsideal for guests, caretakers, or rental income. Equestrian features include 2 fenced pastures with matted double run-ins, a paddock with a single matted shed, ~95x198 Olympia Footing arena (fenced with sand/rubber footing), and a ~60 round pen. The vintage 3BR, 1.5BA farmhouse offers rustic charm, storage, a cellar, and a relaxing front porch with serene views. A newer guest house (separately addressed) features 1BR + office/bonus roomideal for family, guests, or rental. Enjoy ~1 acre of Pinot Noir vines, fully fenced and producing excellent estate wineperfect for personal use or boutique winemaking. Mid Pen has plans to add a lot and access to the La Honda Open Space Perserve, that is right across the street. This is more than a propertyits a lifestyle sanctuary just ~20 mins to Hwy 280 and 30 mins to Half Moon Bay.

11120 La Honda RD, Woodside

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

Sold listing courtesy of David Cline from CBR
$699,000
2 Beds ⋅ 1 Baths ⋅ ML82018470 MLS ⋅ Kings Mountain Association BLDG.
Tucked along Skyline Boulevard, this 2-bedroom, 1-bath Woodside condo with its own private one car garage and laundry offers a lifestyle thats becoming increasingly hard to find: quiet, privacy, and nature; without giving up proximity to Silicon Valley and the Peninsula. Only 10-15 minutes to hwy 280 and set among towering redwoods, open sky, an ocean view and steps away from trails. This home features a spacious, light-filled layout with comfortable living areas that feel both grounded and welcoming. Whether youre starting your morning surrounded by nature or coming home after a long day below the hill, this property delivers a sense of retreat that most condos simply cant. This is Woodside living at an attainable level; ideal for a first-time buyer, down-sizer, or anyone craving a peaceful escape with real long-term value. Inventory in this area is limited, and opportunities like this dont come along often. If youve been waiting for the right way into Woodside; this is it.

14826 Skyline BLVD 3, Woodside

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

$1,500,000
1 Beds ⋅ 1 Baths ⋅ ML82016775 MLS

4214 Jefferson AVE, Woodside

Listed by Sternsmith Group, 650-678-5455 from Compass
(If provided) CoList: from

Sold listing courtesy of Zach Arrington from 991248
$3,005,000
4 Beds ⋅ 3 Baths ⋅ ML82009528 MLS
Western hill views take center stage... at this updated farmhouse on 1.2 acres, just minutes from the heart of Woodside. The multi-level home, set back in complete privacy, is filled with character, featuring gleaming hardwood floors and generous gathering spaces, all with expansive windows oriented to the views. The kitchen and family room combination opens directly to a spacious view-side deck for indoor/outdoor living. There are 4 bedrooms and 2.5 baths, including a main-level primary suite and three bedrooms upstairs. A 3-stall barn connects to fenced pastures, there is ample room for a dog run or chickens, and additional highlights include a charming playhouse and an oversized one-car garage with laundry. Located just 1.5 miles from the town center and with access to acclaimed Woodside Elementary School (K-8), this property celebrates rural tranquility and offers the opportunity to enjoy as-is or thoughtfully renovate for the future.

1207 Godetia DR, Woodside

Listed by Erika Demma, 650-888-6558 from Compass
(If provided) CoList: Deborah Kehrberg from Compass

Sold listing courtesy of The Patty Dwyer Group from APR
$2,037,000
4 Beds ⋅ 2 Baths ⋅ ML82008982 MLS
Perched on a peaceful mountain with breathtaking views of the Pacific Ocean, this updated 4-bedroom, 2-bath home offers the perfect blend of privacy and convenience. Just minutes from Half Moon Bay and San Mateo, this gated property is tucked within the cozy Kings Mountain community and designed for flexible living. With two spacious living rooms, two kitchens, and a bonus room, the home has excellent potential for separate living spaces; ideal for multigenerational living or guest quarters. The main kitchen features sleek Bosch appliances and modern finishes, while large windows throughout the primary living space capture breathtaking ocean vistas. Enjoy outdoor entertaining and evening sunsets on the deck, soak in the hot tub under the stars, and embrace the quiet, coastal mountain lifestyle. Whether you're looking for a serene full-time residence or a versatile retreat with income potential, this home offers comfort, flexibility, and unmatched views in a truly special setting. Just steps from Purisima Creek Redwoods Open Space Preserve and minutes to local favorites like The Mountain House and Alice's Restaurant, this home offers nature, charm, and versatility in one stunning package.

12960 Skyline BLVD, Woodside

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

Sold listing courtesy of Emily Baratzadeh from CBR
$1,775,000
3 Beds ⋅ 3 Baths ⋅ ML81993016 MLS
Welcome to 55 Bigtree, a charming retreat nestled among the towering redwoods of Woodside. This historic cabin has been beautifully remodeled and expanded, blending rustic charm with modern comfort. The original structure has been thoughtfully updated with a spacious addition, giving you more room to relax while keeping its timeless character intact. The heart of the home is the stunning great room, featuring soaring ceilings, tons of natural light, and amazing views of the surrounding redwoods. The new kitchen is a dream for any cook, with top-of-the-line appliances, custom cabinetry, and a large center island perfect for meal prep or gathering with friends. Right next to it, the cozy family room is an ideal spot to unwind, with easy access to outdoor living spaces. Step outside and take in the peaceful setting, complete with a partial bay view that adds even more charm to this woodland escape. Sitting on nearly half an acre, theres plenty of space to garden, entertain, or simply soak in the beauty of nature. Plus, you get the benefit of top-rated Portola Valley schools! If youve been looking for a tranquil retreat with modern amenities, this is your chance to call it home. Don't miss out!

55 Big Tree RD, Woodside

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

Sold listing courtesy of Wayne Rivas from AGNC
$685,000
3 Beds ⋅ 2 Baths ⋅ ML81987587 MLS
Price Improvement! Bring your vision, contractor and agent and make us an offer! Picture yourself, immersed in nature, living amongst the redwoods and fruit trees in your own fully fenced, secluded compound. Hidden from the road allowing you the ultimate in privacy. Enjoy the fragrance of fresh air and the Coastal breeze. Sink into soulful bliss and surround yourself in the beauty of nature while enjoying your morning beverage or your telecommute on the sun filled deck. The large great room with stone fireplace is the perfect space to entertain, an additional fireplace in the primary bedroom. Bonus room downstairs. No freeways here, far enough away from the hustle and bustle of the Silicon Valley, yet a short drive to Highways 92 and 280. With a little TLC, this lovely, private and secluded, quiet home would transform into a true gem. Sitting on over a half an acre, this is a real opportunity for the buyer who wants to keep the history and nostalgia of the area while creating a beautiful sanctuary to call their own. Live here or make this your vacation home away from home, moderate drive from the East Bay or San Francisco. Forget Tahoe, live Woodside!

200 Star Hill RD, Woodside

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

Sold listing courtesy of Jazmine Ransom from REEXPERTS
$1,450,000
3 Beds ⋅ 2 Baths ⋅ ML81984955 MLS
Abundant skylights throughout this charming woodsy cabin fill the home with sunlight and create a peaceful, inviting retreat just moments away from the bustle of Silicon Valley. The newly remodeled kitchen offers crisp white counters, cabinets, and a contemporary tile backsplash plus a mudroom laundry area with updated appliances. There are natural hardwood floors and vaulted ceilings in the living room, kitchen, and bedrooms. A large bedroom, full bathroom, kitchenette, and family room on the lower level could be used as a guest suite or ADU with separate entrance. Upgrades include new electrical panel, AC, back-up generator, cast iron wood stoves, and outdoor pizza oven. Multiple fruit trees, a small meadow, and a seasonal creek grace the backyard and are lightly shaded by elegant redwood trees. This one-of-a-kind home is served by Portola Valley's highly acclaimed elementary and middle schools, and is a short stroll to Alices Restaurant, Four Corners, and stunning trails for hiking or biking. Come see all that 223 Blakewood has to offer!

223 Blakewood WAY, Woodside

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

Sold listing courtesy of RECIP from RCIP
$1,099,900
2 Beds ⋅ 1 Baths ⋅ ML81980445 MLS
Welcome to this charming Woodside home, cradled amongst a cathedral of Redwood trees, and loaded with character. Enjoy the relaxing ambiance of this home, featuring Pella windows, vaulted wood ceilings, skylights, and pine wainscoting. With the perfect balance of updated convenience and country charm, this lovely home boasts an open kitchen with an adjacent dining nook, a loft perfect for storage, guests, or office, and a living room with vaulted ceiling, perfect for curling up by the wood burning stove. Outdoor eating area, flagstone patio w/arbor, built-in benches, large shed, extra storage, detached garage

144 Creek TRL, Woodside

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

Sold listing courtesy of Michael Mendenhall from KWSV
$1,801,000
3 Beds ⋅ 2 Baths ⋅ ML81970530 MLS
This private and serene home sits on almost one acre with dramatic views. Approximately 1913 square feet, the single level open floor plan is bright and flowing with vaulted ceilings, hardwood floors and large windows looking to the stunning natural views across the canyon. Living and dining areas open to private decks and yard. Beautifully remodeled and expanded in 2011 with permit, the house has 2 bedrooms and 2 bathrooms with large office also used as a bedroom and an additional office/den. High-end and very functional cabinetry and built-ins. Walk-in pantry and loads of storage. The garage has been converted to workshop/storage. Located in the sought after Skylonda neighborhood and served by the Woodside and Portola Valley Schools it is an easy commute to the heart of the Peninsula.

160 Chapman RD, Woodside

Listed by Karin Bird, 650-207-0940 from Compass
(If provided) CoList: from

Sold listing courtesy of Wayne Rivas from AGNC
$3,485,000
4 Beds ⋅ 3 Baths ⋅ ML81939223 MLS
Do not miss seeing the spectacular views from this serene home located on over an acre and a half of lush and beautiful grounds, close to downtown Woodside, schools and restaurants. Open floor plan with separate family room, dining room and living room with fireplace and a second primary bedroom and bonus room downstairs with a private entrance perfect for an in-law suite or granny unit. Please call TAMMY 650-683-0426

530 Summit Springs RD, Woodside

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

Sold listing courtesy of Tammy T-Cole from APR
$2,850,000
3 Beds ⋅ 2 Baths ⋅ ML81934979 MLS
Serene, very private and very quiet 3+/- acre property, only 5 minutes to Woodside town center surrounded by oaks, redwood and manzanita trees. Set on a knoll the property borders Huddart Park and watershed property and features the highly desirable beautiful western hill views. The 3-bedroom, 2-bath (current 3rd bedroom used as office), inviting home has rustic tones with an abundance of natural light. Large primary bedroom with walk in closet and recently updated en-suite bathroom. Light and bright, well laid out kitchen and updated second bathroom. Multiple outdoor dining and seating areas to enjoy this peaceful natural setting and views, fruit trees and several flat areas for potential other applications. 2 covered horse stalls with runouts, tack room, sand arena/turnout area, larger main barn/workshop, outdoor shower. Barn is aprox. 20'x34' Easy trail access into Huddart Park, Woodside Elementary School, close access to 280 and Sand Hill. Truly must be seen to appreciate.

486 Raymundo DR, Woodside

Listed by Chris Anderson, 650-207-7105 from Compass
(If provided) CoList: from

Sold listing courtesy of Roshan Izadi from APR

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