Woodside Glens Homes for Sale

Welcome to Woodside Glens, a hidden gem nestled in the heart of San Mateo County, California. This enchanting neighborhood combines natural beauty with a strong sense of community, making it an ideal place for families, professionals, and retirees alike. Woodside Glens is known for its picturesque tree-lined streets, spacious lots, and stunning views of the surrounding hills. The tranquil atmosphere invites residents to enjoy leisurely strolls, bike rides, and outdoor activities in the nearby parks and open spaces.

The charm of Woodside Glens extends beyond its scenic landscapes; the neighborhood boasts a rich tapestry of architectural styles, ranging from cozy cottages to elegant contemporary homes. Each property reflects the unique character of its owners while harmonizing with the natural surroundings. Homes for sale in Woodside Glens offer a variety of features, including expansive backyards, modern amenities, and energy-efficient designs, catering to a diverse range of lifestyles and preferences.

Living in Woodside Glens means being part of a close-knit community that values both privacy and connection. Residents enjoy easy access to top-rated schools, local shops, and gourmet dining options, all while being just a short drive from the vibrant cultural scene of nearby cities like Palo Alto and Menlo Park. With its perfect blend of serenity and convenience, Woodside Glens is not just a place to live; it’s a place to thrive. If you’re looking for your dream home in a welcoming environment, explore the enticing homes for sale in Woodside Glens today and discover the lifestyle you’ve always envisioned.

Newest Woodside Glens Homes for Sale

$4,795,000

4 Beds ⋅ 4 Baths ⋅ ML82051662 MLS

Inspired by traditional Norwegian farmstead architecture, this home was extensively rebuilt and expanded in 2002 with views of the western hills and Kite Hill Wildflower Preserve across the street. The home showcases exceptional craftsmanship with solid cedar siding, windows, doors, and screens, a slate roof, old-growth redwood trim, wide-plank Tennessee longleaf pine floors, soapstone countertops, Venetian plaster around the fireplace, and salvaged Douglas fir beams. The flexible 3-level floor plan includes lower-level quarters with kitchenette and private bath, two main-level bedrooms and a bath, plus upstairs primary suite and second suite. Beautifully landscaped grounds feature winding paths, specimen plantings, numerous fruit trees, a rare bamboo grove, pond, flagstone terrace with fireplace, spa, and large chicken coop. Additional features include dual-zone air conditioning, EcoFlow battery backup system and generator, distributed sound, EV charging for 2, and a detached garage. Minutes to Town Center, miles of trails, and acclaimed Woodside Elementary School (K-8).

144 Alta Mesa RD, Woodside

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

$3,695,000

3 Beds ⋅ 3 Baths ⋅ ML82047690 MLS

Classic architecture & beautifully updated interiors define this exceptional home in the Central Woodside, tucked away at the end of a peaceful cul-de-sac just one mile from the Woodside town center. The property offers a distinctive presence with an added sense of privacy & refinement. Freshly painted interiors & hardwood floors introduce warm, inviting spaces filled with natural light. Traditional character is complemented by contemporary finishes, custom cabinetry, granite surfaces, expansive windows, & sliding glass doors opening to the outdoor living areas. Cathedral ceilings enhance the open-concept design, creating wonderful scale for everyday living & entertaining. The flexible floor plan includes 3 bedrooms, a dedicated office, & 2.5 baths, including a spacious primary suite with fireplace, customized walk-in closet, & newly finished bath. There is also expansion & ADU potential (subject to Town approval & applicable development standards). Fully fenced front & rear yards offer expansive areas for entertaining & relaxation with level lawn, expansive deck, paver stone terrace, & large spa, all in a tranquil park-like setting. Access to the excellent Woodside Elementary School (TK-8) further enhances the appeal of this special offering.

63 Ridgecourt, Woodside

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

$5,495,000

4 Beds ⋅ 4 Baths ⋅ ML82046648 MLS

Classic architecture & beautifully curated grounds define this inviting Woodside home set on more than one-third acre moments from the town center. Stone-clad exteriors, newly planted lawns, & a picture-perfect approach introduce interiors that are warm, welcoming, & thoughtfully designed for everyday living. Natural light fills the home through expansive windows, hardwood floors, detailed millwork, & a floor plan that offers both openness & comfortable separation of spaces. Main living areas transition easily from formal rooms to casual gathering spaces, welcoming family room & well-appointed kitchen designed for both function & connection. Lower-level recreation/media room adds flexibility for entertainment or office use. Privately located primary suite with jetted tub & steam shower, bedroom with its own outside entrance & adjacent bath ideal for guest quarters. Outdoor living is a central focus, with a large arbor-covered deck extending from the home & terraced grounds below featuring a play area & garden spaces, all enhanced by refreshed landscaping. Located on a cul-de-sac street in the Woodside Glens neighborhood, with acclaimed Woodside School & offers a combination of traditional appeal, updated comfort, & an exceptionally convenient setting with a true sense of retreat.

103 Toyon CT, Woodside

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

$2,150,000

3 Beds ⋅ 2 Baths ⋅ ML82032924 MLS

BEST VALUE IN WOODSIDE!! Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. The nearly 0.5 acre lot features abundant, verdant scenery and a wrap-around deck to take it all in. The main level boasts a large, open-beam living room anchored by a cozy wood-burning stove, and is surrounded by windows which bring the natural beauty of the Glens inside. The floor plan includes a vintage kitchen, a dining area overlooking the oaks, and two bedrooms -- one featuring its own fireplace. Central air-conditioning provides year-round comfort. Upstairs is a versatile loft with a storage area. The lower level features a large bedroom with a bathroom and shower, an oversize 2-car garage, plus driveway space for 2 additional vehicles. With the large lot, an ADU is possible (buyer to confirm with the town). Located in the district for top-rated Woodside Elementary (K-8) and Woodside High, this home is moments from Woodside Village and offers a convenient commute to the entire Bay Area via Hwy 280. Experience the quintessential Woodside lifestyle in this timeless woodland sanctuary.

235 Hillside DR, Woodside

Listed by Steve Rumberg, 408-981-2383 from Keller Williams Realty-Silicon Valley
(If provided) CoList: from

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The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Fine Group Real Estate are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.